U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C3H8OS2
Molecular Weight 124.225
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIMERCAPROL

SMILES

OCC(S)CS

InChI

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

HIDE SMILES / InChI
Dimercaprol (2, 3-dimercapto-1-propanol) or British anti-Lewisite (BAL), is a colorless or almost colorless liquid chelating agent having a disagreeable, mercaptan-like odor. Dimercaprol was developed at Oxford University during World War II as a means of treating and reversing poisoning from Lewisite, an arsenical gas used in chemical warfare (and thus initially called British anti-Lewisite [BAL]). The sulfhydryl groups of dimercaprol form complexes with certain heavy metals thus preventing or reversing the metallic binding of sulfhydryl-containing enzymes. Parenterally administered dimercaprol is used to treat arsenic, gold, copper and mercury poisoning. It is indicated in acute lead poisoning when used concomitantly with edetate clcium disodium. Dimercaprol is occasionally used in the initial treatment of severe, symptomatic Wilson disease, but generally for a short time only.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
BAL

Approved Use

INDICATIONS BAL in Oil (Dimercaprol Injection USP) is indicated in the treatment of arsenic, gold and mercury poisoning. It is indicated in acute lead poisoning when used concomitantly with Edetate Calcium Disodium Injection USP. Dimercaprol Injection USP is effective for use in acute poisoning by mercury salts if therapy is begun within one or two hours following ingestion. It is not very effective for chronic mercury poisoning. Dimercaprol Injection USP is of questionable value in poisoning caused by other heavy metals such as antimony and bismuth. It should not be used in iron, cadmium, or selenium poisoning because the resulting dimercaprol-metal complexes are more toxic than the metal alone, especially to the kidneys.

Launch Date

1946
Curative
BAL

Approved Use

INDICATIONS BAL in Oil (Dimercaprol Injection USP) is indicated in the treatment of arsenic, gold and mercury poisoning. It is indicated in acute lead poisoning when used concomitantly with Edetate Calcium Disodium Injection USP. Dimercaprol Injection USP is effective for use in acute poisoning by mercury salts if therapy is begun within one or two hours following ingestion. It is not very effective for chronic mercury poisoning. Dimercaprol Injection USP is of questionable value in poisoning caused by other heavy metals such as antimony and bismuth. It should not be used in iron, cadmium, or selenium poisoning because the resulting dimercaprol-metal complexes are more toxic than the metal alone, especially to the kidneys.

Launch Date

1946
Curative
BAL

Approved Use

INDICATIONS BAL in Oil (Dimercaprol Injection USP) is indicated in the treatment of arsenic, gold and mercury poisoning. It is indicated in acute lead poisoning when used concomitantly with Edetate Calcium Disodium Injection USP. Dimercaprol Injection USP is effective for use in acute poisoning by mercury salts if therapy is begun within one or two hours following ingestion. It is not very effective for chronic mercury poisoning. Dimercaprol Injection USP is of questionable value in poisoning caused by other heavy metals such as antimony and bismuth. It should not be used in iron, cadmium, or selenium poisoning because the resulting dimercaprol-metal complexes are more toxic than the metal alone, especially to the kidneys.

Launch Date

1946
Curative
BAL

Approved Use

INDICATIONS BAL in Oil (Dimercaprol Injection USP) is indicated in the treatment of arsenic, gold and mercury poisoning. It is indicated in acute lead poisoning when used concomitantly with Edetate Calcium Disodium Injection USP. Dimercaprol Injection USP is effective for use in acute poisoning by mercury salts if therapy is begun within one or two hours following ingestion. It is not very effective for chronic mercury poisoning. Dimercaprol Injection USP is of questionable value in poisoning caused by other heavy metals such as antimony and bismuth. It should not be used in iron, cadmium, or selenium poisoning because the resulting dimercaprol-metal complexes are more toxic than the metal alone, especially to the kidneys.

Launch Date

1946
PubMed

PubMed

TitleDatePubMed
Inhibition of coupling factor B activity by cadmium ion, arsenite-2,3-dimercaptopropanol, and phenylarsine oxide, and preferential reactivation by dithiols.
1981 Nov 10
Evidence for the involvement of vicinal sulfhydryl groups in insulin-activated hexose transport by 3T3-L1 adipocytes.
1985 Mar 10
Uptake and binding of radiolabelled phenylarsine oxide in 3T3-L1 adipocytes.
1990 Aug 1
2,3 Dimercapto-1-propanol inhibits HIV-1 tat activity, viral production, and infectivity in vitro.
1990 Jul
Phenylarsine oxide inhibits insulin-stimulated protein phosphatase 1 activity and GLUT-4 translocation.
1994 Jul
Treatment of the neurologic manifestations of Wilson's disease.
1995 Apr
Parallel induction of heme oxygenase-1 and chemoprotective phase 2 enzymes by electrophiles and antioxidants: regulation by upstream antioxidant-responsive elements (ARE).
1995 Nov
Electrophile and antioxidant regulation of enzymes that detoxify carcinogens.
1995 Sep 12
Inhibition of tat-mediated HIV-1-LTR transactivation and virus replication by sulfhydryl compounds with chelating properties.
2000 Jul-Aug
Inhibition of NF-kappa B activation by arsenite through reaction with a critical cysteine in the activation loop of Ikappa B kinase.
2000 Nov 17
Inhibition of human squalene monooxygenase by tellurium compounds: evidence of interaction with vicinal sulfhydryls.
2001 Feb
Tributyltin interacts with mitochondria and induces cytochrome c release.
2001 Jun 1
2,3-Dimercaptopropanol inhibits Ca2+ transport in microsomes from brain but not from fast-skeletal muscle.
2001 Mar
BAL modulates glutamate transport in synaptosomes and synaptic vesicles from rat brain.
2001 Mar 5
Induction of heme oxygenase-1 by phenylarsine oxide. Studies in cultured primary liver cells.
2001 Oct
Oxidation of proximal protein sulfhydryls by phenanthraquinone, a component of diesel exhaust particles.
2002 Apr
Purine nucleoside phosphorylase as a cytosolic arsenate reductase.
2002 Nov
Assessment of bismuth thiols and conventional disinfectants on drinking water biofilms.
2003
Interaction between metals and chelating agents affects glutamate binding on brain synaptic membranes.
2003 Dec
A colorimetric microplate assay method for high throughput analysis of lipase activity.
2003 Jul 31
Survival after a lethal dose of arsenic trioxide.
2004
The integrated role of desferrioxamine and phenserine targeted to an iron-responsive element in the APP-mRNA 5'-untranslated region.
2004 Dec
Gas chromatographic-mass spectrometric determination of british anti-lewisite in plasma.
2004 Jul-Aug
2,3-Dimercaptopropanol, 2,3-dimercaptopropane-1-sulfonic acid, and meso-2,3-dimercaptosuccinic acid inhibit delta-aminolevulinate dehydratase from human erythrocytes in vitro.
2004 Mar
Effects of chelating agents on distribution and excretion of terbium in mice.
2005
Synthesis and optical properties of thiol-stabilized PbS nanocrystals.
2005 Feb 1
Bismuth-dithiol inhibition of the Escherichia coli rho transcription termination factor.
2005 Mar
Redox regulation of the nutrient-sensitive raptor-mTOR pathway and complex.
2005 Nov 25
TXM13 human melanoma cells: a novel source for the inhibition kinetics of human tyrosinase and for screening whitening agents.
2006 Feb
Diphenyl diselenide and 2,3-dimercaptopropanol increase the PTZ-induced chemical seizure and mortality in mice.
2006 Feb 15
Complex inhibition of tyrosinase by thiol-composed Cu2+ chelators: a clue for designing whitening agents.
2006 Oct
Depolarization-evoked secretion requires two vicinal transmembrane cysteines of syntaxin 1A.
2007 Dec 5
Quantification of arsenic compounds using derivatization, solvent extraction and liquid chromatography electrospray ionization tandem mass spectrometry.
2008 Dec 15
Phosphatidylinositol kinases as regulators of GA-stimulated alpha-amylase secretion in barley (Hordeum vulgare).
2008 Jun
Coordinate regulation of enzyme markers for inflammation and for protection against oxidants and electrophiles.
2008 Oct 14
Regulation of fast skeletal muscle activity by SERCA1 vicinal-cysteines.
2009
The conquest of Wilson's disease.
2009 Aug
Detoxification of mercury species--an in vitro study with antidotes in human whole blood.
2009 Nov
Pattern-based recognition of thiols and metals using a single squaraine indicator.
2009 Sep 16
Structural, chemical and biological aspects of antioxidants for strategies against metal and metalloid exposure.
2009 Sep-Oct
Display of both N- and C-terminal target fusion proteins on the Aspergillus oryzae cell surface using a chitin-binding module.
2010 Aug
Critical cysteine residues of Kelch-like ECH-associated protein 1 in arsenic sensing and suppression of nuclear factor erythroid 2-related factor 2.
2010 Jan
α-Lipoic acid protects against arsenic trioxide-induced acute QT prolongation in anesthetized guinea pigs.
2013 Apr 5
Reversal effect of monoisoamyl dimercaptosuccinic acid (MiADMSA) for arsenic and lead induced perturbations in apoptosis and antioxidant enzymes in developing rat brain.
2013 Nov
Patents

Patents

Sample Use Guides

By deep intramuscular injection only. For mild arsenic or gold poisoning, 2.5 mg/kg of body weight four times daily for two days, two times on the third day, and once daily thereafter for ten days; for severe arsenic or gold poisoning, 3 mg/kg every four hours for two-days, four times on the third day, then twice daily thereafter for ten days. For mercury poisoning, 5 mg/kg initially, followed by 2.5 mg/kg one or two times daily for ten days. For acute lead encephalopathy, 4 mg/kg body weight is given alone in the first dose and thereafter at four-hour intervals in combination with Edetate Calcium Disodium Injection USP administered at a separate site. For less severe poisoning the dose can be reduced to 3 mg/kg after the first dose. Treatment is maintained for two to seven days depending on clinical response. Successful treatment depends on beginning injections at the earliest possible moment and on the use of adequate amounts at frequent intervals. Other supportive measures should always be used in conjunction with BAL in Oil (Dimercaprol Injection USP) therapy.
Route of Administration: Intramuscular
Name Type Language
DIMERCAPROL
EP   HSDB   INN   MART.   MI   ORANGE BOOK   USP   VANDF   WHO-DD   WHO-IP  
INN  
Official Name English
DIMERCAPROL [VANDF]
Common Name English
DIMERCAPROL [WHO-IP]
Common Name English
2,3-DITHIOPROPANOL
Common Name English
2,3-DIMERCAPTOPROPANOL
Systematic Name English
2,3-DITHIOPROPAN-1-OL
Common Name English
DIMERCAPROLUM [WHO-IP LATIN]
Common Name English
DITHIOGLYCERINE
Systematic Name English
DIMERCAPROL [USP MONOGRAPH]
Common Name English
DIMERCAPROL [HSDB]
Common Name English
DIMERCAPROL [ORANGE BOOK]
Common Name English
1,2-DITHIOGLYCEROL
Systematic Name English
DITHIOGLYCEROL
Systematic Name English
Dimercaprol [WHO-DD]
Common Name English
1,2-DIMERCAPTO-3-PROPANOL
Systematic Name English
BAL
Brand Name English
DIMERCAPROL [MI]
Common Name English
DIMERCAPROL [JAN]
Common Name English
DICAPTOL
Common Name English
2,3,-DIMERCAPTO-1-PROPANOL
Common Name English
3-HYDROXY-1,2-PROPANEDITHIOL
Systematic Name English
PANOBAL
Common Name English
NSC-4646
Code English
dimercaprol [INN]
Common Name English
SULFACTIN
Common Name English
DIMERSOL
Common Name English
NSC-39515
Code English
ANTOXOL
Common Name English
DIMERCAPROL [EP MONOGRAPH]
Common Name English
DIMERCAPROL [MART.]
Common Name English
1-PROPANOL, 2,3-DIMERCAPTO
Common Name English
Classification Tree Code System Code
WHO-VATC QV03AB09
Created by admin on Fri Dec 15 15:03:29 GMT 2023 , Edited by admin on Fri Dec 15 15:03:29 GMT 2023
LIVERTOX NBK548426
Created by admin on Fri Dec 15 15:03:29 GMT 2023 , Edited by admin on Fri Dec 15 15:03:29 GMT 2023
NDF-RT N0000175472
Created by admin on Fri Dec 15 15:03:29 GMT 2023 , Edited by admin on Fri Dec 15 15:03:29 GMT 2023
WHO-ESSENTIAL MEDICINES LIST 4.2
Created by admin on Fri Dec 15 15:03:29 GMT 2023 , Edited by admin on Fri Dec 15 15:03:29 GMT 2023
NCI_THESAURUS C62357
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NDF-RT N0000175473
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WHO-ATC V03AB09
Created by admin on Fri Dec 15 15:03:29 GMT 2023 , Edited by admin on Fri Dec 15 15:03:29 GMT 2023
Code System Code Type Description
EVMPD
SUB07165MIG
Created by admin on Fri Dec 15 15:03:29 GMT 2023 , Edited by admin on Fri Dec 15 15:03:29 GMT 2023
PRIMARY
WIKIPEDIA
Dimercaprol
Created by admin on Fri Dec 15 15:03:29 GMT 2023 , Edited by admin on Fri Dec 15 15:03:29 GMT 2023
PRIMARY
NCI_THESAURUS
C47494
Created by admin on Fri Dec 15 15:03:29 GMT 2023 , Edited by admin on Fri Dec 15 15:03:29 GMT 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
DIMERCAPROL
Created by admin on Fri Dec 15 15:03:29 GMT 2023 , Edited by admin on Fri Dec 15 15:03:29 GMT 2023
PRIMARY Description: A clear, colourless or slightly yellow liquid, with an unpleasant, mercaptan-like odour. Miscibility. Miscible with 20 parts of water; miscible with ethanol (~750 g/l) TS and methanol R.Category: Antidote for arsenic, gold, and mercury poisoning. Storage: Dimercaprol should be kept in a small, well-filled and tightly closed container, protected from light, and stored at atemperature not exceeding 5?C. Definition: Dimercaprol contains not less than 98.5% w/w and not more than 101.5% w/w of C3H8OS2. Identity tests: A. Mix 0.05 mL of cobalt(II) chloride (30 g/l) TS with 5 mL of water and add 0.05 mL of the test liquid; a yellowbrowncolour is produced.B. Dissolve 0.1 mL in 4 mL of water and add a few drops of lead acetate (80 g/l) TS; a yellow precipitate is formed.
CAS
59-52-9
Created by admin on Fri Dec 15 15:03:29 GMT 2023 , Edited by admin on Fri Dec 15 15:03:29 GMT 2023
PRIMARY
PUBCHEM
3080
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PRIMARY
INN
1614
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PRIMARY
FDA UNII
0CPP32S55X
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PRIMARY
CHEBI
64198
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PRIMARY
DAILYMED
0CPP32S55X
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PRIMARY
HSDB
4004
Created by admin on Fri Dec 15 15:03:29 GMT 2023 , Edited by admin on Fri Dec 15 15:03:29 GMT 2023
PRIMARY
DRUG CENTRAL
3150
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PRIMARY
MESH
D004112
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PRIMARY
ChEMBL
CHEMBL1597
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PRIMARY
SMS_ID
100000082658
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PRIMARY
DRUG BANK
DB06782
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PRIMARY
ECHA (EC/EINECS)
200-433-7
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PRIMARY
EPA CompTox
DTXSID5040461
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PRIMARY
RXCUI
3445
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PRIMARY RxNorm
NSC
4646
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PRIMARY
MERCK INDEX
m4501
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PRIMARY Merck Index
NSC
39515
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PRIMARY