Otamixaban

Otamixaban
Systematic (IUPAC) name


Methyl (2R,3R)-2-{3-[amino(imino)methyl]benzyl}-3-{[4-(1-oxidopyridin-4-yl)benzoyl]amino}butanoate
Identifiers
CAS Number	193153-04-7^N
ATC code	none
PubChem	CID 5496659
ChemSpider	4593439^Y
UNII	S173RED00L^Y
ChEMBL	CHEMBL46618^Y
Chemical data
Formula	C₂₅H₂₆N₄O₄
Molar mass	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 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)

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.

Antithrombotics (thrombolytics, anticoagulants and antiplatelet drugs) (B01)

Antiplatelet drugs

Glycoprotein IIb/IIIa inhibitors	Abciximab Eptifibatide Tirofiban Roxifiban Orbofiban

ADP receptor/P2Y₁₂ inhibitors	Thienopyridines Clopidogrel Prasugrel Ticlopidine Nucleotide/nucleoside analogs Cangrelor Elinogrel Ticagrelor

Prostaglandin analogue (PGI2)	Beraprost Iloprost Prostacyclin Treprostinil

COX inhibitors	Acetylsalicylic acid/Aspirin^# Aloxiprin Carbasalate calcium Indobufen Triflusal

Thromboxane inhibitors	Thromboxane synthase inhibitors Dipyridamole (+Aspirin) Picotamide Receptor antagonists Terutroban^†

Phosphodiesterase inhibitors	Cilostazol Dipyridamole Triflusal

Other	Cloricromen Ditazole Vorapaxar

Anticoagulants

Vitamin K antagonists
(inhibit II, VII, IX, X)

Factor Xa inhibitors
(with some II inhibition)

Heparin group/ glycosaminoglycans/ (bind antithrombin)	Low molecular weight heparin Bemiparin Certoparin Dalteparin Enoxaparin Nadroparin Parnaparin Reviparin Tinzaparin^‡ Oligosaccharides Fondaparinux Idraparinux^§ Heparinoids Danaparoid Dermatan sulfate Sulodexide

Direct Xa inhibitors	Xabans Apixaban Betrixaban^† Darexaban^§ Edoxaban Otamixaban^§ Rivaroxaban

Direct thrombin (IIa) inhibitors

Other

Thrombolytic drugs/
fibrinolytics

Non-medicinal

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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