Atracurium besylate

Identification

Summary

Atracurium besylate is a non-depolarizing neuromuscular blocker used to facilitate endotracheal intubation and relax skeletal muscles during surgery.

Generic Name
Atracurium besylate
DrugBank Accession Number
DB00732
Background

A non-depolarizing neuromuscular blocking agent with short duration of action. Its lack of significant cardiovascular effects and its lack of dependence on good kidney function for elimination provide clinical advantage over alternate non-depolarizing neuromuscular blocking agents.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 1243.49
Monoisotopic: 1242.500406156
Chemical Formula
C65H82N2O18S2
Synonyms
  • Atracurium besilate
  • Atracurium besylate
  • Atracurium dibesylate
  • Besilate d'atracurium
  • Besilato de atracurio
External IDs
  • BW 33A
  • BW-33A
  • Wellcome 33-A-74

Pharmacology

Indication

For use, as an adjunct to general anesthesia, to facilitate endotracheal intubation and to provide skeletal muscle relaxation during surgery or mechanical ventilation.

Pharmacology
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Associated Therapies
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Contraindications
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Pharmacodynamics

Atracurium is a nondepolarizing skeletal muscle relaxant. Atracurium can be used most advantageously if muscle twitch response to peripheral nerve stimulation is monitored to assess degree of muscle relaxation. The duration of neuromuscular block produced by Atracurium is approximately one third to one half the duration of block by d-tubocurarine, metocurine, and pancuronium at initially equipotent doses. As with other nondepolarizing neuromuscular blockers, the time to onset of paralysis decreases and the duration of maximum effect increases with increasing doses of Atracurium. Repeated administration of maintenance doses of Atracurium has no cumulative effect on the duration of neuromuscular block if recovery is allowed to begin prior to repeat dosing. Moreover, the time needed to recover from repeat doses does not change with additional doses. Repeat doses can therefore be administered at relatively regular intervals with predictable results.

Mechanism of action

Atracurium antagonizes the neurotransmitter action of acetylcholine by binding competitively with cholinergic receptor sites on the motor end-plate. This antagonism is inhibited, and neuromuscular block reversed, by acetylcholinesterase inhibitors such as neostigmine, edrophonium, and pyridostigmine.

TargetActionsOrganism
ANeuronal acetylcholine receptor subunit alpha-2
antagonist
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

The elimination half-life is approximately 20 minutes.

Clearance

Not Available

Adverse Effects
Adverseeffects
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Toxicity

Excessive doses can be expected to produce enhanced pharmacological effects. Overdosage may increase the risk of histamine release and cardiovascular effects, especially hypotension.

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 Atracurium besylate is combined with 1,2-Benzodiazepine.
AcetazolamideThe risk or severity of adverse effects can be increased when Atracurium besylate is combined with Acetazolamide.
AcetophenazineThe risk or severity of adverse effects can be increased when Atracurium besylate is combined with Acetophenazine.
AcetyldigitoxinThe risk or severity of Cardiac Arrhythmia can be increased when Atracurium besylate is combined with Acetyldigitoxin.
AclidiniumAtracurium besylate may increase the central nervous system depressant (CNS depressant) activities of Aclidinium.
AgomelatineThe risk or severity of adverse effects can be increased when Atracurium besylate is combined with Agomelatine.
AlfentanilThe risk or severity of adverse effects can be increased when Atracurium besylate is combined with Alfentanil.
AlimemazineThe risk or severity of adverse effects can be increased when Atracurium besylate is combined with Alimemazine.
AlloinThe therapeutic efficacy of Alloin can be decreased when used in combination with Atracurium besylate.
AlmotriptanThe risk or severity of adverse effects can be increased when Atracurium besylate is combined with Almotriptan.
Interactions
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Food Interactions
No interactions found.

Products

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Active Moieties
NameKindUNIICASInChI Key
Atracuriumionic2GQ1IRY63P64228-79-1Not applicable
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Atracurium - (for Multiple Dose Vial - With Preservative)Solution10 mg / mLIntravenousIvax Pharmaceuticals IncorporatedNot applicableNot applicableCanada flag
Atracurium - (for Single Dose )Solution10 mg / mLIntravenousIvax Pharmaceuticals IncorporatedNot applicableNot applicableCanada flag
Atracurium Besylate InjectionLiquid10 mg / mLIntravenousAbbott1998-02-112007-07-31Canada flag
Atracurium Besylate InjectionLiquid10 mg / mLIntravenousSandoz Canada Incorporated1998-01-20Not applicableCanada flag
Atracurium Besylate InjectionSolution10 mg / mLIntravenousHospira Healthcare Ulc1998-07-132012-08-03Canada flag
TracriumLiquid10 mg / mLIntravenousAbbvie1990-12-312012-11-03Canada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Atracurium BesylateInjection, solution100 mg/10mLIntravenousAurobindo Pharma Limited2015-04-08Not applicableUS flag
Atracurium BesylateInjection, solution10 mg/1mLIntravenousMeitheal Pharmaceuticals Inc.2018-05-15Not applicableUS flag
Atracurium BesylateInjection, solution10 mg/1mLIntravenousHospira, Inc.2013-02-25Not applicableUS flag
Atracurium BesylateInjection, solution100 mg/10mLIntravenousHospira Worldwide, Inc.1997-03-282009-04-05US flag
Atracurium BesylateInjection, solution50 mg/5mLIntravenousAurobindo Pharma2015-04-08Not applicableUS flag
Atracurium BesylateInjection, solution10 mg/1mLIntravenousMylan Institutional LLC2017-10-192019-08-31US flag
Atracurium BesylateInjection, solution10 mg/1mLIntravenousSagent Pharmaceuticals2012-05-012022-09-30US flag
Atracurium BesylateInjection10 mg/1mLIntravenousBedford Pharmaceuticals1997-09-152013-03-31US flag
Atracurium BesylateInjection, solution10 mg/1mLIntravenousBaxter Laboratories1997-02-172007-05-30US flag
Atracurium BesylateInjection, solution100 mg/10mLIntravenousAuroMedics Pharma LLC2015-04-08Not applicableUS flag

Categories

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
Benzenesulfonic acids and derivatives / Dimethoxybenzenes / Tetrahydroisoquinolines / 1-sulfo,2-unsubstituted aromatic compounds / Benzenesulfonyl compounds / Phenoxy compounds / Anisoles / Aralkylamines / Alkyl aryl ethers / Dicarboxylic acids and derivatives
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Substituents
1-sulfo,2-unsubstituted aromatic compound / Alkyl aryl ether / Amine / Anisole / Aralkylamine / Aromatic heteropolycyclic compound / Arylsulfonic acid or derivatives / Azacycle / Benzenesulfonate / Benzenesulfonyl group
show 30 more
Molecular Framework
Not Available
External Descriptors
quaternary ammonium salt, organosulfonate salt (CHEBI:2915)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
40AX66P76P
CAS number
64228-81-5
InChI Key
XXZSQOVSEBAPGS-UHFFFAOYSA-L
InChI
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
IUPAC Name
1-[(3,4-dimethoxyphenyl)methyl]-2-[3-({5-[(3-{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 dibenzenesulfonate
SMILES
[O-]S(=O)(=O)C1=CC=CC=C1.[O-]S(=O)(=O)C1=CC=CC=C1.COC1=CC2=C(C=C1OC)C(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)C1CC1=CC(OC)=C(OC)C=C1)CC2

References

Synthesis Reference

Steven A. Chamberlin, Ashok V. Bhatia, Deborah A. Davis, Keith A. Drengler, "Process for the preparation and isolation of atracurium besylate." U.S. Patent US5684154, issued September, 1995.

US5684154
General References
Not Available
KEGG Drug
D00758
PubChem Compound
47320
PubChem Substance
46504689
ChemSpider
43068
BindingDB
50149881
RxNav
1219
ChEBI
2915
ChEMBL
CHEMBL1200527
Therapeutic Targets Database
DAP000105
PharmGKB
PA164776840
RxList
RxList Drug Page
Wikipedia
Atracurium_besilate
MSDS
Download (162 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedSupportive CareQuality of Ocular Akinesia (Onset and Duration)1
Not AvailableCompletedOtherSpine Diseases1
Not AvailableRecruitingPreventionOpioid Analgesic Adverse Reaction1
Not AvailableRecruitingTreatmentSmooth muscle relaxation prior to radiological procedures1
Not AvailableUnknown StatusSupportive CareMalignant Neoplasm of Female Breast1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Baxter International Inc.
Dosage Forms
FormRouteStrength
Solution10 mg/1ml
InjectionIntravenous
InjectionIntravenous10 mg/1mL
Injection, solutionIntravenous10 mg/1mL
Injection, solutionIntravenous100 mg/10mL
Injection, solutionIntravenous50 mg/5mL
SolutionIntravenous10 mg / mL
Injection, solutionIntravenous25 mg/2.5ml
Solution
Injection, solutionIntravenous10 mg/ml
Injection, solutionIntravenous
SolutionOral25 mg
LiquidIntravenous10 mg / mL
SolutionIntravenous
InjectionIntravenous10 mg/ml
Prices
Unit descriptionCostUnit
Atracurium 10 mg/ml vial0.96USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)85-90Stenlake, J.B., Waigh, R.D., Dewar,G.H., Urwin, J. and Dhar, N.C.; U.S. Patent 4,179,507 December 18,1979; assigned to BurroughsWellcome Company.
water solubilityMiscibleNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.17e-05 mg/mLALOGPS
logP3.34ALOGPS
logP-0.96ChemAxon
logS-7.5ALOGPS
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 Count28ChemAxon
Refractivity280.68 m3·mol-1ChemAxon
Polarizability104.67 Å3ChemAxon
Number of Rings8ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9907
Blood Brain Barrier+0.9367
Caco-2 permeable+0.6226
P-glycoprotein substrateSubstrate0.8276
P-glycoprotein inhibitor IInhibitor0.5282
P-glycoprotein inhibitor IIInhibitor0.6888
Renal organic cation transporterNon-inhibitor0.5447
CYP450 2C9 substrateNon-substrate0.8354
CYP450 2D6 substrateNon-substrate0.6895
CYP450 3A4 substrateSubstrate0.6913
CYP450 1A2 substrateNon-inhibitor0.9225
CYP450 2C9 inhibitorNon-inhibitor0.9468
CYP450 2D6 inhibitorNon-inhibitor0.8816
CYP450 2C19 inhibitorNon-inhibitor0.9107
CYP450 3A4 inhibitorNon-inhibitor0.8359
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9068
Ames testNon AMES toxic0.7032
CarcinogenicityNon-carcinogens0.9241
BiodegradationNot ready biodegradable0.7843
Rat acute toxicity2.5245 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8459
hERG inhibition (predictor II)Non-inhibitor0.5169
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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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. Jonsson Fagerlund M, Dabrowski M, Eriksson LI: Pharmacological characteristics of the inhibition of nondepolarizing neuromuscular blocking agents at human adult muscle nicotinic acetylcholine receptor. Anesthesiology. 2009 Jun;110(6):1244-52. doi: 10.1097/ALN.0b013e31819fade3. [Article]

Drug created on June 13, 2005 13:24 / Updated on October 24, 2021 16:00