A prodrug form of tizoxanide
Related Products
Active Metabolite(s)
13693Tizoxanide
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Nitazoxanide

Item No. 13692

Technical Information
Formal Name
2-(acetyloxy)-N-(5-nitro-2-thiazolyl)-benzamide
CAS Number
55981-09-4
Synonyms
  • NSC 697855
  • NTZ
Molecular Formula
C12H9N3O5S
Formula Weight
Purity
≥95%
A crystalline solid
DMF: 15 mg/mlDMSO: 20 mg/mlDMSO:PBS (pH 7.2) (1:10): 0.1 mg/ml
λmax
238, 341 nm
SMILES
O=C(NC1=NC=C([N+]([O-])=O)S1)C2=C(OC(C)=O)C=CC=C2
InChi Code
InChI=1S/C12H9N3O5S/c1-7(16)20-9-5-3-2-4-8(9)11(17)14-12-13-6-10(21-12)15(18)19/h2-6H,1H3,(H,13,14,17)
InChi Key
YQNQNVDNTFHQSW-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    Product Description

    Nitazoxanide is a prodrug form of the antiparasitic tizoxanide (Item No. 13693), an inhibitor of pyruvate-ferredoxin oxidoreductase (PFOR).1 It inhibits growth of the parasite C. parvum in MDBK cells when used at a concentration of 10 µg/ml.2 It is active against M. tuberculosis and M. bovis (MIC = 16 µg/ml for both) and bactericidal against replicating and non-replicating M. tuberculosis.1 Nitazoxanide (5 and 10 µM) inhibits replication of severe acute respiratory coronavirus 2 (SARS-CoV-2) and Middle East respiratory syndrome CoV (MERS-CoV).3 It also inhibits viral hemagglutinin N-glycosylation and replication of the influenza strains H1N1 PR8 and WSN, as well as H5N9 A/Ck viruses (EC50s = 1, 0.5, and 1 µg/ml, respectively).4 Nitazoxanide (250 mg/kg) reduces oocyst shedding and parasite burden, but not the severity of diarrhea, in a gnotobiotic piglet model of C. parvum infection.2 Formulations containing nitazoxanide have been used in the treatment of diarrhea caused by G. lamblia or C. parvum.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. de Carvalho, L.P.S., Lin, G., Jiang, X., et alNitazoxanide kills replicating and nonreplicating Mycobacterium tuberculosis and evades resistance. J. Med. Chem. 52(19), 5789-5792 (2009).

    2. Theodos, C.M., Griffiths, J.K., D'Onfro, J., et alEfficacy of nitazoxanide against Cryptosporidium parvum in cell culture and in animal models. Antimicrob. Agents Chemother. 42(8), 1959-1965 (1998).

    3. Mostafa, A., Kandeil, A., Elshaier, Y.A.M.M., et alFDA-approved drugs with potent in vitro antiviral activity against severe acute respiratory syndrome coronavirus 2. Pharmaceuticals (Basel) 13(12), 443 (2020).

    4. Rossignol, J.F., La Frazia, S., Chiappa, L., et alThiazolides, a new class of anti-influenza molecules targeting viral hemagglutinin at the post-translational level. The Journal of Biological Chemisty 284(43), 29798-29808 (2009).