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Tizoxanide
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| Category | Human immunodeficiency Virus (HIV) |
| CAS | 173903-47-4 |
| Description | Tizoxanide is the active metabolite of nitazoxanide, an anti-infective that has been approved for the treatment of diarrhea caused by Giardia lamblia or Crytosporidium parvum. Tizoxanide is active against anaerobic bacteria, protozoan parasites, and viruses. It reduces the growth of the disease-causing parasites, L. mexicana and T. cruzi, in vitro (IC50s = 6.2 and 17.5 μM, respectively), inhibits influenza A replication (EC50s = 0.3-1 μM)3, and inhibits hepatitis B and hepatitis C virus replication (EC50s both = 0.15 μM). |
Product Information
| Synonyms | TIZ; NSC-697856; NSC697856; NSC697856; Tizoxanide; Desacetylnitazoxanide; Desacetyl-nitazoxanide. |
| IUPAC Name | 2-hydroxy-N-(5-nitro-1,3-thiazol-2-yl)benzamide |
| Molecular Weight | 265.25 |
| Molecular Formula | C10H7N3O4S |
| Canonical SMILES | C1=CC=C(C(=C1)C(=O)NC2=NC=C(S2)[N+](=O)[O-])O |
| InChI | InChI=1S/C10H7N3O4S/c14-7-4-2-1-3-6(7)9(15)12-10-11-5-8(18-10)13(16)17/h1-5,14H,(H,11,12,15) |
| InChIKey | FDTZUTSGGSRHQF-UHFFFAOYSA-N |
| Melting Point | >240 °C (dec) |
| Purity | >98% |
| Density | 1.6±0.1 g/cm3 |
| Solubility | 10 mM in DMSO |
| Appearance | White to Off-white Solid |
| Application | Anti-Infective Agents |
| Storage | - 20 °C |
| Complexity | 336 |
| Exact Mass | 265.01572689 |
| Index Of Refraction | 1.750 |
| In Vitro | Tizoxanide (TIZ) induces mild mitochondrial uncoupling and activate AMPK in hepatocytes Tizoxanide (TIZ) inhibits hepatitis C virus (HCV) replication in HCV replicon systems Cell Viability Assay Cell Line: HepG2 cells Concentration: 1-25 µmol/L Incubation Time: 24 Result: Induced mitochondrial uncoupling and AMPK activation not due to the non-specific cytotoxicity in HepG2 cells at concentrations less than 25 µmol/L Immunofluorescence Cell Line: HepG2 cells Concentration: 10 µmol/L Incubation Time: 24 Result: Promoted the nuclear translocation of TFEB by activating AMPK in HepG2 cells RT-PCR Cell Line: HepG2 cells Concentration: 1-25 µmol/L Incubation Time: 24 Result: Induced the increase transcription of SQSTM1/P62 in HepG2 cells Western Blot Analysis Cell Line: HepG2 cells Concentration: 1-25 µmol/L Incubation Time: 24 Result: Activated AMPK and increased phosphorylation of ACC in HepG2 cells Cell Cytotoxicity Assay Cell Line: RP7 cells, NTZ-11 and TIZ-9 cell lines Concentration: The initial drug concentration was 0.02 µM, followed by 0.05, 0.1, 0.5, and 1 µM, and subsequent weekly increases of 1 µM until a final concentration of 11 µM. |
| In Vivo | Tizoxanide (TIZ) induces mild mitochondrial uncoupling and activate AMPK in hepatocytes. Tizoxanide (TIZ) (10 mg/kg; i.v.) can pass the BBB and distribute to the brain tissue. Tizoxanide retains in brain is obviously longer than that in plasma. |
| PSA | 136.28000 |
| Target | Bacterial; HIV; Autophagy; Parasite; IKK; Influenza Virus |
| XLogP3-AA | 3.2 |
