Nitazoxanide

Base Information

• Chemical Name: Nitazoxanide
• CAS No.: 55981-09-4
• Molecular Formula: C12H9N3O5S
• Molecular Weight: 307.287
• Hs Code.: 2934100000
• European Community (EC) Number: 259-931-8
• NSC Number: 760057,697855
• UNII: SOA12P041N
• DSSTox Substance ID: DTXSID5033757
• Nikkaji Number: J126.294G
• Wikipedia: Nitazoxanide
• Wikidata: Q2943789
• NCI Thesaurus Code: C47637
• RXCUI: 31819
• Metabolomics Workbench ID: 42850
• ChEMBL ID: CHEMBL1401
• Mol file: 55981-09-4.mol

Synonyms:2-(Acetolyloxy)-N-(5-nitro-2-thiazolyl)benzamide;Alinia;Colufase;Cryptaz;Daxon;Heliton;nitazoxanide;NTZ;Taenitaz

Chemical Property of Nitazoxanide

Chemical Property:

• Appearance/Colour: Crystalline Solid
• Melting Point: 202 °C
• PKA: 6.18±0.50(Predicted)
• PSA: 142.35000
• Density: 1.532 g/cm³
• LogP: 2.82510
• Storage Temp.: -20°C Freezer
• Solubility.: Soluble in DMSO (>50 mg/ml)
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 307.02629157
• Heavy Atom Count: 21
• Complexity: 428

Purity/Quality:

99% ^*data from raw suppliers

Nitazoxanide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Anthelmintic Agents
• Canonical SMILES: CC(=O)OC1=CC=CC=C1C(=O)NC2=NC=C(S2)[N+](=O)[O-]
• Recent ClinicalTrials: Role of Nitazoxanide and Escitalopram in Patients With Rheumatoid Arthritis
• Recent EU Clinical Trials: A Phase III Randomized Double-Blind Placebo Controlled Trial to Evaluate the Efficacy and Safety of Nitazoxanide and Nitazoxanide plus Oseltamivir in the Treatment of Acute Uncomplicated Influenza
• Description: Nitazoxanide (NT Z) has been approved as an orphan drug for the treatment of diarrhea in children (age, 1–11 years) and is associated with giardiasis, but it also is approved for diarrhea caused by crytosporidiosis in patients with AIDS. Crytosporidiosis is a protozoal infection caused by Cryptosporidi um parvum. The condition is uncommon in healthy individuals but can be life-threatening in immunosuppressed patients and those with HIV infections.
• Uses: Nitazoxanide has been used: to test its anti-viral activity against chikungunya virusas an antiprotozoal agent to test its effect on cell viability in various cancer cell linesto test its effect on human cytomegalovirus (HCMV) infected human fibroblast HFF cells An anthelmintic (cestodes), antiprotozoal (cryptosporidium). Kills Mycobacterium tuberculosis. antihypertensive For the treatment of diarrhea in adults and children caused by the protozoa Giardia lamblia and for the treatment of diarrhea in children caused by the protozoa Cryptosporidium parvum.
• Therapeutic Function: Anthelmintic
• Clinical Use: It is indicated for the treatment of diarrhea caused by G. lamblia or C. parvum.

Technology Process of Nitazoxanide

There total 4 articles about Nitazoxanide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 71.0%

C13H10N2O5S → nitazoxanide (55981-09-4)

Guidance literature:

With nitronium tetrafluoborate; silver carbonate; In N,N-dimethyl acetamide; at 90 ℃; for 12h; regioselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.joc.5b02133

Reference yield:

2-amino-5-nitro-1,3-thiazole (121-66-4,176384-36-4,8023-00-5) + O-acetylsalicyloyl chloride (5538-51-2) → nitazoxanide (55981-09-4)

Guidance literature:

Reference yield:

→ nitazoxanide (55981-09-4)

Guidance literature:

entspr. Amin, Saeurehalogenid;

upstream raw materials:

2-amino-5-nitro-1,3-thiazole

O-acetylsalicyloyl chloride

aspirin

Downstream raw materials:

(2-hydroxybenzoyl)-N-(5-acetamidothiazol-2-yl)amine

C₁₄H₁₃N₃O₄S

C₄₂H₇₀O₃₅*C₁₂H₉N₃O₅S

RM₄₈₅₇

Refernces

• 1、 -. "Thiazole compound as well as preparation method and application thereof". Paragraph 0117-0119; 0121-0123. . Retrieved 2021/08/21.
• 2、 Cavier,Gayral,Guillaumel,et al.. "Research on nitro-derivatives of biological interest. XVI. Structure-activity relationships as protozoocidal, anthelmintic and molluscicidal agents in 2-benzamido 5-nitrothiazole series". . p. 539 - 543. Retrieved 2007/10/07.