2,3-disulfanylbutanedioic acid

• ChemBase编号: 448
• 分子式: C4H6O4S2
• 平均质量: 182.21804
• 单一同位素质量: 181.97075067
• SMILES: SC(C(S)C(=O)O)C(=O)O
• Canonical SMILES: SC(C(C(=O)O)S)C(=O)O
• InChI: InChI=1S/C4H6O4S2/c5-3(6)1(9)2(10)4(7)8/h1-2,9-10H,(H,5,6)(H,7,8)
• InChIKey: ACTRVOBWPAIOHC-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2,3-disulfanylbutanedioic acid
• IUPAC传统名: meso-dimercaptosuccinic acid
• 商标名: Chemet; MPI DMSA Kidney Reagent
• 别名: DMSA; Dimercaptosuccinic acid; Succimer; 2,3-Dithio-meso-tartaric acid; Succimer; meso-2,3-DIMERCAPTOSUCCINIC ACID

登记号

• CAS号: 304-55-2
• EC号: 206-155-2
• PubChem SID: 160963911; 46504680
• PubChem CID: 9354

理论计算性质

JChem

• Acid pKa: 3.3712347
• 质子受体: 4
• 质子供体: 4
• LogD (pH = 5.5): -2.1819494
• LogD (pH = 7.4): -5.1027217
• Log P: 0.25882706
• 摩尔折射率: 38.4674 cm^3
• 极化性: 15.464712 Å^3
• 极化表面积: 74.6 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 0.56
• LOG S: -1.87
• 溶解度: 2.43e+00 g/l

分子性质

理化性质

• 疏水性(logP): -0.3

安全信息

• 保存条件: Room Temperature (15-30°C)
• RTECS编号: WM7650000

详细说明

MP Biomedicals - 02150918

Crystalline
A selective masking agent for cadmium in EDTA titration of zinc.

DrugBank - DB00566

• Drug Groups: approved
• Description: A mercaptodicarboxylic acid used as an antidote to heavy metal poisoning because it forms strong chelates with them. [PubChem]
• Indication: For the treatment of lead poisoning in pediatric patients with blood lead levels above 45 µg/dL. May also be used to treat mercury or arsenic poisoning.
• Pharmacology: Succimer is an orally active, heavy metal chelating agent. It forms water soluble chelates and, consequently, increases the urinary excretion of lead. Succimer is not to be used for prophylaxis of lead poisoning in a lead-containing environment. In addition, the use of succimer should always be accompanied by identification and removal of the source of the lead exposure.
• Toxicity: Oral LD₅₀ in mice is over 5011 mg/kg. Doses of 2300 mg/kg in the rat and 2400 mg/kg in the mouse produced ataxia, convulsions, labored respiration and frequently death. No case of overdosage has been reported in humans. Limited data indicate that succimer is dialyzable.
• Affected Organisms: Humans and other mammals
• Biotransformation: Chemical analysis of succimer and its metabolites (primarily mixed disulfides of L-cysteine) in the urine showed that succimer was rapidly and extensively metabolized however the specific site of biotransformation is not known.
• Absorption: Rapid but variable.
• Half Life: 48 hours
• Elimination: Unabsorbed drug is excreted primarily in feces and absorbed drug is excreted primarily in the urine as metabolites.
• References: Miller AL: Dimercaptosuccinic acid (DMSA), a non-toxic, water-soluble treatment for heavy metal toxicity. Altern Med Rev. 1998 Jun;3(3):199-207. [Pubmed] ; Aaseth J, Jacobsen D, Andersen O, Wickstrom E: Treatment of mercury and lead poisonings with dimercaptosuccinic acid and sodium dimercaptopropanesulfonate. A review. Analyst. 1995 Mar;120(3):853-4. [Pubmed] ; Mann KV, Travers JD: Succimer, an oral lead chelator. Clin Pharm. 1991 Dec;10(12):914-22. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

参考文献

• Martell, A.E., Inorganic Chem. , 4 : 378 (1965).
• Miller AL: Dimercaptosuccinic acid (DMSA), a non-toxic, water-soluble treatment for heavy metal toxicity. Altern Med Rev. 1998 Jun;3(3):199-207. Pubmed
• Aaseth J, Jacobsen D, Andersen O, Wickstrom E: Treatment of mercury and lead poisonings with dimercaptosuccinic acid and sodium dimercaptopropanesulfonate. A review. Analyst. 1995 Mar;120(3):853-4. Pubmed
• Mann KV, Travers JD: Succimer, an oral lead chelator. Clin Pharm. 1991 Dec;10(12):914-22. Pubmed