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304-55-2 molecular structure
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2,3-disulfanylbutanedioic acid

ChemBase ID: 448
Molecular Formular: C4H6O4S2
Molecular Mass: 182.21804
Monoisotopic Mass: 181.97075067
SMILES and InChIs

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

Cite this record

CBID:448 http://www.chembase.cn/molecule-448.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
304-55-2
EC Number
206-155-2
PubChem SID
160963911
46504680
PubChem CID
9354

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
MP Biomedicals
02150918 external link Add to cart Please log in.

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 3.3712347  H Acceptors
H Donor LogD (pH = 5.5) -2.1819494 
LogD (pH = 7.4) -5.1027217  Log P 0.25882706 
Molar Refractivity 38.4674 cm3 Polarizability 15.464712 Å3
Polar Surface Area 74.6 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 0.56  LOG S -1.87 
Solubility (Water) 2.43e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Hydrophobicity(logP)
-0.3 expand Show data source
Storage Condition
Room Temperature (15-30°C) expand Show data source
RTECS
WM7650000 expand Show data source
MSDS Link
Download expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank
MP Biomedicals - 02150918 external link
Crystalline
A selective masking agent for cadmium in EDTA titration of zinc.
DrugBank - DB00566 external link
Item Information
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

REFERENCES

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  • • 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
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PATENTS

PATENTS

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INTERNET

INTERNET

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