Simendan
Basic information
- CAS
131741-08-7- Standard SMILES
CC1CC(=O)NN=C1c1ccc(NN=C(C#N)C#N)cc1- InChIKey
WHXMKTBCFHIYNQ-UHFFFAOYSA-N- Molecular formula
- C14H12N6O
- Average molar mass
- 280.28 g/mol
- Monoisotopic mass
- 280.10725903
Overview
A hydrazone and pyridazine derivative; the levo-form is a phosphodiesterase III inhibitor, calcium-sensitizing agent, and inotropic agent that is used in the treatment of HEART FAILURE.
Names & identifiers
- Preferred name
- Simendan
- IUPAC
- 2-[[4-(4-methyl-6-oxo-4,5-dihydro-1H-pyridazin-3-yl)phenyl]hydrazinylidene]propanedinitrile
- English name
- Simendan
- Molecular formula
- C14H12N6O
- Molecular weight
- 280.28
Names & synonyms
Simendan131741-08-7349552KRHKDTXSID20861357Propanedinitrile, ((4-(1,4,5,6-tetrahydro-4-methyl-6-oxo-3-pyridazinyl)phenyl)hydrazono)-Propanedinitrile, 2-[2-[4-(1,4,5,6-tetrahydro-4-methyl-6-oxo-3-pyridazinyl)phenyl]hydrazinylidene]-((4-(1,4,5,6-tetrahydro-4-methyl-6-oxo-3-pyridazinyl)phenyl)hydrazono)propanedinitrileMesoxalonitrile (+-)-(p-(1,4,5,6-tetrahydro-4-methyl-6-oxo-3-pyridazinyl)phenyl)hydrazonePropanedinitrile, 2-(2-(4-(1,4,5,6-tetrahydro-4-methyl-6-oxo-3-pyridazinyl)phenyl)hydrazinylidene)-simendanumRefChem:183070DTXCID50210096
Show more names
Simendan USP/EP/BPLEVOFLUOROCARBOXYLICACIDLevosimendan Impurity 24rac-Levosimendan (Simendan)2-[[4-(6-keto-4-methyl-4,5-dihydro-1H-pyridazin-3-yl)phenyl]hydrazono]malononitrileR-(-)-4-(1,4,5,6-tetrahydro-4-methyl-6-oxo-3-pyridazinyl)phenyl hydrozono-propanedinitrile
1-cyano-N-(4-(6-hydroxy-4-methyl-4,5-dihydropyridazin-3-yl)phenyl)methanecarbohydrazonoyl cyanideSimendan [INN]Levosimendan Impurity 162-[[4-(4-methyl-6-oxo-4,5-dihydro-1H-pyridazin-3-yl)phenyl]hydrazinylidene]propanedinitrile(4-(4-methyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)phenyl)carbonohydrazonoyl dicyanideUNII-349552KRHK[[4-(1,4,5,6-Tetrahydro-4-methyl-6-oxo-3-pyridazinyl)phenyl]hydrazono]-propanedinitrile[4-(4-Methyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)phenyl]carbonohydrazonoyl dicyanide
Properties
Computed structural properties
- XLogP
- 2.3
- Topological polar surface area
- 113 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 3
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 549
Physicochemical properties
- Melting point
- 238 °C · >238°C (dec.)
- Density
- 1.33 · 1.33±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · Hygroscopic, -20°C Freezer, Under inert atmosphere
- solubility
- DMSO (Slightly), THF (Slightly, Sonicated)
- pka
- 6.12 · 6.12±0.10(Predicted)
- form
- Solid
- color
- Yellow to Dark Yellow
- InChI
- InChI=1S/C14H12N6O/c1-9-6-13(21)19-20-14(9)10-2-4-11(5-3-10)17-18-12(7-15)8-16/h2-5,9,17H,6H2,1H3,(H,19,21)
- InChIKey
- WHXMKTBCFHIYNQ-UHFFFAOYSA-N
- SMILES
- C(#N)/C(=N/NC1=CC=C(C2=NNC(=O)CC2C)C=C1)/C#N
- CAS DataBase Reference
- 131741 · 131741-08-7(CAS DataBase Reference)
- FDA UNII
- 349552 KRHK · 349552KRHK
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
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).
Drugs used to cause dilation of the blood vessels.
Compounds that specifically inhibit PHOSPHODIESTERASE 3.
Applications
UsesSimendan is the racemic mixture of Levosimendan (L378000) which is a positive inotropic agent with vasodilating activity.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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