二巰基丁二酸

二巰基丁二酸
	IUPAC名; meso-2,3-dimercaptosuccinic acid
別名	succimer, APRD01236 (Drugbank), Chemet
識別
CAS號	304-55-2
PubChem	2724354
ChemSpider	2006502
SMILES	O=C(O)[C@@H](S)[C@@H](S)C(=O)O;
InChI	1/C4H6O4S2/c5-3(6)1(9)2(10)4(7)8/h1-2,9-10H,(H,5,6)(H,7,8)/t1-,2+;
InChIKey	ACTRVOBWPAIOHC-XIXRPRMCBX
EINECS	259-952-2
性質
化學式	C4H6O4S2
莫耳質量	182.22 g/mol g·mol⁻¹
熔點	125 °C（398 K）
相關物質
相關化合物	酒石酸
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

2,3-二巰基丁二酸（Dimercaptosuccinic acid、英文縮寫為：DMSA），別名2,3-二巰基琥珀酸，一般簡稱二巰基丁二酸，是一種有機硫化合物，常溫下為白色結晶狀粉末。因分子內含有兩個巰基，所以它帶有巰基化合物特有的臭味。二巰基丁二酸和它的鈉鹽都可以作為解毒劑通過口服或注射治療重金屬中毒。^[2] 二巰基丁二酸有兩種非對映異構體，一種是內消旋體，另一種是外消旋體。內消旋體可作為螯合劑使用，常用其鈉鹽。

合成方法

可由丁炔二酸和硫代硫酸鈉反應得到。^[3]

醫療用途

最初二巰基丁二酸的配合物二巰基丁二酸銻鉀作為藥物被Friedheim 等人引入到血吸蟲病的治療中，通過二巰基丁二酸的鉀鹽與金屬銻離子的絡合可以增加人體對銻的吸收，加強治療效果。^[4] 1957年中國科學院上海藥物研究所的梁猷毅等人首次報道了二巰基丁二酸的鈉鹽作為解毒劑可有效治療酒石酸銻鉀引起的重金屬銻中毒，^[5]^[6] 隨後又發現二巰基丁二酸及其鈉鹽可用於治療砷、鉛、汞、鎘等重金屬中毒，還可以作為促銅排泄藥物治療肝豆狀核變性。^[7] 相對於二巰基丙醇來說，二巰基丁二酸的毒性很小，且對銻的解毒效果更好，因此常代替前者使用。^[2]^[8] 但是，儘管二巰基丁二酸可以穿過小鼠的血腦屏障，它卻不能穿透人體的血腦屏障，^[9] 這使得二巰基丁二酸在人體重金屬中毒治療中有局限性，不能用於清除積存在中樞神經系統中的重金屬元素。^[10]^[11]

參見

參考資料

^ Merck Index, 11th Edition, 8854.
^ ^2.0 ^2.1 Miller AL. Dimercaptosuccinic acid (DMSA), a non-toxic, water-soluble treatment for heavy metal toxicity.. Altern Med Rev. 1998, 3 (3): 199–207. PMID 9630737.
^ US 4550193,Lindemann, Martin K. O. & Lukenbach, Elvin R.,「Process for the preparation of 2,3-dimercaptosuccinic acid and its lower alkyl esters」,指定於Johnson & Johnson Baby Products
^ Friedheim, E. A. H., DaSilva, J. R., Martins, A. V. Treatment of schistosomiasis mansoni with antimony a.a'-dimercapto-potassium succinate (TWSb). Am. J. Trop. Med. Hyg. 1954, 3 (4): 714–27. PMID 13180832.
^ 寻找“还魂丹”――记解毒药二巯基丁二酸的研制. 上海發明協會. 2005-10-26 [2012-08-11]. （原始內容存檔於2012-09-20）.
^ Liang, Y., Chu. C, Tsen, Y., Ting, K. Studies on antibilharzial drugs. Vl. The antidotal effects of sodium dimercaptosuccinate and BAL-glucoside against tartar emetic.. Acta Physiol. Sin. 1957, 21: 24–32.
^ Vasken Aposhian. DMSA and DMPS-water soluble antidotes for heavy metal poisoning.. Ann. Rev. Pharmacol Toxicol. 1983, 23: 193–213. PMID 6307120.
^ H. V. Aposhian. DMSA and DMPS--water soluble antidotes for heavy metal poisoning. Annual Review of Pharmacology and Toxicology. 1983, 23: 193–215 [2019-05-25]. ISSN 0362-1642. PMID 6307120. doi:10.1146/annurev.pa.23.040183.001205. （原始內容存檔於2019-05-12）.
^ Aasath, Jan; Dag Jacobsen, Ole Andersen, Elsa Wickstrøm (March 1995). "Treatment of Mercury and Lead Poisonings with Dimercaptosuccinic Acid (DMSA) and Sodium Dimercaptopropanesulfonate (DMPS)". Analyst 120: 853ff.
^ Rooney, James. The role of thiols, dithiols, nutritional factors and interacting ligands in the toxicology of mercury. Toxicology. 2007, 234 (3): 145–156. PMID 17408840. doi:10.1016/j.tox.2007.02.016.
^ Guzzi, GianPaolo; Caterina A.M. La Porta. Molecular mechanisms triggered by mercury. Toxicology. 2008, 244 (1): 1–12. PMID 18077077. doi:10.1016/j.tox.2007.11.002.

拓展閱讀

Aposhian, H.V.; Aposhian, M.M. Meso-2,3-dimercaptosuccinic acid: Chemical, pharmacological and toxicological properties of an orally effective metal chelating agent. Annual Review of Pharmacology and Toxicology. 1990, 30 (1): 279–306. PMID 2160791. doi:10.1146/annurev.pa.30.040190.001431.
尋找「還魂丹」――記解毒藥二巰基丁二酸的研製（頁面存檔備份，存於網際網路檔案館）

[1] Merck Index, 11th Edition, 8854.

[dmsa-2] 2.0 ^2.1 Miller AL. Dimercaptosuccinic acid (DMSA), a non-toxic, water-soluble treatment for heavy metal toxicity.. Altern Med Rev. 1998, 3 (3): 199–207. PMID 9630737.

[3] US 4550193,Lindemann, Martin K. O. & Lukenbach, Elvin R.,「Process for the preparation of 2,3-dimercaptosuccinic acid and its lower alkyl esters」,指定於Johnson & Johnson Baby Products

[4] Friedheim, E. A. H., DaSilva, J. R., Martins, A. V. Treatment of schistosomiasis mansoni with antimony a.a'-dimercapto-potassium succinate (TWSb). Am. J. Trop. Med. Hyg. 1954, 3 (4): 714–27. PMID 13180832.

[5] 寻找“还魂丹”――记解毒药二巯基丁二酸的研制. 上海發明協會. 2005-10-26 [2012-08-11]. （原始內容存檔於2012-09-20）.

[6] Liang, Y., Chu. C, Tsen, Y., Ting, K. Studies on antibilharzial drugs. Vl. The antidotal effects of sodium dimercaptosuccinate and BAL-glucoside against tartar emetic.. Acta Physiol. Sin. 1957, 21: 24–32.

[7] Vasken Aposhian. DMSA and DMPS-water soluble antidotes for heavy metal poisoning.. Ann. Rev. Pharmacol Toxicol. 1983, 23: 193–213. PMID 6307120.

[8] H. V. Aposhian. DMSA and DMPS--water soluble antidotes for heavy metal poisoning. Annual Review of Pharmacology and Toxicology. 1983, 23: 193–215 [2019-05-25]. ISSN 0362-1642. PMID 6307120. doi:10.1146/annurev.pa.23.040183.001205. （原始內容存檔於2019-05-12）.

[9] Aasath, Jan; Dag Jacobsen, Ole Andersen, Elsa Wickstrøm (March 1995). "Treatment of Mercury and Lead Poisonings with Dimercaptosuccinic Acid (DMSA) and Sodium Dimercaptopropanesulfonate (DMPS)". Analyst 120: 853ff.

[10] Rooney, James. The role of thiols, dithiols, nutritional factors and interacting ligands in the toxicology of mercury. Toxicology. 2007, 234 (3): 145–156. PMID 17408840. doi:10.1016/j.tox.2007.02.016.

[11] Guzzi, GianPaolo; Caterina A.M. La Porta. Molecular mechanisms triggered by mercury. Toxicology. 2008, 244 (1): 1–12. PMID 18077077. doi:10.1016/j.tox.2007.11.002.

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