Otamixaban
{{Drugbox | Verifiedfields = changed | verifiedrevid = 462266309 | IUPAC_name = Methyl (2R,3R)-2-{3-[amino(imino)methyl]benzyl}-3-{[4-(1-oxidopyridin-4-yl)benzoyl]amino}butanoate | image = Otamixaban.svg | image2 = Otamixaban 3D.png
| tradename = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration =
| bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =
| CAS_number_Ref = 
| CAS_number = 193153-04-7
| ATC_prefix = none
| ATC_suffix =
| PubChem = 5496659
| DrugBank_Ref = 
| DrugBank =
| ChemSpiderID_Ref =
| ChemSpiderID = 4593439
| UNII_Ref =
| UNII = S173RED00L
| ChEMBL_Ref =
| ChEMBL = 46618
| C=25 | H=26 | N=4 | O=4
| molecular_weight = 446.498 g/mol
| smiles = O=C(OC)[C@H](Cc1cc(C(=[N@H])N)ccc1)[C@H](NC(=O)c3ccc(c2cc[n+]([O-])cc2)cc3)C
| InChI = 1/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
| InChIKey = PFGVNLZDWRZPJW-OPAMFIHVBD
| StdInChI_Ref =
| StdInChI = 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
| StdInChIKey_Ref =
| StdInChIKey = PFGVNLZDWRZPJW-OPAMFIHVSA-N
}}
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]
References
- ↑ 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.
- ↑ "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.
- ↑ "Sanofi's Investigational Iniparib, Otamixaban Fail To Meet Goals, Ends Programs". RTT news. Retrieved 11 April 2014.