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Dimercaprol



Dimercaprol
Systematic (IUPAC) name
2,3-Dimercaptopropanol
Identifiers
CAS number 59-52-9
ATC code V03AB09
PubChem 3080
Chemical data
Formula C3H8OS2 
Mol. mass 124.227
SMILES search in eMolecules, PubChem
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.

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Legal status
Routes  ?

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 toxic 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.

Additional recommended knowledge

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

References

  • British anti-Lewisite Molecule of the Month, University of Bristol School of Chemistry
  • Casarett and Doull's Toxicology, the basic science of poisons
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Dimercaprol". A list of authors is available in Wikipedia.
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