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Literature DB >> 7202435

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

R G Simmonds, T J Woodage, S M Duff, J N Green.

Abstract

(R)-(-)-benoxaprofen is stereospecifically inverted to the (S)-(+)-enantiomer by rats and humans. The rate of inversion is much faster in rats (t 1/2 ca. 2.5 h) than in humans (t 1/2 108 h). Inversion in rats apparently does not occur in the liver, but can be brought about in vitro by an everted intestinal sac preparation, suggesting that the transformation takes place while passing through the gut wall.

Entities: Chemical Gene Species

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Year: 1980 PMID： 7202435 DOI： 10.1007/BF03189461

Source DB: PubMed Journal: Eur J Drug Metab Pharmacokinet ISSN： 0378-7966 Impact factor: 2.441

10 in total

1. Isomeric inversion of ibuprofen (R)-enantiomer in humans.

Authors: D G Kaiser; G J Vangiessen; R J Reischer; W J Wechter
Journal: J Pharm Sci Date: 1976-02 Impact factor: 3.534

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

Authors: S J Lan; K J Kripalani; A V Dean; P Egli; L T Difazio; E C Schreiber
Journal: Drug Metab Dispos Date: 1976 Jul-Aug Impact factor: 3.922

3. Enzymatic inversion at saturated carbon: nature and mechanism of the inversion of R(-) p-iso-butyl hydratropic acid.

Authors: W J Wechter; D G Loughhead; R J Reischer; G J VanGiessen; D G Kaiser
Journal: Biochem Biophys Res Commun Date: 1974-12-11 Impact factor: 3.575

4. Determination of benoxaprofen [2-(4-chlorophenyl)-alpha-methyl-5-benzoxazoleacetic acid, LRCL 3794] in biological fluids.

Authors: D H Chatfield; T J Woodage
Journal: J Chromatogr Date: 1978-06-01

5. Preliminary studies of absorption and excretion of benoxaprofen in man.

Authors: G L Smith; R A Goulbourn; R A Burt; D H Chatfield
Journal: Br J Clin Pharmacol Date: 1977-10 Impact factor: 4.335

6. The pharmacology of benoxaprofen (2-[4-chlorophenyl]-alpha-methyl-5-benzoxazole acetic acid), LRCL 3794, a new compound with antiinflammatory activity apparently unrelated to inhibition of prostaglandin synthesis.

Authors: C H Cashin; W Dawson; E A Kitchen
Journal: J Pharm Pharmacol Date: 1977-06 Impact factor: 3.765

7. Stereospecific inversion of l-alpha-methylfluorene-2-acetic acid to its d-enantiomer in the dog.

Authors: K J Kripalani; A Z El-Abdin; A V Dean; E C Schreiber
Journal: Xenobiotica Date: 1976-03 Impact factor: 1.908

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

Authors: R J Bopp; J F Nash; A S Ridolfo; E R Shepard
Journal: Drug Metab Dispos Date: 1979 Nov-Dec Impact factor: 3.922

9. Disposition and metabolism of benoxaprofen in laboratory animals and man.

Authors: D H Chatfield; J N Green
Journal: Xenobiotica Date: 1978-03 Impact factor: 1.908

10. The metabolism of shikimate in the rat.

Authors: D Brewster; R S Jones; D V Parke
Journal: Biochem J Date: 1978-02-15 Impact factor: 3.857

10 in total

14 in total

Review 1. Stereoselectivity in clinical pharmacokinetics and drug development.

Authors: D B Campbell
Journal: Eur J Drug Metab Pharmacokinet Date: 1990 Apr-Jun Impact factor: 2.441

Review 2. Enantioselective pharmacodynamics and pharmacokinetics of chiral non-steroidal anti-inflammatory drugs.

Authors: A M Evans
Journal: Eur J Clin Pharmacol Date: 1992 Impact factor: 2.953

3. Influence of probenecid on the urinary excretion rates of the diastereomeric benoxaprofen glucuronides.

Authors: H Spahn; S Iwakawa; L Z Bevet; E T Lin
Journal: Eur J Drug Metab Pharmacokinet Date: 1987 Oct-Dec Impact factor: 2.441

Review 4. Pharmacokinetics of enantiomers of chiral non-steroidal anti-inflammatory drugs.

Authors: F Jamali
Journal: Eur J Drug Metab Pharmacokinet Date: 1988 Jan-Mar Impact factor: 2.441

Review 5. Importance of drug enantiomers in clinical pharmacology.

Authors: K Williams; E Lee
Journal: Drugs Date: 1985-10 Impact factor: 9.546

6. Stereoselective taurine conjugation of (R)-benoxaprofen enantiomer in rats: in vivo and in vitro studies using rat hepatic mitochondria and microsomes.

Authors: Kiminori Mohri; Kenji Okada; Leslie Z Benet
Journal: Pharm Res Date: 2005-01 Impact factor: 4.200

7. Pharmacokinetics of ibuprofen enantiomers in humans following oral administration of tablets with different absorption rates.

Authors: F Jamali; N N Singh; F M Pasutto; A S Russell; R T Coutts
Journal: Pharm Res Date: 1988-01 Impact factor: 4.200