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Merck

L5545

Levosimendan

≥98% (HPLC), calcium sensitizer, powder

Synonym(s):

(-)-OR-1259, (R)-Simendan, 2-[2-[4-[(4R)-1,4,5,6-Tetrahydro-4-methyl-6-oxo-3-pyridazinyl]phenyl]hydrazinylidene]-propanedinitrile, OR 1259, R)-((4-(1,4,5,6-Tetrahydro-4-methyl-6-oxo-3-pyridazinyl)phenyl)hydrazono) propanedintrile

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10 MG

CZK 2,110.00

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About This Item

Empirical Formula (Hill Notation):
C14H12N6O
CAS Number:
141505-33-1
Molecular Weight:
280.28
UNSPSC Code:
12352202
PubChem Substance ID:
329817628
NACRES:
NA.77
MDL number:
MFCD00867135

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Product Name

Levosimendan, ≥98% (HPLC)

SMILES string

C[C@@H]1CC(=O)NN=C1c2ccc(N\N=C(\C#N)C#N)cc2

InChI key

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

assay

≥98% (HPLC)

form

powder

optical activity

[α]/D -500 to -650°, c = 0.5 in THF

color

yellow

solubility

DMSO: ≥20 mg/mL

storage temp.

room temp

Quality Level

100

Gene Information

human ... PDE3A(5139), PDE3B(5140), TNNC1(7134), TNNI3(7137), TNNT2(7139)

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This Item
SML1179SML1563SML2208
Levosimendan ≥98% (HPLC)

Sigma-Aldrich

L5545

Levosimendan

WWL113 ≥98% (HPLC)

Sigma-Aldrich

SML1179

WWL113

BAY-678 ≥98% (HPLC)

Sigma-Aldrich

SML1563

BAY-678

BRD6989 ≥98% (HPLC)

Sigma-Aldrich

SML2208

BRD6989

assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

form

powder

form

powder

form

powder

form

powder

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

-

storage temp.

room temp

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

solubility

DMSO: ≥20 mg/mL

solubility

DMSO: 10 mg/mL, clear

solubility

DMSO: 20 mg/mL, clear

solubility

DMSO: 2 mg/mL, clear

color

yellow

color

white to beige

color

white to light brown

color

white to beige

Application

Levosimendan has been used for screening its anti-human immunodeficiency virus type 1 (HIV-1) property.[1] It has also been used for screening its cytotoxic effects in TP53 mutant and wild-type lung adenocarcinoma cell lines[2]

Biochem/physiol Actions

Levosimendan has a potential to inhibit both acute human immunodeficiency virus type 1 (HIV-1) replication and the reactivation of latent HIV-1 proviruses. Therefore, it is considered to be a promising anti-HIV-1 agent.[1]
Levosimendan is a calcium sensitiser.
Levosimendan is a calcium sensitiser. The compound increases the sensitivity of the heart to calcium, thus increasing cardiac contractility without a rise in intracellular calcium. Levosimendan binds to cardiac troponin C in a calcium-dependent manner and stabilizes troponin C. This is followed by actin-myosin cross-bridges, without increasing myocardial consumption of ATP. Additionally the compound acts as vasodilator by opening an ATP-sensitive potassium channels. Levosimendan is a drug used for treatment of congestive heart failure. Also it can be used to treat calcium channel blocker overdose.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000523222
0000523222
0000472405
0000472405
0000449431

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Claes-Håkan Bergh et al.
European journal of heart failure, 12(4), 404-410 (2010-03-26)
The aim of this study is to compare the effects of a 24 h intravenous infusion of levosimendan and a 48 h infusion of dobutamine on invasive haemodynamics in patients with acutely decompensated chronic NYHA class III-IV heart failure. All
Matti Adam et al.
Scientific reports, 5, 9704-9704 (2015-04-14)
Treatment of decompensated heart failure often includes administration of levosimendan. Myeloperoxidase (MPO) is released during polymorphonuclear neutrophil (PMN) degranulation, and mediates dysregulation of vascular tone in heart failure. We evaluated the effects of levosimendan-treatment on MPO in patients with acute
Saraswati Kache et al.
Pediatric research, 88(5), 705-716 (2020-07-08)
Fewer children than adults have been affected by the COVID-19 pandemic, and the clinical manifestations are distinct from those of adults. Some children particularly those with acute or chronic co-morbidities are likely to develop critical illness. Recently, a multisystem inflammatory
Malin Johansson et al.
Journal of cardiothoracic and vascular anesthesia, 28(4), 960-965 (2013-12-10)
The aim of the present study was to evaluate acute kidney injury (AKI) with cystatin C following transcatheter aortic valve implantation (TAVI) and to assess the impact of postoperative AKI on outcome and late renal function. A prospective study. Single
Chih-Hung Wang et al.
Journal of the American Heart Association, 9(12), e016139-e016139 (2020-06-02)
Background This study investigated whether levosimendan, an inotropic calcium sensitizer, when combined with moderate therapeutic hypothermia, may exert synergistic benefits on post-cardiac arrest myocardial dysfunction and improve outcomes. Methods and Results After 9.5-minute asphyxia-induced cardiac arrest and resuscitation, 48 rats
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