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L5545

Levosimendan

Name: Levosimendan
Brand: SIGMA

≥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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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

Assay:

≥98% (HPLC)

Form:

powder

Quality level:

100

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Properties

Product Name

Levosimendan, ≥98% (HPLC)

Quality Level

100

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

SMILES string

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

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

InChI key

WHXMKTBCFHIYNQ-SECBINFHSA-N

Gene Information

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

Description

Application

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

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.

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

GHS07

signalword

Warning

hcodes

H302 + H312 + H332

pcodes

P261 - P264 - P280 - P301 + P312 - P302 + P352 + P312 - P304 + P340 + P312

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

0000472405

0000449431

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Reversible Covalent Reaction of Levosimendan with Cardiac Troponin C in Vitro and in Situ.

Brittney A Klein et al.

Biochemistry, 57(15), 2256-2265 (2018-03-21)

The development of calcium sensitizers for the treatment of systolic heart failure presents difficulties, including judging the optimal efficacy and the specificity to target cardiac muscle. The thin filament is an attractive target because cardiac troponin C (cTnC) is the

Synergistic Effects of Moderate Therapeutic Hypothermia and Levosimendan on Cardiac Function and Survival After Asphyxia-Induced Cardiac Arrest in Rats.

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

Screening of an FDA-approved compound library identifies levosimendan as a novel anti-HIV-1 agent that inhibits viral transcription

Hayashi T, et al.

Antiviral research, 146, 76-85 (2017)

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Global Trade Item Number

SKU	GTIN
L5545-10MG	04061833958261
L5545-50MG	04061835557585