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Identification
NameDimercaprol
Accession NumberDB06782
TypeSmall Molecule
GroupsApproved
Description

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 is a potentially toxic drug, and its use may be accompanied by multiple side effects.

Structure
Thumb
Synonyms
SynonymLanguageCode
1,2-Dimercapto-3-propanolNot AvailableNot Available
1,2-DithioglycerolNot AvailableNot Available
2,3-DimercaproNot AvailableNot Available
2,3-Dimercapto-1-propanolNot AvailableNot Available
2,3-Dimercaptol-1-propanolNot AvailableNot Available
2,3-DimercaptopropanolNot AvailableNot Available
2,3-DithiopropanolNot AvailableNot Available
2,3-Mercaptopropan-1-olNot AvailableNot Available
2,3-MercaptopropanolNot AvailableNot Available
3-Hydroxy-1,2-propanedithiolNot AvailableNot Available
alpha,beta-DithioglycerolNot AvailableNot Available
BALNot AvailableNot Available
British Anti-LewisiteNot AvailableNot Available
British antilewisiteNot AvailableNot Available
DimercaprolumNot AvailableNot Available
DimercaptopropanolNot AvailableNot Available
DithioglycerineNot AvailableNot Available
DithioglycerolNot AvailableNot Available
SulfactinNot AvailableNot Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Balinjection100 mg/mLintramuscularAkorn, Inc.2012-05-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
Bal In Oil InjectionTaylor Pharmaceuticals
DimavalHeyl
DimercaprolAkorn
TechneScan DMSAMallinckrodt
Brand mixtures
Brand NameIngredients
BalDimercaprol and Butacaine
ZorexDimercaprol and Calcium Pantothenate
SaltsNot Available
Categories
CAS number59-52-9
WeightAverage: 124.225
Monoisotopic: 124.001656258
Chemical FormulaC3H8OS2
InChI KeyWQABCVAJNWAXTE-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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganosulfur compounds
ClassThiols
Sub ClassAlkylthiols
Direct ParentAlkylthiols
Alternative Parents
Substituents
  • Alkylthiol
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment of arsenic, gold and mercury poisoning. Indicated in acute lead poisoning when used concomitantly with edetate calcium disodium (DB00974).
PharmacodynamicsDue to its oily nature, dimercaprol is not absorbed orally and its administration requires 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. Although treatment with dimercaprol increases the excretion of cadmium, there is a concomitant increase in renal cadmium concentration, so its use should be avoided in cases of cadmium toxicity.
Mechanism of actionThe 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.
AbsorptionAfter intra-muscular injection.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationUrine.
Half lifeThe drug has a short half life.
ClearanceNot Available
ToxicityThe 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.
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrateNon-inhibitor0.9071
CYP450 2D6 substrateNon-inhibitor0.9413
CYP450 2C19 substrateNon-inhibitor0.9025
CYP450 3A4 substrateNon-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
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Injectionintramuscular100 mg/mL
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point< 25 °CPhysProp
boiling point140 °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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
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 Reference
  1. Walshe JM: The conquest of Wilson’s disease. Brain. 2009 Aug;132(Pt 8):2289-95. Epub 2009 Jul 13. Pubmed
  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. Pubmed
  3. Flora SJ, Pachauri V: Chelation in metal intoxication. Int J Environ Res Public Health. 2010 Jul;7(7):2745-88. Epub 2010 Jun 28. Pubmed
  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. Pubmed
External Links
ATC CodesV03AB09
AHFS Codes
  • 64:00.00
PDB EntriesNot Available
FDA labelDownload (111 KB)
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Arsenic

Kind: small molecule

Organism: Human

Pharmacological action: yes

Actions: chelator

Components

Name UniProt ID Details

References:

  1. Flora SJ, Pachauri V: Chelation in metal intoxication. Int J Environ Res Public Health. 2010 Jul;7(7):2745-88. Epub 2010 Jun 28. Pubmed

2. Cadmium

Kind: small molecule

Organism: Human

Pharmacological action: yes

Actions: chelator

Components

Name UniProt ID Details

References:

  1. Flora SJ, Pachauri V: Chelation in metal intoxication. Int J Environ Res Public Health. 2010 Jul;7(7):2745-88. Epub 2010 Jun 28. Pubmed

3. Mercury

Kind: small molecule

Organism: Human

Pharmacological action: yes

Actions: chelator

Components

Name UniProt ID Details

References:

  1. Flora SJ, Pachauri V: Chelation in metal intoxication. Int J Environ Res Public Health. 2010 Jul;7(7):2745-88. Epub 2010 Jun 28. Pubmed

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Drug created on September 14, 2010 10:21 / Updated on April 14, 2014 14:48