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Details

Stereochemistry ABSOLUTE
Molecular Formula C14H12N6O
Molecular Weight 280.2847
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEVOSIMENDAN

SMILES

C[C@@H]1CC(=O)NN=C1C2=CC=C(NN=C(C#N)C#N)C=C2

InChI

InChIKey=WHXMKTBCFHIYNQ-SECBINFHSA-N
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)/t9-/m1/s1

HIDE SMILES / InChI

Description

Levosimendan (Simdax) is a novel intravenous agent that exerts inotropic effects through sensitization of myofilaments to calcium and vasodilator effects by binding to cardiac troponin C in a calcium-dependent manner. It also has a vasodilatory effect, by opening adenosine triphosphate (ATP)-sensitive potassium channels in vascular smooth muscle to cause smooth muscle relaxation. Unlike other calcium sensitizing compounds, the binding of levosimendan is highly dependent on the intracellular concentration of calcium, such that calcium sensitivity is enhanced only when the calcium level is elevated. Levosimendan is licensed for the treatment of decompensated heart failure in many countries but not in North America. This drug also passed phase III clinical trials for the prevention of low cardiac output syndrome in pediatric patients after open heart surgery.

CNS Activity

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Troponin C, slow skeletal and cardiac muscles
1
Target ID: P63316
Gene ID: 7134.0
Gene Symbol: TNNC1
Target Organism: Homo sapiens (Human)
Binding Agent
1064
ATP-sensitive inward rectifier potassium channel 11
10
Target ID: Q14654
Gene ID: 3767.0
Gene Symbol: KCNJ11
Target Organism: Homo sapiens (Human)
Opener
34
ATP-sensitive inward rectifier potassium channel 8
9
Target ID: Q15842
Gene ID: 3764.0
Gene Symbol: KCNJ8
Target Organism: Homo sapiens (Human)
Opener
34
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
Simdax

Approved Use

Unknown
Preventing
Phase III
656
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Patents

Patents

JP2001517702A
1
JP2001526205A
1
JP2002512946A
1
JP2003509351A
1
JP2010065060A
1
JP2010083900A
1
JP4493840B2
1
JP4566402B2
1
JP4708648B2
1

Sample Use Guides

In Vivo Use Guide
0.2 micrograms/kg/min is administered intravenously without bolus for 6 hours every two weeks.
Route of Administration: Intravenous
In Vitro Use Guide
Levosimendan down-regulates the expression of the pro-thrombotic and anti-fibrinolytic biomolecules TF and PAI-1 in activated human endothelial cells. Human heart microvascular endothelial cells (HHMEC) and human umbilical vein endothelial cells (HUVEC) were treated with interleukin-1β (IL-1β) (200U/mL) or thrombin (5U/mL) and co-treated with or without levosimendan (0.1-10μM) for 2-24h. In addition, flow experiments were performed. Effects on plasminogen activator inhibitor-1 (PAI-1) and tissue factor (TF) expression and activity were measured by rt-PCR, specific ELISA and flow cytometry.
Name Type Language
LEVOSIMENDAN
INN   MART.   MI   USAN   WHO-DD  
INN   USAN  
Official Name English
(-)-OR-1259
Code English
PROPANEDINITRILE, 2-(2-(4-((4R)-1,4,5,6-TETRAHYDRO-4-METHYL-6-OXO-3-PYRIDAZINYL)PHENYL)HYDRAZINYLIDENE)-
Systematic Name English
LEVOSIMENDAN [USAN]
Common Name English
LEVOSIMENDAN [MART.]
Common Name English
2-(2-(4-((4R)-1,4,5,6-TETRAHYDRO-4-METHYL-6-OXO-3-PYRIDAZINYL)PHENYL)HYDRAZINYLIDENE)PROPANEDINITRILE
Systematic Name English
PROPANEDINITRILE, ((4-(1,4,5,6-TETRAHYDRO-4-METHYL-6-OXO-3-PYRIDAZINYL)PHENYL)HYDRAZONO)-, (R)-
Common Name English
levosimendan [INN]
Common Name English
MESOXALONITRILE (P-((R)-1,4,5,6-TETRAHYDRO-4-METHYL-6-OXO-PYRIDAZINYL)PHENYL)HYDRAZONE
Common Name English
(R)-SIMENDAN
Common Name English
SIMENDAN, (R)-
Common Name English
LEVOSIMENDAN [MI]
Common Name English
SIMDAX
Brand Name English
OR-1259
Code English
(R)-((4-(1,4,5,6-TETRAHYDRO-4-METHYL-6-OXO-3-PYRIDAZINYL)PHENYL)HYDRAZONO) PROPANEDINTRILE
Common Name English
Levosimendan [WHO-DD]
Common Name English
NSC-759644
Code English
Classification Tree Code System Code
WHO-ATC C01CX08
Created by admin on Fri Dec 15 15:44:34 GMT 2023 , Edited by admin on Fri Dec 15 15:44:34 GMT 2023
WHO-VATC QC01CX08
Created by admin on Fri Dec 15 15:44:34 GMT 2023 , Edited by admin on Fri Dec 15 15:44:34 GMT 2023
FDA ORPHAN DRUG 495515
Created by admin on Fri Dec 15 15:44:34 GMT 2023 , Edited by admin on Fri Dec 15 15:44:34 GMT 2023
EU-Orphan Drug EU/3/18/1980
Created by admin on Fri Dec 15 15:44:34 GMT 2023 , Edited by admin on Fri Dec 15 15:44:34 GMT 2023
Code System Code Type Description
DRUG CENTRAL
1576
Created by admin on Fri Dec 15 15:44:34 GMT 2023 , Edited by admin on Fri Dec 15 15:44:34 GMT 2023
PRIMARY
EVMPD
SUB08493MIG
Created by admin on Fri Dec 15 15:44:34 GMT 2023 , Edited by admin on Fri Dec 15 15:44:34 GMT 2023
PRIMARY
USAN
KK-60
Created by admin on Fri Dec 15 15:44:34 GMT 2023 , Edited by admin on Fri Dec 15 15:44:34 GMT 2023
PRIMARY
FDA UNII
C6T4514L4E
Created by admin on Fri Dec 15 15:44:34 GMT 2023 , Edited by admin on Fri Dec 15 15:44:34 GMT 2023
PRIMARY
RXCUI
73107
Created by admin on Fri Dec 15 15:44:34 GMT 2023 , Edited by admin on Fri Dec 15 15:44:34 GMT 2023
PRIMARY RxNorm
EPA CompTox
DTXSID9046445
Created by admin on Fri Dec 15 15:44:34 GMT 2023 , Edited by admin on Fri Dec 15 15:44:34 GMT 2023
PRIMARY
MERCK INDEX
m6795
Created by admin on Fri Dec 15 15:44:34 GMT 2023 , Edited by admin on Fri Dec 15 15:44:34 GMT 2023
PRIMARY Merck Index
DRUG BANK
DB00922
Created by admin on Fri Dec 15 15:44:34 GMT 2023 , Edited by admin on Fri Dec 15 15:44:34 GMT 2023
PRIMARY
PUBCHEM
3033825
Created by admin on Fri Dec 15 15:44:34 GMT 2023 , Edited by admin on Fri Dec 15 15:44:34 GMT 2023
PRIMARY
INN
7020
Created by admin on Fri Dec 15 15:44:34 GMT 2023 , Edited by admin on Fri Dec 15 15:44:34 GMT 2023
PRIMARY
CAS
141505-33-1
Created by admin on Fri Dec 15 15:44:34 GMT 2023 , Edited by admin on Fri Dec 15 15:44:34 GMT 2023
PRIMARY
ChEMBL
CHEMBL2051955
Created by admin on Fri Dec 15 15:44:34 GMT 2023 , Edited by admin on Fri Dec 15 15:44:34 GMT 2023
PRIMARY
SMS_ID
100000092487
Created by admin on Fri Dec 15 15:44:34 GMT 2023 , Edited by admin on Fri Dec 15 15:44:34 GMT 2023
PRIMARY
WIKIPEDIA
LEVOSIMENDAN
Created by admin on Fri Dec 15 15:44:34 GMT 2023 , Edited by admin on Fri Dec 15 15:44:34 GMT 2023
PRIMARY
NCI_THESAURUS
C174653
Created by admin on Fri Dec 15 15:44:34 GMT 2023 , Edited by admin on Fri Dec 15 15:44:34 GMT 2023
PRIMARY
NSC
759644
Created by admin on Fri Dec 15 15:44:34 GMT 2023 , Edited by admin on Fri Dec 15 15:44:34 GMT 2023
PRIMARY
CHEBI
50567
Created by admin on Fri Dec 15 15:44:34 GMT 2023 , Edited by admin on Fri Dec 15 15:44:34 GMT 2023
PRIMARY
ACTIVE MOIETY
Structure of LEVOSIMENDAN
METABOLITE ACTIVE (PARENT)
Structure of OR-1896
NIH
NCATS
PRIVACY ACT
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DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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