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Record Information
Version3.6
Creation Date2012-09-06 15:16:50 UTC
Update Date2016-02-11 01:29:36 UTC
HMDB IDHMDB14706
Secondary Accession NumbersNone
Metabolite Identification
Common NameSuccimer
DescriptionSuccimer is only found in individuals that have used or taken this drug. It is a mercaptodicarboxylic acid used as an antidote to heavy metal poisoning because it forms strong chelates with them. [PubChem]Succimer is a heavy metal chelator. It binds with high specificity to ions of lead in the blood to form a water-soluble complex that is subsequently excreted by the kidneys. Succimer can also chelate mercury, cadmium, and arsenic in this manner.
Structure
Thumb
Synonyms
ValueSource
meso-Dimercaptosuccinic acidKegg
ChemetKegg
meso-2,3-Dimercaptosuccinic acidKegg
meso-DimercaptosuccinateGenerator
meso-2,3-DimercaptosuccinateGenerator
Dimercaptosuccinic acidHMDB
DMSAHMDB
Chemical FormulaC4H6O4S2
Average Molecular Weight182.218
Monoisotopic Molecular Weight181.97075006
IUPAC Name2,3-disulfanylbutanedioic acid
Traditional Namechemet
CAS Registry Number304-55-2
SMILES
OC(=O)C(S)C(S)C(O)=O
InChI Identifier
InChI=1S/C4H6O4S2/c5-3(6)1(9)2(10)4(7)8/h1-2,9-10H,(H,5,6)(H,7,8)
InChI KeyInChIKey=ACTRVOBWPAIOHC-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as thia fatty acids. These are fatty acid derivatives obtained by insertion of a sulfur atom at specific positions in the chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentThia fatty acids
Alternative Parents
Substituents
  • Thia fatty acid
  • Dicarboxylic acid or derivatives
  • 2-mercaptocarboxylic acid
  • Carboxylic acid
  • Carboxylic acid derivative
  • Alkylthiol
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Antidotes
  • Chelating Agents
Application
  • Pharmaceutical
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point193 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.43e+00 g/LNot Available
LogP-0.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.43 mg/mLALOGPS
logP0.56ALOGPS
logP0.26ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)3.37ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area74.6 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity38.47 m3·mol-1ChemAxon
Polarizability15.47 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00566
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00566
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00566
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID8988
KEGG Compound IDC07598
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSuccimer
NuGOwiki LinkHMDB14706
Metagene LinkHMDB14706
METLIN IDNot Available
PubChem Compound9354
PDB IDNot Available
ChEBI ID140459
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Mann KV, Travers JD: Succimer, an oral lead chelator. Clin Pharm. 1991 Dec;10(12):914-22. [1663439 ]
  2. 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. [7741240 ]
  3. Miller AL: Dimercaptosuccinic acid (DMSA), a non-toxic, water-soluble treatment for heavy metal toxicity. Altern Med Rev. 1998 Jun;3(3):199-207. [9630737 ]