All Photos(1)
Synonym(s):
1-methyl-2-[[4-(methylthio)phenoxy]methyl]-5-nitro-1H-imidazole, HOE 239
Empirical Formula (Hill Notation):
C12H13N3O3S
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Assay
≥98% (HPLC)
form
powder
color
light yellow to dark brown
solubility
DMSO: 2 mg/mL, clear
storage temp.
−20°C
SMILES string
CN1C(COC2=CC=C(SC)C=C2)=NC=C1[N+]([O-])=O
Biochem/physiol Actions
Anti Trypanosoma, Leishmania agent.
Fexinidazole is a potent anti-Trypanosoma agent. Trypanosoma species human protozoan pathogens are responsible for sleeping sickness and Chagas disease. In vivo, fexinidazole is oxidized to sulfoxide and sulfone metabolites that are effective in blocking the progression of the parasitic disease visceral leishmaniasis. The mechanism of action appears to be by reductive activation via an NADH-dependent nitroreductase expressed by the parasites.
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Regulatory Information
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Victor Kande Betu Ku Mesu et al.
Lancet (London, England), 391(10116), 144-154 (2017-11-09)
Few therapeutic options are available to treat the late-stage of human African trypanosomiasis, a neglected tropical disease, caused by Trypanosoma brucei gambiense (g-HAT). The firstline treatment is a combination therapy of oral nifurtimox and intravenous eflornithine that needs to be
Alan H Fairlamb et al.
Current medicinal chemistry (2018-04-28)
Interest in nitroheterocyclic drugs for the treatment of infectious diseases has undergone a resurgence in recent years. Here we review the current status of monocyclic and bicyclic nitroheterocyclic compounds as existing or potential new treatments for visceral leishmaniasis, Chagas' disease
Marcel Kaiser et al.
Antimicrobial agents and chemotherapy, 55(12), 5602-5608 (2011-09-14)
Fexinidazole is a 5-nitroimidazole drug currently in clinical development for the treatment of human sleeping sickness (human African trypanosomiasis [HAT]), caused by infection with species of the protozoan parasite Trypanosoma brucei. The compound and its two principal metabolites, sulfoxide and
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