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Identification
NameDisulfiram
Accession NumberDB00822  (APRD00767)
TypeSmall Molecule
GroupsApproved
DescriptionA 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 Identifiers
  • Dupon 4472
  • Dupont Fungicide 4472
  • USAF B-33
Approved 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
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AntabuseTablet250 mg/1OralTeva Women's Health, Inc.2000-12-01Not applicableUs
AntabuseTablet250 mg/1OralPhysicians Total Care, Inc.2004-03-30Not applicableUs
AntabuseTablet500 mg/1OralTeva Women's Health, Inc.2006-02-01Not applicableUs
DisulfiramTablet250 mg/1OralCarilion Materials Management2011-04-01Not applicableUs
DisulfiramTablet250 mg/1OralMylan Pharmaceuticals Inc.2015-03-04Not applicableUs
DisulfiramTablet500 mg/1OralRising Pharmaceuticals, Inc.2011-04-01Not applicableUs
DisulfiramTablet500 mg/1OralTeva Pharmaceuticals USA Inc2011-07-19Not applicableUs
DisulfiramTablet250 mg/1OralAlvogen Inc.2012-08-31Not applicableUs
DisulfiramTablet250 mg/1OralWest Ward Pharmaceuticals Corp.2014-11-04Not applicableUs
DisulfiramTablet500 mg/1OralMylan Pharmaceuticals Inc.2015-03-04Not applicableUs
DisulfiramTablet500 mg/1OralWest Ward Pharmaceuticals Corp.2014-11-04Not applicableUs
DisulfiramTablet500 mg/1OralQualitest Pharmaceuticals2012-12-312016-10-26Us
DisulfiramTablet250 mg/1OralGolden State Medical Supply, Inc.2013-09-11Not applicableUs
DisulfiramTablet250 mg/1OralTeva Pharmaceuticals USA Inc2011-04-15Not applicableUs
DisulfiramTablet250 mg/1OralQualitest Pharmaceuticals2012-12-312016-10-26Us
DisulfiramTablet250 mg/1OralRising Pharmaceuticals, Inc.2011-04-01Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AntabusActavis
AntaethylSanofi
AntalcolSintofarm
AnticolPolfa Warszawa
AntietanolSanofi
ChronolCharoon Bhesaj
EsperalSanofi
Brand mixturesNot Available
SaltsNot Available
Categories
UNIITR3MLJ1UAI
CAS number97-77-8
WeightAverage: 296.539
Monoisotopic: 296.05093141
Chemical FormulaC10H20N2S4
InChI KeyAUZONCFQVSMFAP-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
IndicationFor the treatment and management of chronic alcoholism
Structured Indications
PharmacodynamicsDisulfiram 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 actionDisulfiram 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.
TargetKindPharmacological actionActionsOrganismUniProt ID
Aldehyde dehydrogenase, mitochondrialProteinyes
inhibitor
HumanP05091 details
Dopamine beta-hydroxylaseProteinyes
inhibitor
HumanP09172 details
Related Articles
AbsorptionDisulfiram is absorbed slowly from the gastrointestinal tract (80 to 90% of oral dose).
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic.

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityLD50=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
PathwayCategorySMPDB ID
Disulfiram Action PathwayDrug actionSMP00429
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
AcenocoumarolThe serum concentration of Acenocoumarol can be increased when it is combined with Disulfiram.Approved
AcetaminophenThe metabolism of Acetaminophen can be decreased when combined with Disulfiram.Approved
AlmotriptanThe metabolism of Almotriptan can be decreased when combined with Disulfiram.Approved, Investigational
Ambroxol acefyllinateThe serum concentration of Ambroxol acefyllinate can be increased when it is combined with Disulfiram.Experimental
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
AmitriptylineThe metabolism of Amitriptyline can be decreased when combined with Disulfiram.Approved
AnilineThe metabolism of Aniline can be decreased when combined with Disulfiram.Experimental
AntipyrineThe metabolism of Antipyrine can be decreased when combined with Disulfiram.Approved
AprepitantThe serum concentration of Disulfiram can be increased when it is combined with Aprepitant.Approved, Investigational
AripiprazoleThe serum concentration of Aripiprazole can be increased when it is combined with Disulfiram.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
Benzyl alcoholThe metabolism of Benzyl alcohol can be decreased when combined with Disulfiram.Approved
BexaroteneThe serum concentration of Disulfiram can be decreased when it is combined with Bexarotene.Approved, Investigational
BoceprevirThe metabolism of Disulfiram can be decreased when combined with Boceprevir.Approved
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
BrompheniramineThe metabolism of Brompheniramine can be decreased when combined with Disulfiram.Approved
BupropionThe metabolism of Bupropion can be decreased when combined with Disulfiram.Approved
CaffeineThe metabolism of Caffeine can be decreased when combined with Disulfiram.Approved
CapsaicinThe metabolism of Capsaicin can be decreased when combined with Disulfiram.Approved
CarbamazepineThe metabolism of Disulfiram can be increased when combined with Carbamazepine.Approved, Investigational
CarbinoxamineThe metabolism of Carbinoxamine can be decreased when combined with Disulfiram.Approved
CarbocisteineThe risk or severity of adverse effects can be increased when Disulfiram is combined with Carbocisteine.Approved
CarvedilolThe metabolism of Carvedilol can be decreased when combined with Disulfiram.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
CitalopramThe metabolism of Citalopram 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
ClevidipineThe metabolism of Clevidipine can be decreased when combined with Disulfiram.Approved
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
DacarbazineThe metabolism of Dacarbazine can be decreased when combined with Disulfiram.Approved, Investigational
DalfampridineThe metabolism of Dalfampridine can be decreased when combined with Disulfiram.Approved
DapsoneThe metabolism of Dapsone can be decreased when combined with Disulfiram.Approved, Investigational
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
DexamethasoneThe serum concentration of Disulfiram can be decreased when it is combined with Dexamethasone.Approved, Investigational, Vet Approved
DexmedetomidineThe metabolism of Dexmedetomidine can be decreased when combined with Disulfiram.Approved, Vet Approved
DextromethorphanThe metabolism of Dextromethorphan can be decreased when combined with Disulfiram.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
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
EfavirenzThe serum concentration of Disulfiram can be decreased when it is combined with Efavirenz.Approved, Investigational
EnfluraneThe metabolism of Enflurane can be decreased when combined with Disulfiram.Approved, Vet Approved
EnfuvirtideThe metabolism of Enfuvirtide can be decreased when combined with Disulfiram.Approved, Investigational
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
Eslicarbazepine acetateThe serum concentration of Disulfiram can be decreased when it is combined with Eslicarbazepine acetate.Approved
EstroneThe metabolism of Estrone can be decreased when combined with Disulfiram.Approved
EthanolThe risk or severity of adverse effects can be increased when Disulfiram is combined with Ethanol.Approved
Ethanolamine OleateThe metabolism of Ethanolamine Oleate can be decreased when combined with Disulfiram.Approved
EthosuximideThe metabolism of Ethosuximide can be decreased when combined with Disulfiram.Approved
Ethyl biscoumacetateThe serum concentration of Ethyl biscoumacetate can be increased when it is combined with Disulfiram.Withdrawn
EtoposideThe metabolism of Etoposide can be decreased when combined with Disulfiram.Approved
EtravirineThe serum concentration of Disulfiram can be decreased when it is combined with Etravirine.Approved
FelbamateThe metabolism of Felbamate can be decreased when combined with Disulfiram.Approved
FingolimodThe metabolism of Fingolimod can be decreased when combined with Disulfiram.Approved, Investigational
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 Fluvoxamine can be decreased when combined with Disulfiram.Approved, Investigational
Folic AcidThe metabolism of Folic Acid can be decreased when combined with Disulfiram.Approved, Nutraceutical, Vet Approved
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
GlucosamineThe metabolism of Glucosamine can be decreased when combined with Disulfiram.Approved
HalothaneThe metabolism of Halothane can be decreased when combined with Disulfiram.Approved, Vet Approved
IdelalisibThe serum concentration of Disulfiram can be increased when it is combined with Idelalisib.Approved
IloperidoneThe metabolism of Iloperidone can be decreased when combined with Disulfiram.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
IsofluraneThe metabolism of Isoflurane can be decreased when combined with Disulfiram.Approved, Vet Approved
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
MenadioneThe metabolism of Menadione can be decreased when combined with Disulfiram.Approved, Nutraceutical
MeprobamateThe metabolism of Meprobamate can be decreased when combined with Disulfiram.Approved, Illicit
MethoxyfluraneThe metabolism of Methoxyflurane can be decreased when combined with Disulfiram.Approved, Vet Approved
MetronidazoleThe risk or severity of adverse effects can be increased when Disulfiram is combined with Metronidazole.Approved
MexiletineThe metabolism of Mexiletine can be decreased when 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
MitoxantroneThe metabolism of Mitoxantrone can be decreased when combined with Disulfiram.Approved, Investigational
ModafinilThe serum concentration of Disulfiram can be decreased when it is combined with Modafinil.Approved, Investigational
NafcillinThe serum concentration of Disulfiram can be decreased when it is combined with Nafcillin.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
NicardipineThe metabolism of Nicardipine can be decreased when combined with Disulfiram.Approved
NicotineThe metabolism of Nicotine can be decreased when combined with Disulfiram.Approved
NilotinibThe metabolism of Disulfiram can be decreased when combined with Nilotinib.Approved, Investigational
NilvadipineThe metabolism of Nilvadipine can be decreased when combined with Disulfiram.Approved
OlaparibThe metabolism of Disulfiram can be decreased when combined with Olaparib.Approved
OndansetronThe metabolism of Ondansetron can be decreased when combined with Disulfiram.Approved
OsimertinibThe serum concentration of Disulfiram can be increased when it is combined with Osimertinib.Approved
OxaliplatinThe metabolism of Oxaliplatin can be decreased when combined with Disulfiram.Approved, Investigational
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
ParamethadioneThe metabolism of Paramethadione can be decreased when combined with Disulfiram.Approved
PentobarbitalThe metabolism of Disulfiram can be increased when combined with Pentobarbital.Approved, Vet Approved
PhenacetinThe metabolism of Phenacetin can be decreased when combined with Disulfiram.Withdrawn
PhenindioneThe serum concentration of Phenindione can be increased when it is combined with Disulfiram.Approved
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
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Disulfiram.Approved, Vet Approved
PilocarpineThe metabolism of Pilocarpine can be decreased when combined with Disulfiram.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
ProguanilThe metabolism of Proguanil can be decreased when combined with Disulfiram.Approved
PropofolThe metabolism of Propofol can be decreased when combined with Disulfiram.Approved, Investigational, Vet Approved
QuinidineThe metabolism of Quinidine can be decreased when combined with Disulfiram.Approved
QuinineThe metabolism of Quinine can be decreased when combined with Disulfiram.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
SevofluraneThe metabolism of Sevoflurane can be decreased when combined with Disulfiram.Approved, Vet Approved
SildenafilThe metabolism of Sildenafil can be decreased when combined with Disulfiram.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.Nutraceutical
StiripentolThe serum concentration of Disulfiram can be increased when it is combined with Stiripentol.Approved
SulfadiazineThe metabolism of Sulfadiazine can be decreased when combined with Disulfiram.Approved, Vet Approved
SulfisoxazoleThe metabolism of Disulfiram can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
TamoxifenThe metabolism of Tamoxifen can be decreased when combined with Disulfiram.Approved
TelaprevirThe metabolism of Disulfiram can be decreased when combined with Telaprevir.Approved
TelithromycinThe metabolism of Disulfiram can be decreased when combined with Telithromycin.Approved
ThalidomideThe metabolism of Thalidomide can be decreased when combined with Disulfiram.Approved, Investigational, Withdrawn
TheobromineThe metabolism of Theobromine can be decreased when combined with Disulfiram.Approved
TheophyllineThe serum concentration of Theophylline can be increased when it is combined with Disulfiram.Approved
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
TipranavirThe risk or severity of adverse effects can be increased when Disulfiram is combined with Tipranavir.Approved, Investigational
TirapazamineThe metabolism of Tirapazamine can be decreased when combined with Disulfiram.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
TrabectedinThe metabolism of Trabectedin can be decreased when combined with Disulfiram.Approved, Investigational
TrimethadioneThe metabolism of Trimethadione can be decreased when combined with Disulfiram.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
ZopicloneThe metabolism of Zopiclone can be decreased when combined with Disulfiram.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
ATC CodesP03AA04P03AA54N07BB01
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (50.6 KB)
ADMET
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 )
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.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point71.5 °CPhysProp
boiling point117 °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 RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (8.65 KB)
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-014r-9510000000-2e18f478f9c0f9a2958aView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as organic thiocarbonic acid derivatives. These are organic compounds containing the thiocarbonic acid structure or a derivative thereof.
KingdomOrganic compounds
Super ClassOrganosulfur compounds
ClassThiocarbonyl compounds
Sub ClassOrganic thiocarbonic acid derivatives
Direct ParentOrganic thiocarbonic acid derivatives
Alternative Parents
Substituents
  • Dithiocarbamic acid or derivatives
  • Tertiary amine
  • Thiocarbonic acid derivative
  • Organic disulfide
  • Sulfenyl compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors

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
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
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 or carcinogenic forms.
Gene Name:
CYP2E1
Uniprot ID:
P05181
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
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 unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
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 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23