p-hydroxybenzoic acid (5-nitrofurfurylidene) hydrazide
nifuroxazide
CAS: 965-52-6
Molecular Formula: C12H9N3O5
p-hydroxybenzoic acid (5-nitrofurfurylidene) hydrazide - Names and Identifiers
| Name | nifuroxazide |
| Synonyms | Adral r.c.27-109 Nifurocazide NIFUROXAZIDE nifuroxazide 4-hydroxy-2-(5-nitrofurfurylidene)benzohydrazide (nitro-5'furfurylidene-2')hydroxy-4benzhydrazide (5-Nitro-2-furfurylidene)(4-hydroxybenzoyl)hydrazine p-hydroxybenzoic acid (5-nitrofurfurylidene) hydrazide p-Hydroxybenzoic acid (5-nitrofurfurylidene) hydrazide 4-hydroxy-N'-[(5-nitrofuran-2-yl)methylidene]benzohydrazide 4-hydroxy-benzoicaci((5-nitro-2-furanyl)methylene)hydrazide 4-Hydroxybenzoic Acid 2-[(5-Nitro-2-furanyl)methylene]hydrazide 4-hydroxy-N'-[(1E)-(5-nitrofuran-2-yl)methylidene]benzohydrazide |
| CAS | 965-52-6 |
| EINECS | 213-522-0 |
| InChI | InChI=1/C12H9N3O5/c16-9-3-1-8(2-4-9)12(17)14-13-7-10-5-6-11(20-10)15(18)19/h1-7,16H,(H,14,17)/b13-7+ |
p-hydroxybenzoic acid (5-nitrofurfurylidene) hydrazide - Physico-chemical Properties
| Molecular Formula | C12H9N3O5 |
| Molar Mass | 275.22 |
| Density | 1.3877 (rough estimate) |
| Melting Point | 281-283°C |
| Boling Point | 418.17°C (rough estimate) |
| Solubility | Practically insoluble in water, slightly soluble in ethanol (96 per cent), practically insoluble in methylene chloride. |
| Appearance | neat |
| Color | Yellow |
| BRN | 4264976 |
| pKa | 8.36±0.15(Predicted) |
| Storage Condition | Inert atmosphere,2-8°C |
| Refractive Index | 1.5700 (estimate) |
| In vitro study | Nifuroxazide is a nitrofuran compound inhibitor that inhibits the signal transduction of the STAT transcription factor. Nifuroxazide blocks constitutive phosphorylation of STAT3 by reducing Jak kinase autophosphorylation, thereby reducing myeloma cell viability without affecting normal peripheral blood mononuclear cells. Nifuroxazide was able to reduce the tyrosine phosphorylation of Jak and TYK2 without an effect on EGF receptor tyrosine kinase or Src kinase, indicating the relative specificity of Nifuroxazide for Jak2 and tyk2. Nifuroxazide did not inhibit Akt or MAPK phosphorylation. Nifuroxazide Inhibits Constitutive phosphorylation of STAT3 in MM cells by reducing Jak kinase autophosphorylation and leads to downregulation of target gene Mcl-1 of STAT3. Nifuroxazide caused a decrease in the viability of primary myeloma cells and myeloma cell lines containing STAT3 activation, but did not affect normal peripheral blood mononuclear cells. While bone marrow stromal cells provide a survival signal for myeloma cells, nifuroxazide blocks this survival advantage. Relative to the interaction of STAT3 with other cellular pathways, nifuroxazide in combination with histone deacetylase inhibitor depsipeptide or MEK inhibitor UO126 will show greater cytotoxicity. |
| In vivo study | Compared with the vehicle group, treatment with Nifuroxazide could inhibit tumor growth and tumor weight in a dose-dependent manner, with the inhibition rate of tumor volumes being 43.0% and 62.1% at 25 mg/kg and 50 mg/kg, respectively. It is also shown that Nifuroxazide significantly inhibits the proliferation of nuclear Ki-67-positive cells and induces apoptosis cells of cleaved caspase-3-positive cells. Besides, it is found that treatment with Nifuroxazide could inhibit the expression of MMP-2, MMP-9 and p-Stat3 in A375 tumor tissues. What’s more, Nifuroxazide inhibits the infiltration of MDSCs into the lung, which might be associated with suppression of distant colonization of tumor cells in B16-F10 melanoma metastasis model. |
p-hydroxybenzoic acid (5-nitrofurfurylidene) hydrazide - Risk and Safety
| WGK Germany | 3 |
| RTECS | DH2528300 |
| Toxicity | LD50 intraperitoneal in mouse: 1gm/kg |
p-hydroxybenzoic acid (5-nitrofurfurylidene) hydrazide - Reference Information
| biological activity | Nifuroxazide is a cell-permeable, orally effective nitrofuran antidiarrheal, effectively inhibits the activation of STAT1/3/5 transcriptional activity in cells with IC50 of 3 μm. |
| Target | Value |
| Use | prevention and treatment of Escherichia coli, salmonella, Pasteurella (including reectococcus), Aerobacter, Proteus, intestinal or urinary system diseases caused by necrosis bacteria and Staphylococcus. Can effectively prevent diarrhea, promote animal feed |
Last Update：2024-04-10 22:29:15
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View History
p-hydroxybenzoic acid (5-nitrofurfurylidene) hydrazide
489451-08-3
2H-1,2,4-Benzothiadiazine, 3-(4-piperidinyl)-, 1,1-dioxide
Pentanoic acid, 4-oxo-3-[[(2S)-1-oxo-2-[[(phenylMethoxy)carbonyl]aMino]propyl]aMino]-5-(2,3,5,6-tetrafluorophenoxy)-, 1,1-diMethylethyl ester, (3S)-
4-Piperidinecarboxylic acid, 1-(4,4,4-trifluoro-3-hydroxybutyl)-, ethyl ester
DL-2-AMINO-4-(4-METHYLPHENYL)-4-OXOBUTANOIC ACID HCL
Athinazone Hydrochloride
16-Desoxycucurbitacin V
,4-Dichloro-6,7-dimethyl-7H-pyrrolo[2,3-d]pyrimidine
4H-1-Benzopyran-4-one, 2,3-dihydro-5-hydroxy-7-methoxy-2-methyl-6-(3-methyl-2-buten-1-yl)-
489451-08-3
2H-1,2,4-Benzothiadiazine, 3-(4-piperidinyl)-, 1,1-dioxide
Pentanoic acid, 4-oxo-3-[[(2S)-1-oxo-2-[[(phenylMethoxy)carbonyl]aMino]propyl]aMino]-5-(2,3,5,6-tetrafluorophenoxy)-, 1,1-diMethylethyl ester, (3S)-
4-Piperidinecarboxylic acid, 1-(4,4,4-trifluoro-3-hydroxybutyl)-, ethyl ester
DL-2-AMINO-4-(4-METHYLPHENYL)-4-OXOBUTANOIC ACID HCL
Athinazone Hydrochloride
16-Desoxycucurbitacin V
,4-Dichloro-6,7-dimethyl-7H-pyrrolo[2,3-d]pyrimidine
4H-1-Benzopyran-4-one, 2,3-dihydro-5-hydroxy-7-methoxy-2-methyl-6-(3-methyl-2-buten-1-yl)-