Nitazoxanide

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Cat Number

API0232277

CAS Number

55981-09-4

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CAS Number

55981-09-4

EINECS

259-931-8

Storage

Store at room temperature

Synonyms

Alinia; Nitazoxanida; Benzamide, 2-(acetyloxy)-N-(5-nitro-2-thiazolyl)-; Nitazoxanidum; 2-[(5-nitro-1,3-thiazol-2-yl)carbamoyl]phenyl acetate; 2-(Acetolyloxy)-N-(5-nitro-2-thiazolyl)benzamide

Molecular Formula

C12H9N3O5S

Molecular Weight

307.28

Smiles

CC(=O)OC1=CC=CC=C1C(=O)NC2=NC=C(S2)[N+](=O)[O-]

Appearance

White to off-white solid powder

Melting Point

198-200°C

Relative Density

1.532

General Description

Nitazoxanide is a synthetic nitrothiazolyl-salicylamide derivative, a broad-spectrum antiparasitic and antiviral agent. Its chemical structure is 2-acetoxy-N-(5-nitro-2-thiazolyl)benzamide. Nitazoxanide is a white to off-white powder, practically insoluble in water but soluble in organic solvents. It is a prodrug that is hydrolyzed to its active metabolite, tizoxanide.

Mechanism of Action

Nitazoxanide is hydrolyzed to tizoxanide, which inhibits the enzyme pyruvate:ferredoxin oxidoreductase (PFOR) in anaerobic organisms, disrupting the electron transport chain and energy metabolism. This leads to the inhibition of the growth of parasites and bacteria. The drug also has antiviral activity by inhibiting the assembly of viral proteins.

Application

Nitazoxanide is indicated for the treatment of diarrhea caused by Cryptosporidium parvum and Giardia lamblia in immunocompetent patients. It is also used for the treatment of viral gastroenteritis and for the management of other parasitic infections. The drug is effective in reducing the duration and severity of diarrhea.

Nitazoxanide (NTZ) inhibited human astrovirus replication in vitro with an EC₅₀ of ~1.47 μM, effective against multiple serotypes and clinical isolates, even when added up to 8 hours post‑infection. In vivo, NTZ reduced viral shedding. This is the first identification of an anti‑astrovirus agent, supporting NTZ as a potential clinical therapeutic for astrovirus gastroenteritis.

Fig. 1 Nitazoxanide reduces clinical symptoms and viral titers in turkey poults. (Hargest V, et al., 2020)

References

Hargest V, et al. Astrovirus Replication Is Inhibited by Nitazoxanide In Vitro and In Vivo. J Virol. 2020;94(5):e01706-19.

Nitazoxanide was identified as a moderate STAT3 pathway inhibitor. A series of thiazolide derivatives were synthesized, with eight compounds showing greater potency than nitazoxanide. Derivatives 15 and 24 were more potent than the phase I clinical candidate WP1066. Compound 15 also showed improved in vivo pharmacokinetics and broad-spectrum antiproliferative activity across multiple cancer cell lines. These thiazolides represent promising antitumor agents targeting STAT3.

Fig. 2 Negative regulation of the transcriptional activity of STAT3. (Lü Z, et al., 2021)

References

Lü Z, et al. Structure-Activity Study of Nitazoxanide Derivatives as Novel STAT3 Pathway Inhibitors. ACS Med Chem Lett. 2021;12(5):696-703.

Does Nitazoxanide require protection from light during long-term storage?

Yes, it is photosensitive. UV exposure can cause photodegradation and discoloration of the nitrothiazole ring. Store in light-resistant containers, preferably amber glass.

What is the recommended storage temperature for Nitazoxanide?

Store at controlled room temperature (15-25°C). Avoid excessive heat above 30°C, which can soften the powder and accelerate hydrolysis.

Is Nitazoxanide stable in oral suspension and tablet formulations?

Reconstituted suspensions have limited stability (typically 7 days at room temperature).

How is the impurity tizoxanide (a hydrolysis product) monitored?

This primary degradation product is specifically quantified using a stability-indicating HPLC method, ensuring it remains within pharmacopoeial limits.