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| Pronunciation | /ˈsʌksɪmər/ |
| Trade names | Chemet, others |
| Other names | Dimercaptosuccinic acid DMSA (2R,3S)-2,3-Dimercaptosuccinic acid meso-2,3-Dimercaptosuccinic acid APRD01236 |
| AHFS/Drugs.com | Monograph |
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| ECHA InfoCard | 100.005.597 |
| Chemical and physical data | |
| Formula | C4H6O4S2 |
| Molar mass | 182.21 g·mol−1 |
| 3D model (JSmol) | |
| Melting point | 125 °C (257 °F) |
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Succimer, sold under the brand nameChemet among others, is amedication tool used to treatlead,mercury, andarsenic poisoning.[4] Whenradiolabeled withtechnetium-99m, it is used in many types ofdiagnostic testing.[5]
Common side effects include vomiting, diarrhea, rash, andlow blood neutrophil levels.[4]Liver problems andallergic reactions may also occur with use.[4] Whether use duringpregnancy is safe for the baby is unclear.[6]
Dimercaptosuccinic acid is in thechelating agent family of medications.[4] It binds to a metal atom, leading to increased clearance from the body via theurine.[4] A fullcourse of Succimer lasts for 19 days oforal administration.[4] A second course should be given after more than two weeks break after the first course.[4]
Succimer has been used medically since the 1950s.[7][8] It is on theWorld Health Organization's List of Essential Medicines.[9] In the United States, nogeneric version was available as of 2015.[10]
Succimer is indicated for the treatment oflead 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 theblood–brain barrier of mice,[11] but it is not known if this is also the case in humans.[12] Even if dimercaptosuccinic acid cannot reverse the damages done to the central nervous system, it might prevent further deterioration.[13]
Succimer facilitates urinary excretion of lead, and with sufficiently aggressive treatment, can reduce lead content in the brain.[14] It also increases urinary excretion of copper and zinc.[15] Dimercaptosuccinic acid improved cognitive function inrats that had been exposed to lead, but reduced cognitive function in rats that had not been exposed to lead.[14]
Succimer is an isomer of 2,3-dimercaptosuccinic acid. 2,3-dimercaptosuccinic acid is theorganosulfur compound with theformula HO2CCH(SH)CH(SH)CO2H. This colorless solid contains twocarboxylic acid and twothiol groups, the latter being responsible for its mildly unpleasant odour. It occurs in twodiastereomers, meso and the chiraldl forms.
The 2,3-dimercaptosuccinic acid molecule has twostereocentres (twoasymmetric carbon atoms), and can exist as three differentstereoisomers. The 2S,3S and 2R,3R isomers are a pair ofenantiomers, whereas the 2R,3S isomer (succimer) is ameso compound and thusoptically inactive.
-2%2c3-dimercaptosuccinic-acid-2D-skeletal-A-configurations-labelled.png) | | -2%2c3-dimercaptosuccinic-acid-2D-skeletal-A-configurations-labelled.png) |
-2%2c3-dimercaptosuccinic-acid-2D-skeletal-B-configurations-labelled.png) |  | -2%2c3-dimercaptosuccinic-acid-2D-skeletal-B-configurations-labelled.png) |
| (2R,3R)-2,3-dimercaptosuccinic acid | (2R,3S)-2,3-dimercaptosuccinic acid (meso-2,3-dimercaptosuccinic acid) | (2S,3S)-2,3-dimercaptosuccinic acid |
Dimercaptosuccinic acid[clarification needed] may be prepared by reactingacetylenedicarboxylic acid withsodium thiosulfate[16] orthioacetic acid followed by hydrolysis. The dimethylester is also known.[17]
Meso 2,3-dimercaptosuccinic acid binds to"soft" heavy metals such asHg2+ andPb2+, mobilizing these ions for excretion. It binds to metal cations through the thiol groups, which ionize uponcomplexation.
Dimercaptosuccinic acid was first synthesized byV. L. Nirenburg in theUrals Polytechnic Institute, commissioned by one of the electrical enterprises ofSverdlovsk, Russia, which consumed many tons ofmercury and was looking for a medicine to prevent poisoning of personnel. In 1957, Chinese scientists found thatdimercaptosuccinic acid can effectively treatantimony poisoning due to overdose oftartar emetic.[18] Pronounced protective effect in animal poisoning witharsenic andmercury was first shown byI. E. Okonishnikova in 1962. In 1984, the now-defunct Bock Pharmaceutical Company requested theFDA grant approval fororphan 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 successorSanofi in 1996.[19][20]
