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ximelagatran
EntityQ3570984· pop 10· linked from 180 articles

ximelagatran

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Also known as H 376-95, H 376/95, H 37695, Exarta, Exanta, ethyl 2-[[(1R)-1-cyclohexyl-2- [(2S)-2-[[4-(N'-hydroxycarbamimidoyl) phenyl]methylcarbamoyl]azetidin-1-yl]- 2-oxo-ethyl]amino]acetate, Ximelagatranum, Ethyl 2-[[(1R)-1-cyclohexyl-2- [(2S)-2-[[4-(n'-hydroxycarbamimidoyl) phenyl]methylcarbamoyl]azetidin-1-yl]- 2-oxo-ethyl]amino]acetate

Ximelagatran (Exanta or Exarta, H 376/95) is an anticoagulant that has been investigated extensively as a replacement for warfarin that would overcome the problematic dietary, drug interaction, and monitoring issues associated with warfarin therapy. In 2006, its manufacturer AstraZeneca announced that it would withdraw pending applications for marketing approval after reports of hepatotoxicity (liver damage) during trials, and discontinue its distribution in countries where the drug had been approved (Germany, Portugal, Sweden, Finland, Norway, Iceland, Austria, Denmark, France, Switzerland, A

Research

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Wikidata facts

Mass
473.263819
Has use
medication
Show 6 more facts
chemical formula
C₂₄H₃₅N₅O₅
isomeric SMILES
CCOC(=O)CN[C@H](C1CCCCC1)C(=O)N2CC[C@H]2C(=O)NCC3=CC=C(C=C3)/C(=N/O)/N
canonical SMILES
CCOC(=O)CNC(C1CCCCC1)C(=O)N2CCC2C(=O)NCC3=CC=C(C=C3)C(=NO)N
World Health Organisation international non-proprietary name
ximelagatran
defined daily dose
48
physically interacts with
Coagulation factor II, thrombin
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Encyclopedic overview

5 sections
Contents
  • Method of action
  • Uses
  • Side effects
  • References
  • External links

Ximelagatran (Exanta or Exarta, H 376/95) is an anticoagulant that has been investigated extensively as a replacement for warfarin that would overcome the problematic dietary, drug interaction, and monitoring issues associated with warfarin therapy. In 2006, its manufacturer AstraZeneca announced that it would withdraw pending applications for marketing approval after reports of hepatotoxicity (liver damage) during trials, and discontinue its distribution in countries where the drug had been approved (Germany, Portugal, Sweden, Finland, Norway, Iceland, Austria, Denmark, France, Switzerland, Argentina and Brazil).

==Method of action== Ximelagatran, a direct thrombin inhibitor, was the first member of this class that can be taken orally. It acts solely by inhibiting the actions of thrombin. It is taken orally twice daily, and rapidly absorbed by the small intestine. Ximelagatran is a prodrug, being converted in vivo to the active agent melagatran. This conversion takes place in the liver and many other tissues through hydrolysis and dehydroxylation (replacing the ethyl and hydroxyl groups with hydrogen).

Excerpted from Wikipedia’s “ximelagatran” article, available under the CC BY-SA 4.0 licence.

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