Dimercaprol
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![]() Skeletal formula and ball and stick model of dimercaprol | |
Clinical data | |
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Trade names | BAL in Oil |
Other names | 2,3-Dimercaptopropanol British anti-Lewisite 2,3-Dimercaptopropan-1-ol (no longer recommended[1]) British antilewisite |
AHFS/Drugs.com | Monograph |
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Routes of administration | intramuscular |
ATC code | |
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CompTox Dashboard (EPA) | |
ECHA InfoCard | 100.000.394 |
Chemical and physical data | |
Formula | C3H8OS2 |
Molar mass | 124.225 g mol−1 g·mol−1 |
3D model (JSmol) | |
Density | 1.239 g cm−3 g/cm3 |
Boiling point | 393 °C (739 °F) at 2.0 kPa |
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Dimercaprol, also called British anti-Lewisite (BAL), is a medication used to treat acute poisoning by arsenic, mercury, gold, and lead.[2] May also be used for antimony, thallium, or bismuth poisoning, but the evidence for these uses is not very good.[2][3] It is given by injection into a muscle.[2]
Common side effects include high blood pressure, pain at the site of the injection, vomiting, and fever.[2] It is not recommended in people with peanut allergies.[2] It is unclear if use in pregnancy is safe for the baby.[2] Dimercaprol works by binding with heavy metals.[2]
Dimercaprol was first made during World War II.[4] It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system.[5] In the United States a course of treatment costs more than 200 USD.[6]
Medical uses
Dimercaprol has long been the mainstay of chelation therapy for lead or arsenic poisoning,[7] and it remains an essential drug.[8] Nonetheless, because it can have serious adverse effects, researchers have also pursued development of less toxic analogues.[7]
It is also used as an antidote to the chemical weapon Lewisite.
Mechanism of action
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.[9] 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.[10] Serious side effects include nephrotoxicity and hypertension.
Dimercaprol has been found to form stable chelates in vivo with many other 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 phenylmercury 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]
History
Its original name reflects its origins as a compound secretly developed by British biochemists at Oxford University during World War II[11][12] as an antidote for lewisite, a now-obsolete arsenic-based chemical warfare agent.[11]
References
- ^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 697. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
The prefixes 'mercapto' (–SH), and 'hydroseleno' or selenyl (–SeH), etc. are no longer recommended.
- ^ a b c d e f g "Dimercaprol". The American Society of Health-System Pharmacists. Archived from the original on 21 December 2016. Retrieved 8 December 2016.
{{cite web}}
: Unknown parameter|deadurl=
ignored (|url-status=
suggested) (help) - ^ WHO Model Formulary 2008 (PDF). World Health Organization. 2009. p. 62. ISBN 9789241547659. Archived from the original (PDF) on 13 December 2016. Retrieved 8 December 2016.
{{cite book}}
: Unknown parameter|deadurl=
ignored (|url-status=
suggested) (help) - ^ Greenwood, David (2008). Antimicrobial Drugs: Chronicle of a Twentieth Century Medical Triumph. OUP Oxford. p. 281. ISBN 9780199534845. Archived from the original on 2016-12-20.
{{cite book}}
: Unknown parameter|deadurl=
ignored (|url-status=
suggested) (help) - ^ "WHO Model List of Essential Medicines (19th List)" (PDF). World Health Organization. April 2015. Archived from the original (PDF) on 13 December 2016. Retrieved 8 December 2016.
{{cite web}}
: Unknown parameter|deadurl=
ignored (|url-status=
suggested) (help) - ^ Hamilton, Richart (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 470. ISBN 9781284057560.
- ^ a b Flora, SJ; Pachauri, V (2010), "Chelation in metal intoxication", International Journal of Environmental Research and Public Health, 7 (7): 2745–2788, doi:10.3390/ijerph7072745, PMC 2922724, PMID 20717537.
{{citation}}
: CS1 maint: unflagged free DOI (link) - ^ "WHO Model List of Essential Medicines" (PDF). World Health Organization. October 2013. Archived from the original (PDF) on 23 April 2014. Retrieved 22 April 2014.
{{cite web}}
: Unknown parameter|deadurl=
ignored (|url-status=
suggested) (help) - ^ Goldman M, Dacre JC. (1989) Lewisite: its chemistry, toxicology, and biological effects. Rev Environ Contam Toxicol 110: 75-115
- ^ 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
- ^ a b Domingo Tabangcura, Jr.; G. Patrick Daubert. "British anti-Lewisite". Archived from the original on 2009-02-02.
{{cite web}}
: Unknown parameter|deadurl=
ignored (|url-status=
suggested) (help) - ^ Peters, R; Stocken, L; Thompson, R. (1945). "British Anti-Lewisite (BAL)". Nature. 156 (3969): 616–619. doi:10.1038/156616a0. PMID 21006485.