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Dimercaprol

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Dimercaprol
Skeletal formula of dimercaprol
Ball and stick model of dimercaprol ((2R)-2-sulfanyl)
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IUPAC name
2,3-bis(sulfanyl)propan-1-ol
Other names
2,3-dimercaptopropanol
British anti-Lewisite
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ATC code V03AB09
1732058
59-52-9 7pxY
16495-08-2 (2R)-2-sulfanyl 7pxY
16495-16-2 (2S)-2-sulfanyl 7pxY
ChEMBL ChEMBL1597 7pxY
ChemSpider 2971 7pxY
5342114 (2R)-2-sulfanyl 7pxY
2496803 (2S)-2-sulfanyl 7pxY
DrugBank DB06782 7pxY
EC number 200-433-7
Jmol-3D images Image
KEGG D00167 7pxY
MeSH Dimercaprol
PubChem Template:Chembox PubChem/formatTemplate:Chembox PubChem/formatTemplate:Chembox PubChem/format
RTECS number UB2625000
UN number 2810
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Template:Chem/atomTemplate:Chem/atomTemplate:Chem/atomTemplate:Chem/atomTemplate:Chem/atomTemplate:Chem/atomTemplate:Chem/atom
Molar mass 124.225 g mol−1
Density 1.239 g cm−3
Boiling point Script error: No such module "convert". at 2.0 kPa
log P 0.627
Acidity (pKa) 8.999
Basicity (pKb) 4.998
1.573
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GHS pictograms The skull-and-crossbones pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
H301, H315, H319, H335
P261, P301+310, P305+351+338
EU classification Harmful Xn
R-phrases R22, R36/37/38
S-phrases S26, S36
NFPA 704

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Flash point Script error: No such module "convert".
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Dimercaprol (INN) or British anti-Lewisite (abbreviated BAL), is a compound developed by British biochemists at Oxford University during World War II.[1][2] It was developed secretly as an antidote for lewisite, the now-obsolete arsenic-based chemical warfare agent.[1] Today, it is used medically in treatment of arsenic, mercury, gold, lead, antimony, and other toxic metal poisoning.[3] In addition, it has in the past been used for the treatment of Wilson's disease, a genetic disorder in which the body tends to retain copper.[4]

It is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic health system.[5]

Biochemical function

Arsenic and some other heavy metals act by chemically reacting with adjacent thiol residues on metabolic enzymes, creating a chelate complex that inhibits the affected enzyme's activity.[6] Dimercaprol competes with the thiol groups for binding the metal ion, which is then excreted in the urine.[citation needed]

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.[7] Serious side effects include nephrotoxicity and hypertension.

Dimercaprol has been found to form stable chelates in vivo with many other 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. Dimercaprol 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 dimercaprol 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. Dimercaprol also enhances the toxicity of selenium and tellurium, so it is not to be used to remove these elements from the body.[citation needed]

See also

References

  1. ^ a b Domingo Tabangcura, Jr., G. Patrick Daubert. "British anti-Lewisite". 
  2. ^ Peters, R; Stocken, L; Thompson, R. (1945). "British Anti-Lewisite (BAL)". Nature 156 (3969): 616–619. PMID 21006485. doi:10.1038/156616a0. 
  3. ^ "Dimercaprol". 
  4. ^ Denny-Brown D, PORTER H (December 1951). "The effect of BAL (2,3-dimercaptopropanol) on hepatolenticular degeneration (Wilson's disease)". N. Engl. J. Med. 245 (24): 917–25. PMID 14882450. doi:10.1056/NEJM195112132452401. 
  5. ^ "WHO Model List of Essential Medicines" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014. 
  6. ^ Goldman M, Dacre JC. (1989) Lewisite: its chemistry, toxicology, and biological effects. Rev Environ Contam Toxicol 110: 75-115
  7. ^ Mückter H, Liebl B, Reichl FX et al. (1997) Are we ready to replace dimercaprol (BAL) as an arsenic antidote? Human and Experimental Toxicology 16: 460-465