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Otamixaban

Summary

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
  • Methyl (2R,3R)-2-{3-[amino(imino)methyl]benzyl}-3-{[4-(1-oxidopyridin-4-yl)benzoyl]amino}butanoate
CAS Number
  • 193153-04-7 ☒N
PubChem CID
  • 5496659
ChemSpider
  • 4593439 checkY
UNII
  • S173RED00L
ChEMBL
  • ChEMBL46618 checkY
CompTox Dashboard (EPA)
  • DTXSID40172917 Edit this at Wikidata
Chemical and physical data
FormulaC25H26N4O4
Molar mass446.507 g·mol−1
3D model (JSmol)
  • Interactive image
  • O=C(OC)[C@H](Cc1cc(C(=[N@H])N)ccc1)[C@H](NC(=O)c3ccc(c2cc[n+]([O-])cc2)cc3)C
  • 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 checkY
  • Key:PFGVNLZDWRZPJW-OPAMFIHVSA-N checkY
 ☒NcheckY (what is this?)  (verify)

References edit

  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. 91 (23). American Chemical Society: 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.