2,3-disulfanylbutanedioic acid

• ChemBase ID: 448
• Molecular Formular: C4H6O4S2
• Molecular Mass: 182.21804
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,3-disulfanylbutanedioic acid
• IUPAC Traditional name: meso-dimercaptosuccinic acid
• Brand Name: Chemet; MPI DMSA Kidney Reagent
• Synonyms: DMSA; Dimercaptosuccinic acid; Succimer; 2,3-Dithio-meso-tartaric acid; Succimer; meso-2,3-DIMERCAPTOSUCCINIC ACID

Database IDs

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

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.3712347
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): -2.1819494
• LogD (pH = 7.4): -5.1027217
• Log P: 0.25882706
• Molar Refractivity: 38.4674 cm^3
• Polarizability: 15.464712 Å^3
• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.56
• LOG S: -1.87
• Solubility (Water): 2.43e+00 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): -0.3

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: WM7650000

DETAILS

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

REFERENCES

• 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