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Namespace Prefixes

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Statements

Subject Item
n2:DB00822
rdf:type
n3:Drug
n3: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]
n3:dosage
n29:271B4447-363D-11E5-9242-09173F13E4C5 n29:271B4448-363D-11E5-9242-09173F13E4C5
n3:generalReferences
# Nash T, Rice WG: Efficacies of zinc-finger-active drugs against Giardia lamblia. Antimicrob Agents Chemother. 1998 Jun;42(6):1488-92. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/9624499 # 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":http://www.ncbi.nlm.nih.gov/pubmed/10052908 # Gaval-Cruz M, Weinshenker D: mechanisms of disulfiram-induced cocaine abstinence: antabuse and cocaine relapse. Mol Interv. 2009 Aug;9(4):175-87. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/ 19720750
n3:group
approved
n3:indication
For the treatment and management of chronic alcoholism
n3:manufacturer
n5:271B4442-363D-11E5-9242-09173F13E4C5 n5:271B4443-363D-11E5-9242-09173F13E4C5 n5:271B4441-363D-11E5-9242-09173F13E4C5
owl:sameAs
n7:DB00822 n20:DB00822
dcterms:title
Disulfiram
adms:identifier
n9:3117 n10:46506008 n11:49884-153-01 n12:PA449376 n13:C01692 n14:D00131 n17:DB00822 n18:4659 n19:3005 n28:Disulfiram
n3:mechanismOfAction
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.
n3:packager
n5:271B4437-363D-11E5-9242-09173F13E4C5 n5:271B443F-363D-11E5-9242-09173F13E4C5 n5:271B4440-363D-11E5-9242-09173F13E4C5 n5:271B4439-363D-11E5-9242-09173F13E4C5 n5:271B443A-363D-11E5-9242-09173F13E4C5 n5:271B4438-363D-11E5-9242-09173F13E4C5 n5:271B443D-363D-11E5-9242-09173F13E4C5 n5:271B443E-363D-11E5-9242-09173F13E4C5 n5:271B443B-363D-11E5-9242-09173F13E4C5 n5:271B443C-363D-11E5-9242-09173F13E4C5
n3:synonym
N,N,N',N'-tetraethylthiuram disulfide Antabuse (tn) Tetraethylthiuram Disulfide 1,1'-dithiobis(N,N-diethylthioformamide) Tetraethylthioperoxydicarbonic Diamide Bis(diethylthiocarbamoyl) disulfide Tetraethylthiuram Disulphide Disulfiram
n3:toxicity
LD<sub>50</sub>=8.6g/kg (orally in rats). Symptoms of overdose include irritation, slight drowsiness, unpleasant taste, mild GI disturbances, and orthostatic hypotension.
n3:foodInteraction
Take without regard to meals. Avoid alcohol for up to 14 days after treatment has been stopped.
n3:synthesisReference
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.
n21:hasConcept
n22:M0006600
foaf:page
n16:disulfiram.htm n26:disulfiram.html
n3:IUPAC-Name
n4:271B444D-363D-11E5-9242-09173F13E4C5
n3:InChI
n4:271B4453-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n4:271B4452-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n4:271B444F-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n4:271B4450-363D-11E5-9242-09173F13E4C5
n3:SMILES
n4:271B4451-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n4:271B4461-363D-11E5-9242-09173F13E4C5 n4:271B444B-363D-11E5-9242-09173F13E4C5
n3:logP
n4:271B4464-363D-11E5-9242-09173F13E4C5 n4:271B4449-363D-11E5-9242-09173F13E4C5 n4:271B444C-363D-11E5-9242-09173F13E4C5
n3:logS
n4:271B4465-363D-11E5-9242-09173F13E4C5 n4:271B444A-363D-11E5-9242-09173F13E4C5
n23:hasATCCode
n24:P03AA04 n24:N07BB01
n3:H-Bond-Acceptor-Count
n4:271B4459-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n4:271B445A-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n4:271B4454-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n4:271B4455-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n4:271B4457-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n4:271B4456-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n4:271B4458-363D-11E5-9242-09173F13E4C5
n3:absorption
Disulfiram is absorbed slowly from the gastrointestinal tract (80 to 90% of oral dose).
n3:affectedOrganism
Humans and other mammals
n3:casRegistryNumber
97-77-8
n3:category
n3:containedIn
n27:271B4444-363D-11E5-9242-09173F13E4C5 n27:271B4445-363D-11E5-9242-09173F13E4C5 n27:271B4446-363D-11E5-9242-09173F13E4C5
n3:Bioavailability
n4:271B445D-363D-11E5-9242-09173F13E4C5
n3:Boiling-Point
n4:271B4463-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n4:271B445F-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n4:271B4460-363D-11E5-9242-09173F13E4C5
n3:Melting-Point
n4:271B4462-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n4:271B445C-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n4:271B445B-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n4:271B445E-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n4:271B444E-363D-11E5-9242-09173F13E4C5