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Succimer, sold under the brand name Chemet among others, is a medication tool used to treat lead poisoning, mercury, and arsenic poisoning. When it's radiolabeled with technetium-99m, it's used in many types of .
Common side effects include vomiting, diarrhea, rash, and neutropenia. Liver problems and allergic reactions may also occur with use. Whether use during pregnancy is safe for the baby is unclear.
Dimercaptosuccinic acid is in the chelating agent family of medications. It binds to a metal atom, leading to increased clearance from the body via the urine. A full course of Succimer lasts for 19 days of oral administration. A second course should be given when more than two weeks pass after the first course.
Succimer has been used medically since the 1950s. It is on the World Health Organization's List of Essential Medicines. In the United States, no generic version was available as of 2015.
Succimer facilitates urinary excretion of lead, and with sufficiently aggressive treatment, can reduce lead content in the brain. It also increases urinary excretion of copper and zinc. Dimercaptosuccinic acid improved cognitive function in that had been exposed to lead, but reduced cognitive function in rats that had not been exposed to lead.
The 2,3-dimercaptosuccinic acid molecule has two (two asymmetric carbon atoms), and can exist as three different . The 2 S,3 S and 2 R,3 R isomers are a pair of , whereas the 2 R,3 S isomer (succimer) is a meso compound and thus Optical activity.
Meso 2,3-dimercaptosuccinic acid binds to HSAB theory heavy metals such as Hg2+ and lead, mobilizing these ions for excretion. It binds to metal cations through the thiol groups, which ionize upon complexation.
(2025). 9781284057560, Jones & Bartlett Learning. ISBN 9781284057560
Medical uses
Succimer is indicated for the treatment of lead poisoning in children with blood level measured above 45 μg/dL. The use of dimercaptosuccinic acid is not approved for prevention of lead poisoning in anticipation of exposure in known lead-contaminated environments. Dimercaptosuccinic acid can cross the blood–brain barrier of mice, but it is not known if this is also the case in humans. Even if dimercaptosuccinic acid cannot reverse the damages done to the central nervous system, it might prevent further deterioration.
Chemistry
Succimer is an isomer of 2,3-dimercaptosuccinic acid. 2,3-dimercaptosuccinic acid is the organosulfur compound with the Chemical formula HO2CCH(SH)CH(SH)CO2H. This colorless solid contains two carboxylic acid and two thiol groups, the latter being responsible for its mildly unpleasant odour. It occurs in two diastereomers, meso and the chiral dl forms.
(2 S,3 S)-2,3-dimercaptosuccinic acid
Preparation and reactivity
Dimercaptosuccinic acid may be prepared by reacting acetylenedicarboxylic acid with sodium thiosulfate or thioacetic acid followed by hydrolysis. The dimethyl ester is also known.
History
Dimercaptosuccinic acid was first synthesized by V. L. Nirenburg in the Urals Polytechnic Institute, commissioned by one of the electrical enterprises of Sverdlovsk, Russia, which consumed many tons of mercury and was looking for a medicine to prevent poisoning of personnel. In 1957, Chinese scientists found that dimercaptosuccinic acid can effectively treat antimony poisoning due to overdose of tartar emetic. Pronounced protective effect in animal poisoning with arsenic and mercury was first shown by I. E. Okonishnikova in 1962. In 1984, the now-defunct Bock Pharmaceutical Company requested the FDA grant approval for orphan drug status under the brand name Chemet and the FDA approved of this in 1991. It provided exclusivity until 1998 which was conveyed to the successor Sanofi in 1996.
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