141505-33-1 Usage
Description
Levosimendan is a calcium sensitizer that can cause increased cardiac contractility by binding troponin C (EC50 = 9 nM), promotes vasodilation by activating ATP-sensitive potassium channels on vascular smooth muscle cells (EC50 = 0.28 μM), and performs a cardioprotective function by prompting the opening of mitochondrial potassium channels in cardiomyocytes. It also has been reported to inhibit phosphodiesterases 3 and 4 in left ventricular cardiac tissue with IC50 values of 2.5 nM and 25 μM, respectively. Levosimendan is a positive inotropic agent that acts by sensitizing troponin C to Ca2+, prolonging actin-myosin cross-bridge formation, and therefore increasing contractility. This is an energy-independent process and does not increase myocardial oxygen demand. Levosimendan also causes vasodilation by opening ATP-sensitive K+ channels in vascular smooth muscle, reducing preand afterload, and improving myocardial oxygen supply. It may have a role in the management of acute heart failure and postresuscitation myocardial dysfunction.
Uses
Used in Pharmaceutical Industry:
Levosimendan is used as a positive inotropic agent 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. It increases myocardial contractility by selectively binding to the N-terminus of troponin C and by stabilizing the Ca2+-bound conformation of this contractile protein. It also activates ventricular and arterial adenosine triphosphate-regulated potassium channels, which cause vasodilation in vascular smooth muscle and protect the myocardium against infarction.
Used in Anesthetic Applications:
Levosimendan is used as an anesthetic due to its vasodilating activity and its ability to reduce preand afterload, improving myocardial oxygen supply.
Used in Cardiotonic Applications:
Levosimendan is used as a cardiotonic agent, providing positive inotropic effects without prolonging myocardial relaxation or increasing the incidence of malignant arrhythmias. It has been clinically shown to have a lower risk of mortality in patients with heart failure when compared to placebo and dobutamine.
Used in HIV-1 Research:
Levosimendan has been used for screening its anti-human immunodeficiency virus type 1 (HIV-1) property, exploring its potential in the development of new treatments for the virus.
Used in Cancer Research:
Levosimendan has been used for screening its cytotoxic effects in TP53 mutant and wild-type lung adenocarcinoma cell lines, investigating its potential as a therapeutic agent in cancer treatment.
Chemical Properties:
Levosimendan is a yellow crystalline powder.
Brand Name:
Simdax (Orion Pharmaceutica, Finland).
Originator
Orion (Finland)
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.
Check Digit Verification of cas no
The CAS Registry Mumber 141505-33-1 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,4,1,5,0 and 5 respectively; the second part has 2 digits, 3 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 141505-33:
(8*1)+(7*4)+(6*1)+(5*5)+(4*0)+(3*5)+(2*3)+(1*3)=91
91 % 10 = 1
So 141505-33-1 is a valid CAS Registry Number.
InChI:InChI=1/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
141505-33-1Relevant articles and documents
PROCESS FOR PREPARING LEVOSIMENDAN AND INTERMEDIATES FOR USE IN THE PROCESS
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, (2011/02/24)
In an embodiment, the present invention provides a process for preparing (-)-6-(4- aminophenyl)-5-methylpyridazin-3-(2H)-one, which process comprises: a) reacting racemic 6-(4-aminophenyl)-4,5-dihydro-5-methyl-3-(2H)-pyridazinone of formula (Il) with a chiral tartaric acid derivative to obtain a diastereomeric salt of (-)-6-(4- aminophenyl)-4,5-dihydro-5-methyl-3-(2H)-pyridazinone and the chiral tartaric acid derivative; and b) reacting the diastereomeric salt with a base to obtain (-)-6-(4- aminophenyl)-4,5-dihydro-5-methyl-3-(2H)-pyridazinone. The (-)-6-(4-aminophenyl)-4,5- dihydro-5-methyl-3-(2H)-pyridazinone may be used to prepare levosimendan.
