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Identification
Name Dimercaprol
Accession Number DB06782
Type small molecule
Groups approved
Description

Dimercaprol is a traditional chelating agent developed by British biochemists at Oxford University during World War II. It was developed as an experimental antidote against the arsenic-based poison gas Lewisite. It has been used clinically since 1949 in arsenic, cadmium and mercury poisoning. 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. Dimercaprol is a potentially toxic drug, and its use may be accompanied by multiple side effects.
Structure Thumb
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Synonyms
2,3-Dimercapro
2,3-Dimercaptopropanol
BAL
British Anti-Lewisite
Salts Not Available
Brand names
Name Company
Bal In Oil Injection Taylor Pharmaceuticals
Dimercaprol Akorn
Brand mixtures Not Available
Categories
  • Chelating Agents
CAS number 59-52-9
Weight Average: 124.225
Monoisotopic: 124.001656258
Chemical Formula C3H8OS2
InChI Key InChIKey=WQABCVAJNWAXTE-UHFFFAOYSA-N
InChI
InChI=1S/C3H8OS2/c4-1-3(6)2-5/h3-6H,1-2H2
Plain Text
IUPAC Name
2,3-disulfanylpropan-1-ol
SMILES
OCC(S)CS
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes Not Available
Substructures Not Available
Pharmacology
Indication For the treatment of arsenic, gold and mercury poisoning. Indicated in acute lead poisoning when used concomitantly with edetate calcium disodium (DB00974).
Pharmacodynamics Due to its oily nature, dimercaprol is not absorbed orally and its administration requires deep intra-muscular injection that is extremely painful and allergenic. It was found to mobilize and relocate lead to the brain, increasing its neurotoxic effects. Although treatment with dimercaprol increases the excretion of cadmium, there is a concomitant increase in renal cadmium concentration, so its use should be avoided in cases of cadmium toxicity.
Mechanism of action The sulfhydryl groups of dimercaprol form complexes with certain heavy metals thus preventing or reversing the metallic binding of sulfhydryl-containing enzymes. The complex is excreted in the urine.
Absorption After intra-muscular injection.
Volume of distribution Not Available
Protein binding Not Available
Metabolism Not Available
Route of elimination Urine.
Half life The drug has a short half life.
Clearance Not Available
Toxicity The intramuscular LD50 in rats is approximately 105 mg/kg; intraperitoneally 140 mg/kg. The intraperitoneal LD80 in mice is approximately 125 mg/kg. Dimercaprol has been shown in animal experiments to increase brain deposition of arsenite, organic mercury compounds and increase the toxicity of cadmium and lead. Dimercaprol has been shown to induce seizure in animal studies and also is nephrotoxic.
Affected organisms Not Available
Pathways Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers Not Available
Dosage forms
Form Route Strength
Injection Intramuscular 100 mg/mL
Prices Not Available
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point < 25 °C PhysProp
boiling point 140 °C at 4.00E+01 mm Hg PhysProp
water solubility 8.7E+004 mg/L MERCK INDEX (1996)
pKa 8.62 (at 25 °C) SARGEANT,EP & DEMPSEY,B (1979)
Predicted Properties
Property Value Source
water solubility 2.76e+00 g/l ALOGPS
logP 0.58 ALOGPS
logP 0.21 ChemAxon
logS -1.6 ALOGPS
pKa (strongest acidic) 9.58 ChemAxon
pKa (strongest basic) -2.8 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 1 ChemAxon
hydrogen donor count 3 ChemAxon
polar surface area 20.23 ChemAxon
rotatable bond count 2 ChemAxon
refractivity 32.91 ChemAxon
polarizability 12.88 ChemAxon
References
Synthesis Reference Not Available
General Reference
  1. Walshe JM: The conquest of Wilson’s disease. Brain. 2009 Aug;132(Pt 8):2289-95. Epub 2009 Jul 13. Pubmed
  2. Boscolo M, Antonucci S, Volpe AR, Carmignani M, Di Gioacchino M: Acute mercury intoxication and use of chelating agents. J Biol Regul Homeost Agents. 2009 Oct-Dec;23(4):217-23. Pubmed
  3. Flora SJ, Pachauri V: Chelation in metal intoxication. Int J Environ Res Public Health. 2010 Jul;7(7):2745-88. Epub 2010 Jun 28. Pubmed
  4. Andersen O: Chemical and biological considerations in the treatment of metal intoxications by chelating agents. Mini Rev Med Chem. 2004 Jan;4(1):11-21. Pubmed
External Links
Resource Link
KEGG Drug D00167 Link_out
KEGG Compound C02924 Link_out
PubChem Compound 3080 Link_out
PubChem Substance 99443293 Link_out
ChemSpider 2971 Link_out
ChEBI 554382 Link_out
ChEMBL 554382 Link_out
PharmGKB PA165958406 Link_out
Wikipedia http://en.wikipedia.org/wiki/Dimercaprol Link_out
ATC Codes
  • V03AB09
AHFS Codes
  • 64:00.00
PDB Entries Not Available
FDA label show (111 KB)
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Arsenic

Pharmacological action: yes
Actions: chelator

References:
  1. Flora SJ, Pachauri V: Chelation in metal intoxication. Int J Environ Res Public Health. 2010 Jul;7(7):2745-88. Epub 2010 Jun 28. Pubmed

2. Cadmium

Pharmacological action: yes
Actions: chelator

References:
  1. Flora SJ, Pachauri V: Chelation in metal intoxication. Int J Environ Res Public Health. 2010 Jul;7(7):2745-88. Epub 2010 Jun 28. Pubmed

3. Mercury

Pharmacological action: yes
Actions: chelator

References:
  1. Flora SJ, Pachauri V: Chelation in metal intoxication. Int J Environ Res Public Health. 2010 Jul;7(7):2745-88. Epub 2010 Jun 28. Pubmed
Comments
Drug created on September 14, 2010 10:21 / Updated on February 08, 2013 16:24