# Stibophen

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Stibophen
> Markdown URL: https://mediated.wiki/source/Stibophen.md
> Source: https://en.wikipedia.org/wiki/Stibophen
> Source revision: 1329520085
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{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](/source/anthelmintic) originally developed by [Bayer](/source/Bayer) that is used as a treatment for [schistosomiasis](/source/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](/source/intramuscular_injection). It is classified as a trivalent [antimony](/source/antimony) compound. Brand names include Fouadin/Fuadin (named in honor of [Fuad I](/source/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](/source/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](/source/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 vein](/source/mesenteric_vein_(disambiguation))s<!--intentional link to DAB page--> and undergo [hepatic shift](/source/hepatic_shift), die, and are [phagocytose](/source/phagocytose)d by liver cells.{{citation needed|date=December 2013}}

== References ==
{{reflist|2}}

{{Anthelmintics}}

Category:Antiparasitic agents
Category:Sulfonates
Category:Antimony(III) compounds

{{antiinfective-drug-stub}}

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Adapted from the Wikipedia article [Stibophen](https://en.wikipedia.org/wiki/Stibophen) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Stibophen?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.