Fexinidazole

Fexinidazole
Clinical data
Other names
  • Fexinidazole Winthrop
  • HOE 239
License data
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Identifiers
IUPAC name
  • 1-Methyl-2-{[4-(methylsulfanyl)phenoxy]methyl}-5-nitro-1H-imidazole
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.207.619
Chemical and physical data
FormulaC12H13N3O3S
Molar mass279.31 g·mol−1
3D model (JSmol)
SMILES
  • [O-] [N+](=O)c1cnc(n1C)COc2ccc(SC)cc2
InChI
  • 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
  • Key:MIWWSGDADVMLTG-UHFFFAOYSA-N

Fexinidazole is a medication used to treat African trypanosomiasis (sleeping sickness) caused by Trypanosoma brucei gambiense.[3] It is effective against both first and second stage disease.[3] It is taken by mouth.[4]

Common side effects include nausea, vomiting, headache, and trouble sleeping.[5] Other side effects may include QT prolongation, psychosis, and low white blood cells.[6] It is unclear if use during pregnancy or breast feeding is safe.[6] Fexinidazole is in the antiparasitic and the nitroimidazole family of medications.[4] It is believed to work by turning on certain enzymes within the parasites that result in their death.[5]

Fexinidazole was first described in 1978.[7] It was given a positive opinion by the European Medicines Agency in 2018.[5] It is on the World Health Organization's List of Essential Medicines.[8][9] Fexinidazole was developed for sleeping sickness by the Drugs for Neglected Diseases initiative in collaboration with Sanofi.[10] Fexinidazole was approved for medical use in the United States in July 2021.[1]

  1. ^ a b "Fexinidazole: FDA-Approved Drugs". U.S. Food and Drug Administration. Retrieved 16 July 2021.
  2. ^ "Fexinidazole tablet". DailyMed. U.S. National Library of Medicine. Retrieved 20 August 2021.
  3. ^ a b "Fexinidazole Winthrop H-W-2320". European Medicines Agency. 22 January 2019. Archived from the original on 18 January 2021. Retrieved 12 November 2019.
  4. ^ a b Deeks ED (February 2019). "Fexinidazole: First Global Approval". Drugs. 79 (2): 215–220. doi:10.1007/s40265-019-1051-6. PMID 30635838. S2CID 57772417.
  5. ^ a b c "Fexinidazole Winthrop (fexinidazole)" (PDF). EMA. Archived from the original (PDF) on 2 January 2021. Retrieved 12 November 2019.
  6. ^ a b "Fexinidazole Winthrop" (PDF). EMA. Archived from the original (PDF) on 12 November 2019. Retrieved 12 November 2019.
  7. ^ Mowbray CE (2017). "Antileishmanial Drug Discovery: Past, Present, and Future Perspectives". In Gil C, Rivas L (eds.). Drug Discovery for Leishmaniasis. Royal Society of Chemistry. p. 30. ISBN 978-1-78801-258-4.
  8. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  9. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
  10. ^ "Fexinidazole – DNDi". www.dndi.org. 31 December 2004. Retrieved 12 November 2019.
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