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Questions and Answers
Which characteristic of functional groups can significantly influence the lipid solubility of a drug?
What is the primary benefit of using water-soluble salts in drug formulation?
Which type of functional group is most likely to act as a hydrogen bond acceptor?
How do electronic effects of functional groups primarily influence a drug's behavior?
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Which factor is NOT typically influenced by the overall solubility of a drug molecule?
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What is the total carbon count for Aspirin?
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Which of the following compounds is estimated to have the highest solubilizing potential relative to its carbon content?
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Which compound contains an arylamidine functional group?
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What is the carbon content range for Codeine phosphate?
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Which formulation indicates that a compound is likely to be soluble in water?
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What is the function of 1-octanol in the context of drug solubility analysis?
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Which compound contains a hydroxy group aiding in hydrogen bonding?
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How many carbons does Anileridine hydrochloride contribute towards the total?
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Which functional groups are most likely to contribute to the lipid solubility of a drug molecule?
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What does the structure of a salt consist of?
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Which of the following functional groups does NOT typically enhance lipid solubility?
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Which of the following is an accurate description of the chemical nature of salts?
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Which functional group combination is likely to be least effective in enhancing a drug's lipid solubility?
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Which functional group is a hydrogen bond donor?
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Which of the following functional groups primarily serves as hydrogen bond acceptors?
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What is the nature of the bonding in heterocyclic nitrogens like pyridine?
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Which of the following statements is correct regarding thiols?
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Among the following, which group is considered lipid soluble?
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Which functional group is NOT a hydrogen bond donor?
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What role do unionized carboxylic acids play in hydrogen bonding?
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Which functional group has the potential for the highest hydrogen bond formation due to both accepting and donating?
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Which compound is known for its gastroprotective properties by functioning as an acid?
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What functional groups can a compound have that allows it to act both as an acid and a base?
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What is the approximate pKa value of a strong acid?
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Which of the following compounds is a known beta-lactam antibiotic?
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Which statement best describes how pH affects the behavior of a compound with both acidic and basic properties?
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Which compound is NOT commonly associated with acid-base reactions?
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When in an acidic environment, which ion is primarily favored by a compound like Phenobarbital?
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What is a characteristic feature of compounds like Cimetidine and Penicillin G?
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Which of the following statements about Penicillin G is NOT accurate?
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In terms of acid-base chemistry, what role does the sodium ion (Na+) play?
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What mechanism allows compounds with multiple functional groups to switch roles between acids and bases?
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Which compound is primarily used in the treatment of conditions like peptic ulcers due to its acid-reducing effects?
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Which term describes the functional property of a compound that allows it to donate protons (H+)?
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Which compound's structure can be modified to enhance its efficacy against bacterial resistance?
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Study Notes
Functional Groups (FG)
- FGs contribute to specific properties and behaviors of compounds and drugs, allowing them to produce biological responses.
Chemical Properties of FGs
- Electronic Effects: Resonance and inductive effects influence the electron distribution within a molecule.
- Steric Effects: The size and shape of a functional group can hinder or promote interactions with other molecules.
- Acid-base Properties: Some FGs can act as acids or bases, influencing their solubility and biological activity.
- Chirality: The presence of chiral centers in a molecule leads to different stereoisomers, each with potentially unique properties.
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Solubility Effects:
- Water solubility: FGs with the ability to form hydrogen bonds contribute to water solubility, making it easier for drugs to dissolve in body fluids.
- Lipid solubility: FGs that lack hydrogen bonding and are more hydrophobic tend to be lipid-soluble, facilitating passage through biological membranes.
- Salt Formation: Drugs can form salts with acids or bases, altering their solubility and improving their absorption and distribution.
Solubility Effects (continued)
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Hydrogen Bond Acceptors: These FGs are capable of accepting a hydrogen bond, contributing to water solubility.
- Examples: Ketones, esters, ethers, and heterocyclic nitrogens (like pyridine).
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Hydrogen Bond Donors: Contribute to water solubility by donating a hydrogen bond.
- Examples: Thiol, heterocyclic nitrogens (pyrrole ring), hydroxyl, phenol, amide, and primary and secondary amines.
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Lipid Soluble Functional Groups: Lack the ability to ionize or form hydrogen bonds, resulting in greater lipid solubility.
- Examples: Aromatic rings, alkyl chains (aliphatic chains), alicyclic rings (cyclopentyl and cyclohexyl), and halogens.
Salt Formation
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Salts: Ionic compounds formed by the reaction of an acid and a base.
- Consist of a positively charged cation and a negatively charged anion.
- Example: Sodium chloride (NaCl).
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Salt Formation in Drugs:
- Drugs with acidic functional groups can form salts with bases, improving their water solubility and bioavailability.
- Conversely, drugs with basic functional groups can form salts with acids, enhancing their solubility.
Partition Coefficient (Experimental Approach)
- Partition coefficient (P or log P): A measure of a compound's relative solubility in a lipid phase (like 1-octanol) compared to a water phase.
- Octanol-water system: Used as a model for passive transport through biological membranes because 1-octanol mimics the properties of a lipid membrane.
- P value interpretation: A high P value indicates greater lipid solubility and easier membrane penetration.
Key Points
- Analyze drug structure to determine the number of chiral carbons and their absolute configuration.
- Predict the salt formation and water solubility of a drug by analyzing its functional groups and calculating the empirical Log P.
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Description
Explore the various functional groups and their significant contributions to the properties of compounds and drugs. Understand how electronic effects, steric effects, and acid-base characteristics influence biological responses and solubility. This quiz covers essential concepts about chirality and solubility in biological systems.
