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=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

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 2778		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 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 8.1898563E11

T_1/2

Value	Dose	Co-administered	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 unknown	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN 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
Prolonged weakness after cisatracurium infusion: a case report.	1998 Jul	9671384
Effects of pretreatment with cisatracurium, rocuronium, and d-tubocurarine on succinylcholine-induced fasciculations and myalgia: a comparison with placebo.	1999 Dec	10680105
Severe anaphylactic reaction to cisatracurium.	1999 Feb	9972775
Prevention of succinylcholine-induced fasciculation and myalgia: a meta-analysis of randomized trials.	2005 Oct	16192781
Distinct pharmacologic properties of neuromuscular blocking agents on human neuronal nicotinic acetylcholine receptors: a possible explanation for the train-of-four fade.	2006 Sep	16931985
Acute coronary syndrome in cisatracurium-induced anaphylactic shock: Kounis syndrome.	2008 Dec	19097966
[Type IV anaphylactic reaction and ST-elevation acute coronary syndrome due to coronary vasospasm secondary to administration of cisatracurium].	2008 Jun-Jul	18570839

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 `Fri Dec 15 15:45:22 UTC 2023` Edited by `admin` on `Fri Dec 15 15:45:22 UTC 2023`
Record UNII	QX62KLI41N
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

CISATRACURIUM

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