disulfiram Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
928 97-77-8

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • disulfiram
  • tetraethylthiram disulfide
A carbamate derivative used as an alcohol deterrent. It is a relatively nontoxic substance when administered alone, but markedly alters the intermediary metabolism of alcohol. When alcohol is ingested after administration of disulfiram, blood acetaldehyde concentrations are increased, followed by flushing, systemic vasodilation, respiratory difficulties, nausea, hypotension, and other symptoms (acetaldehyde syndrome). It acts by inhibiting aldehyde dehydrogenase.
  • Molecular weight: 296.52
  • Formula: C10H20N2S4
  • CLOGP: 3.88
  • LIPINSKI: 0
  • HAC: 2
  • HDO: 0
  • TPSA: 6.48
  • ALOGS: -4.37
  • ROTB: 7

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.20 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.20 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 24.09 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 80 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
Aug. 28, 1951 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
Intentional self-injury 108.17 34.50 34 1002 24132 46660894
Drug interaction 45.92 34.50 37 999 203057 46481969
Drug abuse 42.90 34.50 23 1013 63385 46621641
Suicide attempt 34.52 34.50 19 1017 55017 46630009

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
Milk-alkali syndrome 115.57 30.22 21 1741 518 29950198
Alcohol intolerance 99.92 30.22 18 1744 422 29950294
Drug abuse 65.30 30.22 47 1715 82025 29868691
Metabolic alkalosis 48.57 30.22 12 1750 1312 29949404
Hypertonia neonatal 45.41 30.22 9 1753 355 29950361
Hypercalcaemia 43.62 30.22 19 1743 12476 29938240
Sopor 42.61 30.22 18 1744 10973 29939743
Intentional overdose 38.12 30.22 26 1736 41455 29909261
Drug interaction 37.60 30.22 52 1710 199516 29751200
Agitation neonatal 36.13 30.22 9 1753 1016 29949700
Intentional self-injury 35.91 30.22 17 1745 13515 29937201
Alcohol interaction 35.64 30.22 11 1751 2731 29947985
Psychotic disorder 33.82 30.22 19 1743 21496 29929220
Alcoholism 33.27 30.22 11 1751 3403 29947313
Depressed level of consciousness 32.85 30.22 23 1739 38199 29912517

Pharmacologic Action:

SourceCodeDescription
ATC N07BB01 NERVOUS SYSTEM
OTHER NERVOUS SYSTEM DRUGS
DRUGS USED IN ADDICTIVE DISORDERS
Drugs used in alcohol dependence
ATC P03AA04 ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
ECTOPARASITICIDES, INCL. SCABICIDES, INSECTICIDES AND REPELLENTS
ECTOPARASITICIDES, INCL. SCABICIDES
Sulfur containing products
ATC P03AA54 ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
ECTOPARASITICIDES, INCL. SCABICIDES, INSECTICIDES AND REPELLENTS
ECTOPARASITICIDES, INCL. SCABICIDES
Sulfur containing products
MeSH PA D065086 Acetaldehyde Dehydrogenase Inhibitors
MeSH PA D000427 Alcohol Deterrents
MeSH PA D002491 Central Nervous System Agents
MeSH PA D004791 Enzyme Inhibitors
FDA MoA N0000000183 Acetyl Aldehyde Dehydrogenase Inhibitors
FDA EPC N0000175679 Aldehyde Dehydrogenase Inhibitor
CHEBI has role CHEBI:24127 fungicides
CHEBI has role CHEBI:35487 nad-dependent 4-hydroxynonenal dehydrogenase inhibitors
CHEBI has role CHEBI:35610 cytostatic
CHEBI has role CHEBI:37733 bche inhibitor
CHEBI has role CHEBI:48422 angiostatic agents
CHEBI has role CHEBI:50276 topoisomerase i inhibitors
CHEBI has role CHEBI:68495 type i programmed cell-death inducer
CHEBI has role CHEBI:73240 nuclear factor kappa-light-chain-enhancer of activated b cells inhibitors
CHEBI has role CHEBI:78444 carboxylic esterase inhibitors

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Alcoholism indication 7200002
Cirrhosis of liver contraindication 19943007 DOID:5082
Chronic glomerulonephritis contraindication 20917003
Alcohol intoxication contraindication 25702006
Hypothyroidism contraindication 40930008 DOID:1459
Conduction disorder of the heart contraindication 44808001
Chronic heart failure contraindication 48447003
Nephritis contraindication 52845002 DOID:10952
Coronary arteriosclerosis contraindication 53741008 DOID:3393
Psychotic disorder contraindication 69322001
Diabetes mellitus contraindication 73211009 DOID:9351
Epilepsy contraindication 84757009 DOID:1826
Disease of liver contraindication 235856003 DOID:409
Cognitive Impairment following Traumatic Brain Injury contraindication

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
Aldehyde dehydrogenase, mitochondrial Enzyme INHIBITOR WOMBAT-PK CHEMBL
D(4) dopamine receptor GPCR Ki 5.96 DRUG MATRIX
Mu-type opioid receptor GPCR Ki 5.85 DRUG MATRIX
D(1A) dopamine receptor GPCR Ki 5.97 DRUG MATRIX
D(2) dopamine receptor GPCR Ki 5.12 DRUG MATRIX
Alpha-2A adrenergic receptor GPCR Ki 5.74 DRUG MATRIX
Sodium-dependent noradrenaline transporter Transporter Ki 4.16 DRUG MATRIX
5-hydroxytryptamine receptor 2B GPCR Ki 4.66 DRUG MATRIX
5-hydroxytryptamine receptor 6 GPCR Ki 5.13 DRUG MATRIX
Alpha-2B adrenergic receptor GPCR Ki 5.83 DRUG MATRIX
D(3) dopamine receptor GPCR Ki 6.43 DRUG MATRIX
Sodium-dependent dopamine transporter Transporter Ki 5.43 DRUG MATRIX
Adenosine receptor A3 GPCR Ki 6.70 DRUG MATRIX
Kappa-type opioid receptor GPCR Ki 5.61 DRUG MATRIX
Cytochrome P450 1A2 Enzyme IC50 5.40 DRUG MATRIX
Amine oxidase [flavin-containing] A Enzyme IC50 4.86 DRUG MATRIX
cAMP-specific 3',5'-cyclic phosphodiesterase 4A Enzyme IC50 5.32 DRUG MATRIX
C-C chemokine receptor type 5 GPCR Ki 4.74 DRUG MATRIX
C-X-C chemokine receptor type 2 GPCR Ki 5.38 DRUG MATRIX
C-C chemokine receptor type 2 GPCR Ki 6.02 DRUG MATRIX
Mitogen-activated protein kinase 3 Kinase IC50 5.82 DRUG MATRIX
Sodium/nucleoside cotransporter 1 Transporter Ki 5.24 DRUG MATRIX
C-C chemokine receptor type 4 GPCR Ki 5.36 DRUG MATRIX
Monoglyceride lipase Enzyme IC50 5.90 CHEMBL
Translocator protein Transporter WOMBAT-PK
Arachidonate 15-lipoxygenase Enzyme IC50 4.79 DRUG MATRIX
5-hydroxytryptamine receptor 1B GPCR Ki 5.67 DRUG MATRIX
Membrane-associated progesterone receptor component 1 Membrane receptor Ki 4.33 DRUG MATRIX
Aldehyde dehydrogenase, mitochondrial Enzyme IC50 4.40 CHEMBL
Bifunctional protein GlmU Unclassified IC50 4.07 CHEMBL

External reference:

IDSource
4018494 VUID
N0000146816 NUI
D00131 KEGG_DRUG
4018494 VANDF
C0012772 UMLSCUI
CHEBI:4659 CHEBI
CHEMBL964 ChEMBL_ID
DB00822 DRUGBANK_ID
D004221 MESH_DESCRIPTOR_UI
3117 PUBCHEM_CID
7168 IUPHAR_LIGAND_ID
1781 INN_ID
TR3MLJ1UAI UNII
3554 RXNORM
2848 MMSL
4623 MMSL
d01389 MMSL
000752 NDDF
387212009 SNOMEDCT_US
39516004 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Disulfiram HUMAN PRESCRIPTION DRUG LABEL 1 0054-0356 TABLET 250 mg ORAL ANDA 17 sections
Disulfiram HUMAN PRESCRIPTION DRUG LABEL 1 0054-0357 TABLET 500 mg ORAL ANDA 17 sections
Disulfiram HUMAN PRESCRIPTION DRUG LABEL 1 0093-5035 TABLET 250 mg ORAL ANDA 18 sections
Disulfiram HUMAN PRESCRIPTION DRUG LABEL 1 0093-5036 TABLET 500 mg ORAL ANDA 18 sections
Disulfiram HUMAN PRESCRIPTION DRUG LABEL 1 47781-607 TABLET 250 mg ORAL ANDA 18 sections
Antabuse HUMAN PRESCRIPTION DRUG LABEL 1 51285-523 TABLET 250 mg ORAL ANDA 18 sections
Antabuse HUMAN PRESCRIPTION DRUG LABEL 1 51285-524 TABLET 500 mg ORAL ANDA 18 sections
Antabuse HUMAN PRESCRIPTION DRUG LABEL 1 54868-5034 TABLET 250 mg ORAL ANDA 18 sections
Disulfiram HUMAN PRESCRIPTION DRUG LABEL 1 60429-196 TABLET 250 mg ORAL ANDA 17 sections
Disulfiram HUMAN PRESCRIPTION DRUG LABEL 1 64980-171 TABLET 250 mg ORAL ANDA 17 sections
Disulfiram HUMAN PRESCRIPTION DRUG LABEL 1 64980-172 TABLET 500 mg ORAL ANDA 17 sections
Disulfiram HUMAN PRESCRIPTION DRUG LABEL 1 68151-2694 TABLET 250 mg ORAL ANDA 17 sections