Stibophen
Clinical data
ATC code
Identifiers
  • Pentasodium 2-(2-oxido-3,5-disulfonatophenoxy)-1,3,2-benzodioxastibole-5,7-disulfonate
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.007.630 Edit 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 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

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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

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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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📚 Artikel Terkait di Wikipedia

Moxidectin

thiazole Niridazole thioxanthone Hycanthone Lucanthone antimony compounds Stibophen Tartar emetic‡ Anticestodals (taeniacides) Binds tubulin benzimidazole

List of drugs used to treat schistosomiasis

hycanthone lucanthone metrifonate niridazole oltipraz oxamniquine praziquantel stibophen Schistosomiasis vaccine Schistosomicides at the U.S. National Library

Metalloid

compounds are poisonous. Two antimony compounds, sodium stibogluconate and stibophen, are used as antiparasitical drugs. Elemental tellurium is not considered

Elaeophora schneideri

hydrochloride healed the skin lesions. For elimination of the nematodes, fuadin (stibophen), diethylcarbamazine and piperazine hexahydrate have been suggested. However

ATC code P02

Arpraziquantel P02BB01 Metrifonate P02BX01 Bithionol P02BX02 Niridazole P02BX03 Stibophen P02BX04 Triclabendazole P02CA01 Mebendazole P02CA02 Tiabendazole P02CA03