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Details

Stereochemistry ABSOLUTE
Molecular Formula C53H72N2O12.2C6H5O3S
Molecular Weight 1243.479
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CISATRACURIUM BESYLATE

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
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
Molecular Formula C6H5O3S
Molecular Weight 157.167
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Severe anaphylactic reaction to cisatracurium.
1999 Feb
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%).
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:56:05 GMT 2023
Edited
by admin
on Fri Dec 15 15:56:05 GMT 2023
Record UNII
80YS8O1MBS
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CISATRACURIUM BESYLATE
MI   ORANGE BOOK   USAN   USP-RS   VANDF  
USAN  
Official Name English
CISATRACURIUM BESILATE
INN   MART.   WHO-DD  
INN  
Official 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)-, BENZENESULFONATE (1:2)
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)-, DIBENZENESULFONATE
Common Name English
CISATRACURIUM BESILATE [MART.]
Common Name English
CISATRACURIUM BESYLATE [MI]
Common Name English
CISATRACURIUM BESILATE [EP MONOGRAPH]
Common Name English
51W89
Code 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-, DIBENZENESULPHONATE, (1R-(1.ALPHA.,2.ALPHA.(1'R*,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-, DIBENZENESULFONATE, (1R-(1.ALPHA.,2.ALPHA.(1'R*,2'R*)))-
Common Name English
CISATRACURIUM (AS BESILATE)
Common Name English
CISATRACURIUM BESYLATE [VANDF]
Common Name English
51W-89
Code English
Cisatracurium besilate [WHO-DD]
Common Name English
CISATRACURIUM BESYLATE [USP MONOGRAPH]
Common Name English
CISATRACURIUM BESYLATE [USAN]
Common Name English
CISATRACURIUM BESYLATE [USP-RS]
Common Name English
CISATRACURIUM BESYLATE [ORANGE BOOK]
Common Name English
51-W89
Code English
NIMBEX
Brand Name English
(1R,2R)-2-(2-Carboxyethyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-veratrylisoquinolinium benzenesulfonate, pentamethylene ester
Common Name English
cisatracurium besilate [INN]
Common Name English
51-W-89
Code English
Classification Tree Code System Code
NCI_THESAURUS C66886
Created by admin on Fri Dec 15 15:56:05 GMT 2023 , Edited by admin on Fri Dec 15 15:56:05 GMT 2023
Code System Code Type Description
MERCK INDEX
m2129
Created by admin on Fri Dec 15 15:56:05 GMT 2023 , Edited by admin on Fri Dec 15 15:56:05 GMT 2023
PRIMARY Merck Index
USAN
FF-81
Created by admin on Fri Dec 15 15:56:05 GMT 2023 , Edited by admin on Fri Dec 15 15:56:05 GMT 2023
PRIMARY
SMS_ID
100000090476
Created by admin on Fri Dec 15 15:56:05 GMT 2023 , Edited by admin on Fri Dec 15 15:56:05 GMT 2023
PRIMARY
FDA UNII
80YS8O1MBS
Created by admin on Fri Dec 15 15:56:05 GMT 2023 , Edited by admin on Fri Dec 15 15:56:05 GMT 2023
PRIMARY
WIKIPEDIA
CISATRACURIUM BESILATE
Created by admin on Fri Dec 15 15:56:05 GMT 2023 , Edited by admin on Fri Dec 15 15:56:05 GMT 2023
PRIMARY
EPA CompTox
DTXSID10895045
Created by admin on Fri Dec 15 15:56:05 GMT 2023 , Edited by admin on Fri Dec 15 15:56:05 GMT 2023
PRIMARY
DRUG BANK
DB00565
Created by admin on Fri Dec 15 15:56:05 GMT 2023 , Edited by admin on Fri Dec 15 15:56:05 GMT 2023
PRIMARY
RXCUI
136561
Created by admin on Fri Dec 15 15:56:05 GMT 2023 , Edited by admin on Fri Dec 15 15:56:05 GMT 2023
PRIMARY RxNorm
EVMPD
SUB07480MIG
Created by admin on Fri Dec 15 15:56:05 GMT 2023 , Edited by admin on Fri Dec 15 15:56:05 GMT 2023
PRIMARY
NCI_THESAURUS
C47451
Created by admin on Fri Dec 15 15:56:05 GMT 2023 , Edited by admin on Fri Dec 15 15:56:05 GMT 2023
PRIMARY
DAILYMED
80YS8O1MBS
Created by admin on Fri Dec 15 15:56:05 GMT 2023 , Edited by admin on Fri Dec 15 15:56:05 GMT 2023
PRIMARY
PUBCHEM
62886
Created by admin on Fri Dec 15 15:56:05 GMT 2023 , Edited by admin on Fri Dec 15 15:56:05 GMT 2023
PRIMARY
CAS
96946-42-8
Created by admin on Fri Dec 15 15:56:05 GMT 2023 , Edited by admin on Fri Dec 15 15:56:05 GMT 2023
PRIMARY
CHEBI
3721
Created by admin on Fri Dec 15 15:56:05 GMT 2023 , Edited by admin on Fri Dec 15 15:56:05 GMT 2023
PRIMARY
ChEMBL
CHEMBL1201248
Created by admin on Fri Dec 15 15:56:05 GMT 2023 , Edited by admin on Fri Dec 15 15:56:05 GMT 2023
PRIMARY
INN
7389
Created by admin on Fri Dec 15 15:56:05 GMT 2023 , Edited by admin on Fri Dec 15 15:56:05 GMT 2023
PRIMARY
RS_ITEM_NUM
1134118
Created by admin on Fri Dec 15 15:56:05 GMT 2023 , Edited by admin on Fri Dec 15 15:56:05 GMT 2023
PRIMARY
Related Record Type Details
Structure of CISATRACURIUM
PARENT -> SALT/SOLVATE
Structure of BENZENESULFONIC ACID
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of 2,2′-[(3-methylpentane-1,5-diyl)bis[oxy(3-oxopropane-3,1-diyl)]]bis[(1R,2R)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolinium]
IMPURITY -> PARENT
Structure of N-DESMETHYL ATRACURIUM
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of (1R,2S)-2-(3,11-DIOXO-4,10-DIOXA-12-TRIDECENYL)-(1,2,3,4-TETRAHYDRO-6,7-DIMETHOXY-2-METHYL-1-VERATRYLISOQUINOLINIUM)
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of (1R,1R,2S,2S)-2,2-(3,11-DIOXO-4,10-DIOXATRIDECAMETHYLENE)BIS(1,2,3,4-TETRAHYDRO-6,7-DIMETHOXY-2-METHYL-1-VERATRYLISOQUINOLINIUM).
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of 2,2′-[1,6-Hexanediylbis[oxy(3-oxo-3,1-propanediyl)]]bis[1-[(3,4-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methylisoquinolinium], (1R,1′R,2R,2′R)-
IMPURITY -> PARENT
Structure of (1R,1R,2R,2R)-2,2-(3,7,15-TRIOXO-4,8,14-TRIOXA-HEPTADECAMETHYLENE)BIS(1,2,3,4-TETRAHYDRO-6,7-DIMETHOXY-2-METHYL-1-VERATRYLISOQUINOLINIUM)
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of (1R,2R)-2-[3-[[5-(acetyloxy)pentyl]oxy]]-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-3-oxopropyl-1,2,3,4-tetrahydroisoquinolinium
IMPURITY -> PARENT
Structure of ATRACURIUM, (1R,2R,1'R,2'S)-(±)-
IMPURITY -> PARENT
Structure of LAUDANOSINE, (R)-
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of (1R,2R)-1,2,3,4-TETRAHYDRO-2-(9-HYDROXY-3-OXO-4-OXANONYL)-6,7-DIMETHOXY-2-METHYL-1-VERATRYLISOQUINOLINIUM
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of (R)-1,2,3,4-TETRAHYDRO-6,7-DIMETHOXY-2,2-DIMETHYL-1-VERATRYLISOQUINOLINIUM
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of (R,R)-N,N'-DIDEMETHYL ATRACURIUM
IMPURITY -> PARENT
Structure of (1R,2R)-1,2,3,4-TETRAHYDRO-6,7-DIMETHOXY-2-(2-(METHOXYCARBONYL)ETHYL)-2-METHYL-1-VERATRYLISOQUINOLINIUM
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of (1R,2S)-1-[(3,4-dimethoxyphenyl)methyl]-2-[3-[(5-hydroxypentyl)oxy]-3-oxopropyl]-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolinium
IMPURITY -> PARENT
Structure of (1R,2R)-2-(2-CARBOXYETHYL)-1,2,3,4-TETRAHYDRO-6,7-DIMETHOXY-2-METHYL-1-VERATRYLISOQUINOLINIUM
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
Structure of CISATRACURIUM
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