Vesnarinone (HCID 5663)

Names & identifiers

Preferred name: Vesnarinone
IUPAC: 6-[4-(3,4-dimethoxybenzoyl)piperazin-1-yl]-3,4-dihydro-1H-quinolin-2-one
English name: VESNARINONE
Molecular formula: C22H25N3O4
Molecular weight: 395.45

Names & synonyms

vesnarinone81840-15-5OPC-8212Arkin-ZVesnarinonaArkinArkin ZVesnarinonumDRG-02105COW40EV8MDTXSID802314111-(3,4-Dimethoxybenzoyl)-4-(1,2,3,4-tetrahydro-2-oxo-6-quinolinyl)piperazine

Show more names

OPC 8212CS-21390PC-8212PiteranometozineVesnarinone(OPC8212)VESNARINONE USP/EP/BPOPC8212OPC 8212Vesnarinone, 10 mM in DMSO

pieranometazine6-(4-((3,4-dimethoxyphenyl)carbonyl)piperazin-1-yl)-1,2,3,4-tetrahydroquinolin-2-one6-{4-[(3,4-dimethoxyphenyl)carbonyl]piperazin-1-yl}-1,2,3,4-tetrahydroquinolin-2-oneRefChem:9018293,4-dihydro-6-(4-(3,4-dimethoxybenzoyl)-1-piperazinyl)-2-1H-quinolinoneDTXCID801539023,4-Dihydro-6-(4-(3,4-dimethoxybenzoyl)-1-pip-erazinyl)-2(1H)-quinolinonePiperazine, 1-(3,4-dimethoxybenzoyl)-4-(1,2,3,4-tetrahydr-o-2-oxo-6-quinolinyl)

Database identifiers

CAS: 81840-15-5
PubChem CID: 5663
DTXSID: DTXSID80231411
ChEMBL: CHEMBL17423
ChEBI: CHEBI:31237
UNII: 5COW40EV8M
Nikkaji: J22.952K

Properties

Computed structural properties

XLogP: 2.1
Topological polar surface area: 71.1 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 5
Rotatable bonds: 4
Heavy atoms: 29
Formal charge: 0
Complexity: 593

Physicochemical properties

Melting point: 238.1 · 238.1-239.5° (Tominaga); mp 238.1-239.8° (Shimizu)
Boiling point: 519.41 °C · 519.41°C (rough estimate)
Density: 1.2414 · 1.2414 (rough estimate)
refractive index: 1.65 · 1.6500 (estimate)
storage temp.: -20 °C · Store at -20°C
solubility: 9.84 · 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 · 2.86(at 25℃)
color: White to off-white
FDA UNII: 5 COW40EV8M · 5COW40EV8M
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H315-H319-H335
Precautionary statements: 261 · P261-P305+P351+P338

Safety & regulation

Safety data

Signal word: Warning
Symbol(GHS): GHS07
Hazard statements: H302-H315-H319-H335
Precautionary statements: P261-P305+P351+P338

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 5 items

Substances that augment, stimulate, activate, potentiate, or modulate the immune response at either the cellular or humoral level. The classical agents (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contain bacterial antigens. Some are endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Their mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy of many biological response modifiers is related to their antigen-specific immunoadjuvanticity.

Substances that inhibit or prevent the proliferation of NEOPLASMS.

Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly.

Agents that have a strengthening effect on the heart or that can increase cardiac output. They may be CARDIAC GLYCOSIDES; SYMPATHOMIMETICS; or other drugs. They are used after MYOCARDIAL INFARCT; CARDIAC SURGICAL PROCEDURES; in SHOCK; or in congestive heart failure (HEART FAILURE).

Compounds which inhibit or antagonize the biosynthesis or actions of phosphodiesterases.

Cellular LocationsMembrane

Applications · 3 items

DescriptionVesnarinone 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.

DescriptionVesnarinone is an inhibitor of phosphodiesterase 3 (PDE3; IC50s = 10.7 and 13.2 μM for PDE3A and PDE3B, respectively). It also inhibits ether-a-go-go-related gene 1 (ERG1) channels (IC50 = 1.1 μM in HEK293T cells expressing human ERG1). Vesnarinone (3-300 μM) increases contractile tension in isolated ventricular muscles of dog, cat, rabbit, and guinea pig in a dose-dependent manner. Oral and i.v. administration of vesnarinone increases right ventricular pressure with no effect on heart rate in dog models of tricuspid insufficiency- and pulmonary stenosis-induced congestive heart failure. It also increases contractility and coronary flow while decreasing heart rate in a guinea pig model of aortic stenosis-induced congestive heart failure. Formulations containing vesnarinone have been used for the treatment of congestive heart failure.

UsesCardiotonic.