Dimercaprol

Dimercaprol
Dimercaprol
Identifiers
CAS number 59-52-9 YesY, 16495-08-2 (2R)-2-sulfanyl YesY, 16495-16-2 (2S)-2-sulfanyl YesY
PubChem 3080, 6971262 (2R)-2-sulfanyl, 3246063 (2S)-2-sulfanyl
ChemSpider 2971 YesY, 5342114 (2R)-2-sulfanyl YesY, 2496803 (2S)-2-sulfanyl YesY
UNII 0CPP32S55X YesY
EC number 200-433-7
UN number 2810
DrugBank DB06782
KEGG D00167 YesY
MeSH Dimercaprol
ChEMBL CHEMBL1597 YesY
RTECS number UB2625000
ATC code V03AB09
Beilstein Reference 1732058
Jmol-3D images Image 1
Properties
Molecular formula C3H8S2O
Molar mass 124.225 g mol-1
Exact mass 124.001656258 g mol-1
Density 1.239 g cm-3
Boiling point

120 °C, 393 K, 248 °F (at 2.0 kPa)

log P 0.627
Acidity (pKa) 8.999
Basicity (pKb) 4.998
Refractive index (nD) 1.573
Hazards
GHS pictograms The skull-and-crossbones pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
GHS hazard statements H301, H315, H319, H335
GHS precautionary statements P261, P301+310, P305+351+338
EU classification Harmful Xn
R-phrases R22, R36/37/38
S-phrases S26, S36
NFPA 704
NFPA 704.svg
1
2
0
Flash point 112 °C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Dimercaprol (INN) or British anti-Lewisite (abbreviated BAL), is a compound developed by British biochemists at Oxford University during World War II.[1][2] It was developed secretly as an antidote for lewisite, the now-obsolete arsenic-based chemical warfare agent.[3] Today, it is used medically in treatment of arsenic, mercury, gold and lead, and other toxic metal poisoning.[4] In addition, it has in the past been used for the treatment of Wilson's disease, a genetic disorder in which the body tends to retain copper.[5]

Biochemical function

Arsenic and some other heavy metals act by chemically reacting with adjacent thiol residues on metabolic enzymes, creating a chelate complex that inhibits the affected enzyme's activity.[6] Dimercaprol competes with the thiol groups for binding the metal ion, which is then excreted in the urine.[citation needed]

Dimercaprol is itself toxic, with a narrow therapeutic range and a tendency to concentrate arsenic in some organs. Other drawbacks include the need to administer it by painful intramuscular injection.[7] Serious side effects include nephrotoxicity and hypertension.

Dimercaprol has been found to form stable chelates in vivo with many other toxic metals including inorganic mercury, antimony, bismuth, cadmium, chromium, cobalt, gold, and nickel. However, it is not necessarily the treatment of choice for toxicity to these metals. Dimercaprol has been used as an adjunct in the treatment of the acute encephalopathy of lead toxicity. It is a potentially toxic drug, and its use may be accompanied by multiple side effects. Although treatment with dimercaprol will increase the excretion of cadmium, there is a concomitant increase in renal cadmium concentration, so that its use in case of cadmium toxicity is to be avoided. It does, however, remove inorganic mercury from the kidneys; but is not useful in the treatment of alkylmercury or phenyl mercury toxicity. Dimercaprol also enhances the toxicity of selenium and tellurium, so it is not to be used to remove these metals from the body.[citation needed]

See also

References

  1. ^ Domingo Tabangcura, Jr., G. Patrick Daubert. "British anti-Lewisite". http://www.chm.bris.ac.uk/motm/bal/development.html. 
  2. ^ Peters, R; Stocken, L; Thompson, R. (1945). "British Anti-Lewisite (BAL)". Nature 156 (3969): 616–619. doi:10.1038/156616a0. PMID 21006485. 
  3. ^ Domingo Tabangcura, Jr., G. Patrick Daubert. "British anti-Lewisite". http://www.chm.bris.ac.uk/motm/bal/development.html. 
  4. ^ "Dimercaprol". http://www.drugs.com/dict/dimercaprol.html. 
  5. ^ Denny-Brown D, PORTER H (December 1951). "The effect of BAL (2,3-dimercaptopropanol) on hepatolenticular degeneration (Wilson's disease)". N. Engl. J. Med. 245 (24): 917–25. doi:10.1056/NEJM195112132452401. PMID 14882450. 
  6. ^ Goldman M, Dacre JC. (1989) Lewisite: its chemistry, toxicology, and biological effects. Rev Environ Contam Toxicol 110: 75-115
  7. ^ Mückter H, Liebl B, Reichl FX et al. (1997) Are we ready to replace dimercaprol (BAL) as an arsenic antidote? Human and Experimental Toxicology 16: 460-465

Wikimedia Foundation. 2010.

Игры ⚽ Поможем сделать НИР

Look at other dictionaries:

  • Dimercaprol — Saltar a navegación, búsqueda Dimercaprol …   Wikipedia Español

  • dimercaprol — Antagonista de metales pesados. Se prescribe en el tratamiento de la enfermedad de Wilson y en el tratamiento de la intoxicación aguda por arsénico, mercurio u oro, así como en las sobredosis de diuréticos mercuriales, sales de arsénico o de …   Diccionario médico

  • dimercaprol — ● dimercaprol ou dimercaptopropanol nom masculin Médicament utilisé dans le traitement d intoxications par des métaux lourds …   Encyclopédie Universelle

  • Dimercaprol — Strukturformel (R) Form (links) und (S) Form (rechts) …   Deutsch Wikipedia

  • Dimercaprol — BAL British Anti Lewisite Dimercaprol Général No CAS 59 52 9 …   Wikipédia en Français

  • dimercaprol — /duy meuhr kap rawl, rol/, n. Chem. a colorless, oily, viscous liquid, C3H8OS2, originally developed as an antidote to lewisite and now used in treating bismuth, gold, mercury, and arsenic poisoning. Also called BAL, British Anti Lewisite. [1945… …   Universalium

  • dimercaprol — noun Etymology: di + mercaptan + propane + 1 ol Date: 1947 a compound C3H8OS2 developed as an antidote against lewisite and used to treat arsenic, mercury, and gold poisoning called also BAL …   New Collegiate Dictionary

  • dimercaprol — noun The mercaptan 2,3 dimercaptopropanol used as an antidote to arsenic poisoning …   Wiktionary

  • dimercaprol — A chelating agent, developed as an antidote for lewisite and other arsenical poisons. It acts by competing for the metal with the essential SH groups in the pyruvate oxidase system of the cells and forms, with arsenic, a stable, relatively… …   Medical dictionary

  • Dimercaprol — Di|mer|ca|p|rol [Kurzw. aus 2,3 Dimercaptopropan 1 ol], das; s; Syn.: BAL: HSH2C CH(SH) CH2OH; chelatisierend wirkendes Antidot bei Vergiftungen durch Verb. des As (z. B. Lewisit), Sb, Hg u. Co sowie in der Komplexometrie eingesetzte ölige Verb.… …   Universal-Lexikon

Share the article and excerpts

Direct link
Do a right-click on the link above
and select “Copy Link”