Otamixaban

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Otamixaban


Systematic (IUPAC) name
Methyl (2R,3R)-2-{3-[amino(imino)methyl]benzyl}-3-{[4-(1-oxidopyridin-4-yl)benzoyl]amino}butanoate
Clinical data
Legal status	?
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
Mol. 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
N (what is this?) (verify)

Otamixaban (INN) is an experimental 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]

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."

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

Antiplatelet drugs

Glycoprotein IIb/IIIa inhibitors	Abciximab Eptifibatide Tirofiban

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 antagonist Terutroban^†

Phosphodiesterase inhibitors	Cilostazol Dipyridamole Triflusal

Other	Cloricromen Ditazole

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 heparinoid Danaparoid Dermatan sulfate Sulodexide

Direct Xa inhibitors	xabans Apixaban Betrixaban Darexaban Edoxaban Otamixaban Rivaroxaban

Direct thrombin (II) inhibitors

bivalent: Hirudin
- Bivalirudin
- Desirudin
- Lepirudin
univalent: Argatroban
Dabigatran
Melagatran^‡
Ximelagatran^‡

Other

Thrombolytic drugs/
fibrinolytics

Non-medicinal

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^‡Withdrawn from market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

M: MYL

cell/phys (coag, heme, immu, gran), csfs

rbmg/mogr/tumr/hist, sysi/epon, btst

drug (B1/2/3+5+6), btst, trns

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