Ximelagatran

Ximelagatran
Clinical data
Trade namesExanta
Pregnancy
category
  • Uncategorized
Routes of
administration		Oral (tablets)
ATC code
Legal status
Legal status
  • Withdrawn from market
Pharmacokinetic data
Bioavailability20%
Metabolismto melagatran
Elimination half-life3–5 hours
ExcretionRenal (80%)
Identifiers
  • ethyl 2-[[(1R)-1-cyclohexyl-2-
    [(2S)-2-[[4-(N'-hydroxycarbamimidoyl)
    phenyl]methylcarbamoyl]azetidin-1-yl]-
    2-oxo-ethyl]amino]acetate
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC24H35N5O5
Molar mass473.574 g·mol−1 (429 g/mol after conversion)
3D model (JSmol)
  • O=C(NCc1ccc(C(=N\O)\N)cc1)[C@H]3N(C(=O)[C@H](NCC(=O)OCC)C2CCCCC2)CC3
  • InChI=1S/C24H35N5O5/c1-2-34-20(30)15-26-21(17-6-4-3-5-7-17)24(32)29-13-12-19(29)23(31)27-14-16-8-10-18(11-9-16)22(25)28-33/h8-11,17,19,21,26,33H,2-7,12-15H2,1H3,(H2,25,28)(H,27,31)/t19-,21+/m0/s1 checkY
  • Key:ZXIBCJHYVWYIKI-PZJWPPBQSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Ximelagatran (Exanta or Exarta, H 376/95) is an anticoagulant that has been investigated extensively as a replacement for warfarin[1] 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).[2]

  1. ^ Hirsh J, O'Donnell M, Eikelboom JW (July 2007). "Beyond unfractionated heparin and warfarin: current and future advances". Circulation. 116 (5): 552–560. doi:10.1161/CIRCULATIONAHA.106.685974. PMID 17664384.
  2. ^ "AstraZeneca Decides to Withdraw Exanta" (Press release). AstraZeneca. February 14, 2006. Retrieved 2012-07-16.