Otamixaban

Otamixaban (INN) is an experimental injectable anticoagulant direct factor Xa inhibitor[1] that was investigated for the treatment for acute coronary syndrome. In 2013, Sanofi announced that it had ended development of the drug candidate after poor performance in a Phase III clinical trial.[2][3]

Otamixaban
Clinical data
ATC code
  • none
Identifiers
IUPAC name
  • Methyl (2R,3R)-2-{3-[amino(imino)methyl]benzyl}-3-{[4-(1-oxidopyridin-4-yl)benzoyl]amino}butanoate
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC25H26N4O4
Molar mass446.507 g·mol−1
3D model (JSmol)
SMILES
  • O=C(OC)[C@H](Cc1cc(C(=[N@H])N)ccc1)[C@H](NC(=O)c3ccc(c2cc[n+]([O-])cc2)cc3)C
InChI
  • InChI=1S/C25H26N4O4/c1-16(22(25(31)33-2)15-17-4-3-5-21(14-17)23(26)27)28-24(30)20-8-6-18(7-9-20)19-10-12-29(32)13-11-19/h3-14,16,22H,15H2,1-2H3,(H3,26,27)(H,28,30)/t16-,22-/m1/s1 Y
  • Key:PFGVNLZDWRZPJW-OPAMFIHVSA-N Y
 NY (what is this?)  (verify)

References
  1. Guertin KR, Choi YM (2007). "The discovery of the Factor Xa inhibitor otamixaban: from lead identification to clinical development". Curr. Med. Chem. 14 (23): 2471–81. doi:10.2174/092986707782023659. PMID 17979700.
  2. "AstraZeneca, Sanofi Cut Programs". Chemical & Engineering News. American Chemical Society. 91 (23): 17. June 10, 2013. Sanofi is ending development on two compounds, the anticancer compound iniparib and the anticoagulant otamixaban, both of which flunked Phase III studies.
  3. "Sanofi's Investigational Iniparib, Otamixaban Fail To Meet Goals, Ends Programs". RTT news. Retrieved 11 April 2014.
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