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Fexinidazole

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Fexinidazole
Names
IUPAC name
1-Methyl-2-{[4-(methylsulfanyl)phenoxy]methyl}-5-nitro-1H-imidazole
Other names
HOE 239
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.207.619 Edit this at Wikidata
UNII
  • InChI=1S/C12H13N3O3S/c1-14-11(13-7-12(14)15(16)17)8-18-9-3-5-10(19-2)6-4-9/h3-7H,8H2,1-2H3
  • [O-][N+](=O)c1cnc(n1C)COc2ccc(SC)cc2
Properties
C12H13N3O3S
Molar mass 279.31 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Fexinidazole is an antiparasitic agent.[1] It has activity against Trypanosoma cruzi, Tritrichomonas foetus, Trichomonas vaginalis, Entamoeba histolytica,[1] Trypanosoma brucei,[2] and Leishmania donovani.[3] The biologically relevant active metabolites in vivo are the sulfoxide and sulfone [3][4]

Fexinidazole was discovered by the German pharmaceutical company Hoechst AG, but its development as a pharmaceutical was halted in the 1980s.[5] Fexinidazole is now being studied through a collaboration between Sanofi and the Drugs for Neglected Diseases Initiative for the treatment of Chagas disease and human African trypanosomiasis (sleeping sickness).[6][7] Fexinidazole is the first drug candidate for the treatment of advanced-stage sleeping sickness in thirty years.[8]

References

  1. ^ a b Raether, W; Seidenath, H (1983). "The activity of fexinidazole (HOE 239) against experimental infections with Trypanosoma cruzi, trichomonads and Entamoeba histolytica". Annals of Tropical Medicine and Parasitology. 77 (1): 13–26. PMID 6411009.
  2. ^ Jennings, FW; Urquhart, GM (1983). "The use of the 2 substituted 5-nitroimidazole, Fexinidazole (Hoe 239) in the treatment of chronic T. brucei infections in mice". Zeitschrift für Parasitenkunde. 69 (5): 577–581. doi:10.1007/bf00926669. PMID 6636983.
  3. ^ a b Wyllie, S; Patterson, S; Stojanovski, L; Simeons, FRC; Norval, S; Kime, R; Read, RD; Fairlamb, AH (2012). "The anti-trypanosome drug fexinidazole shows potential for treating visceral leishmaniasis". Science Translational Medicine. 4 (119): 119re1. doi:10.1126/scitranslmed.3003326. PMC 3457684. PMID 22301556.
  4. ^ Sokolova, AY; Wyllie, S; Patterson, S; Oza, SL; Read, RD; Fairlamb, AH (2010). "Cross-resistance to nitro drugs and implications for treatment of human African trypanosomiasis". Antimicrobial Agents and Chemotherapy. 54 (7): 2893–900. doi:10.1128/AAC.00332-10. PMID 20439607.
  5. ^ "Jump-Start on Slow Trek to Treatment for a Disease". New York Times. January 8, 2008. {{cite web}}: Italic or bold markup not allowed in: |publisher= (help)
  6. ^ "Fexinidazole Progresses into Clinical Development". DNDi Newsletter. November 2009.
  7. ^ "Sanofi-aventis and DNDi enter into a Collaboration Agreement on a New Drug for Sleeping Sickness, Fexinidazole". DNDi. May 18, 2009.
  8. ^ Torreele, E; Bourdin Trunz, B; Tweats, D; Kaiser, M; Brun, R; Mazué, G; Bray, MA; Pécoul, B (2010). Boelaert, Marleen (ed.). "Fexinidazole--a new oral nitroimidazole drug candidate entering clinical development for the treatment of sleeping sickness". PLOS Neglected Tropical Diseases. 4 (12): e923. doi:10.1371/journal.pntd.0000923. PMC 3006138. PMID 21200426.{{cite journal}}: CS1 maint: unflagged free DOI (link)
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