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Details

Stereochemistry RACEMIC
Molecular Formula C53H72N2O12.2C6H5O3S
Molecular Weight 1243.479
Optical Activity ( + / - )
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ATRACURIUM BESYLATE, (1R,1'R,2R,2'R)-(±)-

SMILES

[O-]S(=O)(=O)C1=CC=CC=C1.[O-]S(=O)(=O)C2=CC=CC=C2.COC3=C(OC)C=C(C[C@@H]4C5=CC(OC)=C(OC)C=C5CC[N@+]4(C)CCC(=O)OCCCCCOC(=O)CC[N@@+]6(C)CCC7=CC(OC)=C(OC)C=C7[C@H]6CC8=CC(OC)=C(OC)C=C8)C=C3

InChI

InChIKey=XXZSQOVSEBAPGS-DONVQRBFSA-L
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

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including www.ncbi.nlm.nih.gov/pubmed/9349062

Cisatracurium is a cis-cis isomer of atracurium and five time as potent as atracurium. The drug is approved by FDA and marketed under the name Nimbex. It is indicated as an adjunct to general anesthesia, to facilitate tracheal intubation, and to provide skeletal muscle relaxation due to its antagonistic properties toward nicotinic acetylcholine receptors.

Originator

Sources: ISBN-13: 978-1461484400
Curator's Comment: Now part of GlaxoSmithKline.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
54.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
NIMBEX

Approved Use

Cisatracurium besylate injection is an intermediate-onset/intermediate-duration neuromuscular blocking agent indicated for inpatients and outpatients as an adjunct to general anesthesia, to facilitate tracheal intubation, and to provide skeletal muscle relaxation during surgery or mechanical ventilation in the ICU.

Launch Date

1995
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
22 min
0.1 mg/kg 1 times / day steady-state, intravenous
dose: 0.1 mg/kg
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered:
CISATRACURIUM unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
PubMed

PubMed

TitleDatePubMed
Prolonged weakness after cisatracurium infusion: a case report.
1998 Jul
Effects of pretreatment with cisatracurium, rocuronium, and d-tubocurarine on succinylcholine-induced fasciculations and myalgia: a comparison with placebo.
1999 Dec
Severe anaphylactic reaction to cisatracurium.
1999 Feb
[Precurarization of succinylcholine with cisatracurium: the influence of the precurarization interval].
2002 Sep
Acute motor axonal polyneuropathy after a cisatracurium infusion and concomitant corticosteroid therapy.
2004 Feb
Prevention of succinylcholine-induced fasciculation and myalgia: a meta-analysis of randomized trials.
2005 Oct
Distinct pharmacologic properties of neuromuscular blocking agents on human neuronal nicotinic acetylcholine receptors: a possible explanation for the train-of-four fade.
2006 Sep
Acute coronary syndrome in cisatracurium-induced anaphylactic shock: Kounis syndrome.
2008 Dec
[Type IV anaphylactic reaction and ST-elevation acute coronary syndrome due to coronary vasospasm secondary to administration of cisatracurium].
2008 Jun-Jul
Patents

Sample Use Guides

The recommended initial doses is 0.2 mg/kg, however it should be individualized. A dose of 0.03 mg/kg is recommended for maintenance of neuromuscular block during prolonged surgical procedures.
Route of Administration: Intravenous
Human umbilical vein endothelial cells were incubated with 0, 0.96, 3.2, 9.6, 32, and 96 microM of cisatracurium for 72 h and the drug (3.2 microM) decreased the cell count to 50% (SD, 8.6%).
Name Type Language
ATRACURIUM BESYLATE, (1R,1'R,2R,2'R)-(±)-
Common Name English
ISOQUINOLINIUM, 2,2'-(1,5-PENTANEDIYLBIS(OXY(3-OXO-3,1-PROPANEDIYL)))BIS(1-((3,4-DIMETHOXYPHENYL)METHYL)-1,2,3,4-TETRAHYDRO-6,7-DIMETHOXY-2-METHYL-, (1R,1'R,2R,2'R)-REL, DIBENZENESULFONATE
Common Name English
Code System Code Type Description
FDA UNII
Y78PS7MEDE
Created by admin on Fri Dec 15 15:46:47 GMT 2023 , Edited by admin on Fri Dec 15 15:46:47 GMT 2023
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PUBCHEM
62886
Created by admin on Fri Dec 15 15:46:47 GMT 2023 , Edited by admin on Fri Dec 15 15:46:47 GMT 2023
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