CAS 141505-33-1|(-)-OR-1259|R)-((4-(1,4,5,6-Tetrahydro-4-methyl-6-oxo-3-pyridazinyl)phenyl)hydrazono) propanedintrile|1-cyano-N-{4-[(4R)-4-methyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl]phenyl}methan...

基本信息

化学结构

分子式

C₁₄H₁₂N₆O

分子量

280.28468

精确质量

280.10725903

电荷

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)/t9-/m1/s1

InChIKey

WHXMKTBCFHIYNQ-SECBINFHSA-N

Canonic Smiles

N#CC(=NNc1ccc(cc1)C1=NNC(=O)C[C@H]1C)C#N

Isomeric Smiles

O=C1NN=C([C@@H](C1)C)c1ccc(NN=C(C#N)C#N)cc1

计算属性

JChem

Acid pKa

10.534338

质子受体

质子供体

LogD (pH = 5.5)

2.0628319

LogD (pH = 7.4)

2.159906

Log P

2.1616182

摩尔折射率

77.6308

极化性

27.841526

极化表面积

113.43

可自由旋转的化学键

里宾斯基五规则

true

ALOGPS 2.1

Log P

2.69

LOG S

-3.5

溶解度

8.81e-02 g/l

数据来源

学术数据

产品目录

数据来源

名称和标识

IUPAC标准名

1-cyano-N-{4-[(4R)-4-methyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl]phenyl}methanecarbohydrazonoyl cyanide

IUPAC传统名

levosimendan

别名

Levosimendan(-)-OR-12592-[2-[4-[(4R)-1,4,5,6-Tetrahydro-4-methyl-6-oxo-3-pyridazinyl]phenyl]hydrazinylidene]-propanedinitrileR)-((4-(1,4,5,6-Tetrahydro-4-methyl-6-oxo-3-pyridazinyl)phenyl)hydrazono) propanedintrile(R)-SimendanOR 1259SimdaxOR-1259Levosimendan[[4-[(4R)-1,4,5,6-Terahydro-4-methyl-6-oxo-3-pyridazinyl]phenyl]hydrazono]propanedinitrileLevosimedan

商标名

SimdaxSimendan

名称和标识

数据登录号

PubChem SID

CAS号

PubChem CID

MDL号

数据登录号

化合物性质

产品相关信息

Empirical Formula (Hill Notation)

C14H12N6O

纯度

≥98% (HPLC)

质检报告

下载链接

化合物性质

分子相关蛋白质

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分子图谱

暂无数据

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描述信息

DrugBank

DB00922

Drug Groups

approved; investigational

Description

Levosimendan is a calcium sensitiser used in the management of acutely decompensated congestive heart failure. It increases the sensitivity of the heart to calcium, thus increasing cardiac contractility without a rise in intracellular calcium. Levosimendan exerts its effect by increasing calcium sensitivity of myocytes 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.

Indication

For short term treatment of acutely decompensated severe chronic heart failure (CHF). Also being investigated for use/treatment in heart disease.

Pharmacology

Levosimendan is a new Ca²⁺-sensitizing inotropic agent. Ca²⁺ 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 Ca²⁺ 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.

Affected Organisms

Humans and other mammals

Biotransformation

Complete metabolism, with some active metabolites (OR-1855 and OR-1896) possibly extending the drug's haemodynamic effects.

Absorption

The bioavailability of oral levosimendan is 85 ± 6% in healthy volunteers and 84 ± 4% in patients.

Half Life

Eliminination half-life is approximately 1 hour.

Protein Binding

98% bound to plasma protein.

References

• [Link]

• Mebazaa A, Nieminen MS, Packer M, Cohen-Solal A, Kleber FX, Pocock SJ, Thakkar R, Padley RJ, Poder P, Kivikko M: Levosimendan vs dobutamine for patients with acute decompensated heart failure: the SURVIVE Randomized Trial. JAMA. 2007 May 2;297(17):1883-91. [Pubmed]

• Kasikcioglu HA, Cam N: A review of levosimendan in the treatment of heart failure. Vasc Health Risk Manag. 2006;2(4):389-400. [Pubmed]

External Links

• [Wikipedia]

描述信息

参考文献

PubChem文献

数据源提供

• Link

• Kasikcioglu HA, Cam N: A review of levosimendan in the treatment of heart failure. Vasc Health Risk Manag. 2006;2(4):389-400. Pubmed

• Sandell, E.-P., et al.: J. Cardiovasc. Pharmacol., 26, S57 (1995)

• Pagel, P.S., et al.: Cardiovasc. Drug Rev., 14, 286 (1995)

参考文献