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

Molecular Formula C3H8OS2
Molecular Weight 124.225
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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
Arsenic poisoning in livestock.
1991 Jun
Treatment of the neurologic manifestations of Wilson's disease.
1995 Apr
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
Syntaxin 1A modulates the voltage-gated L-type calcium channel (Ca(v)1.2) in a cooperative manner.
2003 Aug 1
Interaction between metals and chelating agents affects glutamate binding on brain synaptic membranes.
2003 Dec
Synthesis and optical properties of thiol-stabilized PbS nanocrystals.
2005 Feb 1
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
The conquest of Wilson's disease.
2009 Aug
Reaction of the catalytic cysteine of betaine aldehyde dehydrogenase from Pseudomonas aeruginosa with arsenite-BAL and phenylarsine oxide.
2009 Mar 16
Structural, chemical and biological aspects of antioxidants for strategies against metal and metalloid exposure.
2009 Sep-Oct
Synthesis, X-Ray Structure, and Characterization of Catena-bis(benzoate)bis{N,N-bis(2-hydroxyethyl)glycinate}cadmium(II).
2010
Display of both N- and C-terminal target fusion proteins on the Aspergillus oryzae cell surface using a chitin-binding module.
2010 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
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:03:29 GMT 2023
Edited
by admin
on Fri Dec 15 15:03:29 GMT 2023
Record UNII
0CPP32S55X
Record Status Validated (UNII)
Record Version
  • Download
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
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
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ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
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ACTIVE MOIETY