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Details

Stereochemistry ACHIRAL
Molecular Formula C22H25N3O4
Molecular Weight 395.4516
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VESNARINONE

SMILES

COC1=C(OC)C=C(C=C1)C(=O)N2CCN(CC2)C3=CC=C4NC(=O)CCC4=C3

InChI

InChIKey=ZVNYJIZDIRKMBF-UHFFFAOYSA-N
InChI=1S/C22H25N3O4/c1-28-19-7-3-16(14-20(19)29-2)22(27)25-11-9-24(10-12-25)17-5-6-18-15(13-17)4-8-21(26)23-18/h3,5-7,13-14H,4,8-12H2,1-2H3,(H,23,26)

HIDE SMILES / InChI

Molecular Formula C22H25N3O4
Molecular Weight 395.4516
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Vesnarinone is a new and novel inotropic drug that has unique and complex mechanisms of action. It inhibits phosphodiesterase, thereby leading to increased intracellular calcium, and also affects numerous myocardial ion channels, resulting in the prolongation of the opening time of sodium channels and the decrease in the delayed outward and inward rectifying potassium current. In vitro, it has also demonstrated significant effects on cytokine production, which may account for some of its observed clinical benefits. Hemodynamic studies in humans with congestive heart failure reveal that vesnarinone can improve ventricular function. Placebo-controlled studies in large numbers of patients with heart failure have suggested a morbidity and mortality benefit with a 60 mg daily dose. In Japan, vesnarinone was approved in June 1990 and first marketed in September 1990.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
6.2 µM [IC50]
1.096 µM [IC50]
10.4 µM [IC50]
13.2 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Arkin-Z
Primary
Unknown
Primary
Unknown

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
60 mg of vesnarinone per day resulted in lower morbidity and mortality and improved the quality of life of patients with congestive heart failure
Route of Administration: Oral
In Vitro Use Guide
Vesnarinone (0–300 uM) inhibits tumor necrosis factor (TNF)a-induced expression of nuclear factor kB target genes in 293T cells
Substance Class Chemical
Record UNII
5COW40EV8M
Record Status Validated (UNII)
Record Version