N-(3-chloro-4-{3,9-diazatricyclo[8.4.0.03,7]tetradeca-1(10),4,6,11,13-pentaene-9-carbonyl}phenyl)-5-fluoro-2-methylbenzamide

• ChemBase ID: 172358
• Molecular Formular: C27H21ClFN3O2
• Molecular Mass: 473.9259432
• Monoisotopic Mass: 473.13063283
• SMILES: c12c(Cn3c(CN1C(=O)c1ccc(cc1Cl)NC(=O)c1c(ccc(c1)F)C)ccc3)cccc2
• Canonical SMILES: Fc1ccc(c(c1)C(=O)Nc1ccc(c(c1)Cl)C(=O)N1Cc2cccn2Cc2c1cccc2)C
• InChI: InChI=1S/C27H21ClFN3O2/c1-17-8-9-19(29)13-23(17)26(33)30-20-10-11-22(24(28)14-20)27(34)32-16-21-6-4-12-31(21)15-18-5-2-3-7-25(18)32/h2-14H,15-16H2,1H3,(H,30,33)
• InChIKey: PPHTXRNHTVLQED-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(3-chloro-4-{3,9-diazatricyclo[8.4.0.0^3,^7]tetradeca-1(10),4,6,11,13-pentaene-9-carbonyl}phenyl)-5-fluoro-2-methylbenzamide
• IUPAC Traditional name: lixivaptan
• Synonyms: VPA 985; WAY-VPA 985; Lixivaptan; N-[3-Chloro-4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]-5-fluoro-2-methyl-benzamide

Database IDs

• CAS Number: 168079-32-1
• PubChem SID: 164228268
• PubChem CID: 172997

CALCULATED PROPERTIES

• Acid pKa: 10.541978
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 5.9805074
• LogD (pH = 7.4): 5.9802136
• Log P: 5.980511
• Molar Refractivity: 133.0035 cm^3
• Polarizability: 49.026756 Å^3
• Polar Surface Area: 54.34 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - L469275

Drug used in the treatment and prevention of cardiovascular diseases.

REFERENCES

• Lo, R., et al.: Curr. Clin. Pharmacol., 3, 156 (2008)
• Ghali, J., et al.: Cardiol., 111, 147 (2008)