Dimercaprol: Difference between revisions

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{{Short description|Chemical compound}}
{{Short description|Antidote for certain metal poisonings}}
{{MCN|date=October 2025}}
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==Medical uses==
==Medical uses==
Dimercaprol has long been the mainstay of [[chelation therapy]] for lead or arsenic poisoning,<ref name="pmid_20717537">{{cite journal | vauthors = Flora SJ, Pachauri V | title = Chelation in metal intoxication | journal = International Journal of Environmental Research and Public Health | volume = 7 | issue = 7 | pages = 2745–2788 | date = July 2010 | pmid = 20717537 | pmc = 2922724 | doi = 10.3390/ijerph7072745 | doi-access = free }}</ref> and it is an essential drug.<ref name="WHO21st" /> It is also used as an antidote to the chemical weapon [[Lewisite]]. Nonetheless, because it can have serious [[adverse effect]]s, researchers have also pursued development of less toxic analogues,<ref name="pmid_20717537"/> such as [[succimer]].
Dimercaprol has long been the mainstay of [[chelation therapy]] for lead or arsenic poisoning,<ref name="pmid_20717537">{{cite journal | vauthors = Flora SJ, Pachauri V | title = Chelation in metal intoxication | journal = International Journal of Environmental Research and Public Health | volume = 7 | issue = 7 | pages = 2745–2788 | date = July 2010 | pmid = 20717537 | pmc = 2922724 | doi = 10.3390/ijerph7072745 | doi-access = free }}</ref> and it is an essential drug.<ref name="WHO21st" /> It is also used as an antidote to the [[organometallic]] chemical weapon [[Lewisite]]. Nonetheless, because it can have serious [[adverse effect]]s, researchers have also pursued development of less toxic analogues,<ref name="pmid_20717537"/> such as [[succimer]].


[[Wilson's disease]] is a [[genetic disorder]] in which [[copper]] builds up inside the [[liver]] and other tissues.  Dimercaprol is a copper chelating agent that has been approved by the FDA to treat Wilson's disease.<ref>{{cite journal | vauthors = Leggio L, Addolorato G, Abenavoli L, Gasbarrini G | title = Wilson's disease: clinical, genetic and pharmacological findings | journal = International Journal of Immunopathology and Pharmacology | volume = 18 | issue = 1 | pages = 7–14 | date = 2005 | pmid = 15698506 | doi = 10.1177/039463200501800102 | s2cid = 26059921 }}</ref>
[[Wilson's disease]] is a [[genetic disorder]] in which [[copper]] builds up inside the [[liver]] and other tissues.  Dimercaprol is a copper chelating agent that has been approved by the FDA to treat Wilson's disease.<ref>{{cite journal | vauthors = Leggio L, Addolorato G, Abenavoli L, Gasbarrini G | title = Wilson's disease: clinical, genetic and pharmacological findings | journal = International Journal of Immunopathology and Pharmacology | volume = 18 | issue = 1 | pages = 7–14 | date = 2005 | pmid = 15698506 | doi = 10.1177/039463200501800102 | s2cid = 26059921 }}</ref>


Dimercaprol also shows effectiveness against [[snakebite]] by potently antagonizing the activity of [[Zinc|Zn]]<sup>2+</sup>-dependent [[snake venom]] [[Metalloproteinase|metalloproteinases]] ''[[in vitro]]''.<ref>{{cite journal | vauthors = Albulescu LO, Hale MS, Ainsworth S, Alsolaiss J, Crittenden E, Calvete JJ, Evans C, Wilkinson MC, Harrison RA, Kool J, Casewell NR | display-authors = 6 | title = Preclinical validation of a repurposed metal chelator as an early-intervention therapeutic for hemotoxic snakebite | journal = Science Translational Medicine | volume = 12 | issue = 542 | date = May 2020 | pmid = 32376771 | pmc = 7116364 | doi = 10.1126/scitranslmed.aay8314 }}</ref>
Dimercaprol also shows effectiveness against [[snakebite]] by chelating the zinc ions needed for the activity of [[snake venom]] [[Metalloproteinase|metalloproteinases]] ''[[in vitro]]''.<ref>{{cite journal | vauthors = Albulescu LO, Hale MS, Ainsworth S, Alsolaiss J, Crittenden E, Calvete JJ, Evans C, Wilkinson MC, Harrison RA, Kool J, Casewell NR | display-authors = 6 | title = Preclinical validation of a repurposed metal chelator as an early-intervention therapeutic for hemotoxic snakebite | journal = Science Translational Medicine | volume = 12 | issue = 542 | date = May 2020 | article-number = eaay8314 | pmid = 32376771 | pmc = 7116364 | doi = 10.1126/scitranslmed.aay8314 }}</ref>


== Mechanism of action ==
== Mechanism of action ==
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Dimercaprol is itself toxic, with a narrow [[therapeutic index|therapeutic range]] and a tendency to concentrate arsenic in some organs. Other drawbacks include the need to administer it by painful [[intramuscular injection]]<ref name="pmid9292286">{{cite journal | vauthors = Mückter H, Liebl B, Reichl FX, Hunder G, Walther U, Fichtl B | title = Are we ready to replace dimercaprol (BAL) as an arsenic antidote? | journal = Human & Experimental Toxicology | volume = 16 | issue = 8 | pages = 460–465 | date = August 1997 | pmid = 9292286 | doi = 10.1177/096032719701600807 | bibcode = 1997HETox..16..460M | s2cid = 44772701 }}</ref> Serious side effects include [[nephrotoxicity]] and [[hypertension]].
Dimercaprol is itself toxic, with a narrow [[therapeutic index|therapeutic range]] and a tendency to concentrate arsenic in some organs. Other drawbacks include the need to administer it by painful [[intramuscular injection]]<ref name="pmid9292286">{{cite journal | vauthors = Mückter H, Liebl B, Reichl FX, Hunder G, Walther U, Fichtl B | title = Are we ready to replace dimercaprol (BAL) as an arsenic antidote? | journal = Human & Experimental Toxicology | volume = 16 | issue = 8 | pages = 460–465 | date = August 1997 | pmid = 9292286 | doi = 10.1177/096032719701600807 | bibcode = 1997HETox..16..460M | s2cid = 44772701 }}</ref> Serious side effects include [[nephrotoxicity]] and [[hypertension]].


Dimercaprol has been found to form stable chelates ''in vivo'' with many other metals including inorganic [[mercury (element)|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|date=May 2008}}
Dimercaprol has been found to form stable chelates ''in vivo'' with many other metals including inorganic [[mercury (element)|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 urinary excretion of cadmium, use in case of cadmium toxicity is to be avoided as the drug-cadmium complex is rather nephrotoxic. It does, however, remove inorganic mercury from the kidneys; Dimercaprol should not be used to treat [[organomercury]] poisoning. 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|date=May 2008}}


==History==
==History==
The original name of dimercaprol reflects its origins as a [[chemical compound|compound]] secretly developed by British biochemists at [[Oxford University]] in the beginning of the [[World War II]], with the first synthesis in July 1940<ref name="chm.bris">{{cite web |url=http://www.chm.bris.ac.uk/motm/bal/development.html | vauthors = Tabangcura Jr D, Daubert GP |title=British anti-Lewisite |url-status=live |archive-url=https://web.archive.org/web/20090202114257/http://www.chm.bris.ac.uk/motm/bal/development.html |archive-date=2009-02-02 }}</ref><ref>{{cite journal | vauthors = Peters RA, Stocken LA, Thompson RH | title = British anti-lewisite (BAL) | journal = Nature | volume = 156 | issue = 3969 | pages = 616–619 | year = 1945 | pmid = 21006485 | doi = 10.1038/156616a0 | s2cid = 4129186 | bibcode = 1945Natur.156..616P }}</ref> as an [[antidote]] for [[lewisite]], a now-obsolete [[arsenic]]-based [[chemical warfare agent]].<ref name="chm.bris" />
The original name of dimercaprol reflects its origins as a [[chemical compound|compound]] secretly developed by British biochemists at [[Oxford University]] in the beginning of the [[World War II]], with the first synthesis in July 1940<ref name="chm.bris">{{cite web |url=http://www.chm.bris.ac.uk/motm/bal/development.html | vauthors = Tabangcura Jr D, Daubert GP |title=British anti-Lewisite |url-status=live |archive-url=https://web.archive.org/web/20090202114257/http://www.chm.bris.ac.uk/motm/bal/development.html |archive-date=2009-02-02 }}</ref><ref>{{cite journal | vauthors = Peters RA, Stocken LA, Thompson RH | title = British anti-lewisite (BAL) | journal = Nature | volume = 156 | issue = 3969 | pages = 616–619 | year = 1945 | pmid = 21006485 | doi = 10.1038/156616a0 | s2cid = 4129186 | bibcode = 1945Natur.156..616P }}</ref> as an [[antidote]] for [[lewisite]], a now-obsolete [[organoarsenic]] [[chemical warfare agent]].<ref name="chm.bris" />


== See also ==
== See also ==
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== External links ==
== External links ==
* {{cite web | url = https://druginfo.nlm.nih.gov/drugportal/name/dimercaprol | publisher = U.S. National Library of Medicine | work = Drug Information Portal | title = Dimercaprol }}
* {{cite web | url = https://druginfo.nlm.nih.gov/drugportal/name/dimercaprol | archive-url = https://web.archive.org/web/20200729221444/https://druginfo.nlm.nih.gov/drugportal/name/dimercaprol | url-status = dead | archive-date = July 29, 2020 | publisher = U.S. National Library of Medicine | work = Drug Information Portal | title = Dimercaprol }}


{{Antidotes}}
{{Antidotes}}

Latest revision as of 16:17, 9 October 2025

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| _datapage = Dimercaprol (data page) | _vaccine_target=_type_not_vaccine | _legal_all=Rx-only | _ATC_prefix_supplemental=V03 | _has_EMA_link = | CAS_number=59-52-9 | PubChem=3080 | ChemSpiderID=2971 | ChEBI= | ChEMBL=1597 | DrugBank=DB06782 | KEGG=D00167 | _hasInChI_or_Key=yes | UNII=0CPP32S55X | _hasJmol02 = |_hasMultipleCASnumbers = |_hasMultiplePubChemCIDs = |_hasMultipleChEBIs =

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Common side effects include high blood pressure, pain at the site of the injection, vomiting, and fever.[2] It is not recommended for people with peanut allergies as it is typically formulated as a suspension in peanut oil.[2] It is unclear if use in pregnancy is safe for the baby.[2] Dimercaprol is a chelator and works by binding with heavy metals.[2] It has a very pungent odor.

Dimercaprol was first made during World War II.[4] It is on the World Health Organization's List of Essential Medicines.[5]

Medical uses

Dimercaprol has long been the mainstay of chelation therapy for lead or arsenic poisoning,[6] and it is an essential drug.[5] It is also used as an antidote to the organometallic chemical weapon Lewisite. Nonetheless, because it can have serious adverse effects, researchers have also pursued development of less toxic analogues,[6] such as succimer.

Wilson's disease is a genetic disorder in which copper builds up inside the liver and other tissues. Dimercaprol is a copper chelating agent that has been approved by the FDA to treat Wilson's disease.[7]

Dimercaprol also shows effectiveness against snakebite by chelating the zinc ions needed for the activity of snake venom metalloproteinases in vitro.[8]

Mechanism of action

Arsenic and some other heavy metals act by chelating 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.Script error: No such module "Unsubst".

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 urinary excretion of cadmium, use in case of cadmium toxicity is to be avoided as the drug-cadmium complex is rather nephrotoxic. It does, however, remove inorganic mercury from the kidneys; Dimercaprol should not be used to treat organomercury poisoning. Dimercaprol also enhances the toxicity of selenium and tellurium, so it is not to be used to remove these elements from the body.Script error: No such module "Unsubst".

History

The original name of dimercaprol reflects its origins as a compound secretly developed by British biochemists at Oxford University in the beginning of the World War II, with the first synthesis in July 1940[11][12] as an antidote for lewisite, a now-obsolete organoarsenic chemical warfare agent.[11]

See also

References

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External links

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