Literature DB >> 18442220

Is the required therapeutic effect always achieved by racemic switch of proton-pump inhibitors?

Quan Zhou, Xiao-Feng Yan, Wen-Sheng Pan, Su Zeng.   

Abstract

Many of the drugs currently used in medical practice are racemates. The enantiomers of a racemic drug differ in pharmacodynamics and/or pharmacokinetics, thus in some cases it is preferable to develop pure enantiomers by racemic switch. In a recent study by Pai et al, dexrabeprazole [R(+)-rabeprazole] (10 mg) was found to be more effective than rabeprazole (20 mg) in the treatment of gastroesophageal reflux disease. We read with great interest in this study and discussed whether such racemic switch would be applicable to other proton-pump inhibitors (PPIs). A literature review indicates that stereoselective pharmacokinetics, rather than stereoselective pharmacological activity, is the main cause of differences in clinical efficacy between pure enantiomer and racemic PPI. Racemic switches of PPI provide the therapeutic advantages such as reducing metabolic load on the body, simplifying pharmacokinetics, providing benefit to the non-responders to standard dose of racemate, more homogenous response to treatment and better efficacy with equal safety. Further studies in quantitative structure-activity relationships (QSARs) are needed to address the fact that the preferred enantiomer of PPI is not always in the same absolute configuration, i.e. S-form is for omeprazole, pantoprazole and tenatoprazole whereas R-form is for lansoprazole and rabeprazole.

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Year:  2008        PMID: 18442220      PMCID: PMC2708384          DOI: 10.3748/wjg.14.2617

Source DB:  PubMed          Journal:  World J Gastroenterol        ISSN: 1007-9327            Impact factor:   5.742


  10 in total

Review 1.  Effects of stereochemical aspects on drug interaction in pharmacokinetics.

Authors:  Quan Zhou; Tong-Wei Yao; Su Zeng
Journal:  Acta Pharmacol Sin       Date:  2002-05       Impact factor: 6.150

Review 2.  Enantioselective disposition of lansoprazole and rabeprazole in human plasma.

Authors:  Masatomo Miura
Journal:  Yakugaku Zasshi       Date:  2006-06       Impact factor: 0.302

3.  Pharmacodynamic comparison of pantoprazole enantiomers: inhibition of acid-related lesions and acid secretion in rats and guinea-pigs.

Authors:  Hong Cao; Min-Wei Wang; Li-Xin Sun; Takashi Ikejima; Zhi-Qing Hu; Wei-Hua Zhao
Journal:  J Pharm Pharmacol       Date:  2005-07       Impact factor: 3.765

4.  Pharmacokinetics and pharmacodynamics of esomeprazole, the S-isomer of omeprazole.

Authors:  T Andersson; K Röhss; E Bredberg; M Hassan-Alin
Journal:  Aliment Pharmacol Ther       Date:  2001-10       Impact factor: 8.171

5.  Differential stereoselective pharmacokinetics of pantoprazole, a proton pump inhibitor in extensive and poor metabolizers of pantoprazole--a preliminary study.

Authors:  M Tanaka; H Yamazaki; H Hakusui; N Nakamichi; H Sekino
Journal:  Chirality       Date:  1997       Impact factor: 2.437

6.  Comparative clinical trial of S-pantoprazole versus racemic pantoprazole in the treatment of gastro-esophageal reflux disease.

Authors:  Vikas G Pai; Nitin V Pai; Hemant P Thacker; Jaisingh K Shinde; Vijay P Mandora; Subhash S Erram
Journal:  World J Gastroenterol       Date:  2006-10-07       Impact factor: 5.742

7.  Pharmacokinetic differences between the enantiomers of lansoprazole and its metabolite, 5-hydroxylansoprazole, in relation to CYP2C19 genotypes.

Authors:  M Miura; H Tada; N Yasui-Furukori; T Uno; K Sugawara; T Tateishi; T Suzuki
Journal:  Eur J Clin Pharmacol       Date:  2004-09-23       Impact factor: 2.953

Review 8.  Cytochrome P450 pharmacogenetics in drug development: in vitro studies and clinical consequences.

Authors:  A David Rodrigues; Thomas H Rushmore
Journal:  Curr Drug Metab       Date:  2002-06       Impact factor: 3.731

9.  Randomized, double-blind, comparative study of dexrabeprazole 10 mg versus rabeprazole 20 mg in the treatment of gastroesophageal reflux disease.

Authors:  Vikas Pai; Nitin Pai
Journal:  World J Gastroenterol       Date:  2007-08-14       Impact factor: 5.742

10.  Concentration dependent stereoselectivity of propafenone N-depropylation metabolism with human hepatic recombinant CYP1A2.

Authors:  Q Zhou; T W Yao; Y N Yu; S Zeng
Journal:  Pharmazie       Date:  2003-09       Impact factor: 1.267

  10 in total
  1 in total

1.  Efficacy of S-pantoprazole 10 mg in the Symptom Control of Non-erosive Reflux Disease: A Phase III Placebo-controlled Trial.

Authors:  Yu Kyung Cho; Myung-Gyu Choi; Hyojin Park; Ji Won Kim; Dong Ho Lee; Kwang Hyun Ko; Sang Gyun Kim; Hwoon-Yong Jung; Su Jin Hong; Yong Chan Lee; Si Hyung Lee
Journal:  J Neurogastroenterol Motil       Date:  2021-04-30       Impact factor: 4.924

  1 in total

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