Chapter 31. Enantioselectivity in Drug Metabolism

Handbook of Psychopharmacology

1988 • 2,778 citations

Benzodiazepine Receptor: Demonstration in the Central Nervous System

1977 • 1,705 citations

Benzo[ a ]pyrene Diol Epoxides as Intermediates in Nucleic Acid Binding in Vitro and in Vivo

1976 • 584 citations

Microsomes and drug oxidation

1969 • 451 citations

Handbook of psychopharmacology, vol. 16

1985 • 366 citations

Insecticide Biochemistry and Physiology

1976 • 314 citations

Drug Metabolism: Chemical and Biochemical Aspects

1976 • 310 citations

Warfarin STEREOCHEMICAL ASPECTS OF ITS METABOLISM AND THE INTERACTION WITH PHENYLBUTAZONE

1974 • 287 citations

Enzymatic conversion of benzo(a)pyrene leading predominantly to the diol-epoxide r-7,t-8-dihydroxy-t-9,10-oxy-7,8,9,10-tetrahydrobenzo(a)pyrene through a single enantiomer of r-7, t-8-dihydroxy-7,8-dihydrobenzo(a)pyrene.

1976 • 270 citations

Metabolism of benzo[a]pyrene VI. Stereoselective metabolism of benzo[a]pyrene and benzo[a]pyrene 7,8-dihydrodiol to diol epoxides

1977 • 263 citations

Benzo[a]pyrene-nucleic acid derivative found in vivo: structure of a benzo[a]pyrenetetrahydrodiol epoxide-guanosine adduct

1976 • 244 citations

Mutagenicity and cytotoxicity of benzo(a)pyrene benzo-ring epoxides.

1976 • 232 citations

The Metabolism of Ibuprofen

1973 • 215 citations

Studies on the optical enantiomorphs of warfarin in man

1974 • 215 citations

Stereospecific and Nonstereospecific Effects of (+)- and (—)-Morphine: Evidence for a New Class of Receptors?

1977 • 164 citations

Synthesis and reactions of the highly mutagenic 7,8-diol 9,10-epoxides of the carcinogen benzo[a]pyrene

1977 • 162 citations

Molecular geometry and adrenergic drug activity.

1974 • 146 citations

The Influence of Stereochemical Factors on Drug Disposition

1974 • 145 citations

Absolute configuration of a ribonucleic acid adduct formed in vivo by metabolism of benzo[a]pyrene

1977 • 141 citations

Microsomes and Drug Oxidations

1977 • 131 citations

On the pharmacology of the ketamine enantiomorphs in the rat.

1977 • 118 citations

Insecticide biochemistry and physiology

1977 • 117 citations

Drug Metabolism Concepts

1977 • 111 citations

Plasma half-lives, plasma metabolites and anticoagulant efficacies of the enantiomers of warfarin in man

1973 • 109 citations

Stereospecific radioimmunoassay for propranolol isomers.

1976 • 97 citations

Cyclodiene epoxide ring hydration by microsomes from mammalian liver and houseflies

1970 • 95 citations

Psychotherapeutic Drugs

1976 • 91 citations

The enantiomers of phenprocoumon: Pharmacodynamic and pharmacokinetic studies

1976 • 82 citations

GLC Determination of Ibuprofen [dl-2-(p-Isobutylphenyl)propionic Acid] Enantiomers in Biological Specimens

1975 • 74 citations

Drug Metabolism Concepts

1977 • 63 citations

Studies on a ketone reductase in human and rat liver and kidney soluble fraction using warfarin as a substrate

1975 • 60 citations

Pharmacokinetics of dextro-, leavo- and racemic propranolol in man

1972 • 60 citations

Warfarin—stereochemical aspects of its metabolism by rat liver microsomes

1976 • 58 citations

Disposition of (15,16-3H)naltrexone in the central nervous system of the rat.

1976 • 54 citations

Pharmacokinetics of the warfarin enantiomers in rats

1974 • 54 citations

Stereochemistry of Metabolism of Amphetamines: Use of (–)-α-Methoxy-α-(trifluoromethyl)phenylacetyl Chloride for GLC Resolution of Chiral Amines

1977 • 53 citations

The role of dihydropyrimidinase in the metabolism of some hydantoin and succinimide drugs.

1974 • 52 citations

Metabolic Fate of Hexobarbital (HBj

1972 • 49 citations

Observations on the differential metabolism and biological activity of the optical isomers of cyclophosphamide

1976 • 49 citations

Reaction Pathways ofin vivoStereoselective Conversion of Ethylbenzene to (-)-Mandelic Acid

1976 • 45 citations

Quantitative determination of enantiomeric compounds. I—simultaneous measurement of the optical isomers of amphetamine in human plasma and saliva using chemical ionization mass spectrometry

1977 • 42 citations

Metabolism of four resmethrin isomers by liver microsomes

1975 • 38 citations

Hydroxylation of amphetamine to parahydroxyamphetamine by rat liver microsomes

1974 • 36 citations

Studies of the metabolism of 5,5-diphenylhydantoin relating principally to the stereoselectivity of the hydroxylation reactions in man and the dog.

1976 • 35 citations

Relative pharmacological potency in mice of optical isomers of Δ1-tetrahydrocannabinol

1974 • 34 citations

Inversion of optical configuration of alpha-methylfluorene-2-acetic acid (cicloprofen) in rats and monkeys.

1976 • 34 citations

Absolute configuration of (+)-cyclophosphamide. A crystal and molecular structure determination by x-ray diffraction

1977 • 33 citations

The urinary excretion profiles of naltrexone in man, monkey, rabbit, and rat.

1976 • 32 citations

Stereoselective drug distribution and anticoagulant potency of the enantiomers of phenprocoumon in rats

1977 • 31 citations

Absolute configuration of the major metabolite of 5,5-diphenylhydantoin,5-(4'-hydroxyphenyl)-5-phenylhydantoin

1975 • 31 citations

In Vitro Hydrolysis of Oxazepam Succinate Half-Ester by a Stereospecific Soluble Esterase from Different Animal Species

1974 • 28 citations

Excretion and stereoselective biotransformations of dl-, d- and l-norgestrel in women.

1975 • 26 citations

Pharmacokinetics of (+)-, (−)- and (±)-hexobarbitone in man after oral administration

1973 • 26 citations

Thep-Hydroxylation of Amphetamine and Phentermine by Rat Liver Microsomes

1975 • 25 citations

The Metabolism of Amphetaminein vitroby Rabbit Liver Preparations: A Comparison ofR(−) andS(+) Enantiomers

1977 • 24 citations

N-Hydroxylation of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane by rabbit liver microsomes

1975 • 24 citations

Preliminary characterization of enzymes for reduction of naloxone and naltrexone in rabbit and chicken liver.

1976 • 23 citations

Stereoselectivity and Differential Metabolism in vivo of Dextro and Laevo-Methadone-1-3H

1973 • 23 citations

Effect of phenobarbital treatment on the stereochemistry of the in vitro metabolism of ethylbenzene

1973 • 23 citations

In vitro O-demethylation of the psychotomimetic amine, 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane

1977 • 22 citations

Absolute Configuration of the Cancerostatic S()‐Cyclophosphamide

1977 • 22 citations

The difference in activity between (+)- and (-)-methadone is intrinsic and not due to a difference in metabolism

1975 • 21 citations

In vitro stereoselective metabolism of the psychotomimetic amine, 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane. An apparent enantiomeric interaction

1977 • 19 citations

Effect of l-propoxyphene on plasma levels and analgesic activity of d-propoxyphene in the rat.

1976 • 19 citations

Stereochemical aspects and metabolite formation in the in vivo metabolism of the psychotomimetic amine, 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane

1974 • 19 citations

Metabolism of optically active barbiturates. II. S (-)--pentobarbital.

1970 • 18 citations

Stereospecific Inversion ofl-α-Methylfluorene-2-acetic Acid to itsd-Enantiomer in the Dog

1976 • 18 citations

Application of deuterium labelling mass spectrometry in a study of the metabolism of the enantiomers of cyclophosphamide

1977 • 17 citations

Activation Energies of α-C-Oxidation andN-Oxidation ofN-Alkyl-Substituted Amphetamines by Rat Liver Microsomes.: Stereochemistry and Deuterium Isotope Effects

1974 • 17 citations

Stereoselective Demethylation of the Enantiomers of Nefopam, an Experimental Antidepressant and Skeletal Muscle Relaxant

1974 • 16 citations

Pharmacokinetics of the enantiomers of hexobarbital studied in the same intact rat and in the same isolated perfused rat liver

1974 • 16 citations

N-Hydroxylation of pentobarbital in man.

1977 • 16 citations

Metabolic and pharmacodynamic interactions of enantiomers of propoxyphene and methorphan

1974 • 15 citations

Application of chemical ionization mass spectrometry to the study of stereoselective in vitro metabolism of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane

1976 • 15 citations

Buffer catalysis of the racemization reaction of some 5-phenylhydantoins and its relation to the in vivo metabolism of ethotoin.

1976 • 15 citations

Determination of optically active thiopental, thiamylal, and their metabolites in human urine.

1977 • 14 citations

A Reappraisal of the Stereoselective Metabolism of Nicotine to Nicotine-l'-N-oxide

1976 • 14 citations

Metabolism of the (+)-, (±)-, and (-)-Enantiomers of α-Methylfluorene-2-acetic Acid (Cicloprofen) in Rats

1977 • 13 citations

Stereoisomerism and Drug Action in the Nervous System

1973 • 13 citations

Mass spectra ofN-[(S)-α-methoxy-α-(trifluoromethyl)phenylacetyl] derivatives of chiral amines. Stereochemistry of amphetamine metabolism in the rat

1978 • 13 citations

Stereoselective biotransformations of dl-norgestrel and its enantiomers in the African green monkey.

1974 • 12 citations

Some observations on the chemical and stereochemical specificity of the de-alkylation of organophosphorus esters by a hepatic glutathione transferase

1977 • 12 citations

Interactions of the Hexobarbital Enantiomers with Rat Liver Microsomes

1973 • 12 citations

Biotransformation of D(-)-ephedrine and L(+)-ephedrine in the rabbit, in vivo and in vitro.

1977 • 12 citations

Identification of diastereomeric propranolol-O-glucuronides by gas chromatography-mass spectrometry

1975 • 12 citations

Cardiovascular actions of a new metabolite of propranolol: isopropylamine.

1974 • 12 citations

Amobarbital metabolism in man determination ofN-hydroxyamobarbital and 3′-hydroxyamobarbital in urine by gas chromatography chemical ionization mass spectrometry

1977 • 12 citations

Kinetics of microsomal metabolism and binding of enantiomerically related substrates.

1973 • 11 citations

Metabolism of R-(+)-and S-(minus)-pentobarbital by hepatic microsomes from male rats.

1975 • 11 citations

STEREOSELECTIVE BINDING IN CARDIAC TISSUE OF THE ENANTIOMERS OF BENZETIMIDE, AN ANTIMUSCARINIC DRUG

1976 • 10 citations

Stereochemical course in vivo of alpha-methyldopa decarboxylation in rat brains

1977 • 8 citations

The interrelationship between hepatic microsomal cholesterol 7[alpha]-hydroxylase and mixed function oxidase systems /

1976 • 7 citations

The metabolism of d-, l- and dl-methadone in the isolated perfused rat liver.

1977 • 7 citations

The metabolism and antitumour activity of the enantiomers of cis- and trans-4-methylcyclophosphamide

1977 • 6 citations

D-オキサゼパムヘミスクシネートナトリウム塩(D-7-クロロ-1,3-ジヒドロ-3-ヘミスクシニルオキシ-5-フェニル-2H-1,4-ベンゾジアセピン-2-オン)の活性の,二重盲検交差試験による,ラセミ型の活性との比較

1976 • 4 citations

カイラルと非カイラルな1,3-ジヒドロ-2H-1,4-ベンゾジアゼピン-2-オンの酵素による生化学的変換の立体特異性

1974 • 3 citations