Nitazoxanide - ≥98% , Pyruvate:ferredoxin oxidoreductase inhibitor, CAS No.55981-09-4, Pyruvate:ferredoxin oxidoreductase inhibitor

CAS: 55981-09-4 Cat. No.: N159057 Peso molecular: 307.28 Número EC: 259-931-8

GRADE & PURITY ≥98%

Synonyms

Nitazoxamide | Nitazoxanida [INN-Spanish] | Nitazoxanidum | Nitazoxanidum [INN-Latin] | Alinia | Nitazoxanida | 2-[(5-nitro-1,3-thiazol-2-yl)carbamoyl]phenyl acetate | 2-((5-nitrothiazol-2-yl)carbamoyl)phenyl acetate | Daxon

Storage

Store at 2-8°C

Shipped In

Wet ice

Descripción general

Nitazoxanide, an anthelmintic agent, exhibits a broad spectrum of activities against a wide variety of helminths, protozoa, and enteric bacteria infecting animals and humans. Nitazoxanide inhibits Giardia lamblia trophozoite proliferation in axenic culture with an IC50 of 2.4 μM. Nitazoxanide can be used for the research of parasitic gastroenteritis. Nitazoxanide shows anti-Japanese encephalitis virus (JEV) activity in a mouse model.

Specifications

Sinónimos

Nitazoxamide | Nitazoxanida [INN-Spanish] | Nitazoxanidum | Nitazoxanidum [INN-Latin] | Alinia | Nitazoxanida | 2-[(5-nitro-1, 3-thiazol-2-yl)carbamoyl]phenyl acetate | 2-((5-nitrothiazol-2-yl)carbamoyl)phenyl acetate | Daxon

Especificaciones y pureza

≥98%

Mecanismos bioquímicos y fisiológicos

Nitazoxanide (NTZ) promotes autophagy by acting on kinase based signaling pathways and acts on mammalian target of rapamycin complex 1 (mTORC1) in Mycobacteria. It has anti-viral property and effectively halts entry and release of chikungunya virus in in

Condiciones de almacenamiento de almacenamiento

Store at 2-8°C

Enviado en

Wet ice

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Tipo de acción

INHIBITOR

Mecanismo de acción

Pyruvate:ferredoxin oxidoreductase inhibitor

Nota

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Pureza

≥98%

Propiedades del producto

• ALogP: 2

Nombres e identificadores

• Pubchem Sid: 504753611
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504753611
• Sonrisas canónicas: CC(=O)OC1=CC=CC=C1C(=O)NC2=NC=C(S2)[N+](=O)[O-]
• IUPAC Name: [2-[(5-nitro-1,3-thiazol-2-yl)carbamoyl]phenyl] acetate
• InChIKey: YQNQNVDNTFHQSW-UHFFFAOYSA-N
• 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)
• Isómeros SMILES: CC(=O)OC1=CC=CC=C1C(=O)NC2=NC=C(S2)[N+](=O)[O-]
• WGK Alemania: 3
• Peso molecular: 307.28
• Reaxy-Rn: 1225475
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1225475&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Clase Benzene and substituted derivatives
      • Subclass Benzoic acids and derivatives
        • Level5 Hydroxybenzoic acid derivatives
          • Level6 Salicylic acid and derivatives
            • Level7 Acylsalicylic acids and derivatives
              • Level8 Acylsalicylamides

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Clase: Benzene and substituted derivatives
• Subclass: Benzoic acids and derivatives
• Intermediate Tree Nodes: Hydroxybenzoic acid derivatives - Salicylic acid and derivatives - Acylsalicylic acids and derivatives
• Direct Parent: Acylsalicylamides
• Alternative Parents: Phenol esters Benzamides Phenoxy compounds Benzoyl derivatives Nitroaromatic compounds Nitrothiazoles 2,5-disubstituted thiazoles Heteroaromatic compounds Secondary carboxylic acid amides Carboxylic acid esters Monocarboxylic acids and derivatives Azacyclic compounds Propargyl-type 1,3-dipolar organic compounds Organic oxoazanium compounds Organic zwitterions Hydrocarbon derivatives Organonitrogen compounds Carbonyl compounds Organopnictogen compounds Organic oxides
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Acylsalicylamide - Phenol ester - Benzamide - Phenoxy compound - Nitroaromatic compound - Benzoyl - Nitrothiazole - 2,5-disubstituted 1,3-thiazole - Azole - Thiazole - Heteroaromatic compound - Organic nitro compound - Secondary carboxylic acid amide - Carboxamide group - Carboxylic acid ester - C-nitro compound - Organoheterocyclic compound - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Allyl-type 1,3-dipolar organic compound - Azacycle - Carboxylic acid derivative - Organic oxoazanium - Monocarboxylic acid or derivatives - Organic nitrogen compound - Organic oxide - Organonitrogen compound - Organooxygen compound - Hydrocarbon derivative - Carbonyl group - Organopnictogen compound - Organic oxygen compound - Organic zwitterion - Aromatic heteromonocyclic compound
• Descripción: This compound belongs to the class of organic compounds known as acylsalicylamides. These are o-acylated derivatives of salicylamide.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Objetivos asociados (humanos)

F2 Tclin Thrombin (11687 Activities)

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ESR1 Tclin Estrogen receptor alpha (17718 Activities)

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NR3C1 Tclin Glucocorticoid receptor (14987 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PGR Tclin Progesterone receptor (8562 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRB2 Tclin Beta-2 adrenergic receptor (11824 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRB1 Tclin Beta-1 adrenergic receptor (6630 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)

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AR Tclin Androgen Receptor (11781 Activities)

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CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

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VDR Tclin Vitamin D receptor (26531 Activities)

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DRD2 Tclin Dopamine D2 receptor (23596 Activities)

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GABRA1 Tclin GABA receptor alpha-1 subunit (399 Activities)

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TSHR Tclin Thyroid stimulating hormone receptor (29986 Activities)

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MAOA Tclin Monoamine oxidase A (11911 Activities)

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CNR1 Tclin Cannabinoid CB1 receptor (20913 Activities)

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DRD1 Tclin Dopamine D1 receptor (9720 Activities)

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ACHE Tclin Acetylcholinesterase (18204 Activities)

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PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

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SLC6A2 Tclin Norepinephrine transporter (10102 Activities)

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HRH2 Tclin Histamine H2 receptor (5428 Activities)

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HTR2A Tclin Serotonin 2a (5-HT2a) receptor (14758 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR2C Tclin Serotonin 2c (5-HT2c) receptor (11471 Activities)

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AVPR2 Tclin Vasopressin V2 receptor (2912 Activities)

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ADORA1 Tclin Adenosine A1 receptor (17603 Activities)

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AGTR1 Tclin Type-1 angiotensin II receptor (5176 Activities)

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SLC6A4 Tclin Serotonin transporter (12625 Activities)

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ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)

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PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)

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HRH1 Tclin Histamine H1 receptor (7573 Activities)

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OPRM1 Tclin Mu opioid receptor (19785 Activities)

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DRD3 Tclin Dopamine D3 receptor (14368 Activities)

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PPARG Tclin Peroxisome proliferator-activated receptor gamma (15191 Activities)

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AVPR1A Tclin Vasopressin V1a receptor (5412 Activities)

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OPRD1 Tclin Delta opioid receptor (15096 Activities)

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OPRK1 Tclin Kappa opioid receptor (16155 Activities)

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HTR3A Tclin Serotonin 3a (5-HT3a) receptor (3366 Activities)

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SLC6A3 Tclin Dopamine transporter (10535 Activities)

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GRIN1 Tclin Glutamate (NMDA) receptor subunit zeta 1 (122 Activities)

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KCNH2 Tclin HERG (29587 Activities)

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CACNA1C Tclin Voltage-gated L-type calcium channel alpha-1C subunit (766 Activities)

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PDE3A Tclin Phosphodiesterase 3A (3309 Activities)

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SLC29A1 Tclin Equilibrative nucleoside transporter 1 (1711 Activities)

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ADRA2B Tclin Alpha-2b adrenergic receptor (4412 Activities)

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CHRM3 Tclin Muscarinic acetylcholine receptor M3 (7750 Activities)

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HTR2B Tclin Serotonin 2b (5-HT2b) receptor (10323 Activities)

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AKR1B1 Tclin Aldose reductase (1404 Activities)

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TBXA2R Tclin Thromboxane A2 receptor (5717 Activities)

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EDNRA Tclin Endothelin receptor ET-A (5008 Activities)

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Objetivos asociados (no humanos)

Npy1r Neuropeptide Y receptor type 1 (8 Activities)

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Cckar Cholecystokinin A receptor (90 Activities)

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Pde4d Phosphodiesterase 4D (4 Activities)

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Ppard Peroxisome proliferator-activated receptor delta (358 Activities)

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Mapk1 MAP kinase ERK2 (650 Activities)

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Hdac6 Histone deacetylase 6 (222 Activities)

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Pkm Pyruvate kinase isozymes M1/M2 (66 Activities)

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Schaalia meyeri (78 Activities)

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Fusobacterium sp. (55 Activities)

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Collinsella aerofaciens (60 Activities)

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Eggerthella lenta (139 Activities)

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Campylobacter jejuni (634 Activities)

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Helicobacter pylori (3113 Activities)

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Pseudomonas aeruginosa (123386 Activities)

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Klebsiella pneumoniae (43867 Activities)

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Bacteroides fragilis (1445 Activities)

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Bacteroides thetaiotaomicron (562 Activities)

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Parabacteroides distasonis (282 Activities)

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Fusobacterium mortiferum (179 Activities)

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Fusobacterium varium (184 Activities)

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Fusobacterium necrophorum (183 Activities)

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Peptoniphilus asaccharolyticus (368 Activities)

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Peptostreptococcus anaerobius (347 Activities)

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Staphylococcus aureus (210822 Activities)

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Staphylococcus epidermidis (22802 Activities)

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Staphylococcus haemolyticus (1695 Activities)

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Staphylococcus hominis (482 Activities)

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Acinetobacter baumannii (41033 Activities)

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Escherichia coli (133304 Activities)

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Bacteroides uniformis (255 Activities)

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Hoylesella loescheii (67 Activities)

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Fusobacterium nucleatum (386 Activities)

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Finegoldia magna (323 Activities)

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Clostridium acetobutylicum (18 Activities)

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Paraclostridium bifermentans (60 Activities)

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Clostridium butyricum (54 Activities)

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Clostridioides difficile (2968 Activities)

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Clostridium perfringens (1165 Activities)

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Clostridium septicum (114 Activities)

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Clostridium sporogenes (139 Activities)

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Clostridium cadaveris (57 Activities)

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Thomasclavelia ramosa (78 Activities)

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Lactiplantibacillus plantarum (102 Activities)

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Mycobacterium tuberculosis (203094 Activities)

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Paeniclostridium sordellii (66 Activities)

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Clostridium tertium (174 Activities)

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Limosilactobacillus fermentum (53 Activities)

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Actinomyces viscosus (309 Activities)

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Eubacterium limosum (41 Activities)

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Cutibacterium acnes (887 Activities)

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Mecanismos de acción

Propiedades químicas y físicas

• Solubilidad: DMSO : ≥ 100 mg/mL (325.44 mM)
• Sensibilidad: heat sensitive
• Punto de fusión (°C): 198.0 - 202.0 °C
• Peso molecular: 307.280 g/mol
• XLogP3: 2.000
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 307.026 Da
• Monoisotopic Mass: 307.026 Da
• Topological Polar Surface Area: 142.000 Ų
• Heavy Atom Count: 21
• Formal Charge: 0
• Complexity: 428.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Referencias

1. Zhanding Cui, Dengliang Li, Yinli Xie, Kai Wang, Ying Zhang, Guohua Li, Qian Zhang, Xiaoxueying Chen, Yue Teng, Shihui Zhao, Jiang Shao, Fan Xingmeng, Yanli Zhao, Dongju Du, Yanbing Guo, Hailong Huang, Hao Dong, Guixue Hu, Shuang Zhang, Yongkun Zhao.  (2020)  Nitazoxanide protects cats from feline calicivirus infection and acts synergistically with mizoribine in vitro.  ANTIVIRAL RESEARCH,      [PMID:32579897] [10.1016/j.antiviral.2020.104827]

2. Cui Zhanding, Liu Jinlong, Xie Chong, Wang Tao, Sun Pu, Wang Jinlong, Li Jiaoyang, Li Guoxiu, Qiu Jicheng, Zhang Ying, Li Dengliang, Sun Ying, Yin Juanbin, Li Kun, Zhao Zhixun, Yuan Hong, Bai Xingwen, Ma Xueqing, Li Pinghua, Fu Yuanfang, Bao Huifang, Li Dong, Zhang Qiang, Liu Zaixin, Cao Yimei, Zhang Jing, Lu Zengjun.  (2024)  High-throughput screening unveils nitazoxanide as a potent PRRSV inhibitor by targeting NMRAL1.  Nature Communications,  15  (1): (1-12).  [PMID:38844461] [10.1038/s41467-024-48807-y]

3. Xianzhe Wang, Yanyan Zhu, Huilin Liu, Xiangchuan Wang, Hongjie Zhang, Xiuping Chen.  (2024)  Nitazoxanide alleviates experimental pulmonary fibrosis by inhibiting the development of cellular senescence.  LIFE SCIENCES,      [PMID:39662775] [10.1016/j.lfs.2024.123302]