metabolism of drugs

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Slide 1: 

AMPHETAMINE METABOLIC PATHWAY: Deamination (followed by oxidation and reduction of the ketone formed) N-oxidation N-dealkylation Hydroxylation of the aromatic ring Hydroxylation of the β-carbon atom Conjugation with glucuronic acid of the phenol and alcohol products from the ketone formed by deamination

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BARBITURATES METABOLIC PATHWAY: Oxidation and complete removal of substituents at carbon 5 N-dealkylation of at N1 and N3 Desulfuration at carbon 2 (Thiobarbiturates) Scission of the barbiturate ring at the 1:6 bond to give substituted malonylureas

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PHENOTHIAZINES METABOLIC PATHWAY: N-dealkylation in the N10 side chain N-oxidation in the N10 side chain Oxidation of the heterocyclic S atom to sulfoxide or sulfone Hydroxylation of one or both aromatic rings Conjugation of phenolic metabolites with glucuronic acid or sulfate Scission of the N10 side chain

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SULPHONAMIDE METABOLIC PATHWAY: Activation at the N4 amino group Conjugation with glucuronic acid sulfate at the N4 amino group Acetylation or conjugation with glucuronic acid at the N1 amino group Hydroxylation and conjugation in the heterocyclic ring, R

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PHENYTOIN METABOLIC PATHWAY: Hydroxylation of one aromatic ring Conjugation of phenolic products with glucuronic acid or sulfate Hydrolytic scission of the hydantoin ring at the bond between carbons 3 and 4 to give 5,5-diphenylhydantoic acid

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MEPERIDINE METABOLIC PATHWAY: Hydrolysis of ester to acid N-dealkylation Hydroxylation of aromatic ring N-oxidation Both N-dealkylation and hydrolysis Conjugation of phenolic products

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PENTAZOCINE METABOLIC PATHWAY: Hydroxylation of terminal methyl groups of the alkenyl side chain to give cis and trans (major) alcohols Oxidation of hydroxymethyl product of the alkenyl side chain to carboxylic acids Reduction of alkenyl side chain and oxidation of terminal methyl group

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COCAINE METABOLIC PATHWAY: Hydrolysis of methyl ester Hydrolysis of benzoate ester N-dealkylation Both hydrolysis and N-dealkylation

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PHENMETRAZINE METABOLIC PATHWAY: Oxidation to lactam Aromatic hydroxylation N-oxidation Conjugation of phenolic products

Slide 10: 

EPHEDRINE METABOLIC PATHWAY: N-dealkylation Oxidative deamination Oxidation of deaminated product to benzoic acid Reduction of deaminated product to 1,2-diol

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PROPRANOLOL METABOLIC PATHWAY: Aromatic hydroxylation at C-4l N-dealkylation Oxidative deamination Oxidation of deaminated product to naphthoxylactic acid Conjugation with glucuronic acid O-dealkylation

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INDOMETHACIN METABOLIC PATHWAY: O-demethylation N-deacylation of p-chlorobenzoyl group Both O-dealkylation and N-deacylation Cojugation of phenolic products with glucuronic acid Other conjugation products

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PHENOXYLATE METABOLIC PATHWAY: Hydrolysis of ester to acid Hydroxylation of one aromatic ring attached to the N-alkyl side chain

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DIAZEPAM METABOLIC PATHWAY: N-dealkylation at N1 Hydroxylation at carbon 3 Conjugation of phenolic products with glucuronic acid Both N-dealkylation of N1 and hydroxylation at carbon 3

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PROSTAGLANDINS METABOLIC PATHWAY: Reduction of double bonds at carbons 5 and 6, and 13 and 14 Oxidation of 15-hydroxyl to ketone β-oxidation of carbons 1,2,3 and 4 ω-oxidation of carbons 20 to acid

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CYPROHEPTADINE METABOLIC PATHWAY: N-dealkylation 10,11-epoxide formation Both N-dealkylation and 10,11-epoxidation

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HYDRALAZINE METABOLIC PATHWAY: N-acetylation with cyclization to a methyl-s-triazolophthalazine N-formylation with cyclization to an s-triazolophthalazine Aromatic hydroxylation of benzene ring Oxidative loss of hydrazinyl group to 1-hydroxy Hydroxylation of methyl of methyl-s- triazolophthalazine Conjugation with glucuronic acid

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METHADONE METABOLIC PATHWAY: Reduction of ketone to hydroxyl Aromatic hydroxylation of one aromatic ring N-dealkylation of alcohol product N-dealkylation with cyclization to pyrrolidine

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LIDOCAINE METABOLIC PATHWAY: N-dealkylation Oxidative cyclization to a 4-imidazolidone N-oxidation of amide N Aromatic hydroxylation ortho to methyl Hydrolysis of amide

Slide 20: 

IMIPRAMINE METABOLIC PATHWAY: N-dealkylaion Hydroxylation at C-11 Aromatic hydroxylation (C-2) N-oxidation Both N-dealkylation and hydroxylation

Slide 21: 

CIMETIDINE METABOLIC PATHWAY: S-oxidation Hydroxylation of 5-methyl

Slide 22: 

VALPROIC ACID METABOLIC PATHWAY: CoA thioester Dehydrogenation to (E) 2-ene Dehydrogenation to (E) 2,4-diene Dehydrogenation to 4-ene 3-Hydroxylation

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PIROXICAM METABOLIC PATHWAY: Pyridine 3l-hydroxylation Hydrolysis of amide Decaboxylation

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CAFFEINE METABOLIC PATHWAY: N3-demethylation N1-demethylation N7-demethylation to theophylline C-8 oxidation to uric acids Imidazole ring opened

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THEOPHYLLINE METABOLIC PATHWAY: N3-demethylation N1-demethylation C-8 oxidation to uric acids Imidazole ring opened 1-Me Xanthine to 1-Me uric acid-xanthine oxidase

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NICOTINE METABOLIC PATHWAY: Pyrrolidine 5l-hydroxylation to continine Pyrrolidine N-oxidation (FMO) N-demethylation (Nornicotine and norcotinine) Pyridine N-methylation 3l-Hydroxylation of cotinine

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IBUPROFEN METABOLIC PATHWAY: CoA thioester and epimerization of R- to S+ enantiomer Methyl hydroxylation to CH2OH CH2OH to COOH Acylglucuronide

Slide 28: 

TAMOXIFEN METABOLIC PATHWAY: N-demethylation 4l-hydroxylation N-oxidation (FMO) 4-O-sulfate 4-O-glucuronide

Slide 29: 

LOVASTATIN METABOLIC PATHWAY: 6l-hydroxylation 3l-side chain hydroxylation 3l-hydroxylation β-oxidation of lactone O-glucuronides

Slide 30: 

CIPROFLOXACIN METABOLIC PATHWAY: Piperazine 3l-hydroxylation N-sulfation `

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