ATRACURIUM BESYLATE, (1R,1'R,2R,2'R)-(±)-

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=CC=C(C[C@@H]4C5=C(CC[N@+]4(C)CCC(=O)OCCCCCOC(=O)CC[N@@+]6(C)CCC7=C(C=C(OC)C(OC)=C7)[C@H]6CC8=CC=C(OC)C(OC)=C8)C=C(OC)C(OC)=C5)C=C3OC

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

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Description

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	Antagonist 2,849		54.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Skeletal muscle relaxation 17	Palliative		Approved 8,583	NIMBEX

C_max

Value	Dose	Co-administered	Analyte	Population
2129.97 ng/mL	0.2 mg/kg single, intravenous		CISATRACURIUM plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
16.6 μg × min/mL	0.1 mg/kg single, intravenous	CISATRACURIUM plasma	Homo sapiens
19.1 μg × min/mL	0.1 mg/kg single, intravenous	CISATRACURIUM plasma	Homo sapiens
1394.04 ng × h/mL	0.2 mg/kg single, intravenous	CISATRACURIUM plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
22 min	0.1 mg/kg 1 times / day steady-state, intravenous	CISATRACURIUM plasma	Homo sapiens
24.4 min	0.1 mg/kg single, intravenous	CISATRACURIUM plasma	Homo sapiens
23.5 min	0.1 mg/kg single, intravenous	CISATRACURIUM plasma	Homo sapiens
29.44 min	0.2 mg/kg single, intravenous	CISATRACURIUM plasma	Homo sapiens

Sourcing

Sourcing

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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

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PubMed

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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
[Precurarization of succinylcholine with cisatracurium: the influence of the precurarization interval].	2002 Sep	12232643
Acute motor axonal polyneuropathy after a cisatracurium infusion and concomitant corticosteroid therapy.	2004 Feb	14722188

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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%).

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Name

Type

Language

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

Preferred Name

English

ATRACURIUM BESYLATE, (1R,1'R,2R,2'R)-(±)-

Common Name

English

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Code System

Code

Type

Description

FDA UNII

Y78PS7MEDE

PRIMARY

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PARENT (SALT/SOLVATE)


					SKE79AOA7L

ATRACURIUM, (1R,1'R,2R,2'R)-(±)-

SUBSTANCE RECORD


					Y78PS7MEDE

ATRACURIUM BESYLATE, (1R,1'R,2R,2'R)-(±)-

SMILES

InChI

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2