Fexinidazole
 | |
| Names | |
|---|---|
| IUPAC name
1-Methyl-2-{[4-(methylsulfanyl)phenoxy]methyl}-5-nitro-1H-imidazole | |
| Other names
HOE 239 | |
| Identifiers | |
59729-37-2  | |
| ChEMBL | ChEMBL1631694 |
| ChemSpider | 62032 |
| |
| Jmol-3D images | Image |
| PubChem | 68792 |
| |
| UNII | 306ERL82IR |
| Properties | |
| Molecular formula |
C12H13N3O3S |
| Molar mass | 279.31 g·mol−1 |
| Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
| Infobox references | |
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
- ↑ 1.0 1.1 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.
- ↑ 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.
- ↑ 3.0 3.1 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.
- ↑ 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.
- ↑ "Jump-Start on Slow Trek to Treatment for a Disease". New York Times. January 8, 2008.
- ↑ "Fexinidazole Progresses into Clinical Development". DNDi Newsletter. November 2009.
- ↑ "Sanofi-aventis and DNDi enter into a Collaboration Agreement on a New Drug for Sleeping Sickness, Fexinidazole". DNDi. May 18, 2009.
- ↑ 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.