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
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 |
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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 |
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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 |
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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 Nov 10 |
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Evidence for the involvement of vicinal sulfhydryl groups in insulin-activated hexose transport by 3T3-L1 adipocytes. | 1985 Mar 10 |
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Uptake and binding of radiolabelled phenylarsine oxide in 3T3-L1 adipocytes. | 1990 Aug 1 |
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2,3 Dimercapto-1-propanol inhibits HIV-1 tat activity, viral production, and infectivity in vitro. | 1990 Jul |
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Phenylarsine oxide inhibits insulin-stimulated protein phosphatase 1 activity and GLUT-4 translocation. | 1994 Jul |
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Treatment of the neurologic manifestations of Wilson's disease. | 1995 Apr |
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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 Nov |
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Electrophile and antioxidant regulation of enzymes that detoxify carcinogens. | 1995 Sep 12 |
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Inhibition of tat-mediated HIV-1-LTR transactivation and virus replication by sulfhydryl compounds with chelating properties. | 2000 Jul-Aug |
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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 |
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Inhibition of human squalene monooxygenase by tellurium compounds: evidence of interaction with vicinal sulfhydryls. | 2001 Feb |
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Tributyltin interacts with mitochondria and induces cytochrome c release. | 2001 Jun 1 |
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2,3-Dimercaptopropanol inhibits Ca2+ transport in microsomes from brain but not from fast-skeletal muscle. | 2001 Mar |
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BAL modulates glutamate transport in synaptosomes and synaptic vesicles from rat brain. | 2001 Mar 5 |
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Induction of heme oxygenase-1 by phenylarsine oxide. Studies in cultured primary liver cells. | 2001 Oct |
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Oxidation of proximal protein sulfhydryls by phenanthraquinone, a component of diesel exhaust particles. | 2002 Apr |
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Purine nucleoside phosphorylase as a cytosolic arsenate reductase. | 2002 Nov |
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Assessment of bismuth thiols and conventional disinfectants on drinking water biofilms. | 2003 |
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Interaction between metals and chelating agents affects glutamate binding on brain synaptic membranes. | 2003 Dec |
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A colorimetric microplate assay method for high throughput analysis of lipase activity. | 2003 Jul 31 |
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Survival after a lethal dose of arsenic trioxide. | 2004 |
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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 Dec |
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Gas chromatographic-mass spectrometric determination of british anti-lewisite in plasma. | 2004 Jul-Aug |
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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 Mar |
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Effects of chelating agents on distribution and excretion of terbium in mice. | 2005 |
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Synthesis and optical properties of thiol-stabilized PbS nanocrystals. | 2005 Feb 1 |
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Bismuth-dithiol inhibition of the Escherichia coli rho transcription termination factor. | 2005 Mar |
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Redox regulation of the nutrient-sensitive raptor-mTOR pathway and complex. | 2005 Nov 25 |
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TXM13 human melanoma cells: a novel source for the inhibition kinetics of human tyrosinase and for screening whitening agents. | 2006 Feb |
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Diphenyl diselenide and 2,3-dimercaptopropanol increase the PTZ-induced chemical seizure and mortality in mice. | 2006 Feb 15 |
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Complex inhibition of tyrosinase by thiol-composed Cu2+ chelators: a clue for designing whitening agents. | 2006 Oct |
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Depolarization-evoked secretion requires two vicinal transmembrane cysteines of syntaxin 1A. | 2007 Dec 5 |
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Quantification of arsenic compounds using derivatization, solvent extraction and liquid chromatography electrospray ionization tandem mass spectrometry. | 2008 Dec 15 |
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Phosphatidylinositol kinases as regulators of GA-stimulated alpha-amylase secretion in barley (Hordeum vulgare). | 2008 Jun |
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Coordinate regulation of enzyme markers for inflammation and for protection against oxidants and electrophiles. | 2008 Oct 14 |
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Regulation of fast skeletal muscle activity by SERCA1 vicinal-cysteines. | 2009 |
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The conquest of Wilson's disease. | 2009 Aug |
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Detoxification of mercury species--an in vitro study with antidotes in human whole blood. | 2009 Nov |
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Pattern-based recognition of thiols and metals using a single squaraine indicator. | 2009 Sep 16 |
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Structural, chemical and biological aspects of antioxidants for strategies against metal and metalloid exposure. | 2009 Sep-Oct |
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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 Aug |
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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 Jan |
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α-Lipoic acid protects against arsenic trioxide-induced acute QT prolongation in anesthetized guinea pigs. | 2013 Apr 5 |
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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
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
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Classification Tree | Code System | Code | ||
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WHO-VATC |
QV03AB09
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NBK548426
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N0000175472
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WHO-ESSENTIAL MEDICINES LIST |
4.2
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C62357
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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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39515
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ACTIVE MOIETY