Organic Chemistry Questions PDF

- What is the major component of lipid bilayers in cellular membranes? A- Proteins b- Cholesterol c- Mucopolysaccharides d- Phosphoglycerides e- Sphingomyelins - Why does the water-saturated octanol in the n-octanol/water partitioning system mimic the physiological aqueous compartments in the...

- What is the major component of lipid bilayers in cellular membranes? A- Proteins b- Cholesterol c- Mucopolysaccharides d- Phosphoglycerides e- Sphingomyelins - Why does the water-saturated octanol in the n-octanol/water partitioning system mimic the physiological aqueous compartments in the body? A- Because octanol is completely immiscible with water b- Because octanol has similar hydrophobic properties as water c- Because water molecules cluster easily around octanol's hydroxy moiety d- Because octanol contains a high concentration of nonpolar components e- Because octanol is highly charged - What is a pharmacophore in drug design? A- A high-throughput screening method b- A computational technique c- A theoretical framework representing essential features for biological activity d- A lead compound with promising biological activity e- A software used for drug optimization - What does Virtual High Throughput Screening (vHTS) involve in drug discovery? A- Experimental assessment of chemical compounds b- Rapid analysis of large chemical databases using computer simulations c- Lead compound optimization d- Pharmacophore generation e- Absorption, Distribution, Metabolism, and Excretion (ADME) modeling - What is the role of lead compounds in drug discovery? A- To serve as starting points for further optimization b- To generate pharmacophores c- To conduct high-throughput screening d- To predict ADME properties e- To model chemical interactions - What does In Silico ADME Modeling predict in drug discovery? A- Biological activity b- Chemical interactions c- Pharmacophores d- ADME properties e- Lead compound optimization - Why are hexane/water and chloroform/water partitioning systems considered poor models for the lipid bilayer/water system in the body? A- They contain a high concentration of water in the organic phase b- They mimic the physiological aqueous compartments well c- They are good approximations of the lipid bilayer/water system d- They lack water in the organic phase e- They are immiscible with water- -What is a disadvantage of intravenous administration in terms of drug distribution? A- Rapid circulation b- Targeted delivery c- Limited tissue deposition d- Unwanted distribution e- Decreased first-pass metabolism - In what form is methylprednisolone sodium succinate typically found for administration? A- Topical ointment b- Oral tablet c- Sterile aqueous suspension d- Injectable solution e-Enteric-coated capsule - Why is acitretin recommended for a woman planning to become pregnant? A- Faster clearance from the body b- Lower teratogenic potential c- Longer biological half-life d- Increased protein binding e- Greater effectiveness against psoriasis - What role does the albumin–drug complex play in a drug's duration of action? A- Decreases drug concentration b- Acts as a reservoir for free drug c- Enhances rapid excretion d- Promotes protein binding e- Accelerates metabolism - What happens to the concentration of the ultra–short-acting, lipophilic barbiturate thiopental in tissue depots? A- Rapidly increases b- Remains constant c- Gradually decrease d- Promotes rapid diffusion e-Enhances pharmacological response -What is the main route of excretion for drugs and their metabolites? A- Enterohepatic circulation b- Excretion in human milk c- Diffusion from tissue depots d- Kidney e-Bile duct 1. In what form does olsalazine, used in ulcerative colitis treatment, reach the colon? A) Active mesalamine B) Inactive forms C) Dimeric form D) Water-soluble form E) Palmitic acid form ANSWER: C 2. How does the prodrug approach enhance the absorption of drugs like enalapril? A) Reducing oral absorption B) Increasing the first-pass effect C) Cleaving the active agent D) Creating inactive metabolites E) Improving oral absorption ANSWER: E 3. Why might parenteral administration be preferred in certain situations? A) Faster drug metabolism B) Limited drug distribution C) Inability to tolerate oral drugs D) Reduced first-pass effect E) Increased tissue depot formation ANSWER: C 4. How can the blood-brain barrier (BBB) impact the distribution of parenterally administered drugs? A) Facilitates brain exposure B) Enhances metabolic reactions C) Limits exposure to the brain D) Increases first-pass metabolism E) Accelerates systemic circulation ANSWER: C 5. How does prodrug design impact the biological half-life of etretinate and acitretin? A) Etretinate has a shorter half-life B) Acitretin has a longer half-life C) Both have similar half-lives D) Etretinate has a longer half-life E) Acitretin has a shorter half-life ANSWER: D 6. How does protein binding impact the passage of drugs from maternal to fetal circulation? A) Facilitates passage to the fetus B) Accelerates excretion C) Retains drugs in maternal circulation D) Reduces drug half-life E) Enhances fetal drug metabolism ANSWER: C 7. What is the significance of tissue depots in drug distribution? A) Enhances drug excretion B) Concentrates drugs in active sites C) Decreases drug half-life D) Promotes rapid diffusion E) Accelerates drug metabolism ANSWER: B 8. How does tocainide differ from lidocaine in terms of half-life? A) Lidocaine has a longer half-life B) Tocainide has a shorter half-life C) Both have similar half-lives D) Lidocaine's half-life is unknown E) Tocainide's half-life is unknown ANSWER: B 9. What responses can drug-receptor association produce in terms of macromolecule configuration? A) Decrease in 3D flexibility B) Unproductive changes C) Antagonistic or blocking responses D) Rigid lock-and-key fit E) Homologous series structure ANSWER: C 10. Provide an example of an inactive parent drug that is converted to an active metabolite. A) Lidocaine B) Sulindac C) Acyclovir D) Phenacetin E) Desipramine ANSWER: B  Class A & B Ministry of Higher Edu. & Sc. Research Subject: Org. Pharm Chem. I Alma'arif University College Date: March/ 26th /2024 Pharmacy Department. Time: 1.0 hour Mid - Exam Second Semester - Third Year 2023-2024 Assist. Prof. Dr. Smeerah Fenjan Hasan Q.I. Select the most appropriate answer for each of the followings by encircling: (There is only one correct answer for each question and your answers should be on the bubble sheet) 1. The followings are considered as site of drug loss except: a. Binding to the required receptor. b. Protein binding. c. Tissue depots. d. Metabolism. e. Excretion. 2. Orally administered drugs have bioavailability less than parenteral dosage form because of __ a. Digestive and bacterial enzymes. b. Protein binding. c. Both a&d. d. First pass effect. e. Tissue depots. 3. Which is not true about olsalazine a. Bioactivated by bacterial flora azo reductase. HOOC COOH b. Dimer of mesalamine. HO N c. Dimer of 5-ASA. N OH d. Bioactivated in the colon by esterase e. Bioactivated in the colon. 4. The followings describe chloramphenicol except: a. Ester prodrug. b. Has enough water solubility. c. Orally active. d. Has unpalatable bitterness. e. Pharmacologically active. 5. To reach the receptor orally administered drug has to partition between the followings except: a. The aqueous environment of the gastrointestinal tract. b. The lipid bilayer cell membrane of the mucosal cells. c. The adipose tissues. d. The lipid bilayer membranes on the venous side of the gastrointestinal tract. e. The aqueous environment of venous circulation. 6. Drugs with high protein binding such as warfarine shows: a. long duration of action. b. High drug activity. c. Low incident of drug- drug interaction. d. short duration of action. e. Fast metabolism. 1 Assist. Prof. Dr. Smeerah Fenjan Hasan 7. One of the following statements is incorrect about Thiopental: a. Ultra–short acting, lipophilic barbiturate b. Concentrate in tissue depots (fat). c. Very short duration of action. d. High protein binding property e. Can pass blood brain barrier (BBB). 8. In the following drugs, compound----------------- can be used in oral, intravenous (IV), and intramuscular (IM) dosage forms. a. I b. II c. I &III d. III e. II & III 9. Drugs with high extent of 1st pass effect show: a. High oral bioavailability. b. Long duration of action. c. Short duration of action. d. Low oral bioavailability. e. High incident of drug -drug interaction. 10. Drugs that undergo enterohepatic circulation show: a. High incident of protein binding. b. Long duration of action. c. Short duration of action. d. Decreased bioavailability. e. High incident of drug -drug interaction. 11. The ability of a chemical compound to give therapeutic effect is related to its…………………Properties 2 Assist. Prof. Dr. Smeerah Fenjan Hasan a. Steric. b. Taste. c. Acidity& basicity. d. Electronic. e. a, c& d 12.How many hydrogen bonding donors in compound III (given below). a. 1 b. 2 c. 4 d. 5 e.3 13. In the Henderson-Hasselbalch equation pKa represents the. a. Concentration of H3O+ ion. b. Acid strength. c. % of ionization. d. Equilibrium constat. e. Concentration of OH- ion. 14. The % of ionization of Aspirin (structure below) (PKa=4.5) at PH= 2.5 is: OCO CH3 COO H a. 99.9% b. 50% c. 9.99% d. 0.99% e. 90.9% 15. ------------ is the equilibrium ratio of both the ionized and un- ionized species of the molecule in n-octanol/water system. a. log D. b. log P. c. log Ka. d. log Kb. e. log (Solute)oct. 16. The science that translates the structural formula of the drug (physicochemical properties) into drug action is: a. Pharmaceutical Technology. b. Pharmaceutical (Medicinal) chemistry. c. Pharmacology. d. Biochemistry. e. Organic chemistry. 17.…………….is study of the correlation between structural changes of the compound and its pharmacological activity. a. Acidic strength. b. Pharmacodynamics. c. QSAR. d. Partition coefficient. e. pharmacokinetics. 18. The followings are methods applied to perform Drug-Design except: 3 Assist. Prof. Dr. Smeerah Fenjan Hasan a. Classification Methods. b. Computational chemistry. c. Silico ADME Modeling. d. Toxicological assay. e. Virtual High Throughput Screening (vHTS). 19. The followings describe Lidocaine except: a. Has significance first-pass effect. b. Used as local anesthetic. c. Used orally for cardiac arrhythmias. d. Used as IV for cardiac arrhythmias. e. Has half-life of less than 2 hours. 20. The diuretic drug ethacrynic acid (structure below), acts by------------------ bond formation with its receptor in the renal tubules. a. Hydrogen. b. Ionic. c. Hydrophobic. d. Ion–dipole. e. Covalent. 21.The following drug receptor (See figure) interaction is known as ------------ bonding a. Covalent. b. Hydrogen. c. Van der Waals. d. Ionic. e. Dipole – dipole 22. Methadone (structure below) exerts its action in ………………………. Ph a. Trans configuration. H3C H b. Extended conformation. CH C C COCH2CH3 H3C c. Bonded folded conformation N H Ph H3C 4 Assist. Prof. Dr. Smeerah Fenjan Hasan d. Cis configuration. e. Rigid geometrical configuration 23. The (-) enantiomer of epinephrine (structure below) is more active than the (+) isomer because it has_________ to the adrenergic receptor. a. The right steric fitness. b. Three points of attachments c. Two points of attachments. d. Both a&b e. The right biodistribution. 24.The followings are true about (-) ephedrine except one: a. The most potent optical isomer among the four optical isomers of ephedrine. b. Is 5 times more potent than (+) pseudoephedrine. c. The least potent optical isomer among the four optical isomers of ephedrine. d. Is 36 times more potent than (-) pseudo ephedrine. e. Is 3 times more potent activity than (+) ephedrine. 25. Acetylcholine interacts with the muscarinic receptor and with acetylcholinesterase in the fully extended structure and in a more folded structure, with the nicotinic receptors (see structures below). This is example of ------------------isomerism. a. Optical. b. Conformational. c. Structural. d. Configurational. e. Geometrical. 26. Different stereoisomers show different biological responses because of the followings except. a. Most receptors are asymmetric. b. Active transport mechanisms involve asymmetric carrier molecules. 5 Assist. Prof. Dr. Smeerah Fenjan Hasan c. The synthetic procedure of different isomers is different. d. The distribution of isomers with different physical properties is different. e. The enzymes responsible for drug metabolism are asymmetric 27. Epinephrine (structure below) exists at physiological pH (7.4) as: a. Negatively charged ion. b. Zwitter ion. c. Unionized species. d. Positively charged. e. 99% ionized at caticholic OH. 28. The followings are Lipinski Rule of Five for poor absorption or permeability of candidate molecule except. a. The molecule is racemic. b. The molecular weight exceeds 500. c. There are more than 5 H-bond donors. d. There are more than 10 H-bond acceptors e. The calculated n-octanol/water partition coefficient exceeds 5. 29. Phenytoin (acidic drug,HA acid; pKa 8.3) injection must be adjusted to pH 12 with sodium hydroxide to: --------------- a. Decrease ionization. b. Maintain physiological pH. c. Increase ionization.? d. Decrease water solubility e. Enhance patient comfort. 30.The followings describe the Purposes of drug metabolism except: a. Converts active parent drug to inactive metabolites. b. Converts inactive parent drug to active metabolite. c. Facilitate drug storage in tissue depots. d. Converts active parent drug to active metabolite. e. Converts toxic compounds to nontoxic metabolite Answer sheet 6 Assist. Prof. Dr. Smeerah Fenjan Hasan Answer Q.I Answer Q.I Answer Q.I (letter) (letter) (letter) 1 a 11 e 21 d 2 c 12 c 22 c 3 d 13 b 23 d 4 a 14 d 24 c 5 c 15 a 25 b 6 a 16 b 26 c 7 d 17 c 27 d 8 d 18 d 28 a 9 d 19 c 29 c 10 b 20 e 30 c Best wishes Head of the Department TheSmeerah Assist. Prof. Dr. Lecturer Fenjan Hasan Assist. Prof. Dr. Ibtisam Tahir 7  Class A Ministry of Higher Edu. & Sc. Research Subject: Org.Pharm. Chem. I Alma'arif University College Date: April. 21st.2024 Pharmacy Department. 3rd Level 2nd Semester C Assit Prf Dr.Smira Fenjan Hasan Quiz -2 Student Name: Q.I: Choose the most appropriate answer by encircling: 1. Conjugation biotransformation is the: A. Direct introduction of the functional group B. Modifying functionalities. C. Aromatic and aliphatic hydroxylation. D. Unmasking an existing functionality. E. Attachment of small, polar, ionizable and endogenous compounds 2. ----------(?)----------is metabolite generated from the following biotransformation. A. Compound II. B. Compound I. C. Compound V. D. Compound IV. E. Compound III. 3 Arene oxide intermediates (structure below) undergo the following metabolic path ways except one. A. spontaneous rearrangement to corresponding arenols. B. Enzymatic conjugation with (GSH). C. Enzymatic hydration to trans-dihydrodiols. D. Acetylation. E. Binds covalently with proteins, (DNA), and (RNA). 1 4. The role of NADPH-dependent CYP reductase is-------: A. Carry one atom of oxygen (O)from O2 and introduced it into the substrate R-H to form R-OH. B. Supply the reducing cofactor NADPH. C. Supply the reducing equivalents (electrons) needed in the overall metabolic oxidation of the substrate. D. Hydrolysis of the substrate. E. Both A&B. 5.The biotransformation shown below is----------: A. Amino acid conjugation. B. Methylation C. Acetylation D. Both C& B E. Glutathione reaction. 6. One of the followings does not describe sulfate conjugation. A. All sulfate conjugates are not toxic. B. Activated coenzyme is PAPS C. Less frequent than glucuronide conjugation. D. Occurs mainly for phenols > alcohols > aromatic amines > N-hydroxyl. E. Used to conjugate endogenous compounds such as steroids,heparin. 7. The enzyme that catalysis the following biotransformation is------------------: A. Epoxide hydrases. B. Amidase. C. ADH. D. P-450 E. Esterase 2  8. One of the followings does not describe glutathione reaction (GSH). A. Important pathway for detoxifying chemically reactive compounds. B. Protects vital cellular constituents against chemically reactive species. C. The substrates should be nucleophilic. D. GSH adducts are excreted as mercapturic acid derivatives. E. It is a tripeptide γ-glutamyl-cysteinyl glycine 9. Decreased rate of metabolism of the drug will cause----------------------of the drug. A. Increases the intensity. B. Decreases the intensity. C. Both A and E. D. Decreases the duration. E. Increases the duration. 10 ---------------------- describes the selective metabolism of two or more similar functional groups (e.g., OCH3, OH, NO2) or two or more similar atoms that are positioned in different regions of a molecule. A. Regioselectivity. B. Product stereoselectivity. C. Substrate stereoselectivity. D. Both A and C. E. Both B and C. 11. The following biotransformation warfarin is example on------------------- A. Keto Reduction. B. Aromatic hydroxylation. C. Ester hydrolysis. D. O-dealkylation. E. Alcohol oxidation. 3 12. The enzyme that catalysis the following biotransformation is----------------: A. Epoxide hydrases. B. ADH C.P-450. D. Amidase. E. Esterase 13. The functional groups undergoing glucuronidation in drug metabolism are the followings except one A. Hydroxy (OH) (phenolic and alcoholic hydroxyls) B. Carboxy (COOH). C. Amino (NH2). D. Phosphate (PO4) E. Thiol (SH) and Carbone. 14. The purpose of Methylation and Acetylation biotransformation reactions is: A. Protect the body against biological activity. B. Terminate the biological activity of drugs and xenobiotics. C. Protect the body against chemically reactive compounds or metabolites. D. Facilitate drug elimination. E. Unmasking an existing functionality. 15. ---------(?)----is metabolite generated from the following biotransformation.: A. Compound I. B. Compound IV. C. Compound V. D. Compound II. E. Compound III. 4  BEST WESHIES Answer sheet Answer Q.I Answer Q.I Answer Q.I (letter) (letter) (letter) 1 E 6 A 11 A 2 A 7 C 12 D 3 D 8 C 13 D 4 C 9 C 14 B 5 A 10 A 15 A 5 Quiz 1: 1. When a drug is administered orally, what factors govern its ability to dissolve? a. Type of tablet matrix b. Particle size and surface area c. Nature of crystal form d. All of the above e. None of the above 2. What is olsalazine, used in the treatment of ulcerative colitis? a. Active inhibitor of angiotensin-converting enzyme b. Prodrug cleaved to 5- amino salicylic acid c. Water-soluble prodrug d. Dimer of palmitic acid e. None of the above 3. What is the purpose of adding palmitic acid moiety to chloramphenicol, creating chloramphenicol palmitate? a. Enhance absorption b. Increase water solubility c. Reduce bitterness d. Inactivate digestive enzymes e. Improve stability 4. What is enalapril (in relation to enalaprilic acid)? a. Metabolically inactive compound b. Prodrug c. Water-soluble drug d. Active inhibitor of ACE e. Parenterally administered. 5. In drug distribution, what is the journey that involves partitioning between the aqueous environment of the gastrointestinal tract and the aqueous environment of venous circulation? a. Gastrointestinal mucosal barrier b. Aqueous intracellular environment of GI mucosal cells. c. Venous side of the gastrointestinal tract d. All the above e. None of the above 6. What is the primary purpose of the dimeric form of olsalazine? a. Enhance absorption b.Increase water solubility c. Improve stability d. all the above e. None of the above 7. Which route of administration is NOT mentioned as an alternate route when oral bioavailability is low? a. Parenteral b. Intravenous c. Intramuscular d. all the above e. None of the above 8. The following is NOT considered a cause for parenteral (injectable) dosage forms to be preferred? a. Patients intolerant to oral drugs b. Rapid metabolism in the liver c. Slow distribution in tissues d. All of the above e. None of the above 9. What is the first-pass effect in drug metabolism? a. Rapid distribution throughout the body b. Metabolism in the liver before reaching systemic circulation c. Inability to cross the blood-brain barrier d. Slow distribution from injection sites e. Bypassing the BBB by injecting drugs directly into specific organs 10.What is the purpose of subcutaneous and intramuscular injections in terms of drug distribution when compared with oral administeration? a. Rapid distribution b. Slow distribution from the injection site c. Bypassing the blood-brain barrier d. Circulation in tissue depots e. Targeting specific organs 11.How is methylprednisolone acetate different from methylprednisolone in terms of solubility? a. Methylprednisolone is water-soluble b.Methylprednisolone acetate is essentially water-insoluble c. Methylprednisolone acetate is found in tablets d. Both a and b e. Both b and c 12.What is the purpose of the ester prodrug approach for methylprednisolone succinate? a. Increase water solubility b. Reduce bitterness c. Enhance absorption d. Inactivate esterases e. Improve stability 13.How does acitretin differ from etretinate in terms of terminal half-life? a. Acitretin has a longer half-life b. Etretinate has a shorter half-life c. Both drugs have similar half-lives d. Neither drug has a terminal half-life e. none of the above. 14.What is the role of protein binding in drug solubility? a. Increases unbound (active) drug concentrations b. Acts as a reservoir for pharmacological response c. Limits access to body compartments d. Both a and b e. Both b and c 15.How can protein binding affect drug biodistribution? a. Enhances access to body compartments b. Decreases drug concentrations in specific organs c. Facilitates passage through the placental barrier d. Both a and b e. Both b and c 16.What role does the albumin–drug complex play in drug half-life? a. Prevents rapid excretion b. Increases drug availability for biotransformation c. increases pharmacological response d. Both a and b e. Both b and c 17.In what situation can protein binding lead to clinically significant drug–drug interactions? a. When one drug displaces another from albumin-binding sites b. When both drugs have similar pharmacological effects c. When one drug is water-soluble d. Both a and b e. Both b and c 18.How does the lipophilicity of a drug influence its concentration in tissue depots? a. Lipophilic drugs are less likely to concentrate in depots b. Lipophilic drugs rapidly diffuse out of tissue depots c. Lipophilic drugs are more likely to concentrate in depots d. Lipophilic drugs undergo rapid excretion e. Lipophilic drugs have longer durations of action 19.Why is thiopental's duration of action affected by its lipophilicity and tissue depot distribution? a. It is with high plasma protein binding b. It redistributes into body fat c. It slowly diffuses out of tissue depots d. Both b and c e. All of the above. 20.In the barbiturate series, what structural changes decrease duration of action but increase CNS depression? a. Decreasing lipophilicity b. Increasing lipophilicity c. Nonpolar side chains d. Both a and c e. Both b and c  Form A 1. What role does the liver play in drug metabolism? a. It acts as a reservoir for drugs b. It prevents first-pass metabolism c. It metabolizes drugs to inactive chemicals d. Both b and c e. Both a and c 2. Why is lidocaine impractical to administer orally? a. Rapid metabolism during its initial passage through the liver b. Slow metabolism in the liver c. Inability to cross the blood-brain barrier d. Both a and c e. Both b and c 3. Which is an example of an active parent drug converted to inactive metabolites? a. Lidocaine b. Sulindac c. Azathioprine d. Both b and c e. All of the above 4. What is the primary source of hindrance in drug metabolism for the medicinal chemist, pharmacist, and physician? a. Slow metabolic degradation b. Rapid excretion c. Inconvenience and compliance problems d. Rapid drug absorption e. All of the above 5. Why is it fortunate that the body has the ability to metabolize foreign molecules (xenobiotics)? a. To increase drug concentration in tissue depots b. To prevent chronic exposure to lipophilic chemical pollutants c. To enhance drug stability d. Both a and c e. Both b and c 6. What is a concern for nursing mothers regarding drug excretion? a. Drugs may be excreted in human milk b. Drugs may be ingested by the nursing infant c. Both a and b d. Neither a nor b 7. Why might dosing regimens need to be more frequent in certain situations? a. Formation of the drug–receptor complex is favored b. Partitioning into tissue stores is favored c. Metabolic degradation is favored d. Both b and c e. All of the above 8. What is the primary consequence of lidocaine's rapid metabolism during its initial passage through the liver? a. Increased oral bioavailability b. Extended duration of action c. Impractical oral administration d. Reduced hepatocyte concentration e. Enhanced CNS depression 9. How does the first-pass effect impact the oral administration of certain drugs? a. Decreases the concentration of drugs in the liver b. Increases bioavailability c. Prevents metabolism by hepatic enzymes d. Promotes oral absorption e. Induces rapid excretion 10.How does the presence of neutral fat tissue depots impact the pharmacokinetics of lipophilic drugs? a. Increases the rate of drug metabolism b. Decreases drug concentration in blood c. Enhances drug redistribution d. Prolongs duration of action e. Facilitates rapid excretion  Form A 1. How do un-ionized acids, like carboxylic acids, behave in terms of proton donation? a. They accept protons b. They donate hydroxide ions c. They form ionized conjugate bases d. They have no influence on protonation e. They exhibit weaker basic properties 2. Which of the following compounds is an example of an ionized acid? a. Carboxylic acids b. Ammonium compounds c. Hydrochloric acid d. Ephedrine e. Conjugate acids of carboxylate 3. What is the consequence of a hydrochloric acid solution having a Ka of 1.26 x 10 6? a. There is no unreacted HCl left in the solution b. Hydrochloric acid is a strong base c. The concentration of conjugate base is low d. The solution is neutral e. Hydrochloric acid is a weak acid 4. What does the pKa of ephedrine HCl (pKa = 9.6) indicate about its acid–base properties? a. It is a strong acid b. It has a weak conjugate base c. It is a proton acceptor d. Its conjugate base predominates in solution e. It has weak acidic properties in water 5. What is the general rule for determining a strong acid depending on pKa? a. pKa < 2 b. pKa 4 to 6 c. pKa 8 to 10 d. pKa > 12 e. pKa < 12 6. For a chemical with pKa 4 to 6, what acid–base classification would be appropriate? a. Strong acid b. Weak acid c. Very weak acid d. Strong base e. Neutral compound 7. How does ephedrine behave in terms of proton donation based on its pKa? a. It is a strong proton donor b. It is a weak proton donor c. It is a proton acceptor d. It has no acidic properties e. It forms a strong conjugate base 8. In the context of acid–base properties, what does a pKa > 12 suggest? a. Strong acid b. Strong base c. weak acid d. No basic properties in water e. Weak conjugate base 9. How does ephedrine HCl influence the concentration of its conjugate base in solution? a. The conjugate base concentration is low b. The conjugate base predominates c. Ephedrine HCl has no influence on its conjugate base d. The solution becomes neutral e. Ephedrine HCl is a strong acid 10. What is the role of carboxylate in the acid–base properties of carboxylic acids? a. It is an ionized acid b. It donates protons c. It is a proton acceptor d. It forms un-ionized conjugate bases e. It has no basic properties 11. How does ionized ammonium compounds behave in terms of proton donation? a. They accept protons b. They donate protons c. They form ionized conjugate bases  d. They have no influence on protonation e. They exhibit strong basic properties 12. How does an increase of 1 pH unit from the pKa affect the percent ionization of an HA acid like indomethacin? a. It decreases to 10.9% b. It increases to 90.9% c. It remains at 50% d. It decreases to 9.1% e. It increases to 99% 13. What happens when the medium is made more acidic relative to a drug's pKa value of HA acidic drugs? a. The equilibrium shifts to the right b. The drug becomes more water-soluble c. The concentration of the acid decreases d. The concentration of the conjugate base increases e. The concentration of the conjugate base decreases 14. What is the role of percent ionization in explaining and predicting problems with drug preparations? a. It affects the acid strength of drugs. b. It affects the drug's taste and odor. c. It helps predict pH extremes d. It determines the drug's shelf life e. It controls the drug's structure 15. Why is phenytoin injection adjusted to pH 12 with sodium hydroxide? a. To decrease its ionization b. To decrease water solubility c. To increase its anionic water-soluble form d. To increase its nonionic form e. To decrease the drug's shelf life 16. Why is indomethacin, with a pKa of 4.5, preferred as a suspension buffered at pH 4 to 5? a. To maximize water solubility b. To decrease ionization c. To minimize water solubility d. To decrease the drug's shelf life e. To enhance protein binding 17. How does the pKa of a drug affect its distribution in the aqueous environment of the blood? a. Ionized drugs distribute more rapidly b. Un-ionized drugs distribute more rapidly c. It has no effect on distribution d. It affects protein binding e. It affects the drug's color 18. What is the primary determinant of whether a drug remains in the aqueous environment of the blood or partitions into tissue? a. Drug concentration b. Plasma pH c. Protein binding d. Drug's taste e. pH of tissue depots 19. What does a polyfunctional drug like amoxicillin, with several pKa values, exhibit at physiological pH? a. Complete ionization b. Complete non-ionization c. Partial ionization d. Alternating ionization e. No ionization 20. How does the chemical nature of lipid membranes impact drug partitioning, and why is the n-octanol/water system preferred as a model for biological systems? a. Lipid membranes consist of fatty structures b. Lipid membranes favor hexane/water partitioning c. Lipid membranes are dynamic bilayers with polar and hydrophobic components d. N-octanol/water system enhances drug solubility e. N-octanol/water system has low water content  Class A Ministry of Higher Edu. & Sc. Research Subject: Org.Pharm. Chem. I Alma'arif University College Date: March. 3rd.2024 Pharmacy Department. 3rd Level 2nd Semester A-1 WK Student Name: Quiz I Q.I: Choose the most appropriate answer by encircling: 1. For the orally administered drugs the rate of dissolution is governed by the following factors except a. Drug chemical structure. b. Drug particle size and surface area. c. Nature of the crystal form. d. Type of tablet coating. e. Drug dosing regiment. 2. The followings describe Olsalazine except: a. Pharmacologically active. b. Azo prodrugs. c. Dimer of mesalamine. d. Cleaved by the intestinal bacteria to 5-aminosalicylic acid. e. Not metabolized by digestive enzymes. 3. The followings describe protein bound drug except: a. Increases the passage of the complex from maternal to fetal circulation. b. Increases drug’s duration of action. c. Increases the risk of drug-drug interaction. d. The complex acts as a reservoir to provide free drug at the receptor. e. Protein bound drug can pass through body membranes. 4.The following structures are isostere except: a. b. c. d. e. 5.The following drug – receptor interaction represents---------------bond. a. Ion-dipole. b. Covalent. c. Dipole - dipole. d. Reinforced ionic. e. Ionic. 6. ------------------represents the hydrophobic tail of the bilayer component of the biological cell wall. a. Phosphoglycerides. b. Cephalin. c. Sphingomyelins. d. cis -Unsaturated fatty acids. e. Plasmalogens. 1 7. The-------------is the dose of the drug that produces the desired effect in half of the subjects. a. ED90. b. LD50. c. Ki. d. ED50. e. MIC. 8. The percent of ionization of Tropicamide (basic drug, pka= 5.2. in the eye (pH=4.2) is: --------.-. a.0.99% b. 50% c- 99.09% d. 9.1% e. 90.9% 9. The followings describe drug -receptor interaction except: a. Drug-receptor interaction is an equilibrium process. b. Drug-receptor interaction is flexible key-lock interaction. c. The drug docks with the receptor. d. Drug-receptor association undergo changes in 3DS of the macromolecule. e. Drug-receptor interaction is rigid key-lock interaction. 10. The trans-diethylstilbestrol is estrogenic (95% active), whereas the cis- isomer is only 7% as active (structures below). This is example of ----------------- -isomerism. a. Optical. b. Conformational. c. Structural. d. Configurational. e. Geometrical. Answer sheet Answer Q.I (letter) 1 e. 2 a. 3 a. 4 b. 5 c. 6 d. 7 d. 8 e. 9 e. 10 e 2  Class B Ministry of Higher Edu. & Sc. Research Subject: Org.Pharm. Chem. I Alma'arif University College Date: March. 3rd.2024 Pharmacy Department. 3rd Level 2nd Semester B-1WK s Student Name: Quiz I Q.I: Choose the most appropriate answer by encircling: 1. For the orally administered drugs the rate of dissolution is affected by the followings except: a. Type of tablet matrix. b. Drug PKa c. Drug particle size. d. Drug affinity. e. Type of tablet coating. 2. The followings describe mesalamine except: a. Used in the treatment of ulcerative colitis. b. Azo prodrug. c. Pharmacologically active. d. Inactivated before reaching the colon. e. Metabolized by digestive enzymes. 3. The followings describe tissue depots except: a. Neutral fat constitutes 20% to 50% of body weight. b. Decreases drug’s onset and duration of action c. Increases drug’s onset and duration of action. d. The more lipophilic the drug will concentrate in these depots. e. It is considered as a site of drug loss. 4. The following structures are isostere except: a. -CH3. b. -NH2. c-OH. d. -Br. e. -Cl. 5. The following drug – receptor interaction represents---------------bond. a. Hydrogen. b. Covalent. c. Hydrophobic. d. Reinforced ionic. e. Ionic. 6.------------------represents the hydrophilic head of the bifunctional phospholipids of the bilayer component of the biological cell wall. a. Phosphoglycerides. b. Cephalin. c. Sphingomyelins. d. Galactocerebrosides. e. Plasmalogens. 7. The ---------- is the dose of the drug that kills half of the subjects. a. ED90. b. LD50. c. Ki. d. ED50. e. MIC. 1  8. The percent of ionization of Phenytoin (acidic drug; pKa 8.5) at physiological pH is: --------.-. a.0.99%. b. 50%. c- 99.09%. d. 9.1%. e. 90.9%. 9. Lock and key theory for ligand- receptor interaction assumed that: a. The ligand and the receptor are flexible. b. Only the ligand is flexible. c. Only the receptor is flexible. d. Neither of them is flexible. e. The flexibility has no role in this theory. 10. (-)Epinephrine exhibits 12 to 15 times more vasoconstrictor activity than (+)-epinephrine. This is example of ------------------ isomerism. a. Enantiomerism. b. Conformational isomerism. c. Diastereomerism d. Configurational isomerism. e. Geometrical isomerism. Answer sheet Answer Q.I (letter) 1 d. 2 b. 3 c 4 d. 5 d. 6 a. 7 b. 8 d. 9 a. 10 a. 2  Ministry of Higher Education & Organic Pharmaceutical Scientific Researches Chemistry 퐈 University of Babylon Third Stage / Second Trial College of Pharmacy Time : 1.5 hour Department of Clinical Laboratory Sciences Mid-term exam 2023 – 2024 み૯ɭเﾒ๏เ ઽ૯ท ઽ૯เ 1. drug’s acid–base properties affect its membrane permeability and hence biodistribution characteristics. a. true b. false 2. Acids are compounds that a. Donate a proton b. Accept a proton c. Neither give nor accept a proton d. None of the above are correct 3. Bases are compounds that a. Donate a proton b. Accept a proton c. Neither give nor accept a proton d. None of the above are correct 4. Un-ionized acids (HA acids) donate their protons forming ionized conjugate bases. a. true b. false 5. Ionized acids (BH+ acids) donate proton and yield un-ionized conjugate bases. a. true b. false 6. carboxylic acid drugs donate protons and form carboxylate ions. a. true b. false 7. Sulfanilamide drugs donate protons and form corresponding anions. a. true b. false 8. un-ionized bases donate protons and yield ionized conjugated acids. a. true b. false 9. ionized bases donate protons and yield un-ionized conjugated acids. a. true b. false 10. In vivid acid base reactions take place frequently because Drugs are a. bound to plasma proteins b. deputized in adipose tissue c. Encounter water in all places d. None of the above are correct ㅤㅤㅤㅤㅤㅤㅤㅤㅤ Page 1 of 7 ㅤㅤㅤㅤㅤㅤㅤㅤㅤ ㅤㅤㅤㅤㅤㅤㅤㅤㅤ 11. Water is an amphoteric molecule because a. It reacts with acids b. It reacts with bases c. Neither reacts with acids nor bases d. Reacts with both acids and bases 12. Which of the following statements best describes water amphoteric properties. a. React with acidic drugs to form the strongly acidic hydronium ion (H3O+) b. React with bases to form the strongly basic hydroxide anion (OH-) c. Both (a) and (b) are correct d. None of the above are correct 13. Which of the following parameters useful in predicting the direction of an acid–base reaction? a. Pka of the compound b. PH of the medium c. Type of the compound whether acid or base d. All of the above are correct 14. Which of the following used to predict the extent the reaction goes to completion? a. Pka of the compound b. PH of the medium c. Type of the compound whether acid or base d. All of the above are correct 15. The equilibrium in water for a strong acid, with low pKa values, lies to the right, favoring the formation of conjugate acid and conjugate base. a. true b. false 16. The equilibrium in water for a strong acid, with low pKa values, lies to the left, opposing the formation of conjugate acid and conjugate base. a. true b. false 17. The equilibrium in water for a weak acid, with high pKa value, lies to the left which means: a. The conjugate acid is a better proton donor than the parent acid b. The parent acid is a better proton donor than the conjugate acid c. The conjugate base is a good proton acceptor. d. Both (a) (b) are correct 18. The Ka value for indomethacin, HA acid, is 3.16* 10-5 , Which of the following statements best describes its hydrolysis in water: a. indomethacin is an excellent proton donor b. indomethacin is an excellent proton acceptor c. Its conjugate base is an excellent proton acceptor d. None of the above are correct 19. Saccharine is an HA acid with pKa value of 1.6, all of the following statements apply except: a. It’s a strong acid b. Its conjugate base has no basic properties in water c. It’s an HA acid d. It’s a poor proton donor Page 2 of 7 20. Ephedrine HCl is a BH+ acid with pKa value of 9.6, Which of the following statements best describes its acid base properties? a. It’s a very an excellent proton donor b. Ephedrine is a poor proton acceptor c. Both (a) and (b) are correct d. None of the above are correct 21. A drug has pKa value of 4.8, Which of the following statements best describes its acid Strength? a. It’s a strong acid b. It’s a weak acid c. It’s a very weak acid d. It has no acidic properties 22. indomethacin has pKa value of 4.5, Which of the following statements best describes its acid Strength? a. It’s a strong acid b. It’s a weak acid c. It’s a very weak acid d. It has no acidic properties 23. Ephedrine HCl has pKa value of 4.5, Which of the following statements best describes its acid Strength? a. It’s a strong acid b. It’s a weak acid c. It’s a very weak acid d. It has no acidic properties 24. Studying drug’s acid–base chemistry becomes beneficial as knowing the drug’s pKa, make possible to adjust the pH to achieve ensure : a. maximum water solubility b. maximum lipid solubility c. Both (a) (b) are correct d. None of the above are correct 25. Acids are divided into two types, HA and BH+, depending on the basis of the acid strength of the acid or conjugate base. a. true b. false 26. Following its administration a drug do which of the following before reaching its site of action? a. Avoid alternate sites of attachment and storage b. pass through biological membranes c. avoid significant metabolic destruction d. All of the above are correct 27. Factors affecting drug dissolution include which of the following? a. chemical structure b. variation in particle size and particle surface area c. Nature of the crystal form d. type of tablet coating and tablet matrix e. All of the above are correct Page 3 of 7 28. Changing the route of administration of drug under investigation intended for oral use to alternative one in which case of the following? a. no effective alternative for this new drug b. it is more effective than existing products c. It can be administered by one of these alternate route d. All of the above are correct 29. We can modify drug dissolution by which of the following? a. Use another dosage form b. Changing the physical characteristics of the drug c. Both (a) and (b) are correct 30. Example on prodrug approach used to facilitate a drug reaching its desired target is : a. Chloramphenicol b. Enalapril c. mesalamine d. Sulindac 31. Which of the following statements best describes Olsalazine? a. It’s a prodrug of mesalamine b. It’s a dimer of 5-aminosalicylic acid c. cleaved by the intestinal bacterial azoreductase to the active drug d. All of the above are correct 32. Which of the following statements about chloramphenicol palmitate is correct? a. chloramphenicol is water soluble enough (2.5 mg/mL) and produce bitterness b. chloramphenicol palmitate is of limited water solubility (1.05 mg/mL) hence do not interact with bitter taste receptors on the tongue c. palmitic acid moiety is esterified with the primary hydroxyl of chloramphenicol d. All of the above are correct 33. prodrug approach: used to alter the solubility, in order to formulate it in many dosage forms, which statement best describes the situation? a. Methylprednisolone, slightly water-insoluble, formulated as tablets b. Methylprednisolone sodium succinate, water insoluble, formulated as topical ointments c. Methylprednisolone acetate, water-soluble, formulated as IV injection d. All of the above are correct 34. All of the following drugs act by forming a covalent bonds with the receptors except: a. Penicillin G b. Epinephrine c. organic phosphates d. ethacrynic acid 35. most drugs acting by forming which of the following bonds? a. Hydrogen bonds b. Ionic bonds, c. Ion–dipole and dipole–dipole interactions. d. van der Waals e. All of the above are correct Page 4 of 7 36. Ionizable functional groups that form ionic bonds at physiological pH include which of the following? a. carboxylic acid group b. sulfonamido group c. aliphatic amino groups d. All of the above are correct 37. Ionizable functional groups that form ionic bonds At any pH include which of the following? a. carboxylic acid group b. quaternary ammonium group c. aliphatic amino groups d. All of the above are correct 38. Groups that form dipole-dipole or ion-dipole interactions include which of the following? a. nitrile group b ether group c. Amide group d. All of the above are correct 39. Groups that form hydrogen bonds interactions include which of the following? a. carbonyl group b. hydroxyl group c. amino, and imino groups d. All of the above are correct 40. which of the following is true about asymmetric molecules? a. they cannot be divided into symmetrical halves b. they are optically active c. usually have chiral center d. all of the above are correct 41. all of the following is true about ephedrine and pseudoephedrine pair except: a. they are diastereomers, have two chiral centers b. they have similar physical properties c. they have different melting points d. they have different Water solubility 42. Optically active isomers that have different biological properties include which of the following? a. (-)-hyoscyamine and (+)-hyoscyamine b. (-)-ephedrine and (+)-ephedrine c. (-)-ephedrine and (+)-pseudoephedrine d. all of the above are correct 43. the pharmacological activity of all of below stereoisomers differ dramatically except: a. (+) morphine and (-) morphine b. dextromethorphan and levomethorphan c. Dextropropoxyphene and Levopropoxyphene d. all of the above are correct 44. which of the below stereoisomers elicit analgesic activity with high risk of drug abuse? a. (-) morphine b. (-) codeine c. Dextropropoxyphene d. both (a) and (b) are correct Page 5 of 7 45. The generic name of all of the following drugs indicates a specific stereoisomer except: a. levodopa b. levamisole c. dexlansoprazole d. Ephedrine 46. Which of the following drugs was originally marketed as racemic mixtures then reintroduced using the active isomer? a. citalopram b. levodopa c. omeprazole d. Both (a) and (b) e. Both (a) and (c) 47. Example on drugs originally approved as racemic mixtures, and later the isomer which has fewer adverse reactions was marketed include which of the following? a. dexlansoprazole b. bupivacaine c. levamisole d. dexmethylphenidate 48. Which of the following statements about bupivacaine is true? a. Act as analgesic b. Levobupivacaine is the R-isomer c. S-isomers is more active than R-isomer d. S-isomer shows less cardiotoxic than R-isomer 49. Which statement about citalopram is correct? a. Escitalopram is the S-isomer b. It’s a selective serotonin reuptake inhibitor , antidepressant c. The R-isomer is less active and causes more side effects d. All of the above are correct 50. The drug's stereoisomers may not be economically feasible to resolve as in case of: a. ibuprofen b. omeprazole c. verapamil d. dextromethorphan 51. Which of the following statements about verapamil is correct? a. it is difficult to conclude whether R or S isomer is better b. S-verapamil is more active and Slowly metabolized c. R-verapamil is Less active and rapidly metabolized d. All of the above are correct 52. For carboxylic acid drugs, which of the following apply? a. the parent acid cross biological membranes b. the conjugate base cross biological membranes c. both parent acid and its conjugate base cross biological membranes d. neither parent acid nor its conjugate base cross biological membranes 53. For ephedrine HCl, which of the following apply? a. the parent acid cross biological membranes b. the conjugate base cross biological membranes c. both parent acid and its conjugate base cross biological membranes d. neither parent acid nor its conjugate base cross biological membranes Page 6 of 7 54. Partition Coefficient is an excellent estimator of drug partitioning in biological systems for drugs absorbed by which of the following mechanism? a. passive diffusion b. carrier mediated transport c. cytosis d. none of the above are correct 55. the n-octanol/water partitioning system seems to mimic the lipid membranes /water systems found in the body because: a. n-octanol phase resembles polar properties to that of the lipid bilayer b. the water phase resembles the physiological aqueous compartments c. both (a) and (b) are correct d. none of the above are correct 56. which of the following is true about asymmetric molecules? a. they cannot be divided into symmetrical halves b. they are optically active c. usually have chiral center d. all of the above are correct 57. all of the following is true about ephedrine and pseudoephedrine pair except: a. they are diastereomers, have two chiral centers b. they have similar physical properties c. they have different melting points d. they have different Water solubility 58. Optically active isomers that have different biological properties include which of the following? a. (-)-hyoscyamine and (+)-hyoscyamine b. (-)-ephedrine and (+)-ephedrine c. (-)-ephedrine and (+)-pseudoephedrine d. all of the above are correct 59. the pharmacological activity of all of below stereoisomers differ dramatically except: a. (+) morphine and (-) morphine b. dextromethorphan and levomethorphan c. Dextropropoxyphene and Levopropoxyphene d. all of the above are correct 60. which of the below stereoisomers elicit analgesic activity with high risk of drug abuse? a. (-) morphine b. (-) codeine c. Dextropropoxyphene d. both (a) and (b) are correct Page 7 of 7  MCQs Exam of Organic Pharmaceutical Chemistry I Al-Ayen Iraqi University Date: 22/4/2024 College of Pharmacy Time: 1.5 hour Department of Pharmaceutical Academic Year: 2023/2024 Chemistry 2nd Semester / Third Stage Examination Notes: This exam is made up of 7 pages. Answer the multiple-choice questions on the provided answer bubble sheet — Use a dry pen ONLY. Choose the correct answer for each of the following questions: (50 marks) 1. Following are the Phase I reactions except ____________ A. Oxidative reactions B. Hydrolytic reactions C. Reductive reactions D. Sulphide reactions E. functionalization reaction 2. Which of the following statements is the closest description of Phase I metabolism? A. Reactions which add a polar molecule to a functional group already present on a drug or one of its metabolites B. Reactions which occur in the blood supply. C. Reactions which add a polar functional group to a drug. D. Reactions which occur in the gut wall. E. involves unmasking or modifying a functional group 3. Which of the following enzymes is not involved in catalyzing Phase I metabolic reaction? A. Flavin-containing monooxygenases B. Oxidation of alkyl groups C. Glucuronyl transferase D. Esterases E. Azo reductase 4. Which of the following reactions is not a Phase I metabolic transformation? A. Reduction of ketones B. Conjugation to alcohols C. Monoamine oxidases D. Esterhydrolysis E. hydrolysis of phosphate ester 5. What is the major end product of oxidation of aromatic carbon atoms? A. Arenols B. Catechol C. Carbinol D. Arene oxide E. Arene epoxide 6. Which enzyme is important in the Phase II reactions? A. Esterase B. Amidases C. Oxidase D. Aldo-keto-reductases E. Acetyl transferase 7. Which of the following groups is least susceptible to cytochrome P450 enzymes? Page 1 of 7  A. Terminal methyl groups B. Epoxide group C. Benzylic carbon atoms D. Quaternary carbon atoms E. Olefinic group 8. Diazepam gets metabolised into Hydroxydiazepam is example of- A. Oxidation at allylic carbon atom B. Oxidation at the carbon alpha to carbonyl and imino group C. Oxidation at benzylic carbon atom D. Aromatic and Side chain Hydroxylation E. A and B 9. __________reaction is most common in drugs having ester or amide functional groups A. Oxidative reactions B. Reduction C. Hydrolysis D. Phase I E. Phase II 10. UDPGA means…. A. Urane diphospho -a- D glucuronic acid B. Uridine diphospho -a- D glucuronic acid C. Uridine diphospho-D glucose amine acid D. Uric diphospho -a- D glucuronic acid E.. Uridine diphospho -a- D glucose amine 11. Which of the following statement is false? A. D-glucuronic acid is easily available B. Several functional groups can be easily linked with the D- glucuronic acid C. Conjugation with D-glucuronic acid occurs to a high degree D. Glucoronidation is the most commom phase II reaction E- Glucoronidation does not require activation 12. Which functional groups are required for the formation of Glucuronide? A. OH and NH2 B. OH, SH and NH2 C. OH, SH, C=O and COOH D. OH, SH, NH2, and COOH E.OH, NH2 and COOH 13. What is the site of first-pass metabolism before molecules reach systemic circulation? A. Kidney B. Throat C. Liver D. Stomach E. Blood 14. What plays a major role in extra-hepatic metabolism and contains CYP3A4 isozyme and P- glycoprotein? A. Kidney B. Lung C. Liver D. Intestine E. Portal circulation 15. Which of the following are protein components of the cytochrome P450 system? A. Heme part of CYP450 B. NADH-CYP450 reductase C. NADPH-CYP450 reductase v1.0 – 2024/2023 ‫كلّيّة الصيدلة‬ Page 2 of 7  D. A and B E. A and C 16. Which of the following statements is not true about cytochrome P450 enzymes? A. They contain haem and magnesium. B. They belong to a general class of enzymes called monooxygenases. C. There are over 30 different cytochrome P450 enzymes. D. Variation in cytochrome P450 enzyme profile between individuals can explain Individual variation in drug susceptibility. E. It can oxidize a wide range of compounds due to its substrate non- specificity 17. What is not a xenobiotic? A. Plant toxins B. Drugs C. Food D. Steroids E. Environmental pollutants 18. Which one of the following is reactive and a known carcinogenic? A. Cytochrome P-450 B. Catechol C. carbinolamine D.Arenol E. Arene oxide 19. Intermediates of aromatic hydroxylation includes the following ,except: A. Arenol B. Epoxide C. Aldehyde D. Dihydrodiol E. Glutathion adducts 20. Oxidation of Tolbutamide is the example of A. Oxidation of Olefin B. Oxidation of Aliphatic carbon C. Oxidation of Benzylic carbon D. Oxidation of Allylic carbon E. B and C 21. Carbon atom adjacent to olefinic double bond is known as A. Alicyclic carbon B. Aliphatic carbon C. Benzylic carbon D. Allylic carbon E. Chiral carbon 22. Hexobarbital can undergo all the following phase I reactions except A. Olefinic oxidation B. N-delakylation C. Allylic oxidation D. N Oxidation E. O-dealkylation 23. Desulphuration of given drug results in ______ A. SH group B. C=O group C. high polar derivatives D. S- dealkylation E. B and D 24. All the phase II reaction required activation except v1.0 – 2024/2023 ‫كلّيّة الصيدلة‬ Page 3 of 7  A. Glucorinide conjugates B. Sulfate Conjugates C. Amino acid Conjugates D. GSH conjugates E. Acetylation 25. Regarding metabolism of aldehyde and ketone, which statement is correct: A. Aldehyde oxidation is more common than ketone B. Ketone oxidation results in carboxylic acid C. Ketone oxidation results in secondary alcohol D. Aldehyde reduction result in chrial or asymmetric carbon E. Aldehyde frequently reduced into carboxylic acid 26. Phase II metabolism consider as a truly detoxifying reaction with few exception. The exception includes A. Glucoronidation B. Sulfation C. Acetylation D. Methylation D. Amino acid conjugations 27. Phase I and phase II metabolism plays a central role in the following except: A. Enhancing renal reabsorption B.Changing lipophilic compounds to hydrophilic ones. C.Detoxification D. Facilitate drug elimination. E. Prodrug activation. 28. Intestinal mucosa is an important site for metabolism of orally administered drugs, this is because: a. It contains CYP3A4 isozyme b. It contains esterase and lipase. c. The role of intestinal bacterial flora in drug metabolism. d. It contains glucuronidase enzymes. e. All the above 29. Concerning CYP 450, all the statements are true except: a. The capital letter in the nomenclature refers to the family. b. It is responsible for the oxidative biotransformation in drug metabolism. c. It is heme protein. d. It is present in many tissue (e.g. liver, lung, kidney and skin). e. It is substrate nonspecific. 30. Concerning aromatic hydroxylation, all the statements are true except: a. Arenols are formed through the spontaneous rearrangement of arene oxide. b. NIH shift of the intramolecular hydride often takes place in the spontaneous rearrangement of arene oxide. c. NH2 substituent to the aromatic ring slows the hydroxylation. d. Arene oxide intermediates are formed when aromatic double bond is epoxidized. e. It is a major route of metabolism of phenyl containing drugs. 31. Regarding arene oxides, all the statements are true except: a. They are toxic intermediates b. They are electrophiles c. They are susceptible to enzymatic hydration to give mercapturic derivatives. d. They are three-membered epoxide ring. e. They are susceptible to nucleophilic attack by water. v1.0 – 2024/2023 ‫كلّيّة الصيدلة‬ Page 4 of 7 32. Hydroxylation of p-chlorobiphenyl would occur mainly at position: a. 1 b. 2 c. 3 d. 4 e. 5 33. Regarding clonidine: a. It undergoes little aromatic hydroxylation. b. The activating groups (Cl, -N+H=C) slow the hydroxylation. c. Replacing (-N+H=C) by (–NH2) would activate the ring. d. Removing the substituted Cl groups would activate the ring. e. a, c and d. 34. Alcofenac is metabolized to dihydroxyalcofenac through: a. aromatic hydroxylation b. olefin oxidation c. allylic oxidation d. benzylic oxidation e. alicyclic oxidation. 35. Concerning styrene epoxide: a. It is reactive species. b. It might cause cellular toxicity. c. It can be detoxified through converting to mercapturic acid derivative by glutathione S- transferase enzyme. d. It can form covalent bonds with proteins and nucleic acids. e. All above 36. Upon oxidation of tolbutamide benzyl carbon, the possible metabolites would be: a. Primary alcohol and aldehyde b. Secondary alcohol and aldehyde c. Ketone and carboxylic acid. d. Tertiary alcohol. e. a and c 37. Concerning the metabolism of amitriptyline, position 1 and 2 could undergo: a. Aromatic oxidation b. Olefin oxidation c. Benzylic oxidation. d. Allylic oxidation. e. Aliphatic oxidation 38. Oxidation at benzyl carbon atom could produce: a. Arene oxide b. Oxirane c. Carbinol v1.0 – 2024/2023 ‫كلّيّة الصيدلة‬ Page 5 of 7  d. Trans-dihydrodiol e. Catechol 39. Concerning the compound in the figure: a. It has 4 benzyl carbon atoms b. It has 3 allylic carbon atoms c. Oxidation at position 1 would produce primary alcohol d. Oxidation at position 3 would produce secondary alcohol. e. Oxidation at position 6 would produce carbinol. 40. Carbinol metabolites of allylic carbon oxidation could be a. Primary, secondary or tertiary alcohol b. Excreated directly through renal system c. Usually oxidized to aldehydes and ketones d. Oxidized to carboxylic acids if they are secondary alcohols. e. All the above. 41. Concerning the compound in the figure: a. Carbon in position 1 can undergo aliphatic oxidation b. Carbon in position 2 can undergo benzylic oxidation c. Carbons in positions 3 can undergo aromatic oxidation d. Oxidation of position 3 would produce secondary alcohol e. All the above 42. Valproic acid undergoes oxidation and the following are possible metabolites except: a. Primary alcohol. b. Secondary alcohol. c. Aldehyde. d. Carboxylic acid. e. Epoxide. 43. Concerning acetohexamide metabolism a. The metabolic pathway is alicyclic hydroxylation b. A & B metabolites represent trans-3-hydroxyacetohexamide and cis-3- hydroxyacetohexamide respectively c. Enzymatic hydroxylation generally occur at carbon 2 of the cyclohexyl group d. Only trans isomers can be formed e. a and b 44. if the metabolism of lipophilic drug was inhibited, this might result in: a- Diminish drug elimination b- Enhance detoxification c- Activation of prodrug d- Increasing kidney clearance. e- All the above. 45. Concerning CYP 450 v1.0 – 2024/2023 ‫كلّيّة الصيدلة‬ Page 6 of 7  a. The heme portion called apoprotein. b. Its name ends with a number that refers to the subfamily. c. It is able to metabolize limited number of substrate. d. It is found in high concentration in the liver. e. All the above. 46. The compound below undergo all the following phase I metabolism, except A. Dealkylation B. aromatic hydroxylation C. hydrolysis D. lactam formation E. benzylic oxidation 47. Metabolism of Nitrogen functionalities is important because A. These groups are found in many natural and synthetic compounds B. Less toxicity of Nitrogen containing compound as compared to other groups C. These groups are easily metabolized D. These groups are highly toxic E. These groups are easily metabolized 48. Primary aliphatic amines are metabolized by A. Oxidative dealkylation B. Oxidative deamination C. N Oxidation D. A and C E. All of them 49. The most common detoxification reaction for arene oxide is: A. Formation of catechol B. Aromatization C. Spontaneous rearrangement to phenolic derivatives D. GSH adduct formation E. hydration to dihydro diol 50. Oxidation of primary alcohol is more important than secondary alcohol, because: A. Primary alcohol oxidized irreversibly to aldehyde B. primary alcohol is more polar than aldehyde c. primary alcohol is oxidized to carboxylic acid irreversibly D. ketone is an inert group E. ketone oxidation produces two isomers GOOD LUCK Examiner Dean of College of Pharmacy Prof. Mazin Nadhim Mousa Assist. Prof. Dr. Qutaiba AlHajjaj v1.0 – 2024/2023 ‫كلّيّة الصيدلة‬ Page 7 of 7