Levosimendan

HCID 3033825CAS 141505-33-1

Grundinformationen

Standard-SMILES
C[C@@H]1CC(=O)NN=C1c1ccc(NN=C(C#N)C#N)cc1
InChIKey
WHXMKTBCFHIYNQ-SECBINFHSA-N
Summenformel
C14H12N6O
Durchschnittliche Molmasse
280,28 g/mol
Monoisotopische Masse
280,107259

Überblick

Levosimendan is a nitrile, a pyridazinone and a hydrazone. It has a role as a vasodilator agent, an anti-arrhythmia drug, a cardiotonic drug and an EC 3.1.4.17 (3',5'-cyclic-nucleotide phosphodiesterase) inhibitor.

Namen und Bezeichner

Bevorzugter Name
Levosimendan
IUPAC
2-[[4-[(4R)-4-methyl-6-oxo-4,5-dihydro-1H-pyridazin-3-yl]phenyl]hydrazinylidene]propanedinitrile
Englischer Name
Levosimendan
Summenformel
C14H12N6O
Molmasse
280.28

Namen und Synonyme

LEVOSIMENDAN141505-33-1Simdax(R)-Simendanlevosimendanum(-)-OR-1259Simendan, (r)-OR-1259OR1259DTXSID9046445NSC-759644CHEBI:50567
Weitere Namen anzeigen
SimdaL-Simendan13C3]-LevosimendanLevosimendanC14H12N60Levosimendan USP/EP/BPLevosimendan - Bio-X ?
C6T4514L4EDTXCID70264451-cyano-N-{4-[(4R)-4-methyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl]phenyl}methanecarbohydrazonoyl cyanide1-cyano-N-(4-((4R)-4-methyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)phenyl)methanecarbohydrazonoyl cyanideRefChem:799036C01CX08663-528-6Levosimedan

Datenbank-Bezeichner

CAS
141505-33-1
PubChem CID
3033825
DTXSID
DTXSID9046445
ChEMBL
CHEMBL2051955
ChEBI
CHEBI:50567
UNII
C6T4514L4E
EC Number
663-528-6
Nikkaji
J550.713H

Eigenschaften

Berechnete Struktureigenschaften

XLogP
2,3
Polarare Oberfläche (TPSA)
113 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
6
Frei drehbare Bindungen
3
Schwere Atome
21

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15
Solubility8.81e-02 g/L
Physical DescriptionSolid

Physikochemische Eigenschaften

Schmelzpunkt
216 · 216-219°C (dec.)
Dichte
1.33 · 1.33±0.1 g/cm3(Predicted)
storage temp.
room temp
Löslichkeit
20 mg/mL · DMSO: ≥20mg/mL
Aggregatzustand
powder
pka
6.3 · 6.3(at 25℃)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Warning

H302 (95.3%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 43 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 4 (95.3%)

Sicherheitsdaten

wgk
3
hs_code
2933.99.7500
RTECS-Nr.
TY1570210
risk_code
20/21/22
Toxizität
LD50 in male, female mice, male rats (mg/kg): 156, 152, 103 orally; 32, 50, 57 i.v. (Pagel)
hazard_code
Xn

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

C - Cardiovascular system

QC - Cardiovascular system

Protein Binding98% bound to plasma protein.
Pharmacodynamics · 1 Eintrag

Levosimendan is a new Ca<sup>2+</sup>-sensitizing inotropic agent. Ca<sup>2+</sup> sensitizers represent a new class of inotropic agents, which overcome the disadvantages associated with currently available inotropic agents in as they are not associated with an increased risk of arrhythmias, cell injury and death due to Ca<sup>2+</sup> overload in myocardial cells; they do not increase the activation energy; and they have the potential to reverse contractile dysfunction under pathophysiologic conditions, such as acidosis or myocardial stunning. Levosimendan has not been approved for use in the U.S. or Canada.

Mechanism of Action · 1 Eintrag

Levosimendan appears to increase myofilament calcium sensitivity by binding to cardiac troponin C in a calcium-dependent manner. This stabilizes the calcium-induced conformational change of troponin C, thereby (1) changing actin-myosin cross-bridge kinetics apparently without increasing the cycling rate of the cross-bridges or myocardial ATP consumption, (2) increasing the effects of calcium on cardiac myofilaments during systole and (3) improving contraction at low energy cost (inotropic effect). Calcium concentration and, therefore, sensitization decline during diastole, allowing normal or improved diastolic relaxation. Levosimendan also leads to vasodilation through the opening of ATP-sensitive potassium channels. By these inotropic and vasodilatory actions, levosimendan increases cardiac output without increasing myocardial oxygen demand. Levosimendan also has a selective phosphodiesterase (PDE)-III inhibitory action that may contribute to the inotropic effect of this compound under certain experimental conditions. It has been reported that levosimendan may act preferentially as a Ca<sup>2+</sup> sensitizer at lower concentrations, whereas at higher concentrations its action as a PDE-III inhibitor becomes more prominent in experimental animals and humans.

Biological Half-LifeEliminination half-life is approximately 1 hour.
Metabolism/MetabolitesComplete metabolism, with some active metabolites (OR-1855 and OR-1896) possibly extending the drug's haemodynamic effects.
Anwendungen · 2 Einträge

BeschreibungLevosimendan was introduced in Sweden as an i.v. infusion for the treatment of acute heart failure or refractory symptoms of chronic heart failure in cases where conventional treatment (e.g., diuretic or ACE inhibitor) is not sufficient. Levosimendan is the (R)- enantiomer of simendan that belongs to the same class as pimobendan (Boehringer Ingelheim).

VerwendenLevosimendan is a positive inotropic agent that acts by sensitising troponin C to Ca2+, prolonging actin-myosin cross-bridge formation and therefore increasing contractility. This is an energy-independent process and therefore does not increase myocardial oxygen demand. Levosimendan also causes vasodilatation by opening ATP-sensitive K+ channels in vascular smooth muscle, reducing pre- and afterload and improving myocardial oxygen supply. It may have a role in the management of acute heart failure and postresuscitation myocardial dysfunction.

Anbieter50 Anbieter

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]
济南百隆化学有限公司[email protected] · [email protected]
广州隽沐生物科技股份有限公司020-36607679; 13502246435 · [email protected]
湖北金梭生物科技有限公司00123456789 · [email protected]

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