Meso 2, 3-dimercaptosuccinic acid

BAL is the standard treatment for poisoning by arsenic compounds and will alleviate some effects from exposure to arsenic vesicants. It may also decrease the severity of skin and eye lesions if applied topically within minutes after decontamination is complete (i.e., within 2-5 minutes postexposure). Additional chelating agents for the treatment of systemic arsenic toxicity include meso-2,3-dimercaptosuccinic acid (DMSA) and 2,3-dimercapto-l-propanesulfonic acid (DMPS). 

Chen, S. et al., Persistent effect of in utero meso-2,3-dimercaptosuccinic acid (DMSA)on immune function and lead-induced immunotoxicity, Toxicology 132,67, 1999. 

Complex 2 also reacts directly with 2,3-dimercapto-l-propanol, or meso-2,3-dimercaptosuccinic acid to give 215 (as a mixture of cis/trans isomers) and 216, respectively.65... 

Henninghausen G, Merkord J. 1985. Meso-2,3-dimercaptosuccinic acid increases the inhibition of glutathione S-transferase activity from rat liver cytosol supernatants by di-n-butyltin dichloride. Arch Toxicol 57 67-68. 

Ercal N, Treeratphan P, Hammond TC, Matthews RH, Grannemann NH, et al. 1996. In vivo indices of oxidative stress in lead-exposed C57BL/6 mice are reduced by treatment with meso-2,3-Dimercaptosuccinic Acid or N-acetylcysteine. Free Radical Biol Med 21 157-161. 

Flora, S.J.S. (1999). Arsenic induced oxidative stress and its reversibility following combined administration of N-acetylcysteine and meso 2,3 dimercaptosuccinic acid in rats. Clin. Exp. Pharmacol. Physiol. 26 865-9. 

Flora, S.J.S., Mehta, A., Rao, P.V.L., Kannan, G.M., Bhaskar, A.S.B., Dube, S.N., Pant, B.P. (2004a). Therapeutic potential of monoisoamyl and monomethyl esters of meso 2,3-dimercaptosuccinic acid in gallium arsenide intoxicated rats. Toxicology 195 127-46. 

Karman, G.M., Flora, S.J.S. (2004). Combined administration of meso 2,3-dimercaptosuccinic acid (DMSA) or monoisoamyl DMSA with an antioxidant for the treatment of chronic experimental arsenic poisoning in rats. Ecotoxicol. Environ. Saf. 58 37-43. 

Saxena, G., Pathak, U., Flora, S.J.S. (2005). Beneficial role of monoesters of meso 2,3-dimercaptosuccinic acid in the mobilization of lead and recovery of tissue oxidative injury in rats. Toxicology 214 39-56. 

Syrup of ipecac (purging solution) and gastric lavage should be administered within 4-6 h of oral exposure to arsenic. Antidotes include 3-5 mg kg BAL (2,3-dimercaptopropanol) administered intramuscularly. Penicilamine has also been administered with optical neuritis as a side effect. Certain synthetic, water-soluble dimercapto compounds (DMSA - meso-2, 3-dimercaptosuccinic acid and 2,3-dimercaptopro-pane-l-sulfonate) have been found effective. 

In acute exposure prompt medical attention is critical. The victim should be immediately removed to fresh air and away from the source of exposure. Oxygen should be provided if there is a respiratory distress. Initial therapy should be directed at stopping the ongoing hemolysis by performing exchange transfusion. Currently there is no other treatment to decrease arsine hemolysis however, studies in vitro have shown that some dithiol chelators (meso-2,3-dimercaptosuccinic acid, DMSA 2,3-dimercapto-l-propanesulfonic acid, DMPS and 2,3-butanedithiol) are effective (see Further Reading). This should be followed by aims to restore renal function or compensate for lost renal function (hemodialysis). This process does not remove any formed arsenic from the exposed body. Administration of dimercaprol (British Anti-Lewisite, BAL) has no effect on arsine hemolysis, but it lowers blood arsenic levels resulting from arsine exposure. The use of chelators must be... 

There does not appear to be an antidote of choice for bismuth toxicity in humans. Gastric lavage can be used within 1 h of exposure. Replace fluids and electrolytes. Monitor renal and liver function for several days and treat failure conventionally. The newer chelating agents, meso-2,3-dimercaptosuccinic acid and D,L-2,3-dimercapto-propane-l-sufonic acid, are being investigated experimentally as antidotes for bismuth toxicity, and the latter has been shown to be effective. In mice, D-penicillamine has proven effective. 

Zalups RK. 1993. Influence of 2,3-dimercaptopropane-1 -sulfonate (dmps) and meso-2,3-dimercaptosuccinic acid (dmsa) on the renal disposition of mercury in normal and uninephrectomized rats exposed to inorganic mercury. J Pharmacol Exper Thera 267(2) 791-800. 

Mei Niu, L., Qun Luo, H., Bing Li, N. (2006). Electrochemical Behavior of Epinephrine at a Meso-2,3-Dimercaptosuccinic Acid Self-Assembled Gold Electrode and Its Analytical Application. Analytical Letters, 39(1), 145-159. doi 10.1080/00032710500423468... 

Roels, H.A., Boeckx, M., Ceulemans, E., Lauwertys, R.R. (1991). Urinary excretion of mercury after occupational exposure to mercury vapour and influence of the chelating agent meso-2,3-dimercaptosuccinic acid (DMSA). British Journal of Industrial Medicine, 28(4), 247-253. doi 10.1136/oem.48.4.247... 

Uceda, M., Choi,Y., Shepherd, J., Guerra, E. (2013). Investigating the influence of meso-2,3-dimercaptosuccinic acid on thiosulphate leaching of bulk gold electrodes. World Gold Conference, 207-214. 

Abbreviations HgCl2, mercuric chloride DMPS, 2,3-dimercapto-l-propane sulfonate DMSA, meso 2,3-dimercaptosuccinic acid GI, gastrointestinal tract RBC red blood cells. 

Aposhian, H.V., and M.M. Aposhian. 1990. Meso-2,3-dimercaptosuccinic acid Chemical, pharmacological and toxicological properties of an orally effective metal chelating agent. Annu. Rev. Toxicol. 30 279-306. 

Medical treatment with chelation uses four different agents British Anti-Lewisite (2,3-dimercaptopropanol), edetate calcium disodium, D-penicillamine, and succimer or meso-2,3-dimercaptosuccinic acid (Roper et al. 1993). British Anti-Lewisite is contraindicated in children allergic to peanuts and in glucose-6-phosphate dehydrogenase deficiency D-penicillamine is contraindicated in penicillin allergy (Roper et al. 1993). 

Forman J, Moline J, Cernichiari E, Sayegh S, Torres JC, Landrigan MM, Hudson J, Adel HN and Landrigan PJ (2000) A cluster of pediatric metallic mercury exposure cases treated with meso-2, 3-dimercaptosuccinic acid (DMSA). Environ Health Perspect 108 575-577. 

Cremin et al. (1999) investigated the efficacy of chelation of lead with meso-2,3-dimercaptosuccinic acid in reducing the lead levels in the brain and its neurotoxicity from chronic oral exposure of the metal in adult rhesus monkeys. Their data, however, indicated that under the conditions of their study succimer treatment did not reduce brain lead levels in the primate model and also the limitations in the use of blood-lead level as an indicator of treatment efficacy. 

A. Oral. Succimer, meso-2,3-dimercaptosuccinic acid, DMSA (Chemet), 100-mg capsules in bottles of 100. 

Maiorino, R.M., Bruce, D.C. Aposhian, H.V. (1989) Determination and metabolism of dithiol chelating agents VI. Isolation and identification of the mixed disulfides of meso-2,3-dimercaptosuccinic acid with L-cysteine in human urine. Toxicol. Appi. Pharmacol. 97, 338. 

Modification of the magnetite surface with meso-2,3-dimercaptosuccinic acid (DMSA) is one of the variants to solve the problems of colloidal system stability in aqueous medium, the material biocompatibility, the immobilization of necessary compounds through thiol and carboxyl functional surface groups. 

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