Dimercaprol
Identification
- Summary
Dimercaprol is a chelating agent used as an antidote to arsenic, gold, and mercury poisoning, as well as acute lead poisoning in combination with edetate calcium disodium.
- Brand Names
- Bal In Oil
- Generic Name
- Dimercaprol
- DrugBank Accession Number
- DB06782
- Background
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 has toxic potential, and its use may be followed by a variety of adverse effects.
- Type
- Small Molecule
- Groups
- Approved
- Structure
- Weight
- Average: 124.225
Monoisotopic: 124.001656258 - Chemical Formula
- C3H8OS2
- Synonyms
- 1,2-dimercapto-3-propanol
- 1,2-dithioglycerol
- 2,3-dimercapto-1-propanol
- 2,3-dimercaptol-1-propanol
- 2,3-dimercaptopropanol
- 2,3-dithiopropanol
- 2,3-mercaptopropan-1-ol
- 2,3-Mercaptopropanol
- 3-hydroxy-1,2-propanedithiol
- BAL
- British anti-lewisite
- British antilewisite
- Dimercaprol
- Dimercaprolum
- Dimercaptopropanol
- Dithioglycerine
- Dithioglycerol
- Sulfactin
- α,β-dithioglycerol
Pharmacology
- Indication
For the treatment of arsenic, gold and mercury poisoning. Indicated in acute lead poisoning when used concomitantly with edetate calcium disodium (DB00974).
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Arsenic poisoning •••••••••••• Used in combination to treat Lead poisoning Regimen in combination with: Edetic acid (DB00974) •••••••••••• Treatment of Acute mercury poisoning •••••••••••• Treatment of Gold poisoning •••••••••••• - Contraindications & Blackbox Warnings
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- Pharmacodynamics
Due to its oily nature, dimercaprol is not absorbed orally and its administration requires a 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. Despite that fact that dimercaprol increases cadmium excretion, there is an associated increase in kidney cadmium concentration. Because of this, dimercaprol must be avoided in patients with 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.
Target Actions Organism AArsenic chelatorHumans ACadmium chelatorHumans AMercury chelatorHumans UAmyloid beta A4 protein Not Available Humans - 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
- Adverse Effects
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- 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.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Abacavir may decrease the excretion rate of Dimercaprol which could result in a higher serum level. Aceclofenac Aceclofenac may decrease the excretion rate of Dimercaprol which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Dimercaprol which could result in a higher serum level. Acetaminophen Acetaminophen may decrease the excretion rate of Dimercaprol which could result in a higher serum level. Acetazolamide Acetazolamide may increase the excretion rate of Dimercaprol which could result in a lower serum level and potentially a reduction in efficacy. - Food Interactions
- No interactions found.
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- International/Other Brands
- Bal In Oil Injection (Taylor Pharmaceuticals) / Dimaval (Heyl) / Dimercaprol (Akorn) / TechneScan DMSA (Mallinckrodt)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Bal Injection 100 mg/1mL Intramuscular Akorn 2012-05-01 Not applicable US BAL in Oil Injection 100 mg/1mL Intramuscular Taylor Pharmaceuticals 2007-08-03 Not applicable US Bal In Oil 3ml Ampules/10 Solution 100 mg / mL Intramuscular Taylor Pharmaceuticals 1995-12-31 2020-12-10 Canada
Categories
- ATC Codes
- V03AB09 — Dimercaprol
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as alkylthiols. These are organic compounds containing the thiol functional group linked to an alkyl chain.
- Kingdom
- Organic compounds
- Super Class
- Organosulfur compounds
- Class
- Thiols
- Sub Class
- Alkylthiols
- Direct Parent
- Alkylthiols
- Alternative Parents
- Primary alcohols / Hydrocarbon derivatives
- Substituents
- Alcohol / Aliphatic acyclic compound / Alkylthiol / Hydrocarbon derivative / Organic oxygen compound / Organooxygen compound / Primary alcohol
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- primary alcohol, dithiol (CHEBI:64198) / a small molecule (23-DIMERCAPTOPROPAN-1-OL)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 0CPP32S55X
- CAS number
- 59-52-9
- InChI Key
- WQABCVAJNWAXTE-UHFFFAOYSA-N
- InChI
- InChI=1S/C3H8OS2/c4-1-3(6)2-5/h3-6H,1-2H2
- IUPAC Name
- 2,3-disulfanylpropan-1-ol
- SMILES
- OCC(S)CS
References
- Synthesis Reference
Peppel, W.J. and Signaigo, F.K.; U.S. Patent 2,402,665; June 25,1946; assigned to E.I. du Pont de Nemwrs & Company.
- General References
- Walshe JM: The conquest of Wilson's disease. Brain. 2009 Aug;132(Pt 8):2289-95. doi: 10.1093/brain/awp149. Epub 2009 Jul 13. [Article]
- 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. [Article]
- Flora SJ, Pachauri V: Chelation in metal intoxication. Int J Environ Res Public Health. 2010 Jul;7(7):2745-88. doi: 10.3390/ijerph7072745. Epub 2010 Jun 28. [Article]
- 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. [Article]
- FDA Approved Drug Products: BAL in Oil (dimercaprol) for intravenous injection [Link]
- External Links
- Human Metabolome Database
- HMDB0015677
- KEGG Drug
- D00167
- KEGG Compound
- C02924
- PubChem Compound
- 3080
- PubChem Substance
- 99443293
- ChemSpider
- 2971
- BindingDB
- 50103608
- 3445
- ChEBI
- 64198
- ChEMBL
- CHEMBL1597
- PharmGKB
- PA165958406
- Wikipedia
- Dimercaprol
- FDA label
- Download (111 KB)
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Solution Intramuscular 50 mg/1ml Injection Intramuscular 100 mg/1mL Solution Intramuscular 100 mg / mL - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) < 25 °C PhysProp boiling point (°C) 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 2.76 mg/mL 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 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 32.91 m3·mol-1 Chemaxon Polarizability 12.88 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.922 Blood Brain Barrier + 0.7436 Caco-2 permeable - 0.5646 P-glycoprotein substrate Non-substrate 0.7655 P-glycoprotein inhibitor I Non-inhibitor 0.9769 P-glycoprotein inhibitor II Non-inhibitor 0.9838 Renal organic cation transporter Non-inhibitor 0.9355 CYP450 2C9 substrate Non-substrate 0.8031 CYP450 2D6 substrate Non-substrate 0.8659 CYP450 3A4 substrate Non-substrate 0.8388 CYP450 1A2 substrate Inhibitor 0.8792 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9413 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.9674 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8851 Ames test Non AMES toxic 0.837 Carcinogenicity Non-carcinogens 0.5788 Biodegradation Ready biodegradable 0.6332 Rat acute toxicity 2.6518 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9667 hERG inhibition (predictor II) Non-inhibitor 0.9257
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0006-9000000000-02d345f6932e4df7ae4c Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0abc-9600000000-28a9f506995ad75cd26b Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-00di-1900000000-9f2b9614668b0e995b2b Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-00dl-9000000000-887e5da384d6b233f53d Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-9000000000-5853d8bcc14a7103b23c Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-9000000000-a3f1c63b67caba3118ff Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-00di-9000000000-5c70a6f869370463e39f Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 114.6421239 predictedDarkChem Lite v0.1.0 [M-H]- 127.134 predictedDeepCCS 1.0 (2019) [M+H]+ 115.1951239 predictedDarkChem Lite v0.1.0 [M+H]+ 129.15697 predictedDeepCCS 1.0 (2019) [M+Na]+ 114.7242239 predictedDarkChem Lite v0.1.0 [M+Na]+ 137.1988 predictedDeepCCS 1.0 (2019)
Targets
References
- Flora SJ, Pachauri V: Chelation in metal intoxication. Int J Environ Res Public Health. 2010 Jul;7(7):2745-88. doi: 10.3390/ijerph7072745. Epub 2010 Jun 28. [Article]
References
- Flora SJ, Pachauri V: Chelation in metal intoxication. Int J Environ Res Public Health. 2010 Jul;7(7):2745-88. doi: 10.3390/ijerph7072745. Epub 2010 Jun 28. [Article]
References
- Flora SJ, Pachauri V: Chelation in metal intoxication. Int J Environ Res Public Health. 2010 Jul;7(7):2745-88. doi: 10.3390/ijerph7072745. Epub 2010 Jun 28. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Transition metal ion binding
- Specific Function
- Functions as a cell surface receptor and performs physiological functions on the surface of neurons relevant to neurite growth, neuronal adhesion and axonogenesis. Involved in cell mobility and tra...
- Gene Name
- APP
- Uniprot ID
- P05067
- Uniprot Name
- Amyloid beta A4 protein
- Molecular Weight
- 86942.715 Da
References
- Venti A, Giordano T, Eder P, Bush AI, Lahiri DK, Greig NH, Rogers JT: The integrated role of desferrioxamine and phenserine targeted to an iron-responsive element in the APP-mRNA 5'-untranslated region. Ann N Y Acad Sci. 2004 Dec;1035:34-48. [Article]
Drug created at September 14, 2010 16:21 / Updated at May 21, 2024 02:58