Metabolism and disposition of the thienopyridine antiplatelet drugs ticlopidine, clopidogrel, and prasugrel in humans

J Clin Pharmacol. 2010 Feb;50(2):126-42. doi: 10.1177/0091270009343005. Epub 2009 Nov 30.

Abstract

Ticlopidine, clopidogrel, and prasugrel are thienopyridine prodrugs that inhibit adenosine-5'-diphosphate (ADP)-mediated platelet aggregation in vivo. These compounds are converted to thiol-containing active metabolites through a corresponding thiolactone. The 3 compounds differ in their metabolic pathways to their active metabolites in humans. Whereas ticlopidine and clopidogrel are metabolized to their thiolactones in the liver by cytochromes P450, prasugrel proceeds to its thiolactone following hydrolysis by carboxylesterase 2 during absorption, and a portion of prasugrel's active metabolite is also formed by intestinal CYP3A. Both ticlopidine and clopidogrel are subject to major competing metabolic pathways to inactive metabolites. Thus, varying efficiencies in the formation of active metabolites affect observed effects on the onset of action and extent of inhibition of platelet aggregation (IPA). Knowledge of the CYP-dependent formation of ticlopidine and clopidogrel thiolactones helps explain some of the observed drug-drug interactions with these molecules and, more important, the role of CYP2C19 genetic polymorphism on the pharmacokinetics of and pharmacodynamic response to clopidogrel. The lack of drug interaction potential and the absence of CYP2C19 genetic effect result in a predictable response to thienopyridine antiplatelet therapy with prasugrel. Current literature shows that greater ADP-mediated IPA is associated with significantly better clinical outcomes for patients with acute coronary syndrome.

Publication types

  • Research Support, Non-U.S. Gov't
  • Review

MeSH terms

  • Acute Coronary Syndrome / drug therapy
  • Aryl Hydrocarbon Hydroxylases / genetics
  • Aryl Hydrocarbon Hydroxylases / metabolism
  • Blood Platelets / drug effects
  • Clopidogrel
  • Cytochrome P-450 CYP2C19
  • Drug Interactions
  • Humans
  • Piperazines / metabolism*
  • Piperazines / therapeutic use
  • Platelet Aggregation / drug effects*
  • Platelet Aggregation Inhibitors / metabolism
  • Platelet Aggregation Inhibitors / therapeutic use
  • Polymorphism, Genetic
  • Prasugrel Hydrochloride
  • Pyridines / metabolism*
  • Pyridines / therapeutic use
  • Thiophenes / metabolism*
  • Thiophenes / therapeutic use
  • Ticlopidine / analogs & derivatives*
  • Ticlopidine / metabolism*
  • Ticlopidine / therapeutic use

Substances

  • Piperazines
  • Platelet Aggregation Inhibitors
  • Pyridines
  • Thiophenes
  • thienopyridine
  • Clopidogrel
  • Aryl Hydrocarbon Hydroxylases
  • CYP2C19 protein, human
  • Cytochrome P-450 CYP2C19
  • Prasugrel Hydrochloride
  • Ticlopidine