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Details

Stereochemistry ABSOLUTE
Molecular Formula C53H72N2O12
Molecular Weight 929.145
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 2

SHOW SMILES / InChI
Structure of CISATRACURIUM

SMILES

COC1=C(OC)C=C(C[C@@H]2C3=CC(OC)=C(OC)C=C3CC[N@+]2(C)CCC(=O)OCCCCCOC(=O)CC[N@@+]4(C)CCC5=CC(OC)=C(OC)C=C5[C@H]4CC6=CC(OC)=C(OC)C=C6)C=C1

InChI

InChIKey=YXSLJKQTIDHPOT-LJCJQEJUSA-N
InChI=1S/C53H72N2O12/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/h14-17,30-35,42-43H,11-13,18-29H2,1-10H3/q+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

Burroughs Wellcome Fund
41
Sources: ISBN-13: 978-1461484400
Curator's Comment: Now part of GlaxoSmithKline.

Approval Year

1995
196
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2778
 54.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Approved
8429
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
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/20551Orig1s026lbl.pdf
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
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:140621
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:140621
ZINC
ZINC000238809664
http://zinc15.docking.org/substances/ZINC000238809664
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
Complete recovery from prolonged cardiac arrest following self-administration of cisatracurium.
2005 Jan
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
Cisatracurium in "weakening doses" assists in weaning from sedation and withdrawal following extended use of inhaled isoflurane.
2007 Jan
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

Patents

EP2283005 A2
4
US20110185796 A1
4

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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
CISATRACURIUM
VANDF   WHO-DD  
Common Name English
CISATRACURIUM ION
Common Name English
(1R,2R,1'R,2'R)-2,2'-(PENTANE-1,5-DIYLBIS(OXY(3-OXOPROPANE-3,1-DIYL)))BIS(1-(3,4-DIMETHOXYBENZYL)-6,7-DIMETHOXY-2-METHYL-1,2,3,4-TETRAHYDROISOQUINOLINIUM)
Common Name English
CISATRACURIUM CATION
Common Name English
Cisatracurium [WHO-DD]
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,2R,1'R,2'R)-
Common Name English
CISATRACURIUM [VANDF]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175720
Created by admin on Fri Dec 15 15:45:22 GMT 2023 , Edited by admin on Fri Dec 15 15:45:22 GMT 2023
WHO-ATC M03AC11
Created by admin on Fri Dec 15 15:45:22 GMT 2023 , Edited by admin on Fri Dec 15 15:45:22 GMT 2023
NDF-RT N0000175732
Created by admin on Fri Dec 15 15:45:22 GMT 2023 , Edited by admin on Fri Dec 15 15:45:22 GMT 2023
WHO-VATC QM03AC11
Created by admin on Fri Dec 15 15:45:22 GMT 2023 , Edited by admin on Fri Dec 15 15:45:22 GMT 2023
NCI_THESAURUS C66886
Created by admin on Fri Dec 15 15:45:22 GMT 2023 , Edited by admin on Fri Dec 15 15:45:22 GMT 2023
Code System Code Type Description
LACTMED
Cisatracurium
Created by admin on Fri Dec 15 15:45:22 GMT 2023 , Edited by admin on Fri Dec 15 15:45:22 GMT 2023
PRIMARY
DAILYMED
QX62KLI41N
Created by admin on Fri Dec 15 15:45:22 GMT 2023 , Edited by admin on Fri Dec 15 15:45:22 GMT 2023
PRIMARY
EPA CompTox
DTXSID60873212
Created by admin on Fri Dec 15 15:45:22 GMT 2023 , Edited by admin on Fri Dec 15 15:45:22 GMT 2023
PRIMARY
EVMPD
SUB01319MIG
Created by admin on Fri Dec 15 15:45:22 GMT 2023 , Edited by admin on Fri Dec 15 15:45:22 GMT 2023
PRIMARY
NCI_THESAURUS
C77365
Created by admin on Fri Dec 15 15:45:22 GMT 2023 , Edited by admin on Fri Dec 15 15:45:22 GMT 2023
PRIMARY
DRUG CENTRAL
661
Created by admin on Fri Dec 15 15:45:22 GMT 2023 , Edited by admin on Fri Dec 15 15:45:22 GMT 2023
PRIMARY
FDA UNII
QX62KLI41N
Created by admin on Fri Dec 15 15:45:22 GMT 2023 , Edited by admin on Fri Dec 15 15:45:22 GMT 2023
PRIMARY
CAS
96946-41-7
Created by admin on Fri Dec 15 15:45:22 GMT 2023 , Edited by admin on Fri Dec 15 15:45:22 GMT 2023
PRIMARY
MESH
C101584
Created by admin on Fri Dec 15 15:45:22 GMT 2023 , Edited by admin on Fri Dec 15 15:45:22 GMT 2023
PRIMARY
SMS_ID
100000087946
Created by admin on Fri Dec 15 15:45:22 GMT 2023 , Edited by admin on Fri Dec 15 15:45:22 GMT 2023
PRIMARY
DRUG BANK
DB00565
Created by admin on Fri Dec 15 15:45:22 GMT 2023 , Edited by admin on Fri Dec 15 15:45:22 GMT 2023
PRIMARY
RXCUI
319864
Created by admin on Fri Dec 15 15:45:22 GMT 2023 , Edited by admin on Fri Dec 15 15:45:22 GMT 2023
PRIMARY RxNorm
WIKIPEDIA
Cisatracurium
Created by admin on Fri Dec 15 15:45:22 GMT 2023 , Edited by admin on Fri Dec 15 15:45:22 GMT 2023
PRIMARY
PUBCHEM
62887
Created by admin on Fri Dec 15 15:45:22 GMT 2023 , Edited by admin on Fri Dec 15 15:45:22 GMT 2023
PRIMARY
ACTIVE MOIETY
Structure of CISATRACURIUM
METABOLITE ACTIVE (PARENT)
Structure of LAUDANOSINE
SALT/SOLVATE (PARENT)
Structure of CISATRACURIUM BESYLATE
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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