stibophen
{{Short description|Chemical compound}}
{{Drugbox
| Watchedfields = changed
| verifiedrevid = 387475262
| IUPAC_name = Pentasodium 2-(2-oxido-3,5-disulfonatophenoxy)-1,3,2-benzodioxastibole-5,7-disulfonate
| image = Stibophen.png
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| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 23940-36-5
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = EF31LJY4KN
| ATC_prefix = P02
| ATC_suffix = BX03
| PubChem = 16683091
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
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| ChemSpiderID = 17615576
| chemical_formula =
| C=12 | H=4 | Na=5 | O=16 | S=4 | Sb=1
| 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+]
| StdInChI = 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
| StdInChIKey = ZDDUXABBRATYFS-UHFFFAOYSA-F
}}
Stibophen is an anthelmintic originally developed by Bayer that is used as a treatment for schistosomiasis{{cite journal | vauthors = Miller MJ, Lyon HP | title = Treatment of vesical schistosomiasis with stibophen | journal = The American Journal of Tropical Medicine and Hygiene | volume = 4 | issue = 6 | pages = 1049–56 | date = November 1955 | pmid = 13268811 | doi = 10.4269/ajtmh.1955.4.1049 }} 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).{{cite journal | vauthors = Khalil M, Betache MH | title = Treatment of Bilharziasis With a New Compound 'Fouadin.' | journal = Lancet | volume = 215 | issue = 5553 | pages = 234–35 | date = February 1930 | doi = 10.1016/S0140-6736(00)87344-4 }}{{cite journal | vauthors = Williamson TV, Dodson AI | title = The Specific Effect of 'Fouadin' (Fuadin) on Granuloma Inguinale: Preliminary Report | journal = JAMA | volume = 100 | issue = 21 | pages = 1671–76 | date = May 1933 | doi = 10.1001/jama.1933.02740210019007 }}
Mechanism of action
Stibophen inhibits the enzyme phosphofructokinase, which the worms need for glycolysis,{{cite journal | vauthors = Bueding E, Mansour JM | title = The relationship between inhibition of phosphofructokinase activity and the mode of action of trivalent organic antimonials on Schistosoma mansoni | journal = British Journal of Pharmacology and Chemotherapy | volume = 12 | issue = 2 | pages = 159–65 | date = June 1957 | pmid = 13446367 | pmc = 1509678 | doi = 10.1111/j.1476-5381.1957.tb00114.x }} at least partly by binding to the sulfhydryl (–SH) group of the enzyme.{{cite journal | vauthors = Su JG, Mansour JM, Mansour TE | title = Purification, kinetics and inhibition by antimonials of recombinant phosphofructokinase from Schistosoma mansoni | journal = Molecular and Biochemical Parasitology | volume = 81 | issue = 2 | pages = 171–8 | date = October 1996 | pmid = 8898332 | doi = 10.1016/0166-6851(96)02702-8 | doi-access = free }} 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|date=December 2013}}