Problem_Set_II_-_metabolism - i Reduction of ketone to...

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Pharmaceutical Chemistry 306 Problem Set II – Chemical Aspects of Drug Metabolism For Questions 1 –3, Draw the structure of major intermediates and products in each of the pathways. And classify each in terms of phase I (oxidative or reductive or hydrolytic) or phase II reactions. 1. Amphetamine is known to undergo the following metabolic reactions. i) Deamination ii) Deamination followed by reduction iii) Hydroxylation of the aromatic ring iv) Hydroxylation of the β -carbon atom v) Conjugation with glucuronic acid 2. Cocaine is known to undergo the following metabolic reactions. i) Hydrolysis of methyl ester ii) Hydrolysis of benzoate ester iii) N-dealkylation iv) Both hydrolysis and N-dealkylation 3. Methadone is known to undergo the following metabolic reactions.
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Unformatted text preview: i) Reduction of ketone to hydroxyl ii) Aromatic hydroxylation of one aromatic ring iii) N-dealkylation of alcohol product iv) N-dealkylation with cyclization to pyrrolidine. 4. Predict the conjugation pathways for p-aminosalicylic acid. 5. Match the following conjugation pathways with cosubstrates and give the name of enzyme involved in each. Methylation Glutathione Acetylation Glycine Sulfation UDP-glucruonate Glucuronidation Acetyl-CoA Mercapturic acid formation S-Adenosylmethione (SAM) Amino acid conjugation 3’-Phosphoadenosine-5’-phosphosulfate (PAPS) NH 2 CH 3 α β Amphetamine N COOCH 3 O O Cocaine CH 3 O CH 3 N(CH 3 ) 2 Methadone H 2 N COOH OH p-aminosalicylic acid...
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