4-(4-{[(2R,3R)-3-[(3-carbamimidoylphenyl)methyl]-4-methoxy-4-oxobutan-2-yl]carbamoyl}phenyl)pyridin-1-ium-1-olate

• ChemBase ID: 175947
• Molecular Formular: C25H26N4O4
• Molecular Mass: 446.49834
• Monoisotopic Mass: 446.19540533
• SMILES: c1[n+](ccc(c1)c1ccc(cc1)C(=O)N[C@@H]([C@@H](Cc1cc(C(=N)N)ccc1)C(=O)OC)C)[O-]
• Canonical SMILES: COC(=O)[C@@H]([C@H](NC(=O)c1ccc(cc1)c1cc[n+](cc1)[O-])C)Cc1cccc(c1)C(=N)N
• 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
• InChIKey: PFGVNLZDWRZPJW-OPAMFIHVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(4-{[(2R,3R)-3-[(3-carbamimidoylphenyl)methyl]-4-methoxy-4-oxobutan-2-yl]carbamoyl}phenyl)pyridin-1-ium-1-olate
• IUPAC Traditional name: otamixaban
• Synonyms: (αR)-3-(Aminoiminomethyl)-α-[(1R)-1-[[4-(1-oxido-4-pyridinyl)benzoyl]amino]ethyl]benzenepropanoic Acid Methyl Ester; [R-(R*,R*)]-3-(Aminoiminomethyl)-α-[1-[[4-(1-oxido-4-pyridinyl)benzoyl]amino]ethyl]benzenepropanoic Acid Methyl Ester; FXV 673; Methyl (2R,3R)-2-[3-Amidinobenzyl]-3-[[4-(1-oxido-4-pyridinyl)benzoyl]amino]butanoate; Otamixaban

Database IDs

• CAS Number: 193153-04-7
• PubChem SID: 164231857
• PubChem CID: 5496659

CALCULATED PROPERTIES

• Acid pKa: 14.9449
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -0.879095
• LogD (pH = 7.4): -0.86946535
• Log P: 1.5362507
• Molar Refractivity: 137.6168 cm^3
• Polarizability: 48.764984 Å^3
• Polar Surface Area: 130.73 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - O712500

A potent (Ki = 0.5 nM), selective, rapid acting, competitive and reversible fXa inhibitor that effectively inhibits both free and prothrombinase-bound fXa. Clinical studies show that it is efficacious, safe and well tolerated in humans and therefore has c

REFERENCES

• Guertin, K.R. et al.: Curr. Med. Chem., 14, 2471 (2007)
• Hinder, M. et al.: Clin. Pharmacol. Therap., 80, 691 (2007)
• Hinder, M. et al.: Thromb. Haemost., 95, 224 (2007)