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Stibophen

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Stibophen
Clinical data
ATC code
Identifiers
  • Pentasodium 2-(2-oxido-3,5-disulfonatophenoxy)-1,3,2-benzodioxastibole-5,7-disulfonate
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
ECHA InfoCard100.007.630Edit this at Wikidata
Chemical and physical data
FormulaC12H4Na5O16S4Sb
Molar mass769.10 g·mol−1
3D model (JSmol)
  • 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=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
  • Key:ZDDUXABBRATYFS-UHFFFAOYSA-F
  (verify)

Stibophen is ananthelmintic originally developed byBayer that is used as a treatment forschistosomiasis[1] byintramuscular injection. It is classified as a trivalentantimony compound. Brand names include Fouadin/Fuadin (named in honor ofFuad I of Egypt, who had enthusiastically supported its research and development).[2][3]

Mechanism of action

[edit]

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 veins and undergohepatic shift, die, and arephagocytosed by liver cells.[citation needed]

References

[edit]
  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.
Antiplatyhelmintic agents
Antitrematodals
(schistosomicides)
Bindstubulin
AChE inhibitor
Other/unknown
Anticestodals
(taeniacides)
Bindstubulin
Other/unknown
Antinematodal agents
(including
macrofilaricides)
Bindstubulin
Glutamate-gated chloride channel,GABA receptor
NMDA
Other/unknown
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