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
SMILES
OCC(S)CS
InChI
InChIKey=WQABCVAJNWAXTE-UHFFFAOYSA-N
InChI=1S/C3H8OS2/c4-1-3(6)2-5/h3-6H,1-2H2
| 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
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | BAL Approved UseINDICATIONS 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 Date1946 |
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| Curative | BAL Approved UseINDICATIONS 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 Date1946 |
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| Curative | BAL Approved UseINDICATIONS 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 Date1946 |
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| Curative | BAL Approved UseINDICATIONS 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 Date1946 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Reversal effect of monoisoamyl dimercaptosuccinic acid (MiADMSA) for arsenic and lead induced perturbations in apoptosis and antioxidant enzymes in developing rat brain. | 2013-11 |
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| α-Lipoic acid protects against arsenic trioxide-induced acute QT prolongation in anesthetized guinea pigs. | 2013-04-05 |
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| Effects of selenite and chelating agents on mammalian thioredoxin reductase inhibited by mercury: implications for treatment of mercury poisoning. | 2011-01 |
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| Structural, chemical and biological aspects of antioxidants for strategies against metal and metalloid exposure. | 2010-08-19 |
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| Display of both N- and C-terminal target fusion proteins on the Aspergillus oryzae cell surface using a chitin-binding module. | 2010-08 |
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| Chelation in metal intoxication. | 2010-07 |
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| Critical cysteine residues of Kelch-like ECH-associated protein 1 in arsenic sensing and suppression of nuclear factor erythroid 2-related factor 2. | 2010-01 |
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| Synthesis, X-Ray Structure, and Characterization of Catena-bis(benzoate)bis{N,N-bis(2-hydroxyethyl)glycinate}cadmium(II). | 2010 |
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| Acute mercury intoxication and use of chelating agents. | 2009-12-17 |
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| Detoxification of mercury species--an in vitro study with antidotes in human whole blood. | 2009-11 |
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| Pattern-based recognition of thiols and metals using a single squaraine indicator. | 2009-09-16 |
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| The conquest of Wilson's disease. | 2009-08 |
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| Reaction of the catalytic cysteine of betaine aldehyde dehydrogenase from Pseudomonas aeruginosa with arsenite-BAL and phenylarsine oxide. | 2009-03-16 |
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| Regulation of fast skeletal muscle activity by SERCA1 vicinal-cysteines. | 2009 |
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| Quantification of arsenic compounds using derivatization, solvent extraction and liquid chromatography electrospray ionization tandem mass spectrometry. | 2008-12-15 |
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| Coordinate regulation of enzyme markers for inflammation and for protection against oxidants and electrophiles. | 2008-10-14 |
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| Phosphatidylinositol kinases as regulators of GA-stimulated alpha-amylase secretion in barley (Hordeum vulgare). | 2008-06 |
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| Selective masking and demasking for the stepwise complexometric determination of aluminium, lead and zinc from the same solution. | 2008-03-06 |
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| Depolarization-evoked secretion requires two vicinal transmembrane cysteines of syntaxin 1A. | 2007-12-05 |
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| Complex inhibition of tyrosinase by thiol-composed Cu2+ chelators: a clue for designing whitening agents. | 2006-10 |
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| Photochemistry of the [Fe4(mu3-S)3(NO)7]- complex in the presence of S-nucleophiles: a spectroscopic study. | 2006-05 |
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| Microarray analysis of mouse ear tissue exposed to bis-(2-chloroethyl) sulfide: gene expression profiles correlate with treatment efficacy and an established clinical endpoint. | 2006-04 |
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| Diphenyl diselenide and 2,3-dimercaptopropanol increase the PTZ-induced chemical seizure and mortality in mice. | 2006-02-15 |
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| TXM13 human melanoma cells: a novel source for the inhibition kinetics of human tyrosinase and for screening whitening agents. | 2006-02 |
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| Redox regulation of the nutrient-sensitive raptor-mTOR pathway and complex. | 2005-11-25 |
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| Toxicity induced by Hg2+ on choline acetyltransferase activity from E. electricus (L.) electrocytes: the protective effect of 2,3 dimercapto-propanol (BAL). | 2005-04 |
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| 2,3-Dimercaptopropanol, 2,3-dimercaptopropane-1-sulfonic acid and meso-2,3-dimercaptosuccinic acid acute administration diferentially change biochemical parameters in mice. | 2005-04 |
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| 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. | 2005-04 |
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| Bismuth-dithiol inhibition of the Escherichia coli rho transcription termination factor. | 2005-03 |
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| Synthesis and optical properties of thiol-stabilized PbS nanocrystals. | 2005-02-01 |
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| Effects of chelating agents on distribution and excretion of terbium in mice. | 2005 |
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| The integrated role of desferrioxamine and phenserine targeted to an iron-responsive element in the APP-mRNA 5'-untranslated region. | 2004-12 |
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| Gas chromatographic-mass spectrometric determination of british anti-lewisite in plasma. | 2004-07-09 |
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| 2,3-Dimercaptopropanol, 2,3-dimercaptopropane-1-sulfonic acid, and meso-2,3-dimercaptosuccinic acid inhibit delta-aminolevulinate dehydratase from human erythrocytes in vitro. | 2004-03 |
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| Chemical and biological considerations in the treatment of metal intoxications by chelating agents. | 2004-01 |
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| Survival after a lethal dose of arsenic trioxide. | 2004 |
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| Interaction between metals and chelating agents affects glutamate binding on brain synaptic membranes. | 2003-12 |
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| Syntaxin 1A modulates the voltage-gated L-type calcium channel (Ca(v)1.2) in a cooperative manner. | 2003-08-01 |
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| A colorimetric microplate assay method for high throughput analysis of lipase activity. | 2003-07-31 |
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| Assessment of bismuth thiols and conventional disinfectants on drinking water biofilms. | 2003 |
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| Parallel induction of heme oxygenase-1 and chemoprotective phase 2 enzymes by electrophiles and antioxidants: regulation by upstream antioxidant-responsive elements (ARE). | 1995-11 |
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| Electrophile and antioxidant regulation of enzymes that detoxify carcinogens. | 1995-09-12 |
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| Treatment of the neurologic manifestations of Wilson's disease. | 1995-04 |
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| Phenylarsine oxide inhibits insulin-stimulated protein phosphatase 1 activity and GLUT-4 translocation. | 1994-07 |
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| Effects of phenylarsine oxide on insulin-stimulated system A amino acid uptake in skeletal muscle. | 1991-10 |
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| Arsenic poisoning in livestock. | 1991-06 |
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| Uptake and binding of radiolabelled phenylarsine oxide in 3T3-L1 adipocytes. | 1990-08-01 |
|
| 2,3 Dimercapto-1-propanol inhibits HIV-1 tat activity, viral production, and infectivity in vitro. | 1990-07 |
|
| Evidence for the involvement of vicinal sulfhydryl groups in insulin-activated hexose transport by 3T3-L1 adipocytes. | 1985-03-10 |
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| Inhibition of coupling factor B activity by cadmium ion, arsenite-2,3-dimercaptopropanol, and phenylarsine oxide, and preferential reactivation by dithiols. | 1981-11-10 |
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
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on
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| Record UNII |
0CPP32S55X
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| Record Status |
Validated (UNII)
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| Classification Tree | Code System | Code | ||
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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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SUB07165MIG
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Dimercaprol
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C47494
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DIMERCAPROL
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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. | ||
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0CPP32S55X
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64198
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100000082658
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DB06782
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200-433-7
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4646
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m4501
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39515
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ENANTIOMER -> RACEMATE | |||
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ENANTIOMER -> RACEMATE |
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ACTIVE MOIETY |