Succimer

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(Redirected from
Dimercaptosuccinic acid
)
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Succimer
Clinical data
Pronunciation/ˈsʌksɪmər/
Trade namesChemet, others
Other namesDimercaptosuccinic acid
DMSA
(2R,3S)-2,3-Dimercaptosuccinic acid
meso-2,3-Dimercaptosuccinic acid
APRD01236
AHFS/Drugs.comMonograph
License data
ATC code
Legal status
Legal status
Identifiers
  • (2R,3S)-2,3-disulfanylbutanedioic acid
JSmol)
Melting point125 °C (257 °F)
  • O=C(O)[C@@H](S)[C@@H](S)C(=O)O
  • 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+ ☒N
  • Key:ACTRVOBWPAIOHC-XIXRPRMCSA-N

Succimer, sold under the brand name Chemet among others, is a

diagnostic testing.[5] A full course of Succimer lasts for 19 days of oral administration.[4] A second course should be given when more than two weeks pass after the first course.[4]

Common side effects include vomiting, diarrhea, rash, and

allergic reactions may also occur with use.[4] Whether use during pregnancy is safe for the baby is unclear.[6] Dimercaptosuccinic acid is in the chelating agent family of medications.[4] It works by binding with lead and a number of other heavy metals, allowing them to leave the body in the urine.[4]

Succimer has been used medically since the 1950s.

generic version was available as of 2015.[10]

Medical uses

See also: DMSA scan

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,[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 in rats that had been exposed to lead, but reduced cognitive function in rats that had not been exposed to lead.[14]

Chemistry

Succimer is an isomer of 2,3-dimercaptosuccinic acid. 2,3-dimercaptosuccinic acid is the

diastereomers
, meso and the chiral dl forms.

The 2,3-dimercaptosuccinic acid molecule has two

optically inactive
.

(2R,3R)-2,3-dimercaptosuccinic acid (2R,3S)-2,3-dimercaptosuccinic acid
(meso-2,3-dimercaptosuccinic acid)		 (2S,3S)-2,3-dimercaptosuccinic acid

Preparation and reactivity

Dimercaptosuccinic acid[clarification needed] may be prepared by reacting acetylenedicarboxylic acid with sodium thiosulfate[16] or thioacetic acid followed by hydrolysis. The dimethyl ester is also known.[17]

Meso 2,3-dimercaptosuccinic acid binds to

complexation
.

History

Dimercaptosuccinic acid was first synthesized by

FDA grant approval for orphan drug status under the brand name Chemet and the FDA approved of this in 1991, providing exclusivity until 1998 which was conveyed to the successor Sanofi in 1996.[19][20]

References

  1. ^ "Chemet- succimer capsule". DailyMed. U.S. National Library of Medicine. 12 December 2019. Retrieved 19 June 2022.
  2. ^ "Nephroscan- succimer injection, powder, lyophilized, for solution". DailyMed. U.S. National Library of Medicine. 1 March 2022. Retrieved 19 June 2022.
  3. ^ "Rotop - DMSA- kit for the preparation of technetium tc99m succimer injection injection, powder, lyophilized, for solution". DailyMed. U.S. National Library of Medicine. 9 March 2021. Retrieved 19 June 2022.
  4. ^ a b c d e f g "Succimer". The American Society of Health-System Pharmacists. Archived from the original on 16 January 2017. Retrieved 8 January 2017.
  5. ISBN 9783540278450. Archived
    from the original on 2017-01-13.
  6. ^ "Succimer (Chemet) Use During Pregnancy". www.drugs.com. Archived from the original on 16 January 2017. Retrieved 12 January 2017.
  7. PMID 9630737
    .
  8. ISBN 9780080527574. Archived
    from the original on 2017-01-13.
  9. hdl:10665/325771
    . WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  10. ISBN 9781284057560
    .
  11. PMID 7741240
    .
  12. PMID 18077077
    .
  13. PMID 14585942
    .
  14. ^
    PMID 24113857
    .
  15. PMID 19700440
    .
  16. ^ US 4550193, Lindemann MK, Lukenbach ER, "Process for the preparation of 2,3-dimercaptosuccinic acid and its lower alkyl esters", issued 29 October 1985, assigned to Johnson & Johnson Baby Products 
  17. doi:10.1002/hlca.19610440410
    .
  18. ^ Liang Y, Chu C, Tsen Y, Ting K (1957). "Studies on antibilharzial drugs. Vl. The antidotal effects of sodium dimercaptosuccinate and BAL-glucoside against tartar emetic". Acta Physiol. Sin. 21: 24–32.
  19. ^ "Search Orphan Drug Designations and Approvals". Searchable database for Orphan Designated and or Approved Products. FDA. 2013. Archived from the original on 6 November 2014. Retrieved 5 November 2014.
  20. ^ "Sanofi Buying An American Drug Concern". The New York Times. July 17, 1996. Archived from the original on 6 November 2014. Retrieved 5 November 2014.

Further reading

  • Aposhian HV, Aposhian MM (1990). "meso-2,3-Dimercaptosuccinic acid: chemical, pharmacological and toxicological properties of an orally effective metal chelating agent". Annual Review of Pharmacology and Toxicology. 30 (1): 279–306.
    PMID 2160791
    .
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