Identification

Summary

Cisatracurium is a skeletal muscle relaxant used to facilitate tracheal intubation, muscle relaxation in surgery, or mechanical ventilation.

Brand Names
Nimbex
Generic Name
Cisatracurium
DrugBank Accession Number
DB00565
Background

Cisatracurium is a nondepolarizing skeletal muscle relaxant for intravenous administration. Cisatracurium acts on cholinergic receptors, blocking neuromuscular transmission. This action is antagonized by acetylcholinesterase inhibitors such as neostigmine. The neuromuscular block produced by cisatracurium besylate is readily antagonized by anticholinesterase agents once recovery has started. As with other nondepolarizing neuromuscular blocking agents, the more profound the neuromuscular block at the time of reversal, the longer the time required for recovery of neuromuscular function. Compared to other neuromuscular blocking agents, it is intermediate in its onset and duration of action.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 929.16
Monoisotopic: 928.507428607
Chemical Formula
C53H72N2O12
Synonyms
  • Cisatracurium cation

Pharmacology

Indication

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.

Pharmacology
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Associated Therapies
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Contraindications
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Pharmacodynamics

Cisatracurium Besylate is a nondepolarizing skeletal muscle relaxant for intravenous administration. Cisatracurium Besylate acts on cholinergic receptors, blocking neuromuscular transmission. This action is antagonized by acetylcholinesterase inhibitors such as neostigmine. The neuromuscular block produced by cisatracurium besylate is readily antagonized by anticholinesterase agents once recovery has started. As with other nondepolarizing neuromuscular blocking agents, the more profound the neuromuscular block at the time of reversal, the longer the time required for recovery of neuromuscular function. Compared to other neuromuscular blocking agents, it is intermediate in its onset and duration of action.

Mechanism of action

Cisatracurium Besylate binds to the nicotinic acetycholine (cholinergic) receptors in the motor endplate and blocks access to the receptors. In the process of binding, the receptor is actually activated - causing a process known as depolarization. Since it is not degraded in the neuromuscular junction, the depolarized membrane remains depolarized and unresponsive to any other impulse, causing muscle paralysis.

TargetActionsOrganism
ANeuronal acetylcholine receptor subunit alpha-2
antagonist
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

The binding of cisatracurium to plasma proteins has not been successfully studied due to its rapid degradation at physiologic pH.

Metabolism

The degradation of cisatracurium is largely independent of liver metabolism. Results from in vitro experiments suggest that cisatracurium undergoes Hofmann elimination (a pH and temperature-dependent chemical process) to form laudanosine and the monoquaternary acrylate metabolite. The monoquaternary acrylate undergoes hydrolysis by non-specific plasma esterases to form the monoquaternary alcohol metabolite. The monoquaternary alcohol metabolite can also undergo Hofmann elimination but at a much slower rate than cisatracurium. Laudanosine is further metabolized to desmethyl metabolites which are conjugated with glucuronic acid and excreted in the urine.

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Route of elimination

Biliary and urinary excretion were the major routes of excretion of radioactivity (totaling >90% of the labeled dose within 7 hours of dosing), of which atracurium represented only a minor fraction.

Half-life

Elimination half-life of 22 minutes.

Clearance

Not Available

Adverse Effects
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Toxicity

Overdosage with neuromuscular blocking agents may result in neuromuscular block beyond the time needed for surgery and anesthesia.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when Cisatracurium is combined with 1,2-Benzodiazepine.
AcetazolamideThe risk or severity of adverse effects can be increased when Cisatracurium is combined with Acetazolamide.
AcetophenazineThe risk or severity of adverse effects can be increased when Cisatracurium is combined with Acetophenazine.
AcetyldigitoxinThe risk or severity of Cardiac Arrhythmia can be increased when Cisatracurium is combined with Acetyldigitoxin.
AclidiniumCisatracurium may increase the central nervous system depressant (CNS depressant) activities of Aclidinium.
AgomelatineThe risk or severity of adverse effects can be increased when Cisatracurium is combined with Agomelatine.
AlfentanilThe risk or severity of adverse effects can be increased when Cisatracurium is combined with Alfentanil.
AlimemazineThe risk or severity of adverse effects can be increased when Cisatracurium is combined with Alimemazine.
AlloinThe therapeutic efficacy of Alloin can be decreased when used in combination with Cisatracurium.
AlmotriptanThe risk or severity of adverse effects can be increased when Cisatracurium is combined with Almotriptan.
Interactions
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Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Cisatracurium besylate80YS8O1MBS96946-42-8XXZSQOVSEBAPGS-DONVQRBFSA-L
International/Other Brands
Nimbex Forte (GlaxoSmithKline) / Nimbium (GlaxoSmithKline)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Cisatracurium Besylate InjectionSolution2 mg / mLIntravenousMylan PharmaceuticalsNot applicableNot applicableCanada flag
Cisatracurium Besylate InjectionSolution2 mg / mLIntravenousAccord Healthcare IncNot applicableNot applicableCanada flag
Cisatracurium Besylate InjectionSolution2 mg / mLIntravenousPfizer Canada Ulc2015-06-012019-03-28Canada flag
Cisatracurium Besylate Injection (preservative-free)Solution2 mg / mLIntravenousMylan PharmaceuticalsNot applicableNot applicableCanada flag
Cisatracurium Besylate Injection Multi-doseSolution2 mg / mLIntravenousFresenius KabiNot applicableNot applicableCanada flag
Cisatracurium Besylate Injection Single DoseSolution2 mg / mLIntravenousFresenius KabiNot applicableNot applicableCanada flag
Cisatracurium Omega MultidoseSolution2 mg / mLIntravenousOmega Laboratories Ltd2014-01-20Not applicableCanada flag
Cisatracurium Omega Single DoseSolution2 mg / mLIntravenousOmega Laboratories Ltd2014-01-28Not applicableCanada flag
NimbexInjection10 mg/1mLIntravenousAbbVie Inc.1995-12-15Not applicableUS flag
NimbexLiquid2 mg / mLIntravenousAbbvie1997-04-072016-06-07Canada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Aj-cisatracuriumSolution2 mg / mLIntravenousAgila Jamp Canada IncNot applicableNot applicableCanada flag
Aj-cisatracuriumSolution2 mg / mLIntravenousAgila Jamp Canada IncNot applicableNot applicableCanada flag
CisatracuriumInjection, solution2 mg/1mLIntravenousFresenius Kabi USA, LLC2015-02-26Not applicableUS flag
CisatracuriumInjection, solution2 mg/1mLIntravenousFresenius Kabi USA, LLC2015-02-26Not applicableUS flag
CisatracuriumInjection, solution10 mg/1mLIntravenousFresenius Kabi USA, LLC2015-02-26Not applicableUS flag
Cisatracurium BesylateInjection, solution10 mg/1mLIntravenousHospira, Inc.2021-06-01Not applicableUS flag
Cisatracurium BesylateInjection2 mg/1mLIntravenousSandoz Inc2013-02-282020-12-31US flag
Cisatracurium BesylateInjection10 mg/1mLIntravenousSandoz Inc2012-07-16Not applicableUS flag
Cisatracurium BesylateInjection2 mg/1mLIntravenousSomerset Therapeutics, Llc2019-08-02Not applicableUS flag
Cisatracurium BesylateInjection10 mg/1mLIntravenousCadila Healthcare Limited2020-02-12Not applicableUS flag

Categories

ATC Codes
M03AC11 — Cisatracurium
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Isoquinolines and derivatives
Sub Class
Benzylisoquinolines
Direct Parent
Benzylisoquinolines
Alternative Parents
Tetrahydroisoquinolines / Dimethoxybenzenes / Phenoxy compounds / Anisoles / Alkyl aryl ethers / Aralkylamines / Dicarboxylic acids and derivatives / Tetraalkylammonium salts / Carboxylic acid esters / Azacyclic compounds
show 6 more
Substituents
Alkyl aryl ether / Amine / Anisole / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Benzylisoquinoline / Carbonyl group / Carboxylic acid derivative
show 21 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
QX62KLI41N
CAS number
96946-41-7
InChI Key
YXSLJKQTIDHPOT-LJCJQEJUSA-N
InChI
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
IUPAC Name
(1R,2R)-1-[(3,4-dimethoxyphenyl)methyl]-2-(3-{[5-({3-[(1R,2R)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-2-ium-2-yl]propanoyl}oxy)pentyl]oxy}-3-oxopropyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-2-ium
SMILES
COC1=CC2=C(C=C1OC)[C@@H](CC1=CC(OC)=C(OC)C=C1)[N@@+](C)(CCC(=O)OCCCCCOC(=O)CC[N@@+]1(C)CCC3=C(C=C(OC)C(OC)=C3)[C@H]1CC1=CC(OC)=C(OC)C=C1)CC2

References

General References
  1. GlaxoSmithKline: NIMBEX injection product information [Link]
Human Metabolome Database
HMDB0240286
PubChem Compound
62886
PubChem Substance
46506666
ChemSpider
56615
RxNav
319864
ChEBI
140621
ChEMBL
CHEMBL1201248
ZINC
ZINC000238809664
Therapeutic Targets Database
DAP000196
PharmGKB
PA164744925
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Cisatracurium_besilate
MSDS
Download (25.2 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedNot AvailableNeuromuscular Blockade1
4CompletedBasic ScienceARDS, Human / Critically Ill Patients / Neuromuscular Blockade / Paralysis / Respiratory Distress Syndrome, Adult / Respiratory Failure1
4CompletedPreventionC.Delivery; Surgery (Previous), Gynecological1
4CompletedPreventionCurarization, Postoperative Residual / Residual Neuromuscular Block1
4CompletedPreventionNeuromuscular Blockade / Postoperative Complications1
4CompletedTreatmentRespiratory Distress Syndrome, Acute (ARDS)1
4RecruitingTreatmentIncrease in Intracranial Pressure (ICP) / Traumatic Brain Injury (TBI)1
4Unknown StatusPreventionReaction; Anesthesia1
4Unknown StatusTreatmentAdrenal Suppression / Hemodynamics Instability1
4Unknown StatusTreatmentAnaesthesia therapy / Hemodynamics / Stress Oxidative1

Pharmacoeconomics

Manufacturers
  • Baxter healthcare corp anesthesia and critical care
  • Baxter healthcare corp anesthesia critical care
  • Bedford laboratories div ben venue laboratories inc
  • Hospira inc
  • Marsam pharmaceuticals llc
  • Teva parenteral medicines inc
  • Abbott laboratories
Packagers
  • Abbott Laboratories Ltd.
  • Baxter International Inc.
  • Bedford Labs
  • Ben Venue Laboratories Inc.
  • GlaxoSmithKline Inc.
  • Hospira Inc.
  • Patheon Inc.
  • Teva Pharmaceutical Industries Ltd.
Dosage Forms
FormRouteStrength
Injection, solution2 mg/1ml
Injection, solutionIntravenous bolus5 MG/ML
Injection, solution2 MG/ML
Injection, solution5 MG/ML
Injection, solutionIntravenous bolus2 MG/ML
Injection, solution
Injection, solutionIntravenous10 mg/1mL
Injection, solutionIntravenous2 mg/1mL
Injection, solutionParenteral
InjectionIntravenous10 mg/1mL
InjectionIntravenous10 mg/5mL
InjectionIntravenous2 mg/1mL
InjectionIntravenous20 mg/10mL
InjectionIntravenous200 mg/20mL
Injection, solutionIntravenous10 mg/5mL
Injection, solutionIntravenous20 mg/10mL
Injection, solutionIntravenous200 mg/20mL
SolutionParenteral
Solution2 mg/1ml
Injection, solutionIntravenous bolus
SolutionIntravenous2 mg / mL
InjectionIntravenous10 mg
SolutionIntravenous10 mg
Injection, solutionIntravenous10 mg
Injection, solutionIntravenous150 mg
Injection, solutionIntravenous20 mg
Injection, solutionIntravenous5 mg
Injection, solutionIntravenous50 mg
LiquidIntravenous2 mg / mL
LiquidIntravenous10 mg / mL
InjectionIntravenous
Injection, solutionIntravenous150 mg/30ml
Injection, solutionIntravenous2 mg/ml
Injection, solutionIntravenous
SolutionIntravenous5 mg
Injection, solution5 mg/1ml
Prices
Unit descriptionCostUnit
Nimbex 10 mg/ml vial13.8USD ml
Nimbex 2 mg/ml vial2.91USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5453510No1995-09-262012-09-26US flag
CA2087104No1998-08-182011-07-12Canada flag

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.32e-05 mg/mLALOGPS
logP3.41ALOGPS
logP-0.96ChemAxon
logS-7.6ALOGPS
pKa (Strongest Acidic)19.02ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area126.44 Å2ChemAxon
Rotatable Bond Count26ChemAxon
Refractivity280.68 m3·mol-1ChemAxon
Polarizability104.19 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9847
Blood Brain Barrier+0.9291
Caco-2 permeable-0.5966
P-glycoprotein substrateSubstrate0.6828
P-glycoprotein inhibitor IInhibitor0.7177
P-glycoprotein inhibitor IIInhibitor0.5808
Renal organic cation transporterNon-inhibitor0.5871
CYP450 2C9 substrateNon-substrate0.7994
CYP450 2D6 substrateNon-substrate0.7779
CYP450 3A4 substrateSubstrate0.6527
CYP450 1A2 substrateNon-inhibitor0.8244
CYP450 2C9 inhibitorNon-inhibitor0.7179
CYP450 2D6 inhibitorNon-inhibitor0.791
CYP450 2C19 inhibitorNon-inhibitor0.7048
CYP450 3A4 inhibitorNon-inhibitor0.7338
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8547
Ames testNon AMES toxic0.544
CarcinogenicityNon-carcinogens0.5302
BiodegradationReady biodegradable0.8169
Rat acute toxicity2.6124 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6043
hERG inhibition (predictor II)Inhibitor0.6507
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Targets

Drugtargets2
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insights and accelerate drug research.
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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Drug binding
Specific Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name
CHRNA2
Uniprot ID
Q15822
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-2
Molecular Weight
59764.82 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Tuba Z, Maho S, Vizi ES: Synthesis and structure-activity relationships of neuromuscular blocking agents. Curr Med Chem. 2002 Aug;9(16):1507-36. [Article]

Drug created at June 13, 2005 13:24 / Updated at December 08, 2021 01:57