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
Structure for Atracurium besylate (DB00732)
- 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.
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- Contraindications & Blackbox Warnings
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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.
Target Actions Organism ANeuronal acetylcholine receptor subunit alpha-2 antagonistHumans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Atracurium besylate is combined with 1,2-Benzodiazepine. Acetazolamide The risk or severity of CNS depression can be increased when Atracurium besylate is combined with Acetazolamide. Acetophenazine The risk or severity of CNS depression can be increased when Atracurium besylate is combined with Acetophenazine. Acetyldigitoxin The risk or severity of Cardiac Arrhythmia can be increased when Atracurium besylate is combined with Acetyldigitoxin. Aclidinium The risk or severity of adverse effects can be increased when Atracurium besylate is combined with Aclidinium. Agomelatine The risk or severity of CNS depression can be increased when Atracurium besylate is combined with Agomelatine. Alfentanil The risk or severity of adverse effects can be increased when Atracurium besylate is combined with Alfentanil. Alimemazine The risk or severity of CNS depression can be increased when Atracurium besylate is combined with Alimemazine. Alloin The therapeutic efficacy of Alloin can be decreased when used in combination with Atracurium besylate. Almotriptan The risk or severity of CNS depression can be increased when Atracurium besylate is combined with Almotriptan. 
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- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Active Moieties
Name Kind UNII CAS InChI Key Atracurium ionic 2GQ1IRY63P 64228-79-1 Not applicable - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Atracurium - (for Multiple Dose Vial - With Preservative) Solution 10 mg / mL Intravenous Ivax Pharmaceuticals Incorporated Not applicable Not applicable Canada 
Atracurium - (for Single Dose ) Solution 10 mg / mL Intravenous Ivax Pharmaceuticals Incorporated Not applicable Not applicable Canada Atracurium Besylate Injection Liquid 10 mg / mL Intravenous Abbott 1998-02-11 2007-07-31 Canada Atracurium Besylate Injection Liquid 10 mg / mL Intravenous Sandoz Canada Incorporated 1998-01-20 Not applicable Canada Atracurium Besylate Injection Solution 10 mg / mL Intravenous Hospira Healthcare Ulc 1998-07-13 2012-08-03 Canada Tracrium Liquid 10 mg / mL Intravenous Abbvie 1990-12-31 2012-11-03 Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Atracurium Besylate Injection, solution 10 mg/1mL Intravenous Baxter Laboratories 1997-02-17 2007-05-30 US 
Atracurium Besylate Injection, solution 10 mg/1mL Intravenous Sagent Pharmaceuticals 2012-05-01 2022-09-30 US Atracurium Besylate Injection 10 mg/1mL Intravenous Bedford Pharmaceuticals 2004-10-29 2013-03-31 US Atracurium Besylate Injection, solution 100 mg/10mL Intravenous AuroMedics Pharma LLC 2015-04-08 Not applicable US Atracurium Besylate Injection, solution 100 mg/10mL Intravenous Hospira Worldwide, Inc. 1997-03-28 2009-04-05 US Atracurium Besylate Injection, solution 10 mg/1mL Intravenous Mylan Institutional LLC 2017-10-19 2019-08-31 US Atracurium Besylate Injection, solution 10 mg/1mL Intravenous Hospira, Inc. 2013-05-29 Not applicable US Atracurium Besylate Injection, solution 50 mg/5mL Intravenous Aurobindo Pharma 2015-04-08 Not applicable US Atracurium Besylate Injection, solution 10 mg/1mL Intravenous Meitheal Pharmaceuticals Inc. 2018-05-15 Not applicable US Atracurium Besylate Injection 10 mg/1mL Intravenous Bedford Pharmaceuticals 1997-09-15 2013-03-31 US
Categories
- Drug Categories
- Anticholinergic Agents
- Benzylisoquinolines
- Central Nervous System Depressants
- Cholinergic Agents
- Heterocyclic Compounds, Fused-Ring
- Isoquinolines
- Miscellaneous Skeletal Muscle Relaxants
- Neuromuscular Agents
- Neuromuscular Blocking Agents
- Neuromuscular-Blocking Agents (Nondepolarizing)
- Neurotransmitter Agents
- Nicotinic Antagonists
- Peripheral Nervous System Agents
- 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 show 11 more
- 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
- External Links
- KEGG Drug
- D00758
- PubChem Compound
- 47320
- PubChem Substance
- 46504689
- ChemSpider
- 43068
- BindingDB
- 50149881
- 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
Phase Status Purpose Conditions Count 4 Completed Supportive Care Quality of Ocular Akinesia (Onset and Duration) 1 1 Terminated Treatment Healthy Subjects (HS) 1 0 Completed Screening Entropy Device and How Will Muscle Relaxants Affect it 1 Not Available Completed Other Spine Diseases 1 Not Available Not Yet Recruiting Other Caudal epidural block therapy / Inguinal Hernias / Postoperative pain / Quadratus Lumborum Block / Transversus Abdominis Plane (TAP) Block 1 Not Available Not Yet Recruiting Prevention External Dacryocystorhinostomy Operation / Patient With Nasolacrimal Duct Obstruction 1 Not Available Recruiting Prevention Opioid Analgesic Adverse Reaction 1 Not Available Recruiting Treatment Smooth muscle relaxation prior to radiological procedures therapy 1 Not Available Unknown Status Supportive Care Female Breast Cancer 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Baxter International Inc.
- Dosage Forms
Form Route Strength Solution 10 mg/1ml Injection Intravenous Injection Intravenous 10 mg/1mL Injection, solution Intravenous 10 mg/1mL Injection, solution Intravenous 100 mg/10mL Injection, solution Intravenous 50 mg/5mL Solution Intravenous 10 mg / mL Injection, solution Intravenous 25 mg/2.5ml Solution Injection, solution Intravenous 10 mg/ml Injection Parenteral 10 MG/ML Solution Intravenous Injection, solution Intravenous Solution Oral 25 mg Liquid Intravenous 10 mg / mL Solution Intravenous 25 mg Solution Intravenous 50 mg Injection Intravenous 10 mg/ml Injection Parenteral 25 MG/2.5ML Injection Parenteral 50 MG/5ML - Prices
Unit description Cost Unit Atracurium 10 mg/ml vial 0.96USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 85-90 Stenlake, 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 solubility Miscible Not Available - Predicted Properties
Property Value Source Water Solubility 4.17e-05 mg/mL ALOGPS logP 3.34 ALOGPS logP -0.96 Chemaxon logS -7.5 ALOGPS pKa (Strongest Acidic) 19.02 Chemaxon pKa (Strongest Basic) -4.1 Chemaxon Physiological Charge 2 Chemaxon Hydrogen Acceptor Count 10 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 126.44 Å2 Chemaxon Rotatable Bond Count 28 Chemaxon Refractivity 280.68 m3·mol-1 Chemaxon Polarizability 104.67 Å3 Chemaxon Number of Rings 8 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.9907 Blood Brain Barrier + 0.9367 Caco-2 permeable + 0.6226 P-glycoprotein substrate Substrate 0.8276 P-glycoprotein inhibitor I Inhibitor 0.5282 P-glycoprotein inhibitor II Inhibitor 0.6888 Renal organic cation transporter Non-inhibitor 0.5447 CYP450 2C9 substrate Non-substrate 0.8354 CYP450 2D6 substrate Non-substrate 0.6895 CYP450 3A4 substrate Substrate 0.6913 CYP450 1A2 substrate Non-inhibitor 0.9225 CYP450 2C9 inhibitor Non-inhibitor 0.9468 CYP450 2D6 inhibitor Non-inhibitor 0.8816 CYP450 2C19 inhibitor Non-inhibitor 0.9107 CYP450 3A4 inhibitor Non-inhibitor 0.8359 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9068 Ames test Non AMES toxic 0.7032 Carcinogenicity Non-carcinogens 0.9241 Biodegradation Not ready biodegradable 0.7843 Rat acute toxicity 2.5245 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8459 hERG inhibition (predictor II) Non-inhibitor 0.5169
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Not Available
Targets
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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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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]
- 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 at June 13, 2005 13:24 / Updated at June 05, 2023 06:28