CISATRACURIUM

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 Search

SMILES

COC1=CC=C(C[C@@H]2C3=CC(OC)=C(OC)C=C3CC[N@+]2(C)CCC(=O)OCCCCCOC(=O)CC[N@@+]4(C)CCC5=C(C=C(OC)C(OC)=C5)[C@H]4CC6=CC=C(OC)C(OC)=C6)C=C1OC

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

Molecular Formula	C53H72N2O12
Molecular Weight	929.145
Charge	2
Count

Stereochemistry	MIXED
Additional Stereochemistry	No
Defined Stereocenters	2 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020551s019lbl.pdf
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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Muscle-type nicotinic acetylcholine receptor 65 Target ID: CHEMBL2362997 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020551s019lbl.pdf	Antagonist 2849		54.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Skeletal muscle relaxation 17 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020551s019lbl.pdf	Palliative		Approved 8583	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

C_max

Value	Dose	Co-administered	Analyte	Population
2129.97 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/35065599/	0.2 mg/kg single, intravenous dose: 0.2 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		CISATRACURIUM plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
16.6 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8688259/	0.1 mg/kg single, intravenous dose: 0.1 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	CISATRACURIUM plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
19.1 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8688259/	0.1 mg/kg single, intravenous dose: 0.1 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	CISATRACURIUM plasma	Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1394.04 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/35065599/	0.2 mg/kg single, intravenous dose: 0.2 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	CISATRACURIUM plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
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 plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
24.4 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8688259/	0.1 mg/kg single, intravenous dose: 0.1 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	CISATRACURIUM plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
23.5 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8688259/	0.1 mg/kg single, intravenous dose: 0.1 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	CISATRACURIUM plasma	Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE / MALE food status: UNKNOWN
29.44 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/35065599/	0.2 mg/kg single, intravenous dose: 0.2 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	CISATRACURIUM plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:140621	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:140621
ZINC	ZINC000238809664	http://zinc15.docking.org/substances/ZINC000238809664

PubMed

Title	Date	PubMed
Acute coronary syndrome in cisatracurium-induced anaphylactic shock: Kounis syndrome.	2008-12	19097966
[Type IV anaphylactic reaction and ST-elevation acute coronary syndrome due to coronary vasospasm secondary to administration of cisatracurium].	2008-06-24	18570839
Cisatracurium in "weakening doses" assists in weaning from sedation and withdrawal following extended use of inhaled isoflurane.	2007-01	17251884
Distinct pharmacologic properties of neuromuscular blocking agents on human neuronal nicotinic acetylcholine receptors: a possible explanation for the train-of-four fade.	2006-09	16931985
Prevention of succinylcholine-induced fasciculation and myalgia: a meta-analysis of randomized trials.	2005-10	16192781
Complete recovery from prolonged cardiac arrest following self-administration of cisatracurium.	2005-01	15816581
Acute motor axonal polyneuropathy after a cisatracurium infusion and concomitant corticosteroid therapy.	2004-02	14722188
[Precurarization of succinylcholine with cisatracurium: the influence of the precurarization interval].	2002-09	12232643
Effects of pretreatment with cisatracurium, rocuronium, and d-tubocurarine on succinylcholine-induced fasciculations and myalgia: a comparison with placebo.	1999-12	10680105
Severe anaphylactic reaction to cisatracurium.	1999-02	9972775
Prolonged weakness after cisatracurium infusion: a case report.	1998-07	9671384

Patents

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%).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:07:34 GMT 2025` Edited by `admin` on `Mon Mar 31 18:07:34 GMT 2025`
Record UNII	QX62KLI41N
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CISATRACURIUM ION

Preferred Name

English

CISATRACURIUM

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