Title: Vesnarinone
CAS Registry Number: 81840-15-5
CAS Name: 1-(3,4-Dimethoxybenzoyl)-4-(1,2,3,4-tetrahydro-2-oxo-6-quinolinyl)piperazine
Additional Names: 3,4-dihydro-6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]-2(1H)-quinolinone; 6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril; 1-(1,2,3,4-tetrahydro-2-oxo-6-quinolyl)-4-veratroylpiperazine; piteranometozine
Manufacturers' Codes: OPC-8212
Trademarks: Arkin (Otsuka)
Molecular Formula: C22H25N3O4
Molecular Weight: 395.45
Percent Composition: C 66.82%, H 6.37%, N 10.63%, O 16.18%
Literature References: Positive inotropic agent. Prepn: Y. H. Yang et al., BE 890942; M. Tominaga et al., US 4415572 (1982, 1983 both to Otsuka); M. Tominaga et al., Chem. Pharm. Bull. 32, 2100 (1984). Physicochemical properties: T. Shimizu et al., Arzneim.-Forsch. 34, 334 (1984). Series of articles on mechanism of action and pharmacology: ibid. 342-402. Effects on canine arrhythmias: K. Hashimoto, H. Mitsuhashi, Br. J. Pharmacol. 88, 915 (1986). Metabolism: G. Miyamoto et al., Xenobiotica 18, 1143 (1988). Clinical pharmacokinetics: A. Ohnishi, T. Ishizaki, J. Clin. Pharmacol. 28, 719 (1988). HPLC determn in plasma and urine: G. Miyamoto et al., J. Chromatogr. 338, 450 (1985). Clinical evaluations in congestive heart failure: H. Asanoi et al., J. Am. Coll. Cardiol. 9, 865 (1987); A. M. Feldman et al., Am. Heart J. 116, 771 (1988).
Properties: Colorless granules from ethanol-chloroform, mp 238.1-239.5° (Tominaga); also reported as odorless, tasteless, pale yellow crystalline powder, mp 238.1-239.8° (Shimizu). uv max (methanol, ethanol, chloroform): 271 nm (e = 2.51 ´ 104, 2.52 ´ 104, 2.30 ´ 104, c = 10 mg/ml). % solubility (25°): glacial acetic acid 18.68; chloroform 14.19; benzyl alcohol 5.913; N-methyl-2-pyrrolidone 3.407; DMSO 2.509; 60% sulfolane 1.229; DMF 1.179; dioxane 0.1653; methanol 0.1151; acetone 0.06389; ethanol 0.04005; water 0.002086. pKa 2.86.
Melting point: mp 238.1-239.5° (Tominaga); mp 238.1-239.8° (Shimizu)
pKa: pKa 2.86
Absorption maximum: uv max (methanol, ethanol, chloroform): 271 nm (e = 2.51 ´ 104, 2.52 ´ 104, 2.30 ´ 104, c = 10 mg/ml)
Therap-Cat: Cardiotonic.
Keywords: Cardiotonic. |