ximelagatran   Click here for help

GtoPdb Ligand ID: 6381

Synonyms: H 376-95 | H 376/95
Approved drug
ximelagatran is an approved drug
Compound class: Synthetic organic
Comment: Ximelagatran is a prodrug of the active prothrombin inhibitor melagatran. Applications for approval of ximelagatran were withdrawn in 2006.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 4
Rotatable bonds 13
Topological polar surface area 146.35
Molecular weight 473.26
XLogP 2.39
No. Lipinski's rules broken 1
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Canonical SMILES CCOC(=O)CNC(C(=O)N1CCC1C(=O)NCc1ccc(cc1)C(=NO)N)C1CCCCC1
Isomeric SMILES CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)NCc1ccc(cc1)/C(=N/O)/N)C1CCCCC1
InChI 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
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Summary of Clinical Use Click here for help
Ximelagatran is a prodrug, that is metabolised in the liver to generate a direct thrombin inhibitor. It was investigated as an orally administered prophylactic for deep venous thrombosis, prevention of secondary venous thromboembolism and complications of atrial fibrillation, as a replacement for warfarin. Ximelagatran did receive marketing authorisation in several countries (Germany, Portugal, Sweden, Finland, Norway, Iceland, Austria, Denmark, France, Switzerland, Argentina and Brazil), but the drug was later discontinued by AstraZeneca due to the risk of hepatotoxicity. The FDA informed AstraZeneca that they would not approve ximelagatran in 2004.