Dimercaprol

Dimercaprol

File:Dimercaprol.svg
Clinical data
ATC code	V03AB09 (WHO)
Identifiers
IUPAC name 2,3-Dimercaptopropanol
CAS Number	59-52-9
PubChem CID	3080
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C3H8OS2
Molar mass	124.227
3D model (JSmol)	Interactive image
SMILES OCC(S)CS

Template:Nfpa-float Dimercaprol (INN) or British anti-Lewisite (abbreviated BAL), is a compound developed by British biochemists at Oxford University during World War II. It was developed secretly as an antidote for Lewisite, the now-obsolete arsenic-based chemical warfare agent. Today, it is used medically in treatment of arsenic, mercury and lead, and other heavy metal poisoning. In addition, it is used for the treatment of Wilson's disease, a genetic disorder in which the body tends to retain copper.

Biochemical function

Heavy metals act by chemically reacting with adjacent sulfhydryl residues on metabolic enzymes, creating a chelate complex that inhibits the affected enzyme's activity. Dimercaprol competes with the sulfhydryl groups for binding the metal ion, which is then excreted in the urine.

Dimercaprol is itself toxic, with a narrow therapeutic range and a tendency to concentrate arsenic in some organs. Other drawbacks include the need to administer it by painful intramuscular injection.

BAL has been found to form stable chelates in vivo with many toxic metals including inorganic mercury, antimony, bismuth, cadmium, chromium, cobalt, gold, and nickel. However, it is not necessarily the treatment of choice for toxicity to these metals. BAL has been used as an adjunct in the treatment of the acute encephalopathy of lead toxicity. It is a potentially toxic drug, and its use may be accompanied by multiple side effects. Although treatment with BAL will increase the excretion of cadmium, there is a concomitant increase in renal cadmium concentration, so that its use in case of cadmium toxicity is to be avoided. It does, however, remove inorganic mercury from the kidneys; but is not useful in the treatment of alkylmercury or phenyl mercury toxicity. BAL also enhances the toxicity of selenium and tellurium, so it is not to be used to remove these metals from the body.

See also

• Chelation therapy

References

• British anti-Lewisite Molecule of the Month, University of Bristol School of Chemistry

• Casarett and Doull's Toxicology, the basic science of poisons