Stibophen

Stibophen
Clinical data
ATC code
Identifiers
IUPAC name
  • Pentasodium 2-(2-oxido-3,5-disulfonatophenoxy)-1,3,2-benzodioxastibole-5,7-disulfonate
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
ECHA InfoCard100.007.630
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Chemical and physical data
FormulaC12H4Na5O16S4Sb
Molar mass769.10 g·mol−1
3D model (JSmol)
SMILES
  • C1=C(C=C2C(=C1S(=O)(=O)[O-])O[Sb](O2)OC3=CC(=CC(=C3[O-])S(=O)(=O)[O-])S(=O)(=O)[O-])S(=O)(=O)[O-].[Na+].[Na+].[Na+].[Na+].[Na+]
InChI
  • InChI=1S/2C6H6O8S2.5Na.7H2O.Sb/c2*7-4-1-3(15(9,10)11)2-5(6(4)8)16(12,13)14;;;;;;;;;;;;;/h2*1-2,7-8H,(H,9,10,11)(H,12,13,14);;;;;;7*1H2;/q;;5*+1;;;;;;;;+3/p-8
  • Key:ZDDUXABBRATYFS-UHFFFAOYSA-F
  (verify)

Stibophen is an anthelmintic originally developed by Bayer that is used as a treatment for schistosomiasis[1] by intramuscular injection. It is classified as a trivalent antimony compound. Brand names include Fouadin/Fuadin (named in honor of Fuad I of Egypt, who had enthusiastically supported its research and development)[2][3].

Mechanism of action

Stibophen inhibits the enzyme phosphofructokinase, which the worms need for glycolysis,[4] at least partly by binding to the sulfhydryl (–SH) group of the enzyme.[5] 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

  1. ↑ Miller MJ, Lyon HP (November 1955). "Treatment of vesical schistosomiasis with stibophen". The American Journal of Tropical Medicine and Hygiene. 4 (6): 1049–56. doi:10.4269/ajtmh.1955.4.1049. PMID 13268811.
  2. ↑ Khalil M, Betache MH (February 1930). "Treatment of Bilharziasis With a New Compound 'Fouadin.'". Lancet. 215 (5553): 234–35. doi:10.1016/S0140-6736(00)87344-4.
  3. ↑ Williamson TV, Dodson AI (May 1933). "The Specific Effect of 'Fouadin' (Fuadin) on Granuloma Inguinale: Preliminary Report". JAMA. 100 (21): 1671–76. doi:10.1001/jama.1933.02740210019007.
  4. ↑ Bueding E, Mansour JM (June 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): 159–65. doi:10.1111/j.1476-5381.1957.tb00114.x. PMC 1509678. PMID 13446367.
  5. ↑ Su JG, Mansour JM, Mansour TE (October 1996). "Purification, kinetics and inhibition by antimonials of recombinant phosphofructokinase from Schistosoma mansoni". Molecular and Biochemical Parasitology. 81 (2): 171–8. doi:10.1016/0166-6851(96)02702-8. PMID 8898332.
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