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L5545

Sigma-Aldrich

Levosimendan

≥98% (HPLC)

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
MDL number:
MFCD00867135
UNSPSC Code:
12352202
PubChem Substance ID:
329817628
NACRES:
NA.77

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)

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. 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

Signal Word

Warning

Hazard Statements

H302 + H312 + H332

Hazard Classifications

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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)
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
A Candidate Cell-Selective Anticancer Agent
Probe Reports from the NIH Molecular Libraries Program, 146, 76-85 (2014)
Julia Hasslacher et al.
Critical care (London, England), 15(4), R166-R166 (2011-07-14)
Levosimendan is an extensively investigated inodilator showing also cardioprotective and antiinflammatory effects. The aim of our study was to explore the influence of levosimendan on polymorphonuclear leucocytes (PMN), a main source of reactive oxygen species, in vitro and in patients
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