N-(5-chloropyridin-2-yl)-2-[4-(N,N-dimethylcarbamimidoyl)benzamido]-5-methoxybenzamide

• ChemBase ID: 126139
• Molecular Formular: C23H22ClN5O3
• Molecular Mass: 451.90548
• Monoisotopic Mass: 451.14111727
• SMILES: CN(C)C(=N)c1ccc(cc1)C(=O)Nc1c(cc(cc1)OC)C(=O)Nc1ncc(cc1)Cl
• Canonical SMILES: COc1ccc(c(c1)C(=O)Nc1ccc(cn1)Cl)NC(=O)c1ccc(cc1)C(=N)N(C)C
• InChI: InChI=1S/C23H22ClN5O3/c1-29(2)21(25)14-4-6-15(7-5-14)22(30)27-19-10-9-17(32-3)12-18(19)23(31)28-20-11-8-16(24)13-26-20/h4-13,25H,1-3H3,(H,27,30)(H,26,28,31)
• InChIKey: XHOLNRLADUSQLD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(5-chloropyridin-2-yl)-2-[4-(N,N-dimethylcarbamimidoyl)benzamido]-5-methoxybenzamide
• IUPAC Traditional name: betrixaban
• Synonyms: N-(5-Chloro-2-pyridinyl)-2-[[4-[(dimethylamino)iminomethyl]benzoyl]amino]-5-methoxybenzamide; PRT 054021; Betrixaban

Database IDs

• CAS Number: 330942-05-7
• PubChem SID: 162220480
• PubChem CID: 10275777
• CHEMBL: 512351
• Chemspider ID: 18981107
• Unique Ingredient Identifier: 74RWP7W0J9
• Wikipedia Title: Betrixaban

CALCULATED PROPERTIES

• Acid pKa: 9.1977825
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 1.030337
• LogD (pH = 7.4): 1.3280587
• Log P: 2.7310424
• Molar Refractivity: 138.2914 cm^3
• Polarizability: 46.445236 Å^3
• Polar Surface Area: 107.41 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B329500

A novel anticoagulant. An oral direct inhibitor of factor Xa (FXa) for use in the prevention of venous thromboembolism (VTE).

REFERENCES

• Turpie, A.G.G. et al.: Thromb. Haemost., 101, 68 (2009)
• Gomez-Outes, A. et al.: Curr. Vasc. Pharmacol., 7, 309 (2009)