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2 Medicinal Chemistry 2-Drug Metabolism-Smsrt Ganjil

Drug metabolism involves converting non-polar, lipid soluble compounds into more polar, water soluble compounds so that the body can easily excrete them. This process generally occurs in two phases: phase I involves reactions like oxidation and reduction, while phase II involves conjugating the drug molecule to other compounds like glucuronic acid to increase water solubility. Many factors can influence an individual's drug metabolism, and there are strategies like avoiding interactions and using controlled release formulations to manage how quickly the body metabolizes a drug.

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137 views39 pages

2 Medicinal Chemistry 2-Drug Metabolism-Smsrt Ganjil

Drug metabolism involves converting non-polar, lipid soluble compounds into more polar, water soluble compounds so that the body can easily excrete them. This process generally occurs in two phases: phase I involves reactions like oxidation and reduction, while phase II involves conjugating the drug molecule to other compounds like glucuronic acid to increase water solubility. Many factors can influence an individual's drug metabolism, and there are strategies like avoiding interactions and using controlled release formulations to manage how quickly the body metabolizes a drug.

Uploaded by

Park arima
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© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Medicinal Chemistry 1

Drug Metabolism
Dr. Friardi, Apt
Drug Metabolism

• Most metabolic products are less pharmacologically active


Important exceptions:
• Where the metabolite is more active
(Prodrugs, e.g. Erythromycin-succinate (less irritation of GI) --> Erythromycin)
• Where the metabolite is toxic (acetaminophen)
• Where the metabolite is carcinogenic

• Close relationship between the biotransformation of drugs and normal


biochemical processes occurring in the body:
– Metabolism of drugs involves many pathways associated with the synthesis
of endogenous substrates such as steroid hormones, cholesterol and bile
acids
– Many of the enzymes involved in drug metabolism are principally designed
for the metabolism of endogenous compounds
– These enzymes metabolize drugs only because the drugs resemble the
natural compound
BIMM118
Importance

Drug metabolism is needed to convert non-polar lipophilic compounds (lipid soluble) which the body cannot excrete into more polar hydrophilic compounds (water soluble) which the body can excrete them in
short period of time.
Because if the lipid soluble non-polar compounds are not metabolized to the polar water soluble compounds, they will remain in the blood and tissues and maintain their pharmacological effects for an
indefinite time.
Codeine Morphine
Iproniazid Isoniazid
Drug Metabolism - Phase I

• Phase I Reactions
– Oxidation
– Reduction
– Hydrolytic cleavage
– Alkylation
(Methylation)
– Dealkylation
– Ring cyclization
– N-carboxylation
– Dimerization
– Transamidation
– Isomerization
– Decarboxylation
BIMM118
Drug Metabolism - Phase II

• Conjugation reactions

– Glucuronidation by UDP-
Glucuronosyltransferase:
(on -OH, -COOH, -NH2, -SH groups)
– Sulfation by Sulfotransferase:
(on -NH2, -SO2NH2, -OH groups)
– Acetylation by acetyltransferase:
(on -NH2, -SO2NH2, -OH groups)
– Amino acid conjugation
(on -COOH groups)
– Glutathione conjugation by Glutathione-S-
transferase:
(to epoxides or organic halides)
– Fatty acid conjugation
(on -OH groups)
– Condensation reactions
BIMM118
Conjugating molecules:
Conjugating molecules:
Conjugating molecules:
Factors influencing Drug Metabolism
Strategies to manage drug
metabolism

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