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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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofArsenic poisoning••••••••••••
Used in combination to treatLead poisoningRegimen in combination with: Edetic acid (DB00974)••••••••••••
Treatment ofAcute mercury poisoning••••••••••••
Treatment ofGold 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.

TargetActionsOrganism
AArsenic
chelator
Humans
ACadmium
chelator
Humans
AMercury
chelator
Humans
UAmyloid beta A4 proteinNot AvailableHumans
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.
DrugInteraction
AbacavirAbacavir may decrease the excretion rate of Dimercaprol which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Dimercaprol which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Dimercaprol which could result in a higher serum level.
AcetaminophenAcetaminophen may decrease the excretion rate of Dimercaprol which could result in a higher serum level.
AcetazolamideAcetazolamide 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

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International/Other Brands
Bal In Oil Injection (Taylor Pharmaceuticals) / Dimaval (Heyl) / Dimercaprol (Akorn) / TechneScan DMSA (Mallinckrodt)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
BalInjection100 mg/1mLIntramuscularAkorn2012-05-01Not applicableUS flag
BAL in OilInjection100 mg/1mLIntramuscularTaylor Pharmaceuticals2007-08-03Not applicableUS flag
Bal In Oil 3ml Ampules/10Solution100 mg / mLIntramuscularTaylor Pharmaceuticals1995-12-312020-12-10Canada flag

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
  1. 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]
  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. [Article]
  3. 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]
  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. [Article]
  5. FDA Approved Drug Products: BAL in Oil (dimercaprol) for intravenous injection [Link]
Human Metabolome Database
HMDB0015677
KEGG Drug
D00167
KEGG Compound
C02924
PubChem Compound
3080
PubChem Substance
99443293
ChemSpider
2971
BindingDB
50103608
RxNav
3445
ChEBI
64198
ChEMBL
CHEMBL1597
PharmGKB
PA165958406
Wikipedia
Dimercaprol
FDA label
Download (111 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
SolutionIntramuscular50 mg/1ml
InjectionIntramuscular100 mg/1mL
SolutionIntramuscular100 mg / mL
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)< 25 °CPhysProp
boiling point (°C)140 °C at 4.00E+01 mm HgPhysProp
water solubility8.7E+004 mg/LMERCK INDEX (1996)
pKa8.62 (at 25 °C)SARGEANT,EP & DEMPSEY,B (1979)
Predicted Properties
PropertyValueSource
Water Solubility2.76 mg/mLALOGPS
logP0.58ALOGPS
logP0.21Chemaxon
logS-1.6ALOGPS
pKa (Strongest Acidic)9.58Chemaxon
pKa (Strongest Basic)-2.8Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count1Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area20.23 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity32.91 m3·mol-1Chemaxon
Polarizability12.88 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.922
Blood Brain Barrier+0.7436
Caco-2 permeable-0.5646
P-glycoprotein substrateNon-substrate0.7655
P-glycoprotein inhibitor INon-inhibitor0.9769
P-glycoprotein inhibitor IINon-inhibitor0.9838
Renal organic cation transporterNon-inhibitor0.9355
CYP450 2C9 substrateNon-substrate0.8031
CYP450 2D6 substrateNon-substrate0.8659
CYP450 3A4 substrateNon-substrate0.8388
CYP450 1A2 substrateInhibitor0.8792
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9413
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.9674
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8851
Ames testNon AMES toxic0.837
CarcinogenicityNon-carcinogens0.5788
BiodegradationReady biodegradable0.6332
Rat acute toxicity2.6518 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9667
hERG inhibition (predictor II)Non-inhibitor0.9257
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0006-9000000000-02d345f6932e4df7ae4c
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0abc-9600000000-28a9f506995ad75cd26b
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-1900000000-9f2b9614668b0e995b2b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00dl-9000000000-887e5da384d6b233f53d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9000000000-5853d8bcc14a7103b23c
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9000000000-a3f1c63b67caba3118ff
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-9000000000-5c70a6f869370463e39f
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-114.6421239
predicted
DarkChem Lite v0.1.0
[M-H]-127.134
predicted
DeepCCS 1.0 (2019)
[M+H]+115.1951239
predicted
DarkChem Lite v0.1.0
[M+H]+129.15697
predicted
DeepCCS 1.0 (2019)
[M+Na]+114.7242239
predicted
DarkChem Lite v0.1.0
[M+Na]+137.1988
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Small molecule
Organism
Humans
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. doi: 10.3390/ijerph7072745. Epub 2010 Jun 28. [Article]
Kind
Small molecule
Organism
Humans
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. doi: 10.3390/ijerph7072745. Epub 2010 Jun 28. [Article]
Kind
Small molecule
Organism
Humans
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. 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
  1. 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 March 18, 2024 16:48