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Levosimendan

CAS# 141505-33-1

Levosimendan

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Chemical structure

Levosimendan

3D structure

Chemical Properties of Levosimendan

Cas No. 141505-33-1 SDF Download SDF
PubChem ID 3033825 Appearance Powder
Formula C14H12N6O M.Wt 280.28
Type of Compound N/A Storage Desiccate at -20°C
Synonyms OR1259
Solubility DMSO : ≥ 50 mg/mL (178.39 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name 2-[[4-[(4R)-4-methyl-6-oxo-4,5-dihydro-1H-pyridazin-3-yl]phenyl]hydrazinylidene]propanedinitrile
SMILES CC1CC(=O)NN=C1C2=CC=C(C=C2)NN=C(C#N)C#N
Standard InChIKey WHXMKTBCFHIYNQ-SECBINFHSA-N
Standard 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
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Levosimendan

DescriptionLevosimendan(OR1259) is a calcium sensitiser used in the management of acutely decompensated congestive heart failure. Target: Others Levosimendan is a calcium sensitiser used in the management of acutely decompensated congestive heart failure. Levosimendan is an inodilator indicated for the short-term treatment of acutely decompensated severe chronic heart failure, and in situations where conventional therapy is not considered adequate. Levosimendan has shown preliminary positive effects in a range of conditions requiring inotropic support, including right ventricular failure, cardiogenic shock, septic shock, and Takotsubo cardiomyopathy [1]. The cardiovascular effects of levosimendan are exerted via more than an isolated drug-receptor interaction, and involve favorable energetic and neurohormonal changes that are unique in comparison to other types of inodilators [2]. Levosimendan might reduce mortality in cardiac surgery and cardiology settings of adult patients [3].

References:
[1]. Nieminen, M.S., et al., Levosimendan: current data, clinical use and future development. Heart Lung Vessel, 2013. 5(4): p. 227-245. [2]. Papp, Z., et al., Levosimendan: molecular mechanisms and clinical implications: consensus of experts on the mechanisms of action of levosimendan. Int J Cardiol, 2012. 159(2): p. 82-7. [3]. Landoni, G., et al., Effects of levosimendan on mortality and hospitalization. A meta-analysis of randomized controlled studies. Crit Care Med, 2012. 40(2): p. 634-46.

Levosimendan Dilution Calculator

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Preparing Stock Solutions of Levosimendan

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.5679 mL 17.8393 mL 35.6786 mL 71.3572 mL 89.1965 mL
5 mM 0.7136 mL 3.5679 mL 7.1357 mL 14.2714 mL 17.8393 mL
10 mM 0.3568 mL 1.7839 mL 3.5679 mL 7.1357 mL 8.9197 mL
50 mM 0.0714 mL 0.3568 mL 0.7136 mL 1.4271 mL 1.7839 mL
100 mM 0.0357 mL 0.1784 mL 0.3568 mL 0.7136 mL 0.892 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Levosimendan

Levosimendan is a calcium sensitizer acting through calcium-dependent binding to cardiac troponin C (cTnC), provides treatment for heart failure. Phase 4.

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References on Levosimendan

Levosimendan in Patients with Left Ventricular Dysfunction Undergoing Cardiac Surgery.[Pubmed:28316276]

N Engl J Med. 2017 May 25;376(21):2032-2042.

BACKGROUND: Levosimendan is an inotropic agent that has been shown in small studies to prevent or treat the low cardiac output syndrome after cardiac surgery. METHODS: In a multicenter, randomized, placebo-controlled, phase 3 trial, we evaluated the efficacy and safety of Levosimendan in patients with a left ventricular ejection fraction of 35% or less who were undergoing cardiac surgery with the use of cardiopulmonary bypass. Patients were randomly assigned to receive either intravenous Levosimendan (at a dose of 0.2 mug per kilogram of body weight per minute for 1 hour, followed by a dose of 0.1 mug per kilogram per minute for 23 hours) or placebo, with the infusion started before surgery. The two primary end points were a four-component composite of death through day 30, renal-replacement therapy through day 30, perioperative myocardial infarction through day 5, or use of a mechanical cardiac assist device through day 5; and a two-component composite of death through day 30 or use of a mechanical cardiac assist device through day 5. RESULTS: A total of 882 patients underwent randomization, 849 of whom received Levosimendan or placebo and were included in the modified intention-to-treat population. The four-component primary end point occurred in 105 of 428 patients (24.5%) assigned to receive Levosimendan and in 103 of 421 (24.5%) assigned to receive placebo (adjusted odds ratio, 1.00; 99% confidence interval [CI], 0.66 to 1.54; P=0.98). The two-component primary end point occurred in 56 patients (13.1%) assigned to receive Levosimendan and in 48 (11.4%) assigned to receive placebo (adjusted odds ratio, 1.18; 96% CI, 0.76 to 1.82; P=0.45). The rate of adverse events did not differ significantly between the two groups. CONCLUSIONS: Prophylactic Levosimendan did not result in a rate of the short-term composite end point of death, renal-replacement therapy, perioperative myocardial infarction, or use of a mechanical cardiac assist device that was lower than the rate with placebo among patients with a reduced left ventricular ejection fraction who were undergoing cardiac surgery with the use of cardiopulmonary bypass. (Funded by Tenax Therapeutics; LEVO-CTS ClinicalTrials.gov number, NCT02025621 .).

Prophylactic levosimendan for the prevention of low cardiac output syndrome and mortality in paediatric patients undergoing surgery for congenital heart disease.[Pubmed:28262914]

Cochrane Database Syst Rev. 2017 Mar 6;3:CD011312.

BACKGROUND: Low cardiac output syndrome remains a serious complication, and accounts for substantial morbidity and mortality in the postoperative course of paediatric patients undergoing surgery for congenital heart disease. Standard prophylactic and therapeutic strategies for low cardiac output syndrome are based mainly on catecholamines, which are effective drugs, but have considerable side effects. Levosimendan, a calcium sensitiser, enhances the myocardial function by generating more energy-efficient myocardial contractility than achieved via adrenergic stimulation with catecholamines. Thus potentially, Levosimendan is a beneficial alternative to standard medication for the prevention of low cardiac output syndrome in paediatric patients after open heart surgery. OBJECTIVES: To review the efficacy and safety of the postoperative prophylactic use of Levosimendan for the prevention of low cardiac output syndrome and mortality in paediatric patients undergoing surgery for congenital heart disease. SEARCH METHODS: We identified trials via systematic searches of CENTRAL, MEDLINE, Embase, and Web of Science, as well as clinical trial registries, in June 2016. Reference lists from primary studies and review articles were checked for additional references. SELECTION CRITERIA: We only included randomised controlled trials (RCT) in our analysis that compared prophylactic Levosimendan with standard medication or placebo, in infants and children up to 18 years of age, who were undergoing surgery for congenital heart disease. DATA COLLECTION AND ANALYSIS: Two review authors independently extracted data and assessed risk of bias according to a pre-defined protocol. We obtained additional information from all but one of the study authors of the included studies. We used the five GRADE considerations (study limitations, consistency of effect, imprecision, indirectness, and publication bias) to assess the quality of evidence from the studies that contributed data to the meta-analyses for the prespecified outcomes. We created a 'Summary of findings' table to summarise the results and the quality of evidence for each outcome. MAIN RESULTS: We included five randomised controlled trials with a total of 212 participants in the analyses. All included participants were under five years of age. Using GRADE, we assessed there was low-quality evidence for all analysed outcomes. We assessed high risk of performance and detection bias for two studies due to their unblinded setting. Levosimendan showed no clear effect on risk of mortality (risk ratio (RR) 0.47, 95% confidence interval (CI) 0.12 to 1.82; participants = 123; studies = 3) and no clear effect on low cardiac output syndrome (RR 0.64, 95% CI 0.39 to 1.04; participants = 83; studies = 2) compared to standard treatments. Data on time-to-death were not available from any of the included studies.There was no conclusive evidence on the effect of Levosimendan on the secondary outcomes. The Levosimendan groups had shorter length of intensive care unit stays (mean difference (MD) 0.33 days, 95% CI -1.16 to 1.82; participants = 188; studies = 4; I(2) = 35%), length of hospital stays (0.26 days, 95% CI -3.50 to 4.03; participants = 75; studies = 2), and duration of mechanical ventilation (MD -0.04 days, 95% CI -0.08 to 0.00; participants = 208; studies = 5; I(2) = 0%). The risk of mechanical circulatory support or cardiac transplantation favoured the Levosimendan groups (RR 1.49, 95% CI 0.19 to 11.37; participants = 60; studies = 2). Published data about adverse effects of Levosimendan were limited. A meta-analysis of hypotension, one of the most feared side effects of Levosimendan, was not feasible because of the heterogeneous expression of blood pressure values. AUTHORS' CONCLUSIONS: The current level of evidence is insufficient to judge whether prophylactic Levosimendan prevents low cardiac output syndrome and mortality in paediatric patients undergoing surgery for congenital heart disease. So far, no significant differences have been detected between Levosimendan and standard inotrope treatments in this setting.The authors evaluated the quality of evidence as low, using the GRADE approach. Reasons for downgrading were serious risk of bias (performance and detection bias due to unblinded setting of two RCTs), serious risk of inconsistency, and serious to very serious risk of imprecision (small number of included patients, low event rates).

Levosimendan for Hemodynamic Support after Cardiac Surgery.[Pubmed:28320259]

N Engl J Med. 2017 May 25;376(21):2021-2031.

BACKGROUND: Acute left ventricular dysfunction is a major complication of cardiac surgery and is associated with increased mortality. Meta-analyses of small trials suggest that Levosimendan may result in a higher rate of survival among patients undergoing cardiac surgery. METHODS: We conducted a multicenter, randomized, double-blind, placebo-controlled trial involving patients in whom perioperative hemodynamic support was indicated after cardiac surgery, according to prespecified criteria. Patients were randomly assigned to receive Levosimendan (in a continuous infusion at a dose of 0.025 to 0.2 mug per kilogram of body weight per minute) or placebo, for up to 48 hours or until discharge from the intensive care unit (ICU), in addition to standard care. The primary outcome was 30-day mortality. RESULTS: The trial was stopped for futility after 506 patients were enrolled. A total of 248 patients were assigned to receive Levosimendan and 258 to receive placebo. There was no significant difference in 30-day mortality between the Levosimendan group and the placebo group (32 patients [12.9%] and 33 patients [12.8%], respectively; absolute risk difference, 0.1 percentage points; 95% confidence interval [CI], -5.7 to 5.9; P=0.97). There were no significant differences between the Levosimendan group and the placebo group in the durations of mechanical ventilation (median, 19 hours and 21 hours, respectively; median difference, -2 hours; 95% CI, -5 to 1; P=0.48), ICU stay (median, 72 hours and 84 hours, respectively; median difference, -12 hours; 95% CI, -21 to 2; P=0.09), and hospital stay (median, 14 days and 14 days, respectively; median difference, 0 days; 95% CI, -1 to 2; P=0.39). There was no significant difference between the Levosimendan group and the placebo group in rates of hypotension or cardiac arrhythmias. CONCLUSIONS: In patients who required perioperative hemodynamic support after cardiac surgery, low-dose Levosimendan in addition to standard care did not result in lower 30-day mortality than placebo. (Funded by the Italian Ministry of Health; CHEETAH ClinicalTrials.gov number, NCT00994825 .).

Description

Levosimendan (Simsndan; OR-1259) is a calcium sensitiser used in the management of acutely decompensated congestive heart failure.

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