Advanced search
Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 18, 1988 - Issue 5
Submit an article Journal homepage
17
Views
28
CrossRef citations to date
0
Altmetric
Original Article

Metabolic chiral inversion of anti-inflammatory 2-arylpropionates: Lack of reaction in liver homogenates, and study of methine proton acidity

Joachim M. Mayer School of Pharmacy, University of Lausanne, Place du Cháteau, CH-1005, Lausanne, Switzerland
,
Cecilia Bartolucci School of Pharmacy, University of Lausanne, Place du Cháteau, CH-1005, Lausanne, Switzerland
,
Jean-Michel Maítre School of Pharmacy, University of Lausanne, Place du Cháteau, CH-1005, Lausanne, Switzerland
&
Bernard Testa School of Pharmacy, University of Lausanne, Place du Cháteau, CH-1005, Lausanne, Switzerland
Pages 533-543 | Received 01 Jun 1987, Accepted 13 Dec 1987, Published online: 30 Sep 2009

Citations (28)

Keep up to date with the latest research on this topic with citation updates for this article.

Subscribe to citation updates

Read on this site (2)

Haiping Hao, Guangji Wang & Jianguo Sun. (2005) Enantioselective Pharmacokinetics of Ibuprofen and Involved Mechanisms. Drug Metabolism Reviews 37:1, pages 215-234.
Read now
O. Okazaki, T. Kurata & H. Tachizawa. (1989) Stereoselective Metabolic Disposition of Enantiomers of Ofloxacin in Rats. Xenobiotica 19:4, pages 419-429.
Read now

Articles from other publishers (26)

Walter F. Kean, K.D. Rainsford & W. Watson Buchanan. 2015. Ibuprofen. Ibuprofen 237 312 .
K.D. Rainsford. 2015. Ibuprofen. Ibuprofen 132 236 .
Phillip Jeffrey, Geoffrey T Tucker, Alan Bye, H Kim Crewe & Paul A Wright. (1991) The Site of Inversion of R (–)-Ibuprofen: Studies Using Rat In-situ Isolated Perfused Intestine/liver Preparations . Journal of Pharmacy and Pharmacology 43:10, pages 715-720.
Crossref
Patrick E Hanrahan & Humphrey A Moynihan. (2005) Preparation and stereochemical integrity of certain thioesters of 2-arylpropionic acids and related compounds. Journal of Pharmacy and Pharmacology 57:12, pages 1619-1627.
Crossref
Neal Davies. 2004. Chirality in Drug Design and Development. Chirality in Drug Design and Development.
R. Frihmat, J -M. Cardot, E. Beyssac, M. Boucher & J -M. Aiache. (2000) Bioinversion of ibuprofen enantiomers after administration in dogs: estimation of a novel index. European Journal of Drug Metabolism and Pharmacokinetics 25:3-4, pages 205-211.
Crossref
Hideo Yoshida, Yoshiro Kohno, Hiromi Endo, Jun-ichi Yamaguchi, Kiyomi Fukushima, Toshio Suwa & Masahiro Hayashi. (1997) Mechanistic studies on metabolic chiral inversion of 4-(4-methylphenyl)-2-methylthiomethyl-4-oxobutanoic acid (KE-748), an active metabolite of the new anti-rheumatic agent 2-acetylthiomethyl-4-(4-methylphenyl)-4-oxobutanoic acid (KE-298), in rats. Biochemical Pharmacology 53:2, pages 179-187.
Crossref
Anna Lombard, Valeria Rossetti & Maria Chiara Cassone. (1997) Studies on the in vitro inversion of flurbiprofen. Chirality 9:3, pages 317-319.
Crossref
Assumpta Carabaza, Nuria Suesa, Digna Tost, Jaume Pascual, Manel Gomez, Marta Gutierrez, Elvira Ortega, Xavier Montserrat, Ana M. Garcia, Ricard Mis, Francesc Cabre, David Mauleon & Germano Carganico. (1996) Stereoselective metabolic pathways of ketoprofen in the rat: Incorporation into triacylglycerols and enantiomeric inversion. Chirality 8:2, pages 163-172.
Crossref
J. M. Mayer, B. Testa, M. Roy-de Vos, C. Audergon & J. C. Etter. 1995. Toxicology in Transition. Toxicology in Transition 499 513 .
Keith McCormack. (1994) Non-steroidal anti-inflammatory drugs and spinal nociceptive processing. Pain 59:1, pages 9-43.
Crossref
Stephen D. Hall & Qian Xiaotao. (1994) The role of coenzyme A in the biotransformation of 2-arylpropionic acids. Chemico-Biological Interactions 90:3, pages 235-251.
Crossref
J. M. Mayer & B. Testa. 1994. Pharmacokinetics of Drugs. Pharmacokinetics of Drugs 209 231 .
Saeed Sattari & Fakhreddin Jamali. (2004) Evidence of absorption rate dependency of ibuprofen inversion in the rat. Chirality 6:5, pages 435-439.
Crossref
S. Menzel-Soglowek, G. Geisslinger, J. Mollenhauer & K. Brune. (1992) Metabolic chiral inversion of 2-arylpropionates in rat H4IIE and human Hep G2 hepatoma cells. Biochemical Pharmacology 43:7, pages 1487-1492.
Crossref
Romualda D. Knihinicki, Richard O. Day & Kenneth M. Williams. (1991) Chiral inversion of 2-arylpropionic acid non-steroidal anti-inflammatory drugs—II Racemization and hydrolysis of (R)- and (S)-ibuprofen-CoA thioesters. Biochemical Pharmacology 42:10, pages 1905-1911.
Crossref
Ching-Shih Chen, Woan-Ru Shieh, Pei-Heng Lu, Shawn Harriman & Ching-Yu Chen. (1991) Metabolic stereoisomeric inversion of ibuprofen in mammals. Biochimica et Biophysica Acta (BBA) - Protein Structure and Molecular Enzymology 1078:3, pages 411-417.
Crossref
N. Muller, E. Payan, F. Lapicque, B. Bannwarth & P. Netter. (1990) Pharmacological aspects of chiral nonsteroidal anti-inflammatory drugs. Fundamental & Clinical Pharmacology 4:6, pages 617-634.
Crossref
Kenneth M. Williams. (1990) Enantiomers in arthritic disorders. Pharmacology & Therapeutics 46:2, pages 273-295.
Crossref
G.T. Tucker & M.S. Lennard. (1990) Enantiomer specific pharmacokinetics. Pharmacology & Therapeutics 45:3, pages 309-329.
Crossref
Sylvia Müller, Joachim M. Mayer, Jean‐Claude Etter & Bernard Testa. (2004) Metabolic chiral inversion of ibuprofen in isolated rat hepatocytes. Chirality 2:2, pages 74-78.
Crossref
M. P. Knadler & S. D. Hall. (2004) Stereoselective arylpropionyl‐CoA thioester formation in vitro. Chirality 2:2, pages 67-73.
Crossref
Romualda D. Knihinicki, Kenneth M. Williams & Richard O. Day. (1989) Chiral inversion of 2-arylpropionic acid non-steroidal anti-inflammatory drugs—1. Biochemical Pharmacology 38:24, pages 4389-4395.
Crossref
Joachim M. Mayer, Malcolm Young, Bernard Testa & Jean‐Claude Etter. (2004) Modelling the Metabolic Epimerization of Anti‐inflammatory 2‐Arylpropanoyl‐coenzyme‐A Conjugates: Solvent effects on the 1 H/ 2 H exchange in S ‐[2‐(dimethylamino)ethyl] 2‐phenylpropanethioate . Helvetica Chimica Acta 72:6, pages 1225-1232.
Crossref
F. Jamali, R. Mehvar & F.M. Pasutto. (1989) Enantioselective Aspects of Drug Action and Disposition: Therapeutic Pitfalls. Journal of Pharmaceutical Sciences 78:9, pages 695-715.
Crossref
David R. Webb, Vijendra KR. Singh, H. Hugh Fudenberg, Roger W. Russell, L. Öhman, G. Maluszynska, K.-E. MAgnusson, O. Stendahl, Peter A. Lambert, David H. P. Streeten, Gunnar H. AndersonJrJr, Vickram Ramkumar, George Pierson, Gary L. Stiles, Bernard Testa, Joachm M. Mayer, Duncan Stewart-Tull, Michael Williams, Gary L. Niel, Peter Hambleton, Stephen D. Prior, Andrew Robinson, Jed F. Fisher & Paul A. AristoffBernard Testa & Joachim M. Mayer. 1988. Progress in Drug Research / Fortschritte der Arzneimittelforschung / Progrès des recherches pharmaceutiques. Progress in Drug Research / Fortschritte der Arzneimittelforschung / Progrès des recherches pharmaceutiques 249 303 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Order Reprints Request Corporate Permissions

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

Request Academic Permissions

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.

Related research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.