14 Questions
Which type of prodrug is formed by the reaction of amines to form mannich bases?
Mannich bases
Why are esterases important enzymes for the activation of prodrugs containing carboxylic acids or alcohols?
They can prepare esters with any degree of hydrophilicity or lipophilicity
What is the effect of carriers with aromatic or aliphatic functional groups on the aqueous solubility of ester carrier-linked prodrugs?
Decrease aqueous solubility
Which functional groups can be used to prepare carriers that increase the aqueous solubility of ester carrier-linked prodrugs?
Amino or carboxylic acid functional groups
What is the rare approach for forming prodrugs involving amines?
Amide linkage
Which of the following is NOT a method for increasing the water solubility of an agent as mentioned in the text?
Use of sulfonate prodrugs
What is the main reason for using succinate esters containing ionizable carboxylate in prodrugs?
To avoid the need for immediate dissolution before administration
What is the role of phosphatase enzymes in the hydrolysis of phosphate esters?
They accelerate the hydrolysis process
Which functional group of a drug can be reacted with a carboxylic acid of the carrier to give an amide, according to the text?
Amine
What is the primary reason for using phosphate esters in producing clindamycin phosphate?
To reduce pain at the injection site
When is chemical hydrolysis of the ester function likely to occur?
To some extent
What allows control of the rate and extent of hydrolysis and when the active drug must be revealed at the correct point in its movement through the biological system?
Manipulation of steric and electronic properties of promoiety
What is a potential drawback of succinate esters in solution?
Immediate dissolution required before administration
"Pain after parenteral administration is associated with local irritation caused by" what?
(In)creased water solubility or highly acidic solutions
Study Notes
- Prodrugs are a group of compounds that can be transformed in the body into active drugs.
- Prodrugs are classified according to the functional groups of their parent drugs.
- The most common type of prodrug is formed by carboxylic acids and alcohols, which can be converted into esters.
- Esterases are enzymes responsible for the activation of ester prodrugs in the body.
- Ester carrier-linked prodrugs can be prepared with different carriers to control their hydrophilicity or lipophilicity.
- Hydrolysis of ester prodrugs can be accomplished by esterases in the body, microflora in the gut, or chemical reaction.
- Promoieties such as succinates, phosphates, and sulfonates are used to increase the hydrophilicity of prodrugs.
- Succinate esters are useful for rapid in vivo hydrolysis and are often somewhat unstable in solution.
- Phosphate esters offer another method for increasing the water solubility of agents and are stable in solution.
- Clindamycin phosphate is an example of a prodrug that increases water solubility and reduces pain at the injection site.
- Derivatization of amines to form amides is a less common approach for producing prodrugs.
Test your knowledge on prodrugs and drug delivery systems with this quiz based on lecture 6 by Assist. Lecturer Asmaa Adnan at Al-Nahrain University, College of Pharmacy. Explore the different types of prodrugs formed from functional groups and their chemical bonds.
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