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;
PubChemCID	16683091;
ChemSpider	17615576;
UNII	EF31LJY4KN;
CompTox Dashboard(EPA)	DTXSID10946763;
ECHA InfoCard	100.007.630
Chemical and physical data
Formula	C12H4Na5O16S4Sb
Molar mass	769.10g·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)

Stibophenis ananthelminticoriginally developed byBayerthat is used as a treatment forschistosomiasis^[1]byintramuscular injection.It is classified as a trivalentantimonycompound. Brand names include Fouadin/Fuadin (named in honor ofFuad Iof Egypt, who had enthusiastically supported its research and development).^[2]^[3]

Mechanism of action

Stibophen inhibits the enzymephosphofructokinase,which the worms need for glycolysis,^[4]at least partly by binding to thesulfhydryl(–SH) group of the enzyme.^[5]Inhibiting glycolysis paralyzes the worms, which lose their hold on the wall ofmesenteric veinsand undergohepatic shift,die, and arephagocytosedby liver cells.^{[citation needed]}

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.
^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.
^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.
^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.PMC1509678.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] 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.PMC1509678.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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