(4R)-6-[2-(4-methoxyphenyl)-1H-1,3-benzodiazol-5-yl]-4-methyl-2,3,4,5-tetrahydropyridazin-3-one

• ChemBase ID: 179719
• Molecular Formular: C19H18N4O2
• Molecular Mass: 334.37182
• Monoisotopic Mass: 334.14297584
• SMILES: n1c([nH]c2c1cc(C1=NNC(=O)[C@@H](C1)C)cc2)c1ccc(cc1)OC
• Canonical SMILES: COc1ccc(cc1)c1nc2c([nH]1)ccc(c2)C1=NNC(=O)[C@@H](C1)C
• InChI: InChI=1S/C19H18N4O2/c1-11-9-16(22-23-19(11)24)13-5-8-15-17(10-13)21-18(20-15)12-3-6-14(25-2)7-4-12/h3-8,10-11H,9H2,1-2H3,(H,20,21)(H,23,24)/t11-/m1/s1
• InChIKey: WTNHQTPNWSUDGN-LLVKDONJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-6-[2-(4-methoxyphenyl)-1H-1,3-benzodiazol-5-yl]-4-methyl-2,3,4,5-tetrahydropyridazin-3-one
• IUPAC Traditional name: (4R)-6-[2-(4-methoxyphenyl)-1H-1,3-benzodiazol-5-yl]-4-methyl-2,3,4,5-tetrahydropyridazin-3-one
• Synonyms: Acordi; Acardi; Pimobendan

Database IDs

• CAS Number: 74150-27-9
• PubChem SID: 164235629
• PubChem CID: 28248390

CALCULATED PROPERTIES

• Acid pKa: 11.165449
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.6280305
• LogD (pH = 7.4): 2.6976209
• Log P: 2.6986573
• Molar Refractivity: 104.6832 cm^3
• Polarizability: 37.838036 Å^3
• Polar Surface Area: 79.37 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Partial phosphodiesterase (type III) inhibitor; Vasodilator

Product Information

• Application(s): Shows positive inotropic and vasodilatory activity; Used in the treatment of congestive heart failure

REFERENCES

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• Verdouw, P.D. et al., Eur. J. Pharmacol., 1986, 126, 121, (pharmacol)
• Duncker, D.J. et al., Br. J. Pharmacol., 1987, 91, 609, (pharmacol)
• Chu, K.-M. et al., J. Chromatogr. Sci., 1992, 30, 171, (hplc, sepn)
• Asakura, M. et al., J. Chromatogr., 1993, 614, 135, (hplc, sepn)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 672
• Fitton, A. et al., Drugs Aging, 1994, 4, 417, (rev)
• Remme, W.J. et al., J. Cardiovasc. Pharmacol., 1994, 24, 730, (pharmacol, human)