 | This articleneeds additional citations forverification. Please helpimprove this article byadding citations to reliable sources. Unsourced material may be challenged and removed. Find sources: "Dimercaprol" – news ·newspapers ·books ·scholar ·JSTOR(October 2025) (Learn how and when to remove this message) |
 | |
 Skeletal formula and ball and stick model of dimercaprol | |
| Clinical data | |
|---|---|
| Trade names | BAL in Oil |
| Other names | 2,3-Dimercaptopropanol British Anti-Lewisite 2,3-Dithiopropanol 2,3-Dimercaptopropan-1-ol British antilewisite |
| AHFS/Drugs.com | Monograph |
| License data | |
| Routes of administration | intramuscular |
| ATC code | |
| Legal status | |
| Legal status | |
| Pharmacokinetic data | |
| Excretion | Urine[1] |
| Identifiers | |
| |
| CAS Number |
|
| PubChemCID | |
| DrugBank | |
| ChemSpider | |
| UNII | |
| KEGG | |
| ChEMBL | |
| CompTox Dashboard(EPA) | |
| ECHA InfoCard | 100.000.394 |
| Chemical and physical data | |
| Formula | C3H8OS2 |
| Molar mass | 124.22 g·mol−1 |
| 3D model (JSmol) | |
| Density | 1.239 g/cm3 |
| Boiling point | 393 °C (739 °F) at 2.0 kPa |
| |
| |
Dimercaprol, also calledBritish anti-Lewisite (BAL), is amedication used to treat acute poisoning byarsenic,mercury,gold, andlead.[3] It may also be used forantimony,thallium, orbismuth poisoning, although the evidence for those uses is not very strong.[3][4] It is given byinjection into a muscle.[3]
Common side effects includehigh blood pressure, pain at the site of the injection, vomiting, andfever.[3] It is not recommended for people withpeanut allergies as it is typically formulated as a suspension in peanut oil.[3] It is unclear if use inpregnancy is safe for the baby.[3] Dimercaprol is achelator and works bybinding with heavy metals.[3] It has a very pungent odor.
Dimercaprol was first made duringWorld War II.[5] It is on theWorld Health Organization's List of Essential Medicines.[6]
Dimercaprol has long been the mainstay ofchelation therapy for lead or arsenic poisoning,[7] and it is an essential drug.[6] It is also used as an antidote to theorganometallic chemical weaponLewisite. Nonetheless, because it can have seriousadverse effects, researchers have also pursued development of less toxic analogues,[7] such assuccimer.
Wilson's disease is agenetic disorder in whichcopper builds up inside theliver and other tissues. Dimercaprol is a copper chelating agent that has been approved by the FDA to treat Wilson's disease.[8]
Dimercaprol also shows effectiveness againstsnakebite by chelating the zinc ions needed for the activity ofsnake venommetalloproteinasesin vitro.[9]
Arsenic and some other heavy metals act by chelating with adjacentthiol residues on metabolic enzymes, creating achelate complex that inhibits the affected enzyme's activity.[10] 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 narrowtherapeutic range and a tendency to concentrate arsenic in some organs. Other drawbacks include the need to administer it by painfulintramuscular injection[11] Serious side effects includenephrotoxicity andhypertension.
Dimercaprol has been found to form stable chelatesin vivo with many other metals including inorganicmercury,antimony,bismuth,cadmium,chromium,cobalt,gold, andnickel. 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 treatorganomercury poisoning. Dimercaprol also enhances the toxicity ofselenium andtellurium, so it is not to be used to remove these elements from the body.[citation needed]
The original name of dimercaprol reflects its origins as acompound secretly developed by British biochemists atOxford University in the beginning of theWorld War II, with the first synthesis in July 1940[12][13] as anantidote forlewisite, a now-obsoleteorganoarsenicchemical warfare agent.[12]
The prefixes 'mercapto' (–SH), and 'hydroseleno' or selenyl (–SeH), etc. are no longer recommended.
