Nitazoxanide

Names

[ Name ]:
Nitazoxanide

[Synonym ]:
Cryptaz
Salicylamide, N-(5-nitro-2-thiazolyl)- acetate (ester)
Heliton
Benzamide, 2-(acetyloxy)-N-(5-nitro-2-thiazolyl)-
Alinia
o-(N-(5-Nitrothiazol-2-yl)carbamoyl)phenyl acetate
Nitazoxanida
[14C]-Nitazoxanide
Salicylamide, N-(5-nitro-2-thiazolyl)-, acetate (ester)
EINECS 259-931-8
Colufase
2-(2-Acetoxy)benzamido-5-nitrothiazole
2-[(5-Nitro-1,3-thiazol-2-yl)carbamoyl]phenyl acetate
Nitazoxanide
Nitazoxanidum
Daxon
Nitazoxamide
T5N CSJ BMVR BOV1& DNW
2-(Acetyloxy)-N-(5-nitro-2-thiazolyl)benzamide
o-[N-(5-nitrothiazol-2-yl)carbamoyl]phenyl acetate
MFCD00416599

Biological Activity

[Description]:

Nitazoxanide is a synthetic nitrothiazolyl-salicylamide derivative and an antiprotozoal agent. (IC50 for canine influenza virus ranges from 0.17 to 0.21 μM).Target: OthersNitazoxanide is a synthetic nitrothiazolyl-salicylamide derivative and an antiprotozoal agent. In vitro studies demonstrated much broader activity. Dr. Rossignol co-founded Romark Laboratories, with the goal of bringing nitazoxanide to market as an anti-parasitic drug. Initial studies in the USA were conducted in collaboration with Unimed Pharmaceuticals, Inc. (Marietta, GA) and focused on development of the drug for treatment of cryptosporidiosis in AIDS.The anti-protozoal activity of nitazoxanide is believed to be due to interference with the pyruvate:ferredoxin oxidoreductase (PFOR) enzyme dependent electron transfer reaction which is essential to anaerobic energy metabolism. It has also been shown to have activity against influenza A virus in vitro. The mechanism appears to be by selectively blocking the maturation of the viral hemagglutinin at a stage preceding resistance to endoglycosidase H digestion. This impairs hemagglutinin intracellular trafficking and insertion of the protein into the host plasma membrane.

[Related Catalog]:

Signaling Pathways >> Autophagy >> Autophagy

Signaling Pathways >> Anti-infection >> Influenza Virus

Research Areas >> Infection

[References]

[1]. Rossignol JF, et al. Thiazolides, a new class of anti-influenza molecules targeting viral hemagglutinin at the post-translational level. J Biol Chem. 2009 Oct 23;284(43):29798-808.

[2]. Somvanshi VS, et al. Nitazoxanide: Nematicidal mode of action and drug combination studies. Mol Biochem Parasitol. 2014 Jan 8;193(1):1-8.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Melting Point ]:
202ºC

[ Molecular Formula ]:
C₁₂H₉N₃O₅S

[ Molecular Weight ]:
307.282

[ Exact Mass ]:
307.026276

[ PSA ]:
142.35000

[ LogP ]:
1.79

[ Index of Refraction ]:
1.673

[ Storage condition ]:
-20°C Freezer

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: VN7830000

CHEMICAL NAME :: Salicylamide, N-(5-nitro-2-thiazolyl)-, acetate (ester)

CAS REGISTRY NUMBER :: 55981-09-4

LAST UPDATED :: 199612

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C12-H9-N3-O5-S

MOLECULAR WEIGHT :: 307.30

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >10 gm/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - muscle weakness

REFERENCE :: JJATDK JAT, Journal of Applied Toxicology. (John Wiley & Sons Ltd., Baffins Lane, Chichester, W. Sussex PO19 1UD, UK) V.1- 1981- Volume(issue)/page/year: 5,49,1985

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1350 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - muscle weakness

REFERENCE :: JJATDK JAT, Journal of Applied Toxicology. (John Wiley & Sons Ltd., Baffins Lane, Chichester, W. Sussex PO19 1UD, UK) V.1- 1981- Volume(issue)/page/year: 5,49,1985

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: >10 gm/kg

TOXIC EFFECTS :: Autonomic Nervous System - smooth muscle relaxant (mechanism undefined, spasmolytic)

REFERENCE :: JJATDK JAT, Journal of Applied Toxicology. (John Wiley & Sons Ltd., Baffins Lane, Chichester, W. Sussex PO19 1UD, UK) V.1- 1981- Volume(issue)/page/year: 5,49,1985

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: >10 gm/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - ataxia

REFERENCE :: JJATDK JAT, Journal of Applied Toxicology. (John Wiley & Sons Ltd., Baffins Lane, Chichester, W. Sussex PO19 1UD, UK) V.1- 1981- Volume(issue)/page/year: 5,49,1985 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 44100 mg/kg/14W-C

TOXIC EFFECTS :: Gastrointestinal - changes in structure or function of salivary glands Liver - changes in liver weight Endocrine - changes in spleen weight

REFERENCE :: JJATDK JAT, Journal of Applied Toxicology. (John Wiley & Sons Ltd., Baffins Lane, Chichester, W. Sussex PO19 1UD, UK) V.1- 1981- Volume(issue)/page/year: 5,49,1985

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
22-36/37/38

[ Safety Phrases ]:
26-36

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
2942000000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2934100090

[ Summary ]:
2934100090 other compounds containing an unfused thiazole ring (whether or not hydrogenated) in the structure VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:20.0%

Articles

Validated stability indicating RP-HPLC for quantitation of nitazoxanide in presence of its alkaline degradation products and their characterization by HPLC-tandem mass spectrometry.

J. Chromatogr. Sci. 52(9) , 1071-81, (2014)

A simple and sensitive stability indicating HPLC method was developed and validated for quantitative determination of Nitazoxanide (NTZ), a new antiprotozoal drug, in presence of degradation products ...

Metabolism of nitazoxanide in rats, pigs, and chickens: Application of liquid chromatography coupled to hybrid linear ion trap/Orbitrap mass spectrometer.

J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 1000 , 147-54, (2015)

Nitazoxanide (NTZ) is a nitrothiazole benzamide compound with a broad activity spectrum against parasites, Gram-positive and Gram-negative anaerobic bacteria, and viruses. In this study, hybrid linear...

Tongkat Ali (Eurycoma longifolia): a possible therapeutic candidate against Blastocystis sp.

Parasit. Vectors 8 , 332, (2015)

In the local Malaysian context, herbal plants such as Eurycoma longifolia (Tongkat Ali), Orthosiphon stamineus (MisaiKucing), Ficus deltoidea (Mas Cotek), Zingiber officinale (Halia Bara) and Barringt...