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Cisatracurium Besylate

Neuromuscular-blocking drug CAS# 96946-42-8

Cisatracurium Besylate

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Chemical structure

Cisatracurium Besylate

3D structure

Chemical Properties of Cisatracurium Besylate

Cas No. 96946-42-8 SDF Download SDF
PubChem ID 62886 Appearance Powder
Formula C65H82N2O18S2 M.Wt 1243.48
Type of Compound N/A Storage Desiccate at -20°C
Solubility H2O : ≥ 50 mg/mL (40.21 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name benzenesulfonate;5-[3-[(1R,2R)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-2-ium-2-yl]propanoyloxy]pentyl 3-[(1R,2R)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-2-ium-2-yl]propanoate
SMILES C[N+]1(CCC2=CC(=C(C=C2C1CC3=CC(=C(C=C3)OC)OC)OC)OC)CCC(=O)OCCCCCOC(=O)CC[N+]4(CCC5=CC(=C(C=C5C4CC6=CC(=C(C=C6)OC)OC)OC)OC)C.C1=CC=C(C=C1)S(=O)(=O)[O-].C1=CC=C(C=C1)S(=O)(=O)[O-]
Standard InChIKey XXZSQOVSEBAPGS-DONVQRBFSA-L
Standard InChI InChI=1S/C53H72N2O12.2C6H6O3S/c1-54(22-18-38-32-48(62-7)50(64-9)34-40(38)42(54)28-36-14-16-44(58-3)46(30-36)60-5)24-20-52(56)66-26-12-11-13-27-67-53(57)21-25-55(2)23-19-39-33-49(63-8)51(65-10)35-41(39)43(55)29-37-15-17-45(59-4)47(31-37)61-6;2*7-10(8,9)6-4-2-1-3-5-6/h14-17,30-35,42-43H,11-13,18-29H2,1-10H3;2*1-5H,(H,7,8,9)/q+2;;/p-2/t42-,43-,54-,55-;;/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 Cisatracurium Besylate

DescriptionCisatracurium Besylate is a nondepolarizing neuromuscular blocking agent, antagonizing the action of acetylcholine by inhibiting neuromuscular transmission. Target: AChR alpha-2 Cisatracurium is a neuromuscular-blocking drug or skeletal muscle relaxant in the category of non-depolarizing neuromuscular-blocking drugs, used adjunctively in anesthesia to facilitate endotracheal intubation and to provide skeletal muscle relaxation during surgery or mechanical ventilation. It is a bisbenzyltetrahydroisoquinolinium agent with an intermediate duration of action. Cisatracurium is one of the ten isomers of the parent molecule, atracurium. Moreover, cisatracurium represents approximately 15% of the atracurium mixture [1, 2].

References:
[1]. Dear, G.J., et al., Identification of urinary and biliary conjugated metabolites of the neuromuscular blocker 51W89 by liquid chromatography/mass spectrometry. Rapid Commun Mass Spectrom, 1995. 9(14): p. 1457-64. [2]. Serra, C.S. and A.C. Oliveira, Cisatracurium: myographical and electrophysiological studies in the isolated rat muscle. Fundam Clin Pharmacol, 2006. 20(3): p. 291-8.

Cisatracurium Besylate Dilution Calculator

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Cisatracurium Besylate Molarity Calculator

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Preparing Stock Solutions of Cisatracurium Besylate

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 0.8042 mL 4.021 mL 8.0419 mL 16.0839 mL 20.1049 mL
5 mM 0.1608 mL 0.8042 mL 1.6084 mL 3.2168 mL 4.021 mL
10 mM 0.0804 mL 0.4021 mL 0.8042 mL 1.6084 mL 2.0105 mL
50 mM 0.0161 mL 0.0804 mL 0.1608 mL 0.3217 mL 0.4021 mL
100 mM 0.008 mL 0.0402 mL 0.0804 mL 0.1608 mL 0.201 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 Cisatracurium Besylate

Cisatracurium is a neuromuscular-blocking drug or skeletal muscle relaxant in the category of non-depolarizing neuromuscular-blocking drugs, used adjunctively in anesthesia to facilitate endotracheal intubation and to provide skeletal muscle relaxation du

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References on Cisatracurium Besylate

[Neuromuscular effects of cisatracurium besylate in obese patients].[Pubmed:25534104]

Zhonghua Yi Xue Za Zhi. 2014 Sep 30;94(36):2844-6.

OBJECTIVE: To explore the neuromuscular effects of Cisatracurium Besylate in morbidly obese patients when dosed according to real body weight under total intravenous anesthesia with propofol. METHODS: Thirty-six ASA I-II patients aged 18-65 years scheduled for elective procedures at our hospital during July 2012 to December 2012 were allocated into 2 groups according to body mass index (normal weight: body mass index: <24, overweight: body mass index >28). Anesthesia was induced with target-controlled infusion of propofol (Cp 3 microg/ml) and remifentanil (Ce 3-5 ng/ml). A bolus of cisatracurium 0.2 mg/kg was administered intravenously over 5-10 s as soon as a patient lost consciousness. Neuromuscular block was monitored with TOF-Watch SX (Oaganon, the Netherlands). Single stimulation (0.1 Hz) was applied to ulnar nerve at wrist. The maximal degree of neuromuscular block, onset time, clinical duration and recovery index were recorded. They were intubated and mechanically ventilated when neuromuscular block reached the maximal degree. The intubation condition was evaluated. RESULTS: The average onset time was (164 +/- 25) s in obese group versus (201 +/- 48) s in normal weight group. And there was significant difference between groups (t = 2.83, P < 0.05) . The clinical duration was (68.4 +/- 9.6) min in obese group versus (62.0 +/- 6.5) min in normal weight group. And there was significant difference between groups (t = 2.33, P < 0.05). The recovery index was (15.6 +/- 4.7) min in obese group versus (10.8 +/- 4.2) min in normal weight group. And there was significant difference between groups (t = 3.03, P < 0.05) . Also 75% recovery time was (83.9 +/- 11.5) min in obese group versus (73.0 +/- 9.2) min in normal weight group. And there was significant difference between groups (t = 2.94, P < 0.05). But no differences existed in intubation conditions. CONCLUSION: When dosed according to real body weight, onset time of cisatracurium is shorter while clinical duration and recovery index are prolonged in morbidly obese patients compared with normal weight counterparts.

Autophagic Cell Death and Apoptosis Jointly Mediate Cisatracurium Besylate-Induced Cell Injury.[Pubmed:27058536]

Int J Mol Sci. 2016 Apr 6;17(4):515.

Cisatracurium Besylate is an ideal non-depolarizing muscle relaxant which is widely used in clinical application. However, some studies have suggested that Cisatracurium Besylate can affect cell proliferation. Moreover, its specific mechanism of action remains unclear. Here, we found that the number of GFP-LC3 (green fluoresent protein-light chain 3) positive autophagosomes and the rate of mitochondria fracture both increased significantly in drug-treated GFP-LC3 and MitoDsRed stable HeLa cells. Moreover, cisatracurium promoted the co-localization of LC3 and mitochondria and induced formation of autolysosomes. Levels of mitochondrial proteins decreased, which were reversed by the lysosome inhibitor Bafinomycin A1. Similar results with evidence of dose-dependent effects were found in both HeLa and Human Umbilical Vein Endothelial Cells (HUVECs). Cisatracurium lowered HUVEC viability to 0.16 (OD490) at 100 microM and to 0.05 (OD490) after 48 h in vitro; it increased the cell death rate to 56% at 100 microM and to 60% after 24 h in a concentration- and time-dependent manner (p < 0.01). Cell proliferation decreased significantly by four fold in Atg5 WT (wildtype) MEF (mouse embryonic fibroblast) (p < 0.01) but was unaffected in Atg5 KO (Knockout) MEF, even upon treatment with a high dose of cisatracurium. Cisatracurium induced significant increase in cell death of wild-type MEFs even in the presence of the apoptosis inhibitor zVAD. Thus, we conclude that activation of both the autophagic cell death and cell apoptosis pathways contributes to cisatracurium-mediated cell injury.

Capillary electrophoresis with electrochemiluminescence detection for the simultaneous determination of cisatracurium besylate and its degradation products in pharmaceutical preparations.[Pubmed:25872750]

J Sep Sci. 2015 Jul;38(13):2332-9.

Capillary electrophoresis with electrochemiluminescence detection for the simultaneous analysis of Cisatracurium Besylate and its degradation products (laudanosine, quaternary monoacrylate) in pharmaceutical preparation was developed and fully validated. The significant parameters that influence capillary electrophoresis separation and electrochemiluminescence detection were optimized. The total analysis time of the analytes was 15 min. The linearities of the method were 0.1 approximately 40.0 mug/mL for Cisatracurium Besylate and 0.04 approximately 8.00 mug/mL for laudanosine, with correlation coefficients (r) of 0.999 and 0.998, respectively. The detection limits (S/N = 3) were 83.0 ng/mL for Cisatracurium Besylate and 32.0 ng/mL for laudanosine. The intraday relative standard deviations of the analytes were <3.0%, and the interday relative standard deviations were <8.0%. The developed method was cost-effective, sensitive, fast, and resource-saving, which was suitable for the ingredient analysis in pharmaceutical preparation.

Phlebitis as a consequence of peripheral intravenous administration of cisatracurium besylate in critically ill patients.[Pubmed:27698008]

BMJ Case Rep. 2016 Oct 3;2016. pii: bcr-2016-216448.

This case report series describes 3 cases of Cisatracurium Besylate associated phlebitis after an infusion period of 14-20 hours. No similar cases have been reported in the literature. Association of phlebitis with another neuromuscular blocking agent, atracurium, has been described in the literature. The acidity of atracurium is thought to be the main cause. It is recommended that atracurium is administered only via central venous catheters when indicated to infuse over prolonged periods of time due to the acidity. Cisatracurium is a stereoisomer of atracurium and as such has the same molecular weight. Although cisatracurium also has a similar acidity as atracurium, a recommendation concerning infusion via a central venous catheter is lacking. We suggest prolonged administration of Cisatracurium Besylate only via centrally placed venous catheters or if not possible to careful monitor relevant peripheral intravenous sites to diminish the risks of phlebitis and associated complications or other cutaneous reactions.

Description

Cisatracurium besylate (51W89) is a nondepolarizing neuromuscular blocking agent, antagonizing the action of acetylcholine by inhibiting neuromuscular transmission.

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