Stibophen
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| Systematic (IUPAC) name | |
|---|---|
| Pentasodium 2-(2-oxido-3,5-disulfonatophenoxy)-1,3,2-benzodioxastibole-5,7-disulfonate | |
| Clinical data | |
| Identifiers | |
| 23940-36-5 | |
| P02BX03 | |
| PubChem | CID 16683091 |
| Chemical data | |
| Formula | C12H4Na5O16S4Sb |
| 769.12 g/mol | |
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SMILES
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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.
References
- ↑ 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.
- ↑ 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.
- ↑ 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. doi:10.1016/0166-6851(96)02702-8. PMID 8898332.
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