British anti-Lewisite

ジメルカプロール

WordNet

1. of or relating to or characteristic of Great Britain or its people or culture; "his wife is British"
2. the people of Great Britain (同)British people, Brits
3. not in favor of (an action or proposal etc.)
4. a person who is opposed (to an action or policy or practice etc.); "the antis smelled victory after a long battle"
5. social insect living in organized colonies; characteristically the males and fertile queen have wings during breeding season; wingless sterile females are the workers (同)emmet, pismire

PrepTutorEJDIC

1. 『英国の』;英国人の / 英国民(人)
2. 《話》(特定の慣習・政策・行動などに)反対する人
3. 『アリ』
4. =ain't
5. (次にくる語の発音が母音で始まるときに用いる) / (子音[h]で始まり第1音節に強勢のない語の場合はanを用いることがある.ただし,この場合は[h]を発音しない)

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/06/28 14:24:03」(JST)

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Dimercaprol
IUPAC name 2,3-Disulfanylpropan-1-ol[citation needed]
Other names 2,3-Dimercaptopropanol[citation needed] British anti-Lewisite
Identifiers
CAS number	59-52-9 Y, 16495-08-2 (2R)-2-sulfanyl Y, 16495-16-2 (2S)-2-sulfanyl Y
PubChem	3080, 6971262 (2R)-2-sulfanyl, 3246063 (2S)-2-sulfanyl
ChemSpider	2971 Y, 5342114 (2R)-2-sulfanyl Y, 2496803 (2S)-2-sulfanyl Y
UNII	0CPP32S55X Y
EC number	200-433-7
UN number	2810
DrugBank	DB06782
KEGG	D00167 Y
MeSH	Dimercaprol
ChEMBL	CHEMBL1597 Y
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 Y Key: WQABCVAJNWAXTE-UHFFFAOYSA-N Y
Properties
Molecular formula	C 3H 8S 2O
Molar mass	124.225 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
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
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. It was developed secretly as an antidote for lewisite, the now-obsolete arsenic-based chemical warfare agent. Today, it is used medically in treatment of arsenic, mercury, gold, lead, antimony, and other toxic metal poisoning. 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.

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. 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. 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]}

See also

• Chelation therapy
• Chemical warfare agent
• Toxic metal poisoning

References

UpToDate Contents

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

• 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. 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
• 4. 水銀の毒性および疫学 epidemiology and toxicity of mercury
• 5. 化学テロ：化学兵器への曝露の診断および治療 chemical terrorism diagnosis and treatment of exposure to chemical weapons

English Journal

• A Computational Study of Detoxification of Lewisite Warfare Agents by British Anti-lewisite: Catalytic Effects of Water and Ammonia on Reaction Mechanism and Kinetics.

• Sahu C, Pakhira S, Sen K, Das AK.SourceDepartment of Spectroscopy, Indian Association for the Cultivation of Science , Jadavpur, Kolkata 700032, India.
• The journal of physical chemistry. A.J Phys Chem A.2013 Apr 25;117(16):3496-506. doi: 10.1021/jp312254z. Epub 2013 Apr 11.
• trans-2-Chlorovinyldichloroarsine (lewisite, L agent, Lew-I) acts as a blistering agents. British anti-lewisite (BAL, 2,3-dimercaptopropanol) has long been used as an L-agent antidote. The main reaction channels for the detoxification proceed via breaking of As-Cl bonds and formation of As-S bonds,
• PMID 23540856

• α-Lipoic acid protects against arsenic trioxide-induced acute QT prolongation in anesthetized guinea pigs.

• Kumazaki M, Ando H, Kakei M, Ushijima K, Taniguchi Y, Yoshida M, Yamato S, Washino S, Koshimizu TA, Fujimura A.SourceDivision of Clinical Pharmacology, Department of Pharmacology, Jichi Medical University, 3311-1 Yakushiji, Shimotsuke-shi, Tochigi 329-0498, Japan.
• European journal of pharmacology.Eur J Pharmacol.2013 Apr 5;705(1-3):1-10. doi: 10.1016/j.ejphar.2013.02.027. Epub 2013 Mar 5.
• Clinical use of arsenic trioxide (As2O3), which can induce the remission of relapsed or refractory acute promyelocytic leukemia, is often limited because of its cardiotoxicity. Symptoms of cardiotoxicity include acute cardiac conduction disturbances, such as QT prolongation. The present study was un
• PMID 23474023

• Cardiac conduction block at multiple levels caused by arsenic trioxide therapy.

• Kathirgamanathan K, Angaran P, Lazo-Langner A, Gula LJ.SourceDivision of Cardiology, Department of Medicine, University of Western Ontario, London, Ontario, Canada.
• The Canadian journal of cardiology.Can J Cardiol.2013 Jan;29(1):130.e5-6. doi: 10.1016/j.cjca.2012.04.004. Epub 2012 Jun 8.
• We present a rare case of a woman aged 62 years with refractory acute promyelocytic leukemia treated with arsenic trioxide leading to progressive, multilevel cardiac conduction block. After chelation treatment with dimercaprol, there was normalization of conduction.Copyright © 2013 Canadian Cardiov
• PMID 22683459

Related Links

• British anti-Lewisite :: Introduction

British anti-Lewisite (BAL; dimercaprol; 2,3-dimercaptopropanol) has been in use in the medical community for over 60 years. It is most commonly used as a chelator (remove a heavy metal from the body) in the treatment of poisoning ...

• British anti-Lewisite :: Development

The rediscovery of Lewisite in 1918 was too late for its use as a chemical warfare agent in WWI. However, the allied forces were well-aware of its existence at the start of WWII. At an Oxford laboratory under the keen supervision of Sir ...

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★リンクテーブル★

リンク元	「ジメルカプロール」「BAL」
関連記事	「British」「ant」「anti」

「ジメルカプロール」

　　[★]

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」

　　[★]

• British anti-Lewisite ← ジメルカプロール dimercaprol
• 気管支肺胞洗浄, bronchoalveolar lavage

「British」

　　[★]

• イギリスの

関

England、English、Great Britain、UK、United Kingdom

　 　 　

「ant」

　　[★]

• n.

• アリ

同

ants, stinging

　 　 　

「anti」

　　[★]

• comb form.

• 抗、アンチ