Cisatracurium besilate

Cisatracurium besilate
Clinical data
Trade names	Nimbex
Other names	51W89, cisatracurium besylate (USAN US)
AHFS/Drugs.com	Monograph
License data	US DailyMed: Cisatracurium_besylate;
Pregnancy; category	AU: C;
Routes of; administration	Intravenous
ATC code	M03AC11 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: ℞-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	100% (IV)
Metabolism	80% Hofmann degradation/ liver
Elimination half-life	20–29 minutes
Excretion	10-15% unchanged
Identifiers
	IUPAC name 5-[3-[(1R,2R)-1-[(3,4-Dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-2-yl]propanoyloxy]pentyl 3-[(1R,2R)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-2-yl]propanoate benzenesulfonate (1:2);
CAS Number	96946-42-8 ; 96946-41-7;
PubChem CID	62886; 62887;
DrugBank	DBSALT002671 ; DB00565;
ChemSpider	56614 ; 56615;
UNII	80YS8O1MBS; QX62KLI41N;
KEGG	D00759;
ChEBI	CHEBI:3721 ; CHEBI:140621;
ChEMBL	ChEMBL1200641 ; ChEMBL1201248;
CompTox Dashboard (EPA)	DTXSID10895045 ;
ECHA InfoCard	100.149.509
Chemical and physical data
Formula	C65H82N2O18S2
Molar mass	1243.49 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES [O-]S(=O)(=O)c1ccccc1.[O-]S(=O)(=O)c1ccccc1.O=C(OCCCCCOC(=O)CC[N@@+]2([C@@H](c1c(cc(OC)c(OC)c1)CC2)Cc3ccc(OC)c(OC)c3)C)CC[N@+]5(C)[C@@H](c4cc(OC)c(OC)cc4CC5)Cc6ccc(OC)c(OC)c6;
	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;27-10(8,9)6-4-2-1-3-5-6/h14-17,30-35,42-43H,11-13,18-29H2,1-10H3;21-5H,(H,7,8,9)/q+2;;/p-2/t42-,43-,54-,55-;;/m1../s1 ; Key:XXZSQOVSEBAPGS-DONVQRBFSA-L ;
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Cisatracurium besilate (INN; cisatracurium besylate (USAN); formerly recognized as 51W89;^[1] trade name Nimbex) is a bisbenzyltetrahydroisoquinolinium that has effect as a non-depolarizing neuromuscular-blocking drug, used adjunctively in anesthesia to facilitate endotracheal intubation and to provide skeletal muscle relaxation during surgery or mechanical ventilation. It shows intermediate duration of action. Cisatracurium is one of the ten isomers of the parent molecule, atracurium.^[2] Moreover, cisatracurium represents approximately 15% of the atracurium mixture.^[3]

^ Meretoja OA, Taivainen T, Wirtavuori K (January 1995). "Pharmacodynamic effects of 51W89, an isomer of atracurium, in children during halothane anaesthesia". British Journal of Anaesthesia. 74 (1): 6–11. doi:10.1093/bja/74.1.6. PMID 7880708.
^ Stenlake JB, Waigh RD, Dewar GH, Dhar NC, Hughes R, Chapple DJ, Lindon JC, Ferrige AG (1984). "Biodegradable neuromuscular blocking agents. Part 6. Stereochemical studies on atracurium and related polyalkylene di-esters". Eur J Med Chem. 19 (5): 441–450.
^ Dear GJ, Harrelson JC, Jones AE, Johnson TE, Pleasance S (1995). "Identification of urinary and biliary conjugated metabolites of the neuromuscular blocker 51W89 by liquid chromatography/mass spectrometry". Rapid Communications in Mass Spectrometry. 9 (14): 1457–1464. Bibcode:1995RCMS....9.1457D. doi:10.1002/rcm.1290091425. PMID 8534894.

[1] Meretoja OA, Taivainen T, Wirtavuori K (January 1995). "Pharmacodynamic effects of 51W89, an isomer of atracurium, in children during halothane anaesthesia". British Journal of Anaesthesia. 74 (1): 6–11. doi:10.1093/bja/74.1.6. PMID 7880708.

[Stenlake1984-2] Stenlake JB, Waigh RD, Dewar GH, Dhar NC, Hughes R, Chapple DJ, Lindon JC, Ferrige AG (1984). "Biodegradable neuromuscular blocking agents. Part 6. Stereochemical studies on atracurium and related polyalkylene di-esters". Eur J Med Chem. 19 (5): 441–450.

[Dear1995-3] Dear GJ, Harrelson JC, Jones AE, Johnson TE, Pleasance S (1995). "Identification of urinary and biliary conjugated metabolites of the neuromuscular blocker 51W89 by liquid chromatography/mass spectrometry". Rapid Communications in Mass Spectrometry. 9 (14): 1457–1464. Bibcode:1995RCMS....9.1457D. doi:10.1002/rcm.1290091425. PMID 8534894.

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