Stibophen

Stibophen
Clinical data
ATC code	P02BX03 (WHO) ;
Identifiers
	IUPAC name Pentasodium 2-(2-oxido-3,5-disulfonatophenoxy)-1,3,2-benzodioxastibole-5,7-disulfonate;
CAS Number	23940-36-5;
PubChem CID	16683091;
ChemSpider	17615576;
ECHA InfoCard	100.007.630
Chemical and physical data
Formula	C12H4Na5O16S4Sb
Molar mass	769.12 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	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/c27-4-1-3(15(9,10)11)2-5(6(4)8)16(12,13)14;;;;;;;;;;;;;/h21-2,7-8H,(H,9,10,11)(H,12,13,14);;;;;;71H2;/q;;5+1;;;;;;;;+3/p-8; Key:ZDDUXABBRATYFS-UHFFFAOYSA-F;
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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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[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. doi:10.1016/0166-6851(96)02702-8. PMID 8898332.