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;
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/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 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]

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]}

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. 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] 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. PMC 1509678. 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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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/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)