Chemistry:Stibophen

Short description: Chemical compound

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 Y
PubChem CID	16683091
ChemSpider	17615576
UNII	EF31LJY4KN
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/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
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Stibophen is an anthelmintic originally developed by Bayer that is used as a treatment for schistosomiasis 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).

Mechanism of action

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