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81840-15-5

81840-15-5 Structure

81840-15-5 Structure
IdentificationBack Directory
[Name]

VESNARINONE
[CAS]

81840-15-5
[Synonyms]

Arkin
CS-2139
OPC 8212
0PC-8212
VESNARINONE
Piteranometozine
Vesnarinone(OPC8212)
VESNARINONE USP/EP/BP
OPC8212;OPC 8212;OPC-8212
3,4-Dihydro-6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]-2(1H)-quinolinone
6-[4-(3,4-Dimethoxybenzoyl)-1-piperazinyl]-3,4-dihydro-2(1H)-quinolinone
6-[4-(3,4-dimethoxybenzoyl)piperazin-1-yl]-3,4-dihydro-1H-quinolin-2-one
2(1H)-Quinolinone, 6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]-3,4-dihydro-
[Molecular Formula]

C22H25N3O4
[MDL Number]

MFCD00867124
[MOL File]

81840-15-5.mol
[Molecular Weight]

395.45
Chemical PropertiesBack Directory
[Melting point ]

238.1-239.5° (Tominaga); mp 238.1-239.8° (Shimizu)
[Boiling point ]

519.41°C (rough estimate)
[density ]

1.2414 (rough estimate)
[refractive index ]

1.6500 (estimate)
[storage temp. ]

Store at -20°C
[solubility ]

DMSO:9.84(Max Conc. mg/mL);24.88(Max Conc. mM)
DMSO:PBS (pH 7.2) (1:1):0.5(Max Conc. mg/mL);1.26(Max Conc. mM)
DMF:3.0(Max Conc. mg/mL);7.59(Max Conc. mM)
[form ]

A crystalline solid
[pka]

2.86(at 25℃)
[color ]

White to off-white
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Piperazine-->Formamide-->4-Methylanisole-->3,4-DIHYDROQUINOLIN-2(1H)-ONE
Hazard InformationBack Directory
[Description]

Vesnarinone is a new orally-active positive inotropic agent introduced for the treatment of congestive heart failure. It exerts a positive inotropic effect on the heart and has a peripheral vasodilatory effect. Vesnarinone is claimed not to affect heart rate or aggravate arrhythmia.
[Chemical Properties]

Obtained as colorless granular crystals from ethanol-chloroform, melting point 238.1-239.5°C; also available as an odorless, pale yellow crystalline powder, melting point 238.1-239.8°C. UV absorption maximum (methanol, ethanol, chloroform): 271 nm (ε 25100, 25200, 23000, C = 10 μg/ml). Solubility (% at 25°C): glacial acetic acid 18.68, chloroform 14.19, benzyl alcohol 5.913, N-methyl-2-pyrrolidinone 3.407, dimethyl sulfoxide 2.509, sulfolane 1.229, dimethylformamide 1.179, dioxane 0.1653, methanol 0.1151, acetone 0.06389, ethanol 0.04005, water 0.002086. pKa 2.86.
[Originator]

Otsuka (Japan)
[Uses]

Cardiotonic.
[Definition]

ChEBI: Arkin (TN) is an organic molecular entity.
[Brand name]

Arkin (Otsuka America);Arkin-Z.
[References]

[1] MOHSEN NIKPOUR . Design, synthesis and biological evaluation of 6-(benzyloxy)-4-methylquinolin-2(1H)-one derivatives as PDE3 inhibitors[J]. Bioorganic & Medicinal Chemistry, 2010, 18 2: Pages 855-862. DOI: 10.1016/j.bmc.2009.11.044
[2] Y KATAYAMA. Inhibitory effects of vesnarinone on cloned cardiac delayed rectifier K(+) channels expressed in a mammalian cell line.[J]. Journal of Pharmacology and Experimental Therapeutics, 2000, 294 1: 339-346.
[3] FELDMAN A M. Pharmacologic Properties and Clinical Evaluation of the New Inotropic Agent OPC-8212 (Vesnarinone)[J]. Cardiovascular Therapeutics, 1993, 11 1: 1-11. DOI: 10.1111/j.1527-3466.1993.tb00264.x
[4] MD S E R, FACC  James B Y M  Richard Holubkov PhD, FACC  Jay N C M  B G White PhD, et al. Estrogen is associated with improved survival in aging women with congestive heart failure: analysis of the vesnarinone studies[J]. Journal of the American College of Cardiology, 2000, 36 2: Pages 529-533. DOI: 10.1016/s0735-1097(00)00738-5
Spectrum DetailBack Directory
[Spectrum Detail]

VESNARINONE(81840-15-5)1HNMR
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