atracurium 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |

Stem definitionDrug idCAS RN
neuromuscular blocking agents with rigid structure 259 64228-79-1

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • atracurium
  • tracrium
  • atracurium besylate
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.
  • Molecular weight: 929.16
  • Formula: C53H72N2O12
  • CLOGP: 3.30
  • LIPINSKI: 2
  • HAC: 14
  • HDO: 0
  • TPSA: 126.44
  • ALOGS: -7.63
  • ROTB: 26
  • Status: OFP
    • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

None

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 0 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 8.50 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.65 µM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution) 0.10 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 5.70 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.52 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 0.31 hours Lombardo F, Berellini G, Obach RS

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 -0.040 Moderate 0.70
caco2-efflux Caco-2 efflux ratio (BA/AB) 14.962 Moderate 0.70
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 1.033 10^-6 cm/s Moderate 0.70
dh-clint Dog hepatocyte intrinsic clearance 9.183 uL/min/10^6 cells Moderate 0.70
dppb Dog plasma protein binding (% unbound) 40.280 % Moderate 0.70
fcs-ppb Fetal calf serum protein binding (% unbound) 58.160 % Moderate 0.70
herg hERG pIC50 4.719 pIC50 Moderate 0.70
hh-clint Human hepatocyte intrinsic clearance 6.209 uL/min/10^6 cells Moderate 0.70
hlm-clint Human liver microsomal intrinsic clearance 155.955 uL/min/mg protein Moderate 0.70
hppb Human plasma protein binding (% unbound) 34.060 % Moderate 0.70
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 4.613 Moderate 0.70
mh-clint Mouse hepatocyte intrinsic clearance 61.235 Moderate 0.70
mppb Mouse plasma protein binding (% unbound) 38.030 Moderate 0.70
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 9.311 Moderate 0.70
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pppb Pig plasma protein binding (% unbound) 70.820 % Moderate 0.70
rh-clint Rat hepatocyte intrinsic clearance 39.811 uL/min/10^6 cells Moderate 0.70
rh-fuinc Rat hepatocyte fraction unbound in incubation 78.330 % Moderate 0.70
rppb Rat plasma protein binding (% unbound) 47.010 % Moderate 0.70
solubility-dd Solubility at pH 7.4 in DMSO 872.971 uM Moderate 0.70

Approvals:

DateAgencyCompanyOrphan
Nov. 23, 1983 FDA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Anaphylactic shock 944.79 49.02 218 2921 31399 90593909
Anaphylactic reaction 414.30 49.02 143 2996 87381 90537927
Hypotension 260.59 49.02 153 2986 325244 90300064
Bronchospasm 256.75 49.02 71 3068 20638 90604670
Cardiac arrest 129.61 49.02 66 3073 104869 90520439
Circulatory collapse 84.65 49.02 32 3107 24872 90600436
Wrong product administered 84.46 49.02 24 3115 7641 90617667
Cerebral haemorrhage foetal 77.82 49.02 13 3126 335 90624973
Tachycardia 75.57 49.02 54 3085 157619 90467689
Schizencephaly 71.05 49.02 12 3127 331 90624977
Acute generalised exanthematous pustulosis 66.81 49.02 23 3116 13680 90611628
Skin test positive 65.49 49.02 13 3126 887 90624421
Patent ductus arteriosus 62.71 49.02 17 3122 4552 90620756
Pulseless electrical activity 59.60 49.02 19 3120 8913 90616395
Acute respiratory distress syndrome 56.72 49.02 25 3114 28661 90596647
Anticholinergic syndrome 51.07 49.02 13 3126 2730 90622578
Bradycardia 50.25 49.02 33 3106 83814 90541494
Procedure aborted 49.45 49.02 8 3131 168 90625140

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Anaphylactic shock 604.23 46.04 160 2384 23357 42595434
Bronchospasm 168.41 46.04 52 2492 12833 42605958
Anaphylactic reaction 165.29 46.04 70 2474 42673 42576118
Rash maculo-papular 80.75 46.04 41 2503 37462 42581329
Leukocytosis 80.49 46.04 38 2506 29670 42589121
Eosinophilia 73.84 46.04 37 2507 32862 42585929
Hypotension 73.22 46.04 83 2461 257548 42361243
Hepatic cytolysis 62.61 46.04 31 2513 26813 42591978
Cardiac arrest 58.72 46.04 50 2494 109270 42509521
Hyperthermia malignant 53.44 46.04 15 2529 2643 42616148
Erythema 48.90 46.04 45 2499 108748 42510043
Circulatory collapse 48.39 46.04 25 2519 23611 42595180
Bradycardia 47.71 46.04 40 2504 85444 42533347

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Anaphylactic shock 1489.64 42.71 371 5132 51175 110532621
Anaphylactic reaction 557.38 42.71 210 5293 114090 110469706
Bronchospasm 408.26 42.71 120 5383 30119 110553677
Hypotension 300.72 42.71 230 5273 523619 110060177
Cardiac arrest 169.25 42.71 111 5392 196642 110387154
Circulatory collapse 132.52 42.71 57 5446 42936 110540860
Eosinophilia 101.51 42.71 52 5451 57884 110525912
Tachycardia 98.46 42.71 85 5418 226560 110357236
Bradycardia 90.05 42.71 69 5434 155448 110428348
Rash maculo-papular 81.56 42.71 49 5454 74173 110509623
Shock 76.60 42.71 42 5461 53546 110530250
Stress cardiomyopathy 72.88 42.71 28 5475 15778 110568018
Wrong product administered 71.23 42.71 25 5478 10935 110572861
Leukocytosis 68.25 42.71 39 5464 53789 110530007
Type I hypersensitivity 67.34 42.71 21 5482 6372 110577424
Skin test positive 65.16 42.71 15 5488 1434 110582362
Hyperthermia malignant 63.76 42.71 18 5485 3882 110579914
Erythema 61.43 42.71 74 5429 291373 110292423
Anaphylactoid shock 59.60 42.71 13 5490 973 110582823
Acute generalised exanthematous pustulosis 57.89 42.71 26 5477 21638 110562158
Hepatic cytolysis 57 42.71 35 5468 55018 110528778
Trigemino-cardiac reflex 56.70 42.71 11 5492 460 110583336
Acute respiratory distress syndrome 55.53 42.71 34 5469 53164 110530632
Drug reaction with eosinophilia and systemic symptoms 55.46 42.71 40 5463 82055 110501741
Pulseless electrical activity 54.17 42.71 23 5480 16734 110567062
Oxygen saturation decreased 48.94 42.71 49 5454 156933 110426863
Fatigue 48.80 42.71 3 5500 1215955 109367841
Rhabdomyolysis 47.87 42.71 43 5460 120358 110463438
Procedure aborted 46.33 42.71 8 5495 173 110583623
Unwanted awareness during anaesthesia 45.85 42.71 9 5494 400 110583396
Allergy test negative 45.83 42.71 9 5494 401 110583395
Haemodynamic instability 44.32 42.71 22 5481 22866 110560930
Hypocapnia 43.90 42.71 10 5493 912 110582884
Anaesthetic complication 42.87 42.71 13 5490 3593 110580203

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC M03AC04 MUSCULO-SKELETAL SYSTEM
MUSCLE RELAXANTS
MUSCLE RELAXANTS, PERIPHERALLY ACTING AGENTS
Other quaternary ammonium compounds
CHEBI has role CHEBI:48878 nicotinic antagonist
CHEBI has role CHEBI:51371 muscle relaxant
MeSH PA D003473 Neuromuscular Nondepolarizing Agents
MeSH PA D009465 Neuromuscular Agents
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018678 Cholinergic Agents
MeSH PA D018680 Cholinergic Antagonists
MeSH PA D018733 Nicotinic Antagonists
FDA EPC N0000175720 Nondepolarizing Neuromuscular Blocker
FDA PE N0000175732 Neuromuscular Nondepolarizing Blockade

Related Drugs by ATC class:

M03AC Other quaternary ammonium compounds 10 drugs
cisatracuriumdoxacuriumfazadiniumgallaminehexafluroniummivacuriumpancuroniumpipecuroniumrocuroniumvecuronium

Drug Use | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
Muscle relaxation, function indication 11977004
General anesthesia indication 50697003
Skeletal Muscle Relaxation for Endotracheal Intubation indication
Hypocalcemia contraindication 5291005
Disorder of lung contraindication 19829001 DOID:850
Hypokalemia contraindication 43339004
Low blood pressure contraindication 45007003
Eaton-Lambert syndrome contraindication 56989000 DOID:0050214
Hypermagnesemia contraindication 66978005
Myasthenia gravis contraindication 91637004 DOID:437
Disorder of electrolytes contraindication 237840007
Hypothermia contraindication 386689009
Malignant hyperthermia contraindication 405501007




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

None

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])		Mechanism
action		Bioact sourceMoA source
Acetylcholine receptor Ion channel ANTAGONIST IC50 7.77 WOMBAT-PK CHEMBL
Neuronal acetylcholine receptor subunit alpha-2 Ion channel WOMBAT-PK
Neuronal acetylcholine receptor subunit alpha-7 Ion channel ANTAGONIST IC50 8.25 IUPHAR
Neuronal acetylcholine receptor subunit alpha-3 Ion channel ANTAGONIST IC50 9.05 IUPHAR
Neuronal acetylcholine receptor subunit alpha-4 Ion channel ANTAGONIST IC50 8.10 IUPHAR
Small conductance calcium-activated potassium channel protein 3 Ion channel Ki 5.23 CHEMBL

External reference:

IDSource
2GQ1IRY63P UNII
4019619 VUID
N0000147713 NUI
D00758 KEGG_DRUG
64228-81-5 SECONDARY_CAS_RN
1218 RXNORM
C0004234 UMLSCUI
CHEBI:2914 CHEBI
CHEMBL1360 ChEMBL_ID
47319 PUBCHEM_CID
DB13295 DRUGBANK_ID
CHEMBL1200527 ChEMBL_ID
D001279 MESH_DESCRIPTOR_UI
9537 IUPHAR_LIGAND_ID
DB00732 DRUGBANK_ID
1341 MMSL
397 MMSL
4228 MMSL
d00173 MMSL
4734 INN_ID
4018778 VANDF
4019619 VANDF
002409 NDDF
013420 NDDF
372835000 SNOMEDCT_US
72752006 SNOMEDCT_US
74074008 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Atracurium Besylate HUMAN PRESCRIPTION DRUG LABEL 1 0409-1105 INJECTION, SOLUTION 10 mg INTRAVENOUS ANDA 12 sections
Atracurium Besylate HUMAN PRESCRIPTION DRUG LABEL 1 0409-1109 INJECTION, SOLUTION 10 mg INTRAVENOUS ANDA 12 sections
Atracurium Besylate Human Prescription Drug Label 1 55150-216 INJECTION, SOLUTION 50 mg INTRAVENOUS ANDA 20 sections
Atracurium Besylate Human Prescription Drug Label 1 55150-217 INJECTION, SOLUTION 100 mg INTRAVENOUS ANDA 20 sections
Atracurium Besylate HUMAN PRESCRIPTION DRUG LABEL 1 71288-701 INJECTION, SOLUTION 10 mg INTRAVENOUS ANDA 23 sections
Atracurium Besylate HUMAN PRESCRIPTION DRUG LABEL 1 71288-702 INJECTION, SOLUTION 10 mg INTRAVENOUS ANDA 23 sections