atracurium Indications/Contra | FAERs-F | FAERs-M | Orange Bk | 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: 3.50
  • 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 ┬ÁM/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

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 569.72 43.29 147 2529 20127 46663259
Anaphylactic reaction 236.50 43.29 95 2581 53017 46630369
Bronchospasm 176.77 43.29 56 2620 15651 46667735
Hypotension 175.06 43.29 127 2549 232462 46450924
Oliguria 89.29 43.29 29 2647 8730 46674656
Tachycardia 78.04 43.29 56 2620 99566 46583820
Cardiac arrest 73.51 43.29 52 2624 90347 46593039
Pulseless electrical activity 66.07 43.29 22 2654 7145 46676241
Circulatory collapse 57.56 43.29 27 2649 21597 46661789
Shock 57.29 43.29 27 2649 21818 46661568
Patent ductus arteriosus 57.07 43.29 17 2659 3845 46679541
Infantile apnoea 55.24 43.29 12 2664 764 46682622
Stress cardiomyopathy 52.79 43.29 19 2657 7765 46675621
Foetal exposure during pregnancy 51.33 43.29 28 2648 30719 46652667
Wrong product administered 50.77 43.29 17 2659 5613 46677773
Ventricular fibrillation 48.99 43.29 20 2656 11476 46671910
Post procedural complication 46.09 43.29 21 2655 15708 46667678
Acute respiratory distress syndrome 45.21 43.29 23 2653 21899 46661487
Foetal growth restriction 44.42 43.29 16 2660 6551 46676835
Tonsillar hypertrophy 43.62 43.29 10 2666 814 46682572

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 355.29 39.06 97 1930 13896 29936555
Bronchospasm 190.89 39.06 56 1971 10282 29940169
Anaphylactic reaction 189.40 39.06 71 1956 27911 29922540
Hypotension 74.80 39.06 79 1948 200486 29749965
Circulatory collapse 61.12 39.06 29 1998 20185 29930266
Oxygen saturation decreased 54.89 39.06 35 1992 43405 29907046
Trigemino-cardiac reflex 54.12 39.06 9 2018 111 29950340
Tachycardia 42.37 39.06 37 1990 73702 29876749
Erythema 40.80 39.06 37 1990 77414 29873037
Bradycardia 39.91 39.06 34 1993 65492 29884959
Procedural hypotension 39.80 39.06 10 2017 1015 29949436
Airway complication of anaesthesia 39.46 39.06 7 2020 129 29950322

Pharmacologic Action:

SourceCodeDescription
ATC M03AC04 MUSCULO-SKELETAL SYSTEM
MUSCLE RELAXANTS
MUSCLE RELAXANTS, PERIPHERALLY ACTING AGENTS
Other quaternary ammonium compounds
FDA EPC N0000175720 Nondepolarizing Neuromuscular Blocker
FDA PE N0000175732 Neuromuscular Nondepolarizing Blockade
CHEBI has role CHEBI:48878 agents antinicotiniques
CHEBI has role CHEBI:51371 muscle relaxants
MeSH PA D018678 Cholinergic Agents
MeSH PA D018680 Cholinergic Antagonists
MeSH PA D009465 Neuromuscular Agents
MeSH PA D009466 Neuromuscular Blocking Agents
MeSH PA D003473 Neuromuscular Nondepolarizing Agents
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018733 Nicotinic Antagonists
MeSH PA D018373 Peripheral Nervous System Agents

Drug Use (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

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
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
4018778 VANDF
4019619 VANDF
C0004234 UMLSCUI
CHEBI:2914 CHEBI
CHEMBL1360 ChEMBL_ID
CHEMBL1200527 ChEMBL_ID
DB13295 DRUGBANK_ID
DB00732 DRUGBANK_ID
D001279 MESH_DESCRIPTOR_UI
47319 PUBCHEM_CID
4734 INN_ID
9537 IUPHAR_LIGAND_ID
1218 RXNORM
1341 MMSL
397 MMSL
4228 MMSL
d00173 MMSL
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 25021-659 INJECTION, SOLUTION 10 mg INTRAVENOUS ANDA 22 sections
Atracurium Besylate HUMAN PRESCRIPTION DRUG LABEL 1 25021-659 INJECTION, SOLUTION 10 mg INTRAVENOUS ANDA 22 sections
Atracurium Besylate HUMAN PRESCRIPTION DRUG LABEL 1 25021-672 INJECTION, SOLUTION 10 mg INTRAVENOUS ANDA 22 sections
Atracurium Besylate HUMAN PRESCRIPTION DRUG LABEL 1 25021-672 INJECTION, SOLUTION 10 mg INTRAVENOUS ANDA 22 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