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Importance of Drug Enantiomers in Clinical Pharmacology

Data up to Jan 2025

Published1985
Citations278
References139

Total Citations Per Year

Abstract

References (139)

A physiological approach to hepatic drug clearance

1975 • 1,855 citations

Modification of Parkinsonism — Chronic Treatment with L-Dopa

1969 • 1,253 citations

The specification of asymmetric configuration in organic chemistry

1956 • 784 citations

The Specific Binding of l-Tryptophan to Serum Albumin

1958 • 638 citations

Stereochemistry, a basis for sophisticated nonsense in pharmacokinetics and clinical pharmacology

1984 • 600 citations

The biological properties of the optical isomers of propranolol and their effects on cardiac arrhythmias

1968 • 562 citations

The metabolic chiral inversion of 2-arylpropionic acids—a novel route with pharmacological consequences

1983 • 395 citations

Pharmacological differences between the optical isomers of ibuprofen: evidence for metabolic inversion of the (—)-isomer

1976 • 378 citations

Warfarin STEREOCHEMICAL ASPECTS OF ITS METABOLISM AND THE INTERACTION WITH PHENYLBUTAZONE

1974 • 287 citations

Pharmacokinetics and pharmacodynamics of the enantiomers of warfarin in man

1974 • 265 citations

Inotropic and electrophysiological actions of verapamil and D 600 in mammalian myocardium

1975 • 258 citations

Stereoselective disposition of ibuprofen enantiomers in man.

1985 • 253 citations

Potentiation of Anticoagulant Effect of Warfarin by Phenylbutazone

1967 • 236 citations

Stereoselective disposition of ibuprofen enantiomers in infants.

1994 • 217 citations

The Stereoselective Interaction of Warfarin and Metronidazole in Man

1976 • 216 citations

The Metabolism of Ibuprofen

1973 • 215 citations

Differential stereoselective metabolism of metoprolol in extensive and poor debrisoquin metabolizers

1983 • 215 citations

Studies on the optical enantiomorphs of warfarin in man

1974 • 215 citations

Altered Hepatic Blood Flow and Drug Disposition1

1976 • 209 citations

The disposition of propranolol. 3. Decreased half-life and volume of distribution as a result of plasma binding in man, monkey, dog and rat.

1973 • 205 citations

Mechanism of Action of Barbiturates

1981 • 202 citations

The Disposition of Propranolol

1972 • 188 citations

The Importance of Stereochemistry in the Clinical Pharmacokinetics of the 2-Arylpropionic Acid Non-Steroidal Anti-Inflammatory Drugs

1984 • 187 citations

Methadone in man: Pharmacokinetic and excretion studies in acute and chronic treatment

1975 • 183 citations

Pharmacokinetics of (+)‐, (‐)‐ and (+/‐)‐verapamil after intravenous administration.

1984 • 183 citations

Stereochemistry and biological activity of drugs

1983 • 178 citations

Stereoselective first‐pass metabolism of highly cleared drugs: studies of the bioavailability of L‐ and D‐verapamil examined with a stable isotope technique.

1984 • 177 citations

Absorption, distribution and toxicity of ibuprofen

1969 • 172 citations

Active Transport of L-Dopa in the Intestine

1973 • 157 citations

Serum protein binding as a determinant of warfarin body clearance and anticoagulant effect

1976 • 147 citations

Molecular geometry and adrenergic drug activity.

1974 • 146 citations

The Influence of Stereochemical Factors on Drug Disposition

1974 • 145 citations

A critical evaluation of the application of amino acid racemization to geochronology and geothermometry

1977 • 133 citations

Regional hemodynamic effects of beta-adrenergic blockade with propranolol in the unanesthetized primate

1973 • 126 citations

Chromatographic resolution of enantiomers

1975 • 120 citations

Drug Interactions with Warfarin

1983 • 119 citations

Stereoselective binding of propranolol to human plasma, α1-acid glycoprotein, and albumin

1983 • 113 citations

Stereoselective Interaction of Trimethoprim-Sulfamethoxazole with the Separated Enantiomorphs of Racemic Warfarin in Man

1980 • 112 citations

Phenylbutazone‐warfarin interaction in man: further stereochemical and metabolic considerations.

1983 • 110 citations

Stereoselective Inversion of (R)-Fenoprofen to (S)-Fenoprofen in Humans

1985 • 109 citations

Clinical eftects and pharmacokinetics of racemic methadone and its optical isomers

1977 • 106 citations

Single dose pharmacokinetics and bioavailability of methadone in man studied with a stable isotope method

1981 • 106 citations

Comparative Pharmacokinetics of Coumarin Anticoagulants XIV: Relationship between Protein Binding, Distribution, and Elimination Kinetics of Warfarin in Rats

1975 • 101 citations

Stereospecific radioimmunoassay for propranolol isomers.

1976 • 97 citations

Effects of verapamil on P-R-intervals in relation to verapamil plasma levels following single i.v. and oral administration and during chronic treatment

1980 • 97 citations

Cerebral protection with barbiturates: relation to anesthetic effect.

1978 • 93 citations

Stereospecific assay for (-)- and (+)-propranolol in human and dog plasma.

1980 • 85 citations

Protein binding of warfarin enantiomers in serum of humans and rats

1977 • 84 citations

Stereoselective Interaction of Phenylbutazone with [12C/13C]Warfarin Pseudoracemates in Man

1980 • 83 citations

The enantiomers of phenprocoumon: Pharmacodynamic and pharmacokinetic studies

1976 • 82 citations

Present status of enantiomeric analysis by gas chromatography

1975 • 81 citations

Steric Aspects of Adrenergic Drugs

1970 • 79 citations

Stereospecific inversion of (R)-(−)-benoxaprofen in rat and man

1980 • 78 citations

The participation of ethyl 4-benzyloxybenzoate (BRL 10894) and other aryl-substituted acids in glycerolipid metabolism

1978 • 78 citations

Liquid Chromatographic Determination and Plasma Concentration Profile of Optical Isomers of Ibuprofen in Humans

1984 • 77 citations

Plasma levels of (+) and (−)−propranolol and 4‐hydroxypropranolol after administration of racemic (+/‐)‐propranolol in man.

1982 • 77 citations

The hemodynamic effects of beta adrenergic blockade on the flow-dependent hepatic clearance of propranolol.

1973 • 76 citations

Enhancement of uricosuric properties of indacrinone by manipulation of the enantiomer ratio

1981 • 76 citations

High stereospecificity of the benzodiazepine binding site on human serum albumin. Studies with d- and l-oxazepam hemisuccinate.

1975 • 75 citations

Entero-hepatic cycling of methotrexate estimated by use of the D-isomer as a reference marker

1984 • 73 citations

Pharmacokinetics of the enantiomers of acenocoumarol in man.

1981 • 73 citations

OPTICAL ISOMERIZATION MECHANISM OF R (-)-HYDRATROPIC ACID DERIVATIVES

1981 • 71 citations

Comparative Pharmacokinetics of Coumarin Anticoagulants I

1968 • 69 citations

CRC handbook of stereoisomers : drugs in psychopharmacology

1984 • 69 citations

Pharmacokinetics of warfarin enantiomers: A search for intrasubject correlations

1978 • 69 citations

Stereoselective binding of propranolol enantiomers to human alpha 1‐ acid glycoprotein and human plasma.

1984 • 68 citations

Stereoselective disposition of methadone in man

1979 • 68 citations

Interrelationships between xenobiotic metabolism and lipid biosynthesis

1983 • 67 citations

Racemic Warfarin and Trimethoprim-Sulfamethoxazole Interaction in Humans

1979 • 66 citations

Stereoselective inversion of (R)-(-)-benoxaprofen to the (S)-(+)-enantiomer in humans.

1979 • 64 citations

Coronary Vasodilator and Cardiac Effects of Optical Isomers of Verapamil in the Dog

1980 • 60 citations

Benzodiazepines: Specific competitors for the binding of l-tryptophan to human serum albumin

1975 • 59 citations

Anticoagulant activity of the enantiomers of acenocoumarol.

1978 • 53 citations

Quantitation of Methadone Eenantiomers in Humans Using Stable Isotope-labeled [2H3]-, [2H5]-, and [2H8]methadone

1982 • 50 citations

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

1976 • 49 citations

High-performance Liquid Chromatographic Determination of Stereoselective Disposition of Carprofen in Humans

1981 • 48 citations

The disposition of propranolol. 8. General implications of the effects of liver blood flow on elimination from the perfused rat liver.

1973 • 48 citations

Stereoselective binding of disopyramide to human plasma protein

1984 • 46 citations

Recent advances in methods of direct optical resolution

1984 • 46 citations

Effects of pretreatment with phenobarbitone and phenytoin on the pharmacokinetics and toxicity of misonidazole in mice

1979 • 46 citations

Stereoselective interaction of sulfinpyrazone with racemic warfarin and its separated enantiomorphs in man.

1982 • 46 citations

Optical isomers of verapamil on canine heart

1975 • 43 citations

Relationship of antiarrhythmic to inotropic activity and antiarrhythmic qualities of the optical isomers of verapamil

1976 • 42 citations

Pathways of metabolism of amphetamine and related compounds

1978 • 42 citations

Interaction of warfarin stereoisomers with human albumin

1975 • 41 citations

Optical studies on the mechanism of the interaction of the enantiomers of the antiocagulant drugs phenprocoumon and warfarin with human serum albumin.

1977 • 41 citations

Studies on the Interaction of Warfarin and Clofibrate in Man

1972 • 40 citations

Enzyme Reaction Stereospecificity: A Critical Revie

1972 • 39 citations

Pharmacology of enantiomers and (–) p-OH metabolite of indacrinone

1981 • 38 citations

Side effects of levomethadone and racemic methadone in a maintenance program

1976 • 38 citations

The relation between biological activity and the degree of resolution of optical isomers

1972 • 38 citations

Stereoselective binding of the (-)-enantiomer of propranolol to plasma and extravascular binding sites in the dog.

1983 • 36 citations

Oxidation of (R)- and (S)-propranolol in human and dog liver microsomes. Species differences in stereoselectivity.

1982 • 35 citations

Interaction of secobarbital with warfarin pseudoracemates

1980 • 35 citations

Optical isomers of miscellaneous strong analgetics

1970 • 33 citations

The Effect of D-Timolol On Intraocular Pressure In Patients With Ocular Hypertension

1984 • 33 citations

Respiratory and subjective effects of d- and I-pentazocine

1968 • 32 citations

The binding of the optical isomers of methadone, alpha-methadol, alpha-acetylmethadol and their N-demethylated derivatives to the opiate receptors of rat brain.

1976 • 32 citations

Pharmacokinetic Implications of Stereoselective Changes in Plasma–Protein Binding: Warfarin/Sulfinpyrazone

1984 • 31 citations

Treatment of acute focal cerebral ischemia with propranolol.

1982 • 30 citations

Association between lipid-lowering activity of aryl-substituted carboxylic acids and formation of substituted glycerolipids in rats

1981 • 30 citations

Analgesic and other effects of the d‐ and l‐isomers of pentazocine

1969 • 30 citations

Stereochemical aspects of parachloroamphetamine metabolism

1982 • 29 citations

Pharmacokinetics of the enantiomers of indoprofen in man.

1984 • 29 citations

Determination of moxalactam in human body fluids by liquid chromatographic and microbiological methods

1981 • 28 citations

The disposition of propranolol. VII. The effects of saturable hepatic tissue uptake on drug clearance by the perfused rat liver.

1973 • 27 citations

Epimers of moxalactam: in vitro comparison of activity and stability

1981 • 24 citations

Dynamic interaction between disulfiram and separated enantiomorphs of racemic warfarin

1981 • 24 citations

Effects of Phenylbutazone, Tolbutamide, and Clofibric Acid on Binding of Racemic Warfarin and Its Enantiomers to Human Serum Albumin

1979 • 23 citations

Stereoselective Disposition — Basis for Variability in Response to NSAID’s

1985 • 23 citations

No stereoselective first-pass hepatic extraction of propranolol

1981 • 23 citations

Comparative interaction of sulfinpyrazone and phenylbutazone with racemic warfarin: alteration in vivo of free fraction of plasma warfarin.

1981 • 22 citations

Stereospecific binding of timolol, a beta-adrenergic blocking agent.

1976 • 21 citations

Separation of morphinelike effects by optical resolution. Levo isomers as strong analgetics and narcotic antagonists

1969 • 21 citations

Effect of Pentobarbital on the Formation of Diastereomeric Oxazepam Glucuronides in Man: Analysis by High Performance Liquid Chromatography

1981 • 21 citations

Stereoselective oral bioavailability of (+/-)-propranolol in the dog. A GC-MS study using a stable isotope technique.

1979 • 21 citations

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

1976 • 19 citations

Ticrynafen-racemic warfarin interaction: Hepatotoxic or stereoselective?

1982 • 19 citations

Enantiomers of Indacrinone: A New Approach to Producing an Isouricemic Diuretic

1982 • 18 citations

Antimalarial activity of the optical isomers of chloroquine diphosphate.

1979 • 18 citations

Kinetics of misonidazole enantiomers

1984 • 18 citations

Effects of enantiomers of indacrinone (MK-196) on cation transport by the loop of Henle and distal tubule studied by microperfusion in vivo.

1984 • 17 citations

Interaction of clofibrate with warfarin. I. Effect of clofibrate on the disposition of the optical enantiomorphs of warfarin

1977 • 16 citations

Stereoselectivity in the disposition and metabolism of the uricosuric-diuretic agent, indacrinone, in Rhesus monkeys.

1982 • 16 citations

Some comparative effects of racemic methadone and its optical isomers in rodents.

1974 • 15 citations

The Disposition of Propranolol

2015 • 15 citations

Noninvasive chemical methods of estimating pharmacokinetic parameters

1982 • 14 citations

Stereoisomerism and Drug Action in the Nervous System

1973 • 13 citations

Indacrinone: Natriuretic and Uricosuric Effects of Various Ratios of Its Enantiomers in Healthy Men

1984 • 13 citations

Effects of Verapamil and Its Optical Isomers on Repetitive Slow Responses Induced by Electrical Depolarization in Canine Ventricular Myocardium

1980 • 11 citations

Kinetics of microsomal metabolism and binding of enantiomerically related substrates.

1973 • 11 citations

Optical resolution of some homobenzomorphan derivatives and their pharmacological properties

1979 • 10 citations

The binding of the optical isomers of methadone, alpha-methadol, alpha-acetylmethadol and their N-demethylated derivatives to the opiate receptors of rat brain.

1976 • 9 citations

Effects of phenytoin, phenobarbital, and ascorbic acid on misonidazole elimination

1983 • 9 citations

Stereospecific salivary excretion of tocainide enantiomers in man.

1984 • 8 citations

Comparative Pharmacokinetics of Coumarin Anticoagulants XXXVI: Predicted Steady-State Patterns of Prothrombin Complex Activity Produced by Equieffective Doses of (R)-(+)- and (S)-(−)-Warfarin in Humans

1977 • 8 citations

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

1977 • 6 citations

Propranolol and essential tremor: Rôle of the membrane effect

2009 • 6 citations

Pharmacokinetics and neurochemical effects of pentazocine and its optical isomers.

1973 • 5 citations

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Importance of Drug Enantiomers in Clinical Pharmacology (1985) – Drugs | Metascience Observatory Explorer