{{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 | image_class = skin-invert-image
<!--Clinical data--> | tradename = | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_category = | legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> | legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> | legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C --> | legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> | legal_status = | routes_of_administration =
<!--Pharmacokinetic data--> | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =
<!--Identifiers--> | 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}} | DrugBank = | ChemSpiderID = 17615576
<!--Chemical data--> | 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<ref>{{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 }}</ref> 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).<ref>{{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 }}</ref><ref>{{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 }}</ref>
==Mechanism of action== Stibophen inhibits the enzyme phosphofructokinase, which the worms need for glycolysis,<ref>{{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 }}</ref> at least partly by binding to the sulfhydryl (–SH) group of the enzyme.<ref>{{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 }}</ref> Inhibiting glycolysis paralyzes the worms, which lose their hold on the wall of mesenteric veins<!--intentional link to DAB page--> and undergo hepatic shift, die, and are phagocytosed by liver cells.{{citation needed|date=December 2013}}
== References == {{reflist|2}}
{{Anthelmintics}}
Category:Antiparasitic agents Category:Sulfonates Category:Antimony(III) compounds
{{antiinfective-drug-stub}}