Nitazoxanide
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MedKoo CAT#: 318369

CAS#: 55981-09-4

Description: Nitazoxanide is a broad-spectrum antiparasitic and broad-spectrum antiviral drug that is used in medicine for the treatment of various helminthic, protozoal, and viral infections. It is indicated for the treatment of infection by Cryptosporidium parvum and Giardia lamblia in immunocompetent individuals and has been repurposed for the treatment of influenza. Nitazoxanide has also been shown to have in vitro antiparasitic activity and clinical treatment efficacy for infections caused by other protozoa and helminths. Emerging evidence suggests that it possesses efficacy in treating a number of viral infections as well.


Chemical Structure

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Nitazoxanide
CAS# 55981-09-4

Theoretical Analysis

MedKoo Cat#: 318369
Name: Nitazoxanide
CAS#: 55981-09-4
Chemical Formula: C12H9N3O5S
Exact Mass: 307.03
Molecular Weight: 307.280
Elemental Analysis: C, 46.90; H, 2.95; N, 13.67; O, 26.03; S, 10.44

Price and Availability

Size Price Availability Quantity
1g USD 150 Ready to ship
2g USD 250 Ready to ship
5g USD 450 Ready to ship
25g USD 750 2 Weeks
100g USD 1250 2 Weeks
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Synonym: Nitazoxanide, Alinia, Colufase, Daxon, Nitazoxamide

IUPAC/Chemical Name: [2-[(5-nitro-1,3-thiazol-2-yl)carbamoyl]phenyl] acetate

InChi Key: YQNQNVDNTFHQSW-UHFFFAOYSA-N

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)

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

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Safety Data Sheet (SDS):
Biological target: Nitazoxanide is a synthetic nitrothiazolyl-salicylamide derivative and an antiprotozoal agent.
In vitro activity: Immunofluorescence applied to detect the intracellular viral antigen (E protein) indicated a time-dependent effect, with an important reduction in positively stained cells in the culture treated with 25 μg/mL NTZ (Nitazoxanide) compared to untreated cultures (Fig. 4A). The percentage of infected cells was significantly reduced by 66.9 ± 0.5% at 24 h post-infection when treated with 50 μg/mL NTZ, and by 72.8 ± 0.8% at 48 h post-infection when treated with 12.5 μg/mL NTZ, while at 25 μg/mL NTZ at 48 h post-infection 100% of infection was inhibited as compared to untreated cultures (Fig. 4B, Table 1). Taken together, these results indicate a strong effect of NTZ in inhibiting ZIKV and DENV-2 infection in Vero cells after viral entry, probably at the viral replication step. Reference: Braz J Infect Dis. 2020 Nov-Dec; 24(6): 505–516. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7526660/
In vivo activity: Motivated by remarkable inhibitory effect in 2D and 3D cell culture models, this study then further studied the in vivo therapeutic potential of NTZ (Nitazoxanide) using the orthotopic bladder tumor model. The model was guaranteed according to the bioluminescence signaling. Then mice were randomly divided into two groups and treated with vehicle or NTZ by intragastric administration once per day at a dose of 200 mg/kg according to a recent report. The response of orthotopic bladder tumors to NTZ treatment was monitored using IVIS Lumina system on day 0, 7, 14 and 21. As demonstrated in Fig. 11A,B, the bioluminescence signals in NTZ-treated group were significantly weaker compared with those in vehicle-treated group at each time point. Similarly, the weight of bladders (containing tumors inside) after NTZ treatment were much smaller than those treated with vehicle (Fig. 11C,D). The above results support the inhibition of orthotopic bladder tumor progression in vivo after NTZ administration. Reference: Biochem Pharmacol. 2021 May 4;190:114588. https://pubmed.ncbi.nlm.nih.gov/33957094/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 20.0 65.10

Preparing Stock Solutions

The following data is based on the product molecular weight 307.28 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. de Souza AAA, Torres LR, Lima LRP, de Paula V, Barros JJ, Bonecini-Almeida MDG, Waghabi MC, Gardel MA, Meuser-Batista M, de Souza EM. Inhibition of Brazilian ZIKV strain replication in primary human placental chorionic cells and cervical cells treated with nitazoxanide. Braz J Infect Dis. 2020 Nov-Dec;24(6):505-516. doi: 10.1016/j.bjid.2020.09.001. Epub 2020 Sep 30. PMID: 33010209; PMCID: PMC7526660. 2. Hargest V, Sharp B, Livingston B, Cortez V, Schultz-Cherry S. Astrovirus Replication Is Inhibited by Nitazoxanide In Vitro and In Vivo. J Virol. 2020 Feb 14;94(5):e01706-19. doi: 10.1128/JVI.01706-19. PMID: 31776285; PMCID: PMC7022343. 3. Abd El-Fadeal NM, Nafie MS, K El-Kherbetawy M, El-Mistekawy A, Mohammad HMF, Elbahaie AM, Hashish AA, Alomar SY, Aloyouni SY, El-Dosoky M, Morsy KM, Zaitone SA. Antitumor Activity of Nitazoxanide against Colon Cancers: Molecular Docking and Experimental Studies Based on Wnt/β-Catenin Signaling Inhibition. Int J Mol Sci. 2021 May 14;22(10):5213. doi: 10.3390/ijms22105213. PMID: 34069111. 4. Sun H, Ou T, Hu J, Yang Z, Lei Q, Li Y, Wang G, Li Y, Wu K, Wang S, Wu S. Nitazoxanide impairs mitophagy flux through ROS-mediated mitophagy initiation and lysosomal dysfunction in bladder cancer. Biochem Pharmacol. 2021 May 4;190:114588. doi: 10.1016/j.bcp.2021.114588. Epub ahead of print. PMID: 33957094.
In vitro protocol: 1. de Souza AAA, Torres LR, Lima LRP, de Paula V, Barros JJ, Bonecini-Almeida MDG, Waghabi MC, Gardel MA, Meuser-Batista M, de Souza EM. Inhibition of Brazilian ZIKV strain replication in primary human placental chorionic cells and cervical cells treated with nitazoxanide. Braz J Infect Dis. 2020 Nov-Dec;24(6):505-516. doi: 10.1016/j.bjid.2020.09.001. Epub 2020 Sep 30. PMID: 33010209; PMCID: PMC7526660. 2. Hargest V, Sharp B, Livingston B, Cortez V, Schultz-Cherry S. Astrovirus Replication Is Inhibited by Nitazoxanide In Vitro and In Vivo. J Virol. 2020 Feb 14;94(5):e01706-19. doi: 10.1128/JVI.01706-19. PMID: 31776285; PMCID: PMC7022343.
In vivo protocol: 1. Abd El-Fadeal NM, Nafie MS, K El-Kherbetawy M, El-Mistekawy A, Mohammad HMF, Elbahaie AM, Hashish AA, Alomar SY, Aloyouni SY, El-Dosoky M, Morsy KM, Zaitone SA. Antitumor Activity of Nitazoxanide against Colon Cancers: Molecular Docking and Experimental Studies Based on Wnt/β-Catenin Signaling Inhibition. Int J Mol Sci. 2021 May 14;22(10):5213. doi: 10.3390/ijms22105213. PMID: 34069111. 2. Sun H, Ou T, Hu J, Yang Z, Lei Q, Li Y, Wang G, Li Y, Wu K, Wang S, Wu S. Nitazoxanide impairs mitophagy flux through ROS-mediated mitophagy initiation and lysosomal dysfunction in bladder cancer. Biochem Pharmacol. 2021 May 4;190:114588. doi: 10.1016/j.bcp.2021.114588. Epub ahead of print. PMID: 33957094.

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1: Di Santo N, Ehrisman J. A functional perspective of nitazoxanide as a potential anticancer drug. Mutat Res. 2014 Oct;768:16-21. doi: 10.1016/j.mrfmmm.2014.05.005. Epub 2014 Jun 2. Review. PubMed PMID: 25847384.

2: Rossignol JF. Nitazoxanide: a first-in-class broad-spectrum antiviral agent. Antiviral Res. 2014 Oct;110:94-103. doi: 10.1016/j.antiviral.2014.07.014. Epub 2014 Aug 7. Review. PubMed PMID: 25108173.

3: Nikolova K, Gluud C, Grevstad B, Jakobsen JC. Nitazoxanide for chronic hepatitis C. Cochrane Database Syst Rev. 2014 Apr 6;4:CD009182. doi: 10.1002/14651858.CD009182.pub2. Review. PubMed PMID: 24706397.

4: Pérez-Molina JA, Díaz-Menéndez M, Gallego JI, Norman F, Monge-Maillo B, Ayala AP, López-Vélez R. Evaluation of nitazoxanide for the treatment of disseminated cystic echinococcosis: report of five cases and literature review. Am J Trop Med Hyg. 2011 Feb;84(2):351-6. doi: 10.4269/ajtmh.2011.10-0513. Review. PubMed PMID: 21292913; PubMed Central PMCID: PMC3029196.

5: Bojar H, Knap JP. [Nitazoxanide ("Alinia")--a promising antiparasitic drug]. Wiad Parazytol. 2010;56(1):11-8. Review. Polish. PubMed PMID: 20450003.

6: Sud B, Salvaggio M, Greenfield R, Bronze MS. Part XI. Trimethoprim-sulfamethoxazole, nitrofurantoin, chloramphenicol, metronidazole and tinidazole, rifaximin, and nitazoxanide. J Okla State Med Assoc. 2007 Jul;100(7):267-72. Review. Erratum in: J Okla State Med Assoc. 2007 Oct;100(10):405. Greenfield, Ronald A [corrected to Greenfield, Ronald]. PubMed PMID: 17896614.

7: Anderson VR, Curran MP. Nitazoxanide: a review of its use in the treatment of gastrointestinal infections. Drugs. 2007;67(13):1947-67. Review. PubMed PMID: 17722965.

8: Hemphill A, Mueller J, Esposito M. Nitazoxanide, a broad-spectrum thiazolide anti-infective agent for the treatment of gastrointestinal infections. Expert Opin Pharmacother. 2006 May;7(7):953-64. Review. PubMed PMID: 16634717.

9: Cohen SA. Use of nitazoxanide as a new therapeutic option for persistent diarrhea: a pediatric perspective. Curr Med Res Opin. 2005 Jul;21(7):999-1004. Review. PubMed PMID: 16004666.

10: White CA Jr. Nitazoxanide: a new broad spectrum antiparasitic agent. Expert Rev Anti Infect Ther. 2004 Feb;2(1):43-9. Review. PubMed PMID: 15482170.

11: Bailey JM, Erramouspe J. Nitazoxanide treatment for giardiasis and cryptosporidiosis in children. Ann Pharmacother. 2004 Apr;38(4):634-40. Epub 2004 Feb 27. Review. PubMed PMID: 14990779.