CHEBI:64198 - dimercaprol

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ChEBI Name dimercaprol
ChEBI ID CHEBI:64198
Definition A dithiol that is propane-1,2-dithiol in which one of the methyl hydrogens is replaced by a hydroxy group. a chelating agent originally developed during World War II as an experimental antidote against the arsenic-based poison gas Lewisite, it has been used clinically since 1949 for the treatment of poisoning by arsenic, mercury and gold. It can also be used for treatment of poisoning by antimony, bismuth and possibly thallium, and (with sodium calcium edetate) in cases of acute leaad poisoning. Administration is by (painful) intramuscular injection of a suspension of dimercaprol in peanut oil, typically every 4 hours for 2-10 days depending on the toxicity. In the past, dimercaprol was also used for the treatment of Wilson's disease, a severely debilitating genetic disorder in which the body tends to retain copper, with resultant liver and brain injury.
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Formula C3H8OS2
Net Charge 0
Average Mass 124.22500
Monoisotopic Mass 124.002
InChI InChI=1S/C3H8OS2/c4-1-3(6)2-5/h3-6H,1-2H2
InChIKey WQABCVAJNWAXTE-UHFFFAOYSA-N
SMILES OCC(S)CS
Roles Classification
Chemical Role(s): chelator
A ligand with two or more separate binding sites that can bind to a single metallic central atom, forming a chelate.
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ChEBI Ontology
Outgoing dimercaprol (CHEBI:64198) has role chelator (CHEBI:38161)
dimercaprol (CHEBI:64198) is a dithiol (CHEBI:23853)
dimercaprol (CHEBI:64198) is a primary alcohol (CHEBI:15734)
Incoming dithioglycerophosphocholine (CHEBI:140065) has functional parent dimercaprol (CHEBI:64198)
IUPAC Name
2,3-disulfanylpropan-1-ol
INNs Sources
dimercaprol ChemIDplus
dimercaprolum ChemIDplus
Synonyms Sources
1,2-dimercapto-3-propanol ChemIDplus
1,2-dithioglycerol ChemIDplus
2,3-dimercapto-1-propanol ChemIDplus
2,3-Dimercapto-1-propanol KEGG COMPOUND
2,3-dimercaptol-1-propanol ChemIDplus
2,3-dimercaptopropanol ChemIDplus
2,3-dithiopropanol ChemIDplus
2,3-mercaptopropan-1-ol NIST Chemistry WebBook
2,3-Mercaptopropanol KEGG COMPOUND
3-hydroxy-1,2-propanedithiol ChemIDplus
α,β-dithioglycerol ChemIDplus
BAL ChemIDplus
British anti-Lewisite DrugBank
British anti-lewisite KEGG COMPOUND
British antilewisite ChemIDplus
dimercaptopropanol ChemIDplus
dithioglycerine NIST Chemistry WebBook
dithioglycerol ChemIDplus
sulfactin ChemIDplus
Manual Xrefs Databases
3150 DrugCentral
C02924 KEGG COMPOUND
D00167 KEGG DRUG
DB06782 DrugBank
Dimercaprol Wikipedia
US2402665 Patent
View more database links
Registry Numbers Types Sources
1732058 Reaxys Registry Number Reaxys
59-52-9 CAS Registry Number KEGG COMPOUND
59-52-9 CAS Registry Number NIST Chemistry WebBook
59-52-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
12605205 PubMed citation Europe PMC
14882450 PubMed citation Europe PMC
21006485 PubMed citation Europe PMC
21803782 PubMed citation Europe PMC
9292286 PubMed citation Europe PMC
Last Modified
08 February 2018