Vesnarinone
OPC 8212 · Arkin · CS-2139 · 0PC-8212 · VESNARINONE · Piteranometozine · Vesnarinone(OPC8212) · VESNARINONE USP/EP/BP
Identifiers & Physical Properties
| CAS No. | 81840-15-5 |
|---|---|
| Molecular formula | C22H25N3O4 |
| Average molar mass | 395.5 g/mol |
| Monoisotopic mass | 395.18450629 g/mol |
| SMILES | COc1ccc(C(=O)N2CCN(c3ccc4c(c3)CCC(=O)N4)CC2)cc1OC |
| InChIKey | ZVNYJIZDIRKMBF-UHFFFAOYSA-N |
| PubChem CID | 5663 |
| ChEMBL | CHEMBL17423 |
| ChEBI | CHEBI:31237 |
| DTXSID | DTXSID80231411 |
Chemical & Physical Properties
| XLogP | 2.1 |
|---|---|
| Topological polar surface area | 71.1 |
| Hydrogen bond donors | 1 |
| Hydrogen bond acceptors | 5 |
| Rotatable bonds | 4 |
| Heavy atoms | 29 |
| Formal charge | 0 |
| Complexity | 593 |
| 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 conditions | 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) |
| Physical state | A crystalline solid |
| pKa (acidity coefficient) | 2.86(at 25℃) |
| Color | White to off-white |
| FDA UNII | 5COW40EV8M |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H302-H315-H319-H335 |
| GHS precautionary statements | P261-P305+P351+P338 |
Safety & Regulations
| Signal word | Warning |
|---|---|
| GHS pictogram | GHS07 |
| GHS hazard statements | H302-H315-H319-H335 |
| GHS precautionary statements | P261-P305+P351+P338 |
Applications & Uses
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.
Description
Vesnarinone 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.
Uses
Cardiotonic.