Stibophen

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]

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
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/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)

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.^{[citation needed]}