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;
CompTox Dashboard (EPA)	DTXSID10946763 ;
ECHA InfoCard	100.007.630
Chemical and physical data
Formula	C12H4Na5O16S4Sb
Molar mass	769.10 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;
	(verify)

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 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.
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.
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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[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] 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.

[3] 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.