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SML2524

Sigma-Aldrich

Fexinidazole

≥98% (HPLC)

Synonym(s):

1-methyl-2-[[4-(methylthio)phenoxy]methyl]-5-nitro-1H-imidazole, HOE 239

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About This Item

Empirical Formula (Hill Notation):
C12H13N3O3S
CAS Number:
Molecular Weight:
279.31
MDL number:
UNSPSC Code:
12352200
NACRES:
NA.77

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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

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