2-{[2-(5-carbamimidoyl-2-hydroxyphenoxy)-3,5-difluoro-6-{3-[1-(2H3)methyl-4,5-dihydro-1H-imidazol-2-yl]phenoxy}pyridin-4-yl](methyl)amino}acetic acid

• ChemBase ID: 168919
• Molecular Formular: C25H24F2N6O5
• Molecular Mass: 526.4920664
• Monoisotopic Mass: 526.17762434
• SMILES: c1(cccc(c1)Oc1c(c(c(c(n1)Oc1c(ccc(c1)C(=N)N)O)F)N(CC(=O)O)C)F)C1=NCCN1C
• Canonical SMILES: OC(=O)CN(c1c(F)c(Oc2cccc(c2)C2=NCCN2C)nc(c1F)Oc1cc(ccc1O)C(=N)N)C
• InChI: InChI=1S/C25H24F2N6O5/c1-32-9-8-30-23(32)14-4-3-5-15(10-14)37-24-19(26)21(33(2)12-18(35)36)20(27)25(31-24)38-17-11-13(22(28)29)6-7-16(17)34/h3-7,10-11,34H,8-9,12H2,1-2H3,(H3,28,29)(H,35,36)
• InChIKey: NPNSVNGQJGRSNR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{[2-(5-carbamimidoyl-2-hydroxyphenoxy)-3,5-difluoro-6-{3-[1-(^2H₃)methyl-4,5-dihydro-1H-imidazol-2-yl]phenoxy}pyridin-4-yl](methyl)amino}acetic acid
• IUPAC Traditional name: {[2-(5-carbamimidoyl-2-hydroxyphenoxy)-3,5-difluoro-6-{3-[1-(^2H₃)methyl-4,5-dihydroimidazol-2-yl]phenoxy}pyridin-4-yl](methyl)amino}acetic acid
• Synonyms: N-[2-[5-(aminoiminomethyl)-2-hydroxyphenoxy]-6-[3-[4,5-dihydro-1-(methyl-d3)-1H-imidazol-2-yl]phenoxy]-3,5-difluoro-4-pyridinyl]-N-methylglycine; CI 1031-d3; Fidexaban-d3; ZK 807834-d3; Fidexaban-d3

Database IDs

• PubChem SID: 162263051
• PubChem CID: 71316737

CALCULATED PROPERTIES

• Acid pKa: 2.6557589
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -1.1144699
• LogD (pH = 7.4): -1.1093798
• Log P: -1.0920496
• Molar Refractivity: 145.8637 cm^3
• Polarizability: 49.581528 Å^3
• Polar Surface Area: 157.59 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - F335502

A labelled direct inhibitor of factor Xa (FXa); anticoagulant. It has been shown to reduce ex-vivo arterial thrombus formation and factor-X activity in a dose-dependent manner.

REFERENCES

• Zafar, M.U. et al.: Thromb. Haemost., 97, 487 (2007)
• McClanahan, T.B. et al.: Eur. J. Pharmacol., 432, 187 (2007)
• Chi, L. et al.: Pharmacol., 64, 76 (2007)