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)

None

FDA Adverse Event Reporting System (Male)

None

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
FDA MoA N0000000183 Acetyl Aldehyde Dehydrogenase Inhibitors
FDA EPC N0000175679 Aldehyde Dehydrogenase Inhibitor
MeSH PA D000427 Alcohol Deterrents
CHEBI has role CHEBI:48422 angiogenesis inhibitor
CHEBI has role CHEBI:24127 fungicide
CHEBI has role CHEBI:35610 antineoplastic agent
MeSH PA D002491 Central Nervous System Agents
MeSH PA D004791 Enzyme 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
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
D(4) dopamine receptor GPCR Ki 5.96 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
D004221 MESH_DESCRIPTOR_UI
4018494 VUID
N0000146816 NUI
C0012772 UMLSCUI
D00131 KEGG_DRUG
2848 MMSL
3554 RXNORM
387212009 SNOMEDCT_US
4623 MMSL
d01389 MMSL
39516004 SNOMEDCT_US
4018494 VANDF
000752 NDDF
CHEBI:4659 CHEBI
CHEMBL964 ChEMBL_ID
DB00822 DRUGBANK_ID
TR3MLJ1UAI UNII
1781 INN_ID
7168 IUPHAR_LIGAND_ID
3117 PUBCHEM_CID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Disulfiram HUMAN PRESCRIPTION DRUG LABEL 1 0054-0356 TABLET 250 mg ORAL ANDA 13 sections
Disulfiram HUMAN PRESCRIPTION DRUG LABEL 1 0054-0357 TABLET 500 mg ORAL ANDA 13 sections
Disulfiram HUMAN PRESCRIPTION DRUG LABEL 1 0093-5035 TABLET 250 mg ORAL ANDA 12 sections
Disulfiram HUMAN PRESCRIPTION DRUG LABEL 1 0093-5036 TABLET 500 mg ORAL ANDA 12 sections
Disulfiram HUMAN PRESCRIPTION DRUG LABEL 1 47781-607 TABLET 250 mg ORAL ANDA 12 sections
Antabuse HUMAN PRESCRIPTION DRUG LABEL 1 51285-523 TABLET 250 mg ORAL ANDA 12 sections
Antabuse HUMAN PRESCRIPTION DRUG LABEL 1 51285-524 TABLET 500 mg ORAL ANDA 12 sections
Antabuse HUMAN PRESCRIPTION DRUG LABEL 1 54868-5034 TABLET 250 mg ORAL ANDA 12 sections
Disulfiram HUMAN PRESCRIPTION DRUG LABEL 1 60429-196 TABLET 250 mg ORAL ANDA 12 sections
Disulfiram HUMAN PRESCRIPTION DRUG LABEL 1 64980-171 TABLET 250 mg ORAL ANDA 12 sections
Disulfiram HUMAN PRESCRIPTION DRUG LABEL 1 64980-172 TABLET 500 mg ORAL ANDA 12 sections
Disulfiram HUMAN PRESCRIPTION DRUG LABEL 1 68151-2694 TABLET 250 mg ORAL ANDA 12 sections