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Identification
NameAtracurium besylate
Accession NumberDB00732  (APRD00806)
TypeSmall Molecule
GroupsApproved
Description

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. [PubChem]

Structure
Thumb
Synonyms
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
Atracurium besilate
Atracurium dibesylate
External Identifiers
  • BW 33A
  • BW-33A
  • Wellcome 33-A-74
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Atracurium - (for Single Dose )solution10 mgintravenousIvax Pharmaceuticals IncorporatedNot applicableNot applicableCanada
Atracurium - (for Multiple Dose Vial - With Preservative)solution10 mgintravenousIvax Pharmaceuticals IncorporatedNot applicableNot applicableCanada
Atracurium Besylate Injectionliquid10 mgintravenousSandoz Canada Incorporated1998-01-20Not applicableCanada
Atracurium Besylate Injectionsolution10 mgintravenousHospira Healthcare Corporation1998-07-132012-08-03Canada
Atracurium Besylate Injectionliquid10 mgintravenousAbbott Laboratories, Limited1998-02-112007-07-31Canada
Tracriumliquid10 mgintravenousAbbvie Corporation1990-12-312012-11-03Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Atracurium Besylateinjection, solution10 mg/mLintravenousHospira, Inc.2012-10-18Not applicableUs
Atracurium Besylateinjection, solution50 mg/5mLintravenousAurobindo Pharma Limited2015-04-08Not applicableUs
Atracurium Besylateinjection, solution100 mg/10mLintravenousAuro Medics Pharma Llc2015-04-08Not applicableUs
Atracurium Besylateinjection, solution50 mg/5mLintravenousAuro Medics Pharma Llc2015-04-08Not applicableUs
Atracurium Besylateinjection, solution10 mg/mLintravenousSagent Pharmaceuticals2012-05-01Not applicableUs
Atracurium Besylateinjection, solution10 mg/mLintravenousSagent Pharmaceuticals2012-05-01Not applicableUs
Atracurium Besylateinjection, solution10 mg/mLintravenousHospira, Inc.2012-10-18Not applicableUs
Atracurium Besylateinjection, solution100 mg/10mLintravenousAurobindo Pharma Limited2015-04-08Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII40AX66P76P
CAS number64228-81-5
WeightAverage: 1243.49
Monoisotopic: 1242.500406156
Chemical FormulaC65H82N2O18S2
InChI KeyXXZSQOVSEBAPGS-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
Taxonomy
ClassificationNot classified
Pharmacology
IndicationFor use, as an adjunct to general anesthesia, to facilitate endotracheal intubation and to provide skeletal muscle relaxation during surgery or mechanical ventilation.
PharmacodynamicsAtracurium 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 actionAtracurium 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.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeThe elimination half-life is approximately 20 minutes.
ClearanceNot Available
ToxicityExcessive doses can be expected to produce enhanced pharmacological effects. Overdosage may increase the risk of histamine release and cardiovascular effects, especially hypotension.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Injection, solutionintravenous10 mg/mL
Injection, solutionintravenous100 mg/10mL
Injection, solutionintravenous50 mg/5mL
Liquidintravenous10 mg
Solutionintravenous10 mg
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.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point85-90Stenlake, 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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
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 ReferencesNot Available
External Links
ATC CodesNot Available
AHFS Codes
  • 12:20.00
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (162 KB)
Interactions
Drug Interactions
Drug
AmikacinAmikacin may increase the activities of Atracurium besylate.
AmlodipineAmlodipine may increase the neuromuscular blocking activities of Atracurium besylate.
AmrinoneAmrinone may increase the neuromuscular blocking activities of Atracurium besylate.
ArbekacinArbekacin may increase the activities of Atracurium besylate.
BepridilBepridil may increase the neuromuscular blocking activities of Atracurium besylate.
BetamethasoneAtracurium besylate may increase the adverse neuromuscular activities of Betamethasone.
Botulinum Toxin Type ABotulinum Toxin Type A may increase the neuromuscular blocking activities of Atracurium besylate.
Botulinum Toxin Type BAtracurium besylate may increase the neuromuscular blocking activities of Botulinum Toxin Type B.
CapreomycinCapreomycin may increase the neuromuscular blocking activities of Atracurium besylate.
ClevidipineClevidipine may increase the neuromuscular blocking activities of Atracurium besylate.
ClindamycinClindamycin may increase the neuromuscular blocking activities of Atracurium besylate.
ColistimethateColistimethate may increase the neuromuscular blocking activities of Atracurium besylate.
CorticotropinAtracurium besylate may increase the adverse neuromuscular activities of Corticotropin.
Cortisone acetateAtracurium besylate may increase the adverse neuromuscular activities of Cortisone acetate.
CyclosporineCyclosporine may increase the neuromuscular blocking activities of Atracurium besylate.
DesfluraneDesflurane may increase the neuromuscular blocking activities of Atracurium besylate.
DexamethasoneAtracurium besylate may increase the adverse neuromuscular activities of Dexamethasone.
DigoxinAtracurium besylate may increase the arrhythmogenic activities of Digoxin.
DiltiazemDiltiazem may increase the neuromuscular blocking activities of Atracurium besylate.
DonepezilDonepezil may decrease the neuromuscular blocking activities of Atracurium besylate.
EdrophoniumEdrophonium may decrease the neuromuscular blocking activities of Atracurium besylate.
FelodipineFelodipine may increase the neuromuscular blocking activities of Atracurium besylate.
FludrocortisoneAtracurium besylate may increase the adverse neuromuscular activities of Fludrocortisone.
FlunarizineFlunarizine may increase the neuromuscular blocking activities of Atracurium besylate.
FosphenytoinFosphenytoin may decrease the neuromuscular blocking activities of Atracurium besylate.
FramycetinFramycetin may increase the activities of Atracurium besylate.
GabapentinGabapentin may increase the neuromuscular blocking activities of Atracurium besylate.
GalantamineGalantamine may decrease the neuromuscular blocking activities of Atracurium besylate.
GentamicinGentamicin may increase the activities of Atracurium besylate.
HydrocortisoneAtracurium besylate may increase the adverse neuromuscular activities of Hydrocortisone.
IsofluraneIsoflurane may increase the neuromuscular blocking activities of Atracurium besylate.
IsradipineIsradipine may increase the neuromuscular blocking activities of Atracurium besylate.
KanamycinKanamycin may increase the activities of Atracurium besylate.
KetorolacThe risk or severity of adverse effects can be increased when Ketorolac is combined with Atracurium besylate.
LamotrigineLamotrigine may increase the neuromuscular blocking activities of Atracurium besylate.
LercanidipineLercanidipine may increase the neuromuscular blocking activities of Atracurium besylate.
LincomycinLincomycin may increase the neuromuscular blocking activities of Atracurium besylate.
LithiumLithium may increase the neuromuscular blocking activities of Atracurium besylate.
Magnesium SulfateMagnesium Sulfate may increase the neuromuscular blocking activities of Atracurium besylate.
MethylprednisoloneAtracurium besylate may increase the adverse neuromuscular activities of Methylprednisolone.
MinocyclineMinocycline may increase the neuromuscular blocking activities of Atracurium besylate.
NeomycinNeomycin may increase the activities of Atracurium besylate.
NeostigmineNeostigmine may decrease the neuromuscular blocking activities of Atracurium besylate.
NetilmicinNetilmicin may increase the activities of Atracurium besylate.
NicardipineNicardipine may increase the neuromuscular blocking activities of Atracurium besylate.
NifedipineNifedipine may increase the neuromuscular blocking activities of Atracurium besylate.
NimodipineNimodipine may increase the neuromuscular blocking activities of Atracurium besylate.
NisoldipineNisoldipine may increase the neuromuscular blocking activities of Atracurium besylate.
NitrendipineNitrendipine may increase the neuromuscular blocking activities of Atracurium besylate.
OxytetracyclineOxytetracycline may increase the neuromuscular blocking activities of Atracurium besylate.
PerhexilinePerhexiline may increase the neuromuscular blocking activities of Atracurium besylate.
PhenytoinPhenytoin may decrease the neuromuscular blocking activities of Atracurium besylate.
PhysostigminePhysostigmine may decrease the neuromuscular blocking activities of Atracurium besylate.
Polymyxin B SulfatePolymyxin B Sulfate may increase the neuromuscular blocking activities of Atracurium besylate.
PrednisoloneAtracurium besylate may increase the adverse neuromuscular activities of Prednisolone.
PrednisoneAtracurium besylate may increase the adverse neuromuscular activities of Prednisone.
PrenylaminePrenylamine may increase the neuromuscular blocking activities of Atracurium besylate.
ProcainamideProcainamide may increase the neuromuscular blocking activities of Atracurium besylate.
PyridostigminePyridostigmine may decrease the neuromuscular blocking activities of Atracurium besylate.
QuinidineQuinidine may increase the neuromuscular blocking activities of Atracurium besylate.
QuinineQuinine may increase the neuromuscular blocking activities of Atracurium besylate.
Repository corticotropinAtracurium besylate may increase the adverse neuromuscular activities of Repository corticotropin.
RibostamycinRibostamycin may increase the activities of Atracurium besylate.
RisedronateRisedronate may increase the neuromuscular blocking activities of Atracurium besylate.
RivastigmineRivastigmine may decrease the neuromuscular blocking activities of Atracurium besylate.
SevofluraneSevoflurane may increase the neuromuscular blocking activities of Atracurium besylate.
SpectinomycinSpectinomycin may increase the activities of Atracurium besylate.
SpironolactoneSpironolactone may increase the neuromuscular blocking activities of Atracurium besylate.
StreptomycinStreptomycin may increase the activities of Atracurium besylate.
TacrineTacrine may decrease the neuromuscular blocking activities of Atracurium besylate.
TobramycinTobramycin may increase the activities of Atracurium besylate.
TorasemideTorasemide may decrease the neuromuscular blocking activities of Atracurium besylate.
TriamcinoloneAtracurium besylate may increase the adverse neuromuscular activities of Triamcinolone.
VancomycinVancomycin may increase the neuromuscular blocking activities of Atracurium besylate.
VerapamilVerapamil may increase the neuromuscular blocking activities of Atracurium besylate.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
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
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. [PubMed:17139284 ]
  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. [PubMed:17016423 ]
  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. [PubMed:19417616 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23