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
Phenylarsine oxide inhibits insulin-stimulated protein phosphatase 1 activity and GLUT-4 translocation.
1994 Jul
Parallel induction of heme oxygenase-1 and chemoprotective phase 2 enzymes by electrophiles and antioxidants: regulation by upstream antioxidant-responsive elements (ARE).
1995 Nov
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
Syntaxin 1A modulates the voltage-gated L-type calcium channel (Ca(v)1.2) in a cooperative manner.
2003 Aug 1
The integrated role of desferrioxamine and phenserine targeted to an iron-responsive element in the APP-mRNA 5'-untranslated region.
2004 Dec
Toxicity induced by Hg2+ on choline acetyltransferase activity from E. electricus (L.) electrocytes: the protective effect of 2,3 dimercapto-propanol (BAL).
2005 Apr
2,3-Dimercaptopropanol, 2,3-dimercaptopropane-1-sulfonic acid and meso-2,3-dimercaptosuccinic acid acute administration diferentially change biochemical parameters in mice.
2005 Apr
2,3-Dimercapto-1-propanol does not alter the porphobilinogen synthase inhibition but decreases the mercury content in liver and kidney of suckling rats exposed to HgCl2.
2005 Apr
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
Microarray analysis of mouse ear tissue exposed to bis-(2-chloroethyl) sulfide: gene expression profiles correlate with treatment efficacy and an established clinical endpoint.
2006 Apr
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
Photochemistry of the [Fe4(mu3-S)3(NO)7]- complex in the presence of S-nucleophiles: a spectroscopic study.
2006 May
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
The conquest of Wilson's disease.
2009 Aug
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
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LIVERTOX NBK548426
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NDF-RT N0000175472
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WHO-ESSENTIAL MEDICINES LIST 4.2
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NCI_THESAURUS C62357
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NDF-RT N0000175473
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WHO-ATC V03AB09
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Code System Code Type Description
EVMPD
SUB07165MIG
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PRIMARY
WIKIPEDIA
Dimercaprol
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PRIMARY
NCI_THESAURUS
C47494
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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
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PRIMARY
PUBCHEM
3080
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PRIMARY
INN
1614
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PRIMARY
FDA UNII
0CPP32S55X
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CHEBI
64198
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PRIMARY
DAILYMED
0CPP32S55X
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PRIMARY
HSDB
4004
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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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ECHA (EC/EINECS)
200-433-7
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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