Stibophen

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Stibophen
Systematic (IUPAC) name
Pentasodium 2-(2-oxido-3,5-disulfonatophenoxy)-1,3,2-benzodioxastibole-5,7-disulfonate
Clinical data
Legal status ?
Identifiers
CAS number 23940-36-5
ATC code P02BX03
PubChem CID 16683091
Chemical data
Formula C12H4Na5O16S4Sb 
Mol. mass 769.12 g/mol
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Stibophen is an anthelmintic classified as antimony compound and used as treatment of schistosomiasis[1] by intramuscular injection.

Mechanism of action

Stibophen inhibits the enzyme phosphofructokinase, which the worms need for glycolysis,[2] at least partly by binding to the sulfhydryl (–SH) group of the enzyme.[3] Inhibiting glycolysis paralyzes the worms, which lose their hold on the wall of mesenteric veins and undergo hepatic shift, die, and are phagocytosed by liver cells.[citation needed]

References

  1. Miller, M. J.; Lyon, H. P. (1955). "Treatment of vesical schistosomiasis with stibophen". The American journal of tropical medicine and hygiene 4 (6): 1049–1056. PMID 13268811. 
  2. Bueding, E.; Mansour, J. M. (1957). "The relationship between inhibition of phosphofructokinase activity and the mode of action of trivalent organic antimonials on Schistosoma mansoni". British journal of pharmacology and chemotherapy 12 (2): 159–165. PMC 1509678. PMID 13446367. 
  3. Su, J. G.; Mansour, J. M.; Mansour, T. E. (1996). "Purification, kinetics and inhibition by antimonials of recombinant phosphofructokinase from Schistosoma mansoni". Molecular and biochemical parasitology 81 (2): 171–178. PMID 8898332. 


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