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Identification
Name Succimer
Accession Number DB00566 (APRD01236)
Type small molecule
Groups approved
Description

A mercaptodicarboxylic acid used as an antidote to heavy metal poisoning because it forms strong chelates with them. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Dimercaptosuccinic acid
DMSA
Salts Not Available
Brand names
Name Company
Chemet
MPI DMSA Kidney Reagent
Brand mixtures Not Available
Categories
  • Chelating Agents
  • Antidotes
CAS number 304-55-2
Weight Average: 182.218
Monoisotopic: 181.97075006
Chemical Formula C4H6O4S2
InChI Key InChIKey=ACTRVOBWPAIOHC-UHFFFAOYSA-N
InChI
InChI=1S/C4H6O4S2/c5-3(6)1(9)2(10)4(7)8/h1-2,9-10H,(H,5,6)(H,7,8)
Plain Text
IUPAC Name
2,3-disulfanylbutanedioic acid
SMILES
OC(=O)C(S)C(S)C(O)=O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Keto-Acids
  • Dicarboxylic Acids
Substructures
  • Hydroxy Compounds
  • Acetates
  • Carboxylic Acids and Derivatives
  • Thiols
  • Keto-Acids
  • Dicarboxylic Acids
Pharmacology
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.
Pharmacodynamics 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.
Mechanism of action 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.
Absorption Rapid but variable.
Volume of distribution Not Available
Protein binding Not Available
Metabolism 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.
Route of elimination Unabsorbed drug is excreted primarily in feces and absorbed drug is excreted primarily in the urine as metabolites.
Half life 48 hours
Clearance Not Available
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
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Lundbeck inc
  • Ge healthcare
Packagers
Dosage forms
Form Route Strength
Capsule, coated pellets Oral
Prices
Unit description Cost Unit
Dmsa powder 15.61 USD g
Chemet 100 mg capsule 8.6 USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 193 °C PhysProp
logP -0.3 Not Available
Predicted Properties
Property Value Source
water solubility 2.43e+00 g/l ALOGPS
logP 0.56 ALOGPS
logP 0.26 ChemAxon
logS -1.9 ALOGPS
pKa (strongest acidic) 3.37 ChemAxon
physiological charge -2 ChemAxon
hydrogen acceptor count 4 ChemAxon
hydrogen donor count 4 ChemAxon
polar surface area 74.6 ChemAxon
rotatable bond count 3 ChemAxon
refractivity 38.47 ChemAxon
polarizability 15.47 ChemAxon
References
Synthesis Reference Not Available
General Reference
  1. 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
  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. Pubmed
  3. Mann KV, Travers JD: Succimer, an oral lead chelator. Clin Pharm. 1991 Dec;10(12):914-22. Pubmed
External Links
Resource Link
KEGG Drug D00572 Link_out
KEGG Compound C07598 Link_out
PubChem Compound 9354 Link_out
PubChem Substance 46504680 Link_out
ChemSpider 8988 Link_out
BindingDB 50232640 Link_out
PharmGKB PA451521 Link_out
RxList http://www.rxlist.com/cgi/generic2/succimer.htm Link_out
Drugs.com http://www.drugs.com/cdi/succimer.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Succimer Link_out
ATC Codes
  • V09CA02
  • V09IA03
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS show (60.1 KB)
Interactions
Drug Interactions Searched, but no interactions found.
Food Interactions Not Available
Targets

1. Lead

Pharmacological action: yes
Actions: chelator

References:
  1. Bradberry S, Vale A: Dimercaptosuccinic acid (succimer; DMSA) in inorganic lead poisoning. Clin Toxicol (Phila). 2009 Aug;47(7):617-31. Pubmed
  2. Gracia RC, Snodgrass WR: Lead toxicity and chelation therapy. Am J Health Syst Pharm. 2007 Jan 1;64(1):45-53. Pubmed
  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. Pubmed
  4. Jorgensen FM: Succimer: the first approved oral lead chelator. Am Fam Physician. 1993 Dec;48(8):1496-502. Pubmed
  5. 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
  6. Blanusa M, Varnai VM, Piasek M, Kostial K: Chelators as antidotes of metal toxicity: therapeutic and experimental aspects. Curr Med Chem. 2005;12(23):2771-94. Pubmed
  7. Aposhian HV, Maiorino RM, Gonzalez-Ramirez D, Zuniga-Charles M, Xu Z, Hurlbut KM, Junco-Munoz P, Dart RC, Aposhian MM: Mobilization of heavy metals by newer, therapeutically useful chelating agents. Toxicology. 1995 Mar 31;97(1-3):23-38. Pubmed

2. Mercury

Pharmacological action: yes
Actions: chelator

References:
  1. Ozuah PO: Mercury poisoning. Curr Probl Pediatr. 2000 Mar;30(3):91-9. Pubmed
  2. 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
  3. 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
  4. Blanusa M, Varnai VM, Piasek M, Kostial K: Chelators as antidotes of metal toxicity: therapeutic and experimental aspects. Curr Med Chem. 2005;12(23):2771-94. Pubmed
  5. Aposhian HV, Maiorino RM, Gonzalez-Ramirez D, Zuniga-Charles M, Xu Z, Hurlbut KM, Junco-Munoz P, Dart RC, Aposhian MM: Mobilization of heavy metals by newer, therapeutically useful chelating agents. Toxicology. 1995 Mar 31;97(1-3):23-38. Pubmed

3. Cadmium

Pharmacological action: yes
Actions: chelator

References:
  1. 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
  2. Blanusa M, Varnai VM, Piasek M, Kostial K: Chelators as antidotes of metal toxicity: therapeutic and experimental aspects. Curr Med Chem. 2005;12(23):2771-94. Pubmed
  3. Aposhian HV, Maiorino RM, Gonzalez-Ramirez D, Zuniga-Charles M, Xu Z, Hurlbut KM, Junco-Munoz P, Dart RC, Aposhian MM: Mobilization of heavy metals by newer, therapeutically useful chelating agents. Toxicology. 1995 Mar 31;97(1-3):23-38. Pubmed

4. Arsenic

Pharmacological action: yes
Actions: chelator

References:
  1. 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
  2. Blanusa M, Varnai VM, Piasek M, Kostial K: Chelators as antidotes of metal toxicity: therapeutic and experimental aspects. Curr Med Chem. 2005;12(23):2771-94. Pubmed
  3. Aposhian HV, Maiorino RM, Gonzalez-Ramirez D, Zuniga-Charles M, Xu Z, Hurlbut KM, Junco-Munoz P, Dart RC, Aposhian MM: Mobilization of heavy metals by newer, therapeutically useful chelating agents. Toxicology. 1995 Mar 31;97(1-3):23-38. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19