同: 2,3-dimercaptopropanol, British antilewisite, BAL

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/05/30 17:45:05」(JST)

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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.^[1] Today, it is used medically in treatment of arsenic, mercury, gold, lead, antimony, and other toxic metal poisoning.^[3] 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.^[4]

It is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic health system.^[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 elements from the body.^{[citation needed]}

References

^ ^a ^b Domingo Tabangcura, Jr., G. Patrick Daubert. "British anti-Lewisite".
^ Peters, R; Stocken, L; Thompson, R. (1945). "British Anti-Lewisite (BAL)". Nature 156 (3969): 616–619. doi:10.1038/156616a0. PMID 21006485.
^ "Dimercaprol".
^ 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.
^ "WHO Model List of EssentialMedicines". World Health Organization. October 2013. Retrieved 22 April 2014.
^ Goldman M, Dacre JC. (1989) Lewisite: its chemistry, toxicology, and biological effects. Rev Environ Contam Toxicol 110: 75-115
^ 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

UpToDate Contents

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1. 小児期の鉛中毒：管理 childhood lead poisoning management
2. ヒ素曝露と中毒 arsenic exposure and poisoning
3. 水銀の毒性および疫学 epidemiology and toxicity of mercury
4. 小児期の鉛中毒：臨床症状および診断 childhood lead poisoning clinical manifestations and diagnosis
5. 成人におけるアセトアミノフェン（パラセタモール）中毒：治療 acetaminophen paracetamol poisoning in adults treatment

English Journal

Differences in the substrate binding regions of renal organic anion transporters 1 (OAT1) and 3 (OAT3).

Astorga B, Wunz TM, Morales M, Wright SH, Pelis RM.SourceDept. of Pharmacology, College of Medicine, University of Arizona, Tucson, USA.
American journal of physiology. Renal physiology.Am J Physiol Renal Physiol.2011 Aug;301(2):F378-86. Epub 2011 May 4.
This study examined the selectivity of organic anion transporters OAT1 and OAT3 for structural congeners of the heavy metal chelator 2,3-dimercapto-1-propanesulfonic acid (DMPS). Thiol-reactive reagents were also used to test structural predictions based on a homology model of OAT1 structure. DMPS w
PMID 21543413

Metal mercury poisoning in two boys initially treated for brucellosis in Mashhad, Iran.

Sasan MS, Hadavi N, Afshari R, Mousavi SR, Alizadeh A, Balali-Mood M.SourceDepartment of Pediatrics, Imam Reza Hospital, Mashhad University of Medical Sciences, Mashhad, Iran.
Human & experimental toxicology.Hum Exp Toxicol.2011 Aug 1. [Epub ahead of print]
Elemental mercury (Hg) is the only metal which evaporates in room temperature and its inhalation may cause toxicity. Hg poisoning may occur by mishandling the metal, particularly in children who play with it. Wide-spectrum of the clinical presentations of chronic Hg poisoning may cause misdiagnosis,
PMID 21803782

Differential stability of lead sulfide nanoparticles influences biological responses in embryonic zebrafish.

Truong L, Moody IS, Stankus DP, Nason JA, Lonergan MC, Tanguay RL.SourceNanotoxicology Laboratory, Department of Environmental and Molecular Toxicology, Oregon State University, Corvallis, OR 97331, USA.
Archives of toxicology.Arch Toxicol.2011 Jul;85(7):787-98. Epub 2010 Dec 8.
As the number of nanoparticle-based products increase in the marketplace, there will be increased potential for human exposures to these engineered materials throughout the product life cycle. We currently lack sufficient data to understand or predict the inherent nanomaterial characteristics that d
PMID 21140132

Japanese Journal

Strategies for Safe and Effective Therapeutic Measures for Chronic Arsenic and Lead Poisoning

KALIA Kiran,FLORA Swaran J. S.
Journal of occupational health 47(1), 1-21, 2005-01
… 2, 3-dimercaprol (BAL) has long been the mainstay of chelation therapy for lead or arsenic poisoning. …
NAID 110004568615

Cuprin Sulfate Intoxication with Rhabdomyolysis, Treated with Chelating Agents and Blood Purification

TAKEDA Taichi,YUKIOKA Tetuo,SHIMAZAKI Syuji
Internal medicine 39(3), 253-255, 2000-03
… The patient was successfully treated with dimercaprol, penicillamine, direct hemoperfusion and hemodiafiltration. …
NAID 10006994818

STUDY ON THE MECHANISM BEHIND ADJUVANT ACTION OF DIETHYLETHOXYMETHYLENE MALONATE ENHANCING THE RECTAL ABSORPTION OF CEFMETAZOLE AND LYSOZYME

NISHIHATA TOSHIAKI,MIYAKE MASATOSHI,KAMADA AKIRA
Journal of pharmacobio-dynamics 7(9), 607-613, 1984-09
… Since an increase of cefmetazole transport was found when concentration of nonprotein sulfhydryls in rectal tissue was decreased by the presence of either DEEMM or DEM in the study using in vitro everted sac method and the enhancement of cefmetazole absorption by the coadministration of either DEEMM or DEM was suppressed by the treatment with dimercaprol, membrane permeability of rectal tissue seems to be regulated by the concentration of nonprotein sulfhydryls in rectal tissue. …
NAID 110003637797

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リンク元	「ジメルカプロール」「BAL」

「ジメルカプロール」

Dimercaprol
	IUPAC name 2,3-Disulfanylpropan-1-ol
	Other names 2,3-Dimercaptopropanol; British anti-Lewisite
Identifiers
CAS number	59-52-9 , 16495-08-2 (2R)-2-sulfanyl , 16495-16-2 (2S)-2-sulfanyl
PubChem	3080, 6971262 (2R)-2-sulfanyl, 3246063 (2S)-2-sulfanyl
ChemSpider	2971 , 5342114 (2R)-2-sulfanyl , 2496803 (2S)-2-sulfanyl
UNII	0CPP32S55X
EC number	200-433-7
UN number	2810
DrugBank	DB06782
KEGG	D00167
MeSH	Dimercaprol
ChEMBL	CHEMBL1597
RTECS number	UB2625000
ATC code	V03AB09
Beilstein Reference	1732058
Jmol-3D images	Image 1
	SMILES OCC(S)CS ;
	InChI InChI=1S/C3H8OS2/c4-1-3(6)2-5/h3-6H,1-2H2 ; Key: WQABCVAJNWAXTE-UHFFFAOYSA-N ;
Properties
Molecular formula	C; 3H; 8S; 2O
Molar mass	124.225 g mol-1
Density	1.239 g cm-3
Boiling point	120 °C; 248 °F; 393 K at 2.0 kPa
log P	0.627
Acidity (pKa)	8.999
Basicity (pKb)	4.998
Refractive index (nD)	1.573
Hazards
GHS pictograms
GHS signal word	DANGER
GHS hazard statements	H301, H315, H319, H335
GHS precautionary statements	P261, P301+310, P305+351+338
EU classification	Xn
R-phrases	R22, R36/37/38
S-phrases	S26, S36
NFPA 704	1 2 0
Flash point	112 °C (234 °F; 385 K)
	Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
	Infobox references

　　[★]

英: dimercaprol
ラ: dimercaprolum
同: BAL(British anti-Lewisite)
商: バル

毒ガスのルイサイト(Lewisite)を解毒する薬物として見いだされた
C₃H₈OS₂

１つのヒドロキシル基と２つのSH基をもつ

キレート剤。重金属解毒剤
金属イオンに対して高親和性を有する

作用機序

金属イオン-SH基間の結合を阻害
金属イオンの排泄を促進する

適応

ヒ素、水銀、鉛、銅、ビスマス、クロム、アンチモンの中毒

注意

鉄、カドミウム、セレンの中毒には使用不可

「BAL」

　　[★]

[chm.bris-1] Domingo Tabangcura, Jr., G. Patrick Daubert. "British anti-Lewisite".

[2] Peters, R; Stocken, L; Thompson, R. (1945). "British Anti-Lewisite (BAL)". Nature 156 (3969): 616–619. doi:10.1038/156616a0. PMID 21006485.

[3] "Dimercaprol".

[4] 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.

[5] "WHO Model List of EssentialMedicines". World Health Organization. October 2013. Retrieved 22 April 2014.

[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

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dimercaprol