meso-2,3-Dimercaptosuccinic Acid

• CAT Number: M144065
• CAS Number: 304-55-2
• Molecular Formula: C4H6O4S2
• Molecular Weight: 182.208
• Purity: ≥95%
• Synonyms: Succimer; Dimercaptosuccinic acid; butanedioic acid, 2,2-dimercapto-; (2R,3S)-2,3-Disulfanylsuccinic acid(2R,3S)-2,3-disulfanylbutanedioic acid; meso-2,3-Dimercaptosuccinic acid; DMSA; 2,3-Dithio-meso-tartaric acid; DIM-SA
• Storage: -20°C
• IUPAC Name: (2S,3R)-2,3-bis(sulfanyl)butanedioic acid
• InChI: InChI=1S/C4H6O4S2/c5-3(6)1(9)2(10)4(7)8/h1-2,9-10H,(H,5,6)(H,7,8)/t1-,2+
• InChIKey: ACTRVOBWPAIOHC-XIXRPRMCSA-N
• SMILES: C(C(C(=O)O)S)(C(=O)O)S

meso-2,3-Dimercaptosuccinic Acid is used as a chelating agent and masking agent for cadmium in EDTA titration of zinc. Detoxification of heavy metal.

Reference

1. Annu Rev Pharmacol Toxicol. 1990;30:279-306.

meso-2,3-Dimercaptosuccinic acid: chemical, pharmacological and toxicological
properties of an orally effective metal chelating agent.

Aposhian HV(1), Aposhian MM.

Author information:
(1)Department of Molecular and Cellular Biology, University of Arizona, Tucson
85721.

The primary purpose of this article is to summarize the recent investigations
dealing with the pharmacology and toxicology of meso-2,3-dimercaptosuccinic acid,
an orally effective chelating agent. The need for a better chelating agent for
treating young children and pregnant women with lead intoxication has been
apparent for some time. Preclinical and clinical evidence now indicate that
meso-2,3-dimercaptosuccinic acid, an Orphan Drug, shows the most promise for
being effective in this regard. It has an extracellular distribution that may be
responsible for its low toxicity compared to other dithiols. No attempt has been
made to compare it in a rigorous and thorough manner with other chelating agents.
That has not been the purpose of this review. The advantages of meso-DMSA,
however, compared to CaNa2EDTA for the treatment of lead intoxication, have been
outlined. Significant advances have been made recently in elucidating the
structures of the metal chelates of DMSA. There is a striking difference between
the structures of the lead chelate of meso-DMSA and those of racemic-DMSA. The
former chelates by coordination of one sulfur and one oxygen atom with Pb. The
latter can form chelates via the two sulfur atoms or via one oxygen and one
sulfur atom. Solubility of the lead chelates depends on the ionization of the
noncoordinated thiol and carboxylic acid groups. Bimane derivatization, HPLC, and
fluorescence, as well as gas chromatography can be used for analysis of DMSA in
biological fluids. The acid dissociation constants for meso- and racemic-DMSA
have been summarized from the literature as have the formation constants of some
of the DMSA chelates. DMSA is biotransformed to a mixed disulfide in humans. By
14 hr after DMSA administration (10 mg/kg), only 2.5% of the administered DMSA is
excreted in the urine as unaltered DMSA and 18.1% of the dose is found in the
urine as altered forms of DMSA. Most altered DMSA in the urine is in the form of
a mixed disulfide. It consists of DMSA in disulfide linkages with two molecules
of L-cysteine. One molecule of cysteine is attached to each of the sulfur atoms
of DMSA. The remaining 10% of the altered DMSA was in the form of cyclic
disulfides of DMSA. So far, the mixed disulfide has been found in human but not
in rabbit, mouse, or rat urine. Apparently there are species differences in how
organisms metabolize meso-DMSA.(ABSTRACT TRUNCATED AT 400 WORDS)

DOI: 10.1146/annurev.pa.30.040190.001431
PMID: 2160791 [Indexed for MEDLINE]