CAS 59-52-9|Dimercaprol|BAL|2,3-Dimercapro|Dimercaprol|British Anti-Lewisite|2,3-disulfanylpropan-1-ol|Bal In Oil Injection|2,3-Dimercaptopropanol|BAL|2,3-DIMERCAPTOPROPANOL|2,3-Dimercapto-1-propano...

General Information

Structure

Molecular Formula

C₃H₈OS₂

Molecular Mass

124.22502

Exact Mass

124.00165688

Charge

InChI

InChI=1S/C3H8OS2/c4-1-3(6)2-5/h3-6H,1-2H2

InChIKey

WQABCVAJNWAXTE-UHFFFAOYSA-N

Canonic Smiles

OCC(CS)S

Isomeric Smiles

C(C(CS)S)O

Calculated Properties

JChem

LogD (pH = 7.4)

0.21

LogD (pH = 5.5)

0.21

Log P

0.21

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

9.58

Polar Surface Area

20.23

Polarizability

12.89

Molar Refractivity

32.91

LOG S

-0.66

Data Source

Commercial Catalog

Academic Data

Data Source

Names and Identifiers

Brand Name

DimercaprolBal In Oil Injection

Synonyms

BAL2,3-DimercaproDimercaprolBritish Anti-Lewisite2,3-Dimercaptopropanol2,3-DIMERCAPTOPROPANOL2,3-Dimercapto-1-propanol二硫代甘油2,3-二巯基-1-丙醇Dimercaprol英国抗路易气剂二巯丙醇DMPDithioglycerol2,3-Dimercaptopropanol2,3-二巯基丙醇2,3-Mercaptopropanol1,2-dimercapto-3-propanolBritish antilewisitedithioglycerolBAL1,2-dithioglycerolalpha,beta-dithioglyceroldimercaptopropanol3-hydroxy-1,2-propanedithiolBritish anti-Lewisitedimercaprol2,3-dithiopropanolsulfactin2,3-dimercaptol-1-propanolBritish anti-lewisite2,3-Dimercapto-1-propanoldithioglycerine2,3-dimercapto-1-propanol2,3-dimercaptopropanol2,3-mercaptopropan-1-ol

IUPAC name

2,3-disulfanylpropan-1-ol

IUPAC Traditional name

BAL dimercaprol

International Nonproprietary Name (INN)

dimercaproldimercaprolum

Names and Identifiers

Registration numbers

MDL Number

EC Number

Beilstein Number

CAS Number

ATC CODE

DrugBank ID

CHEMBL

PubChem SID

24893357248640161609679102488309399443293135610754

Merck Index

143209

Unique Ingredient Identifier

MeSH Name

Wikipedia Title

Chemspider ID

KEGG ID

PubChem CID

Patent number

UniProt Database

P07882Q9D7Z6Q9Y2P5P30122O13837Q8TDB6P17649Q9PSN0P19835O23530Q64285Q9ES38Q4LDG0

ACToR Database

59-52-931855-41-1

BKMS React Database

9506610871690880212775104153911179979996725

BRENDA Ligand Database

9111796725108716212775950669088099799104153

CHEBI ID

CHEBI:64198

PubMed Citation Links

929228614882450210064851260520521803782

KEGG DRUG Database

D00167

NMRShiftDB Database

20097917

SureChEMBL Database

SCHEMBL15969

MetaboLights Database

MTBLS1642MTBLS673MTBLS2878

Reaxys Registry

1732058

CompTox Database

DTXSID5040461

Drug Central Database

3,150

Registration numbers

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

MP Biomedicals

05202073

MP Biomedicals Rare Chemical collection

Wikipedia

Dimercaprol

DrugBank

DB06782

Drug Groups

approved

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.

Indication

For the treatment of arsenic, gold and mercury poisoning. Indicated in acute lead poisoning when used concomitantly with edetate calcium disodium (DB00974).

Pharmacology

Due 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.

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.

Absorption

After intra-muscular injection.

Half Life

The drug has a short half life.

Elimination

Urine.

References

• Walshe JM: The conquest of Wilson's disease. Brain. 2009 Aug;132(Pt 8):2289-95. Epub 2009 Jul 13. [Pubmed]

• 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]

• 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]

• 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

• [Wikipedia]

Sigma Aldrich

38520

General description
Visit our Titration Center to learn more.
Other Notes
Chelator for heavy metals; used as antidote to heavy metal poisoning (arsenic, gold, mercury, etc)1,2; Reagent for extracting Cu(II)3; Semi-quantitative det. of Cu(II)4

ChEBI

CHEBI:64198

A dithiol that is propane-1,2-dithiol in which one of the methyl hydrogens is replaced by a hydroxy group. a chelating agent originally developed during World War II as an experimental antidote against the arsenic-based poison gas Lewisite, it has been used clinically since 1949 for the treatment of poisoning by arsenic, mercury and gold. It can also be used for treatment of poisoning by antimony, bismuth and possibly thallium, and (with sodium calcium edetate) in cases of acute leaad poisoning. Administration is by (painful) intramuscular injection of a suspension of dimercaprol in peanut oil, typically every 4 hours for 2-10 days depending on the toxicity. In the past, dimercaprol was also used for the treatment of Wilson's disease, a severely debilitating genetic disorder in which the body tends to retain copper, with resultant liver and brain injury.

Molecule Details

References

PubChem Literature

From Data Sources

• Walshe JM: The conquest of Wilson's disease. Brain. 2009 Aug;132(Pt 8):2289-95. Epub 2009 Jul 13. Pubmed

• 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

• 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

• 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

References

Bioactivity

PubChem BioAssay

Bioactivity

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General Information

Calculated Properties

• RDKit

• JChem

Data Source

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• Brand Name

• Synonyms

• IUPAC name

• IUPAC Traditional name

• International Nonproprietary Name (INN)

Names and Identifiers

Registration numbers

• MDL Number

• EC Number

• Beilstein Number

• CAS Number

• ATC CODE

• DrugBank ID

• CHEMBL

• PubChem SID

• Merck Index

• Unique Ingredient Identifier

• MeSH Name

• Wikipedia Title

• Chemspider ID

• KEGG ID

• PubChem CID

• Patent number

• UniProt Database

• ACToR Database

• BRENDA Database

• BKMS React Database

• BRENDA Ligand Database

• CHEBI ID

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• NMRShiftDB Database

• SureChEMBL Database

• MetaboLights Database

• Reaxys Registry

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Related Proteins

Molecular Spectra

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Molecule Details

References

• PubChem Literature

• From Data Sources

Bioactivity

• PubChem BioAssay

Brand Name

DimercaprolBal In Oil Injection

Synonyms

IUPAC name

2,3-disulfanylpropan-1-ol

IUPAC Traditional name

BAL dimercaprol

International Nonproprietary Name (INN)

dimercaproldimercaprolum

MDL Number

MFCD00004864

Beilstein Number

1732058

Unique Ingredient Identifier

MeSH Name

Wikipedia Title

KEGG ID

Patent number

ACToR Database

CHEBI ID

KEGG DRUG Database

NMRShiftDB Database

SureChEMBL Database

MetaboLights Database

MTBLS1642MTBLS673MTBLS2878

Reaxys Registry

1732058

CompTox Database

DTXSID5040461

Drug Central Database

3,150

MP Biomedicals

05202073

MP Biomedicals Rare Chemical collection

DrugBank

DB06782

Drug Groups

approved

Description

Indication

For the treatment of arsenic, gold and mercury poisoning. Indicated in acute lead poisoning when used concomitantly with edetate calcium disodium (DB00974).

Pharmacology

Toxicity

Absorption

After intra-muscular injection.

Half Life

The drug has a short half life.

Elimination

Urine.

References

• Walshe JM: The conquest of Wilson's disease. Brain. 2009 Aug;132(Pt 8):2289-95. Epub 2009 Jul 13. [Pubmed]

• 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]

• 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]

• 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

• [Wikipedia]

Sigma Aldrich

38520

ChEBI

CHEBI:64198

From Data Sources

• Walshe JM: The conquest of Wilson's disease. Brain. 2009 Aug;132(Pt 8):2289-95. Epub 2009 Jul 13. Pubmed

• 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

• 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

• 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

Product Information

Quality

for spectrophotometric det. of Cu

Grade

for complexometry

Safety Information

Physical Property

Acute toxicity (oral, dermal, inhalation), categories 1,2,3

Acute toxicity (oral, dermal, inhalation), category 4

Skin irritation, category 2

Eye irritation, category 2

Skin sensitisation, category 1

Specific Target Organ Toxicity – Single exposure, category 3

Molecule

ID:4478