Identification

Name
Disulfiram
Accession Number
DB00822  (APRD00767)
Type
Small Molecule
Groups
Approved
Description

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. [PubChem]

Structure
Thumb
Synonyms
  • 1,1'-dithiobis(N,N-diethylthioformamide)
  • Antabuse (tn)
  • Bis(diethylthiocarbamoyl) disulfide
  • Disulfiram
  • N,N,N',N'-tetraethylthiuram disulfide
  • Tetraethylthioperoxydicarbonic Diamide
  • Tetraethylthiuram Disulfide
  • Tetraethylthiuram Disulphide
External IDs
Dupon 4472 / Dupont Fungicide 4472 / ORA-102 / ORA102 / USAF B-33
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Antabuse Tab 0.25gmTablet250 mgOralAyerst Laboratories1966-12-311996-09-10Canada
Antabuse Tab 250mgTablet250 mgOralWyeth Ayerst Canada Inc.1994-12-312001-05-07Canada
Antabuse Tab 500mgTablet500 mgOralWyeth Ayerst Canada Inc.1994-12-312001-05-07Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AntabuseTablet250 mg/1OralPhysicians Total Care, Inc.2004-03-30Not applicableUs
AntabuseTablet250 mg/1OralTeva Women's Health2000-12-01Not applicableUs51285 0523 02 nlmimage10 2f3017d0
AntabuseTablet500 mg/1OralTeva Women's Health2006-02-01Not applicableUs51285 0524 02 nlmimage10 582f2c29
DisulfiramTablet500 mg/1OralQualitest2012-12-312016-10-26Us
DisulfiramTablet250 mg/1OralRising Pharmaceuticals2011-04-01Not applicableUs
DisulfiramTablet500 mg/1OralWest Ward Pharmaceutical2014-11-04Not applicableUs
DisulfiramTablet250 mg/1OralWest Ward Pharmaceutical2014-11-04Not applicableUs
DisulfiramTablet250 mg/1OralMylan Pharmaceuticals2015-03-04Not applicableUs
DisulfiramTablet250 mg/1OralQualitest2012-12-312016-10-26Us
DisulfiramTablet500 mg/1OralRising Pharmaceuticals2011-04-01Not applicableUs
International/Other Brands
Antabus (Actavis) / Antaethyl (Sanofi) / Antalcol (Sintofarm) / Anticol (Polfa Warszawa) / Antietanol (Sanofi) / Chronol (Charoon Bhesaj) / Esperal (Sanofi)
Categories
UNII
TR3MLJ1UAI
CAS number
97-77-8
Weight
Average: 296.539
Monoisotopic: 296.05093141
Chemical Formula
C10H20N2S4
InChI Key
AUZONCFQVSMFAP-UHFFFAOYSA-N
InChI
InChI=1S/C10H20N2S4/c1-5-11(6-2)9(13)15-16-10(14)12(7-3)8-4/h5-8H2,1-4H3
IUPAC Name
N,N-diethyl[(diethylcarbamothioyl)disulfanyl]carbothioamide
SMILES
CCN(CC)C(=S)SSC(=S)N(CC)CC

Pharmacology

Indication

For the treatment and management of chronic alcoholism

Structured Indications
Pharmacodynamics

Disulfiram produces a sensitivity to alcohol which results in a highly unpleasant reaction when the patient under treatment ingests even small amounts of alcohol. Disulfiram blocks the oxidation of alcohol at the acetaldehyde stage during alcohol metabolism following disulfiram intake, the concentration of acetaldehyde occurring in the blood may be 5 to 10 times higher than that found during metabolism of the same amount of alcohol alone. Accumulation of acetaldehyde in the blood produces a complex of highly unpleasant symptoms referred to hereinafter as the disulfiram-alcohol reaction. This reaction, which is proportional to the dosage of both disulfiram and alcohol, will persist as long as alcohol is being metabolized. Disulfiram does not appear to influence the rate of alcohol elimination from the body. Prolonged administration of disulfiram does not produce tolerance; the longer a patient remains on therapy, the more exquisitely sensitive he becomes to alcohol.

Mechanism of action

Disulfiram blocks the oxidation of alcohol at the acetaldehyde stage during alcohol metabolism following disulfiram intake causing an accumulation of acetaldehyde in the blood producing highly unpleasant symptoms. Disulfiram blocks the oxidation of alcohol through its irreversible inactivation of aldehyde dehydrogenase, which acts in the second step of ethanol utilization. In addition, disulfiram competitively binds and inhibits the peripheral benzodiazepine receptor, which may indicate some value in the treatment of the symptoms of alcohol withdrawal, however this activity has not been extensively studied.

TargetActionsOrganism
AAldehyde dehydrogenase, mitochondrial
inhibitor
Human
ADopamine beta-hydroxylase
inhibitor
Human
Absorption

Disulfiram is absorbed slowly from the gastrointestinal tract (80 to 90% of oral dose).

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

Hepatic.

Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity

LD50=8.6g/kg (orally in rats). Symptoms of overdose include irritation, slight drowsiness, unpleasant taste, mild GI disturbances, and orthostatic hypotension.

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Disulfiram Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcenocoumarolThe serum concentration of Acenocoumarol can be increased when it is combined with Disulfiram.Approved
Ambroxol acefyllinateThe serum concentration of Ambroxol acefyllinate can be increased when it is combined with Disulfiram.Experimental, Investigational
AminophyllineThe serum concentration of Aminophylline can be increased when it is combined with Disulfiram.Approved
AmiodaroneThe metabolism of Disulfiram can be decreased when combined with Amiodarone.Approved, Investigational
AprepitantThe serum concentration of Disulfiram can be increased when it is combined with Aprepitant.Approved, Investigational
AtazanavirThe therapeutic efficacy of Disulfiram can be decreased when used in combination with Atazanavir.Approved, Investigational
AtomoxetineThe metabolism of Disulfiram can be decreased when combined with Atomoxetine.Approved
BoceprevirThe metabolism of Disulfiram can be decreased when combined with Boceprevir.Approved, Withdrawn
BortezomibThe metabolism of Disulfiram can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Disulfiram can be decreased when it is combined with Bosentan.Approved, Investigational
CarbamazepineThe metabolism of Disulfiram can be increased when combined with Carbamazepine.Approved, Investigational
CarbocisteineThe risk or severity of adverse effects can be increased when Disulfiram is combined with Carbocisteine.Approved, Investigational
CeritinibThe serum concentration of Disulfiram can be increased when it is combined with Ceritinib.Approved
ChlordiazepoxideThe serum concentration of Chlordiazepoxide can be increased when it is combined with Disulfiram.Approved, Illicit
ChlorzoxazoneThe metabolism of Chlorzoxazone can be decreased when combined with Disulfiram.Approved
ClarithromycinThe metabolism of Disulfiram can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Disulfiram can be decreased when combined with Clemastine.Approved
ClorindioneThe serum concentration of Clorindione can be increased when it is combined with Disulfiram.Experimental
ClotrimazoleThe metabolism of Disulfiram can be decreased when combined with Clotrimazole.Approved, Vet Approved
CobicistatThe metabolism of Disulfiram can be decreased when combined with Cobicistat.Approved
ConivaptanThe serum concentration of Disulfiram can be increased when it is combined with Conivaptan.Approved, Investigational
CrizotinibThe metabolism of Disulfiram can be decreased when combined with Crizotinib.Approved
CyclosporineThe metabolism of Disulfiram can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
DabrafenibThe serum concentration of Disulfiram can be decreased when it is combined with Dabrafenib.Approved
DarunavirThe metabolism of Disulfiram can be decreased when combined with Darunavir.Approved
DasatinibThe serum concentration of Disulfiram can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Disulfiram can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Disulfiram can be decreased when combined with Delavirdine.Approved
DiazepamThe serum concentration of Diazepam can be increased when it is combined with Disulfiram.Approved, Illicit, Vet Approved
DicoumarolThe serum concentration of Dicoumarol can be increased when it is combined with Disulfiram.Approved
DihydroergotamineThe metabolism of Disulfiram can be decreased when combined with Dihydroergotamine.Approved
DiltiazemThe metabolism of Disulfiram can be decreased when combined with Diltiazem.Approved
DiphenadioneThe serum concentration of Diphenadione can be increased when it is combined with Disulfiram.Experimental
DoxycyclineThe metabolism of Disulfiram can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Disulfiram can be decreased when combined with Dronedarone.Approved
DyphyllineThe serum concentration of Dyphylline can be increased when it is combined with Disulfiram.Approved
EnzalutamideThe serum concentration of Disulfiram can be decreased when it is combined with Enzalutamide.Approved
ErythromycinThe metabolism of Disulfiram can be decreased when combined with Erythromycin.Approved, Vet Approved
EthanolThe risk or severity of adverse effects can be increased when Disulfiram is combined with Ethanol.Approved
Ethyl biscoumacetateThe serum concentration of Ethyl biscoumacetate can be increased when it is combined with Disulfiram.Withdrawn
FesoterodineThe serum concentration of the active metabolites of Fesoterodine can be increased when Fesoterodine is used in combination with Disulfiram.Approved
FluconazoleThe metabolism of Disulfiram can be decreased when combined with Fluconazole.Approved
FluindioneThe serum concentration of Fluindione can be increased when it is combined with Disulfiram.Investigational
FluvoxamineThe metabolism of Disulfiram can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe metabolism of Disulfiram can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Disulfiram can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe serum concentration of Fosphenytoin can be increased when it is combined with Disulfiram.Approved
Fusidic AcidThe serum concentration of Disulfiram can be increased when it is combined with Fusidic Acid.Approved
IdelalisibThe serum concentration of Disulfiram can be increased when it is combined with Idelalisib.Approved
ImatinibThe metabolism of Disulfiram can be decreased when combined with Imatinib.Approved
IndinavirThe metabolism of Disulfiram can be decreased when combined with Indinavir.Approved
IsavuconazoniumThe metabolism of Disulfiram can be decreased when combined with Isavuconazonium.Approved, Investigational
IsoniazidThe risk or severity of adverse effects can be increased when Disulfiram is combined with Isoniazid.Approved
IsradipineThe metabolism of Disulfiram can be decreased when combined with Isradipine.Approved
ItraconazoleThe metabolism of Disulfiram can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Disulfiram can be increased when it is combined with Ivacaftor.Approved
KetoconazoleThe metabolism of Disulfiram can be decreased when combined with Ketoconazole.Approved, Investigational
LopinavirThe risk or severity of adverse effects can be increased when Lopinavir is combined with Disulfiram.Approved
LovastatinThe metabolism of Disulfiram can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Disulfiram can be increased when it is combined with Luliconazole.Approved
LumacaftorThe metabolism of Disulfiram can be increased when combined with Lumacaftor.Approved
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Disulfiram.Approved, Investigational
MetronidazoleThe risk or severity of adverse effects can be increased when Metronidazole is combined with Disulfiram.Approved
MifepristoneThe serum concentration of Disulfiram can be increased when it is combined with Mifepristone.Approved, Investigational
MitotaneThe serum concentration of Disulfiram can be decreased when it is combined with Mitotane.Approved
NefazodoneThe metabolism of Disulfiram can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Disulfiram can be decreased when combined with Nelfinavir.Approved
NetupitantThe serum concentration of Disulfiram can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Disulfiram can be increased when combined with Nevirapine.Approved
NilotinibThe metabolism of Disulfiram can be decreased when combined with Nilotinib.Approved, Investigational
OlaparibThe metabolism of Disulfiram can be decreased when combined with Olaparib.Approved
OsimertinibThe serum concentration of Disulfiram can be increased when it is combined with Osimertinib.Approved
PalbociclibThe serum concentration of Disulfiram can be increased when it is combined with Palbociclib.Approved
ParaldehydeThe serum concentration of Paraldehyde can be increased when it is combined with Disulfiram.Approved, Investigational
PentobarbitalThe metabolism of Disulfiram can be increased when combined with Pentobarbital.Approved, Vet Approved
PhenindioneThe serum concentration of Phenindione can be increased when it is combined with Disulfiram.Approved, Investigational
PhenobarbitalThe metabolism of Disulfiram can be increased when combined with Phenobarbital.Approved
PhenprocoumonThe serum concentration of Phenprocoumon can be increased when it is combined with Disulfiram.Approved, Investigational
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Disulfiram.Approved, Vet Approved
PosaconazoleThe metabolism of Disulfiram can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PrimidoneThe metabolism of Disulfiram can be increased when combined with Primidone.Approved, Vet Approved
RanolazineThe metabolism of Disulfiram can be decreased when combined with Ranolazine.Approved, Investigational
RifabutinThe metabolism of Disulfiram can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Disulfiram can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Disulfiram can be increased when combined with Rifapentine.Approved
RitonavirThe risk or severity of adverse effects can be increased when Ritonavir is combined with Disulfiram.Approved, Investigational
SaquinavirThe metabolism of Disulfiram can be decreased when combined with Saquinavir.Approved, Investigational
SertralineThe risk or severity of adverse effects can be increased when Disulfiram is combined with Sertraline.Approved
SildenafilThe metabolism of Disulfiram can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Disulfiram can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Disulfiram can be increased when it is combined with Simeprevir.Approved
St. John's WortThe serum concentration of Disulfiram can be decreased when it is combined with St. John's Wort.Investigational, Nutraceutical
StiripentolThe serum concentration of Disulfiram can be increased when it is combined with Stiripentol.Approved
SulfisoxazoleThe metabolism of Disulfiram can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
TelaprevirThe metabolism of Disulfiram can be decreased when combined with Telaprevir.Approved, Withdrawn
TelithromycinThe metabolism of Disulfiram can be decreased when combined with Telithromycin.Approved
TheophyllineThe serum concentration of Theophylline can be increased when it is combined with Disulfiram.Approved
ThioridazineThe serum concentration of Thioridazine can be increased when it is combined with Disulfiram.Approved, Withdrawn
TiclopidineThe metabolism of Disulfiram can be decreased when combined with Ticlopidine.Approved
TinidazoleThe risk or severity of adverse effects can be increased when Tinidazole is combined with Disulfiram.Approved, Investigational
TioclomarolThe serum concentration of Tioclomarol can be increased when it is combined with Disulfiram.Experimental
TipranavirThe risk or severity of adverse effects can be increased when Disulfiram is combined with Tipranavir.Approved, Investigational
TizanidineThe serum concentration of Tizanidine can be increased when it is combined with Disulfiram.Approved
TocilizumabThe serum concentration of Disulfiram can be decreased when it is combined with Tocilizumab.Approved
VenlafaxineThe metabolism of Disulfiram can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Disulfiram can be decreased when combined with Verapamil.Approved
VoriconazoleThe metabolism of Disulfiram can be decreased when combined with Voriconazole.Approved, Investigational
WarfarinThe serum concentration of Warfarin can be increased when it is combined with Disulfiram.Approved
ZiprasidoneThe metabolism of Disulfiram can be decreased when combined with Ziprasidone.Approved
Food Interactions
  • Avoid alcohol for up to 14 days after treatment has been stopped.
  • Take without regard to meals.

References

Synthesis Reference

Adams, H.S. and Meuser, L.; US.Patent 1,782,111; November 18,1930; assigned to The Naugatuck Chemical Company. Bailey, G.C.; U.S.Patent 1,796,977; March 17,1931; assigned to The Roessler & Hasslacher Chemical Company.

General References
  1. Nash T, Rice WG: Efficacies of zinc-finger-active drugs against Giardia lamblia. Antimicrob Agents Chemother. 1998 Jun;42(6):1488-92. [PubMed:9624499]
  2. Bouma MJ, Snowdon D, Fairlamb AH, Ackers JP: Activity of disulfiram (bis(diethylthiocarbamoyl)disulphide) and ditiocarb (diethyldithiocarbamate) against metronidazole-sensitive and -resistant Trichomonas vaginalis and Tritrichomonas foetus. J Antimicrob Chemother. 1998 Dec;42(6):817-20. [PubMed:10052908]
  3. Gaval-Cruz M, Weinshenker D: mechanisms of disulfiram-induced cocaine abstinence: antabuse and cocaine relapse. Mol Interv. 2009 Aug;9(4):175-87. doi: 10.1124/mi.9.4.6. [PubMed:19720750]
External Links
Human Metabolome Database
HMDB14960
KEGG Drug
D00131
KEGG Compound
C01692
PubChem Compound
3117
PubChem Substance
46506008
ChemSpider
3005
BindingDB
50058655
ChEBI
4659
ChEMBL
CHEMBL964
Therapeutic Targets Database
DAP000012
PharmGKB
PA449376
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Disulfiram
ATC Codes
P03AA54 — Disulfiram, combinationsP03AA04 — DisulfiramN07BB01 — Disulfiram
MSDS
Download (50.6 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Active Not RecruitingTreatmentGlioblastomas1
0Not Yet RecruitingOtherGlioblastomas1
1CompletedNot AvailableDrug Abuse / Human Immunodeficiency Virus (HIV) Infections1
1CompletedTreatmentCancers1
1CompletedTreatmentCocaine Abuse1
1RecruitingTreatmentGlioblastomas1
1RecruitingTreatmentPancreatic Adenocarcinoma Metastatic / Recurrent Pancreatic Carcinoma / Solid Neoplasms / Stage IV Pancreatic Cancer1
1RecruitingTreatmentProstate Cancer1
1Unknown StatusTreatmentAlcohol-Related Disorders / Cocaine-Related Disorders1
1, 2CompletedBasic ScienceHuman Immunodeficiency Virus (HIV)1
1, 2CompletedTreatmentMethamphetamine Dependence1
1, 2CompletedTreatmentStage IV Melanoma1
1, 2RecruitingTreatmentGlioblastoma Multiforme1
1, 2TerminatedBasic ScienceDependence, Cocaine1
1, 2TerminatedTreatmentMetastatic Melanoma1
2CompletedTreatmentAlcohol-Related Disorders / Alcoholism / Cocaine-Related Disorders1
2CompletedTreatmentAlcohol-Related Disorders / Cocaine-Related Disorders1
2CompletedTreatmentCocaine-Related Disorders / Opioid-Related Disorders1
2CompletedTreatmentDependence, Cocaine1
2CompletedTreatmentDependence, Cocaine / Opioid Dependence1
2CompletedTreatmentDependence, Cocaine / Opioid Dependency1
2CompletedTreatmentMelanoma1
2Not Yet RecruitingTreatmentGlioblastoma Multiforme1
2RecruitingTreatmentBreast Neoplasm Female / Metastatic Breast Cancer (MBC)1
2RecruitingTreatmentRecurrent Glioblastoma1
2, 3RecruitingTreatmentGlioblastomas / Gliomas1
4CompletedTreatmentAlcohol Dependence1
4RecruitingBasic ScienceAlcohol Use Disorder (AUD)1
4Unknown StatusTreatmentAlcoholism1
4WithdrawnTreatmentDependence, Cocaine1
Not AvailableCompletedNot AvailableInfection, Human Immunodeficiency Virus I1
Not AvailableCompletedTreatmentCocaine-Related Disorders / Opiate Dependence1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedTreatmentProstate Cancer1

Pharmacoeconomics

Manufacturers
  • Odyssey pharmaceuticals inc
  • Par pharmaceutical inc
  • Watson laboratories inc
Packagers
Dosage forms
FormRouteStrength
TabletOral250 mg
TabletOral500 mg
TabletOral250 mg/1
TabletOral500 mg/1
Prices
Unit descriptionCostUnit
Antabuse 500 mg tablet6.65USD tablet
Antabuse 250 mg tablet4.24USD tablet
Disulfiram powder1.92USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)71.5 °CPhysProp
boiling point (°C)117 °C at 1.70E+01 mm HgPhysProp
water solubility4.09 mg/L (at 25 °C)YALKOWSKY,SH & HE,Y (2003)
logP3.88HANSCH,C ET AL. (1995)
logS-4.86ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility0.0126 mg/mLALOGPS
logP3.88ALOGPS
logP4.16ChemAxon
logS-4.4ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area6.48 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity88.24 m3·mol-1ChemAxon
Polarizability31.6 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9808
Blood Brain Barrier+0.9668
Caco-2 permeable+0.548
P-glycoprotein substrateNon-substrate0.71
P-glycoprotein inhibitor INon-inhibitor0.8236
P-glycoprotein inhibitor IINon-inhibitor0.9884
Renal organic cation transporterNon-inhibitor0.8379
CYP450 2C9 substrateNon-substrate0.8497
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.7558
CYP450 1A2 substrateInhibitor0.9106
CYP450 2C9 inhibitorInhibitor0.8948
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorInhibitor0.8994
CYP450 3A4 inhibitorInhibitor0.796
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5397
Ames testNon AMES toxic0.9132
CarcinogenicityCarcinogens 0.6989
BiodegradationNot ready biodegradable0.9767
Rat acute toxicity2.7419 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8617
hERG inhibition (predictor II)Non-inhibitor0.8823
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (8.65 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-014r-9510000000-2e18f478f9c0f9a2958a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00xr-0904000000-2d29367629d096da4708
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00xr-1914000000-0022574151f222c8050f
MS/MS Spectrum - , positiveLC-MS/MSsplash10-014j-0900000000-07fd862cac7fb47fa007
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00di-0903000000-bb7b2b338b8981b249ac
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00kb-3910100000-263484085094fbdd45da
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as thiuram disulfides. These are organic disulfides that have the general structural formula RN(R')C(=S)SSC(=S)N(R\")R\"', where R-R\"'=alkyl groups.
Kingdom
Organic compounds
Super Class
Organic nitrogen compounds
Class
Organonitrogen compounds
Sub Class
Amines
Direct Parent
Thiuram disulfides
Alternative Parents
Organic disulfides / Sulfenyl compounds / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Thiuram disulfide / Organic disulfide / Sulfenyl compound / Organopnictogen compound / Hydrocarbon derivative / Organosulfur compound / Aliphatic acyclic compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
tertiary amino compound, organic disulfide (CHEBI:4659) / a small molecule (DISULFIRAM)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Electron carrier activity
Specific Function
Not Available
Gene Name
ALDH2
Uniprot ID
P05091
Uniprot Name
Aldehyde dehydrogenase, mitochondrial
Molecular Weight
56380.93 Da
References
  1. Mackenzie IS, Maki-Petaja KM, McEniery CM, Bao YP, Wallace SM, Cheriyan J, Monteith S, Brown MJ, Wilkinson IB: Aldehyde dehydrogenase 2 plays a role in the bioactivation of nitroglycerin in humans. Arterioscler Thromb Vasc Biol. 2005 Sep;25(9):1891-5. Epub 2005 Jul 28. [PubMed:16051882]
  2. Ho MP, Yo CH, Liu CM, Chen CL, Lee CC: Refractive hypotension in a patient with disulfiram-ethanol reaction. Am J Med Sci. 2007 Jan;333(1):53-5. [PubMed:17220694]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
L-ascorbic acid binding
Specific Function
Conversion of dopamine to noradrenaline.
Gene Name
DBH
Uniprot ID
P09172
Uniprot Name
Dopamine beta-hydroxylase
Molecular Weight
69064.45 Da
References
  1. Gaval-Cruz M, Weinshenker D: mechanisms of disulfiram-induced cocaine abstinence: antabuse and cocaine relapse. Mol Interv. 2009 Aug;9(4):175-87. doi: 10.1124/mi.9.4.6. [PubMed:19720750]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
Gene Name
CYP2E1
Uniprot ID
P05181
Uniprot Name
Cytochrome P450 2E1
Molecular Weight
56848.42 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da

Drug created on June 13, 2005 07:24 / Updated on November 07, 2017 01:43