The pharmacodynamics and pharmacokinetics of the oral direct thrombin inhibitor ximelagatran and its active metabolite melagatran: a mini-review

Thromb Res. 2003 Jul 15:109 Suppl 1:S9-15. doi: 10.1016/s0049-3848(03)00249-4.

Abstract

Ximelagatran (Exanta, AstraZeneca) is a novel, oral direct thrombin inhibitor (oral DTI) that is rapidly converted to melagatran, its active form, following absorption. Melagatran has been shown to be a potent, rapidly binding, competitive inhibitor of human alpha-thrombin that inhibits both thrombin activity and generation. Melagatran also effectively inhibits both free and clot-bound thrombin. Melagatran has a wide therapeutic interval that enables it to be administered safely across a wide range of doses with no increased risk of bleeding, in contrast with warfarin whose narrow therapeutic window necessitates monitoring of its pharmacodynamic effect. Although melagatran has all the pharmacodynamic properties required of a new antithrombotic agent, low oral bioavailability that is even further reduced by the concomitant intake of food precludes its development as an oral agent. It was this that propelled the development of its prodrug, ximelagatran, which is 170 times more lipophilic than melagatran and uncharged at intestinal pH. Ximelagatran is therefore much better than melagatran at penetrating the gastrointestinal barrier and, as a consequence, has sufficient bioavailability (20%) for oral administration. Moreover, its pharmacokinetic properties following oral administration are stable and reproducible, with no food interactions and a low potential for drug-drug interactions. These properties allow ximelagatran to be administered twice daily according to a fixed dose regimen without coagulation monitoring. As a consequence of its favourable pharmacokinetic and pharmacodynamic properties, ximelagatran is currently undergoing full-scale clinical development for the prophylaxis and treatment of thromboembolic disorders.

Publication types

  • Review

MeSH terms

  • Azetidines / pharmacokinetics
  • Azetidines / pharmacology*
  • Benzylamines
  • Glycine / analogs & derivatives*
  • Glycine / pharmacology
  • Hemostasis / drug effects
  • Humans
  • Pharmacokinetics
  • Prodrugs / pharmacokinetics
  • Prodrugs / pharmacology*
  • Thrombin / antagonists & inhibitors*
  • Thrombosis / drug therapy
  • Thrombosis / prevention & control

Substances

  • Azetidines
  • Benzylamines
  • Prodrugs
  • melagatran
  • ximelagatran
  • Thrombin
  • Glycine