Structure via PubChem · Public domain (PubChem)
otamixaban
Sign in to saveOtamixaban (INN) is an experimental injectable anticoagulant direct factor Xa inhibitor 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.
Chemical data
- Formula
- C25H26N4O4
- Molecular weight
- 446.5 g/mol
- IUPAC name
- methyl (2R,3R)-2-[(3-carbamimidoylphenyl)methyl]-3-[[4-(1-oxidopyridin-1-ium-4-yl)benzoyl]amino]butanoate
- SMILES
- C[C@H]([C@@H](CC1=CC(=CC=C1)C(=N)N)C(=O)OC)NC(=O)C2=CC=C(C=C2)C3=CC=[N+](C=C3)[O-]
- InChIKey
- PFGVNLZDWRZPJW-OPAMFIHVSA-N
- XLogP
- 2
- Polar surface area
- 131 Ų
- H-bond donors
- 3
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 3
- Molecule type
- Small molecule
- Indications
- acute coronary syndrome, liver disease, kidney disease, coronary artery disease
via ChEMBL · EBI
Research
62 papers- The discovery of the Factor Xa inhibitor otamixaban: from lead identification to clinical development.Current medicinal chemistry · 2007
- Otamixaban in acute coronary syndromes.Lancet (London, England) · 2009
- Drug evaluation: the directly activated Factor Xa inhibitor otamixaban.IDrugs : the investigational drugs journal · 2006
- Otamixaban for the treatment of patients with non-ST-elevation acute coronary syndromes (SEPIA-ACS1 TIMI 42): a randomised, double-blind, active-controlled, phase 2 trial.Lancet (London, England) · 2009
- Synergistic inhibition of SARS-CoV-2 cell entry by otamixaban and covalent protease inhibitors: pre-clinical assessment of pharmacological and molecular properties.Chemical science · 2021
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 446.195
Show 5 more facts
- chemical formula
- C₂₅H₂₆N₄O₄
- Commons category
- Otamixaban
- canonical SMILES
- CC(C(CC1=CC=CC(=C1)C(=N)N)C(=O)OC)NC(=O)C2=CC=C(C=C2)C3=CC=[N+](C=C3)[O-]
- isomeric SMILES
- C[C@H]([C@@H](CC1=CC=CC(=C1)C(=N)N)C(=O)OC)NC(=O)C2=CC=C(C=C2)C3=CC=[N+](C=C3)[O-]
- subject has role
- anticoagulant
via Wikidata · CC0
~2 min read
Encyclopedic overview
1 sectionsContents
- References
{{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 | image_class = skin-invert-image | image2 = Otamixaban 3D.png | image_class2 = bg-transparent
| tradename = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration =
Excerpted from Wikipedia’s “otamixaban” article, available under the CC BY-SA 4.0 licence.