Nitazoxanide (CED0004278)

Record Information

Version

1.0

Creation Date

2016-05-22 04:18:55 UTC

Update Date

2026-08-18 22:11:04 UTC

Accession Number

CHEM017403

Identification

Common Name

Nitazoxanide

Class

Small Molecule

Description

Nitazoxanide is an organic compound with the formula C12H9N3O5S and an average molecular weight of 307.28 g/mol. Nitazoxanide belongs to the benzoic acids and derivatives, a subclass of benzene and substituted derivatives within the organic compounds. This compound is identified as an inhibitor and antagonist of the protein target pyruvate:ferredoxin oxidoreductase (por). It has been found in or released from seven recorded sources, including healthcare, pharmaceuticals, and veterinary products such as antiprotozoals and combinations of antibacterials. Other recorded sources include electrical and electronic equipment, specifically radio transmission systems, electric switches, and electrically stimulated smoking devices. Additionally, it is associated with household cleaning and consumer products, specifically cigar cigarettes, as well as food, food processing, and cookware, specifically the preparation of malt. The recorded exposure route for this substance is oral.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Alinia	Kegg
2-(Acetolyloxy)-N-(5-nitro-2-thiazolyl)benzamide	HMDB
2-Acetyloxy-N-[(5-nitro-2-thiazolyl)]benzamide	HMDB
Nitazoxanid	HMDB
Tizoxanide glucuronide	HMDB
Columbia brand 2 OF nitazoxanide	HMDB
Cryptaz	HMDB
Columbia brand 1 OF nitazoxanide	HMDB
Columbia brand 3 OF nitazoxanide	HMDB
Heliton	HMDB
NTZ	HMDB
Romark brand 1 OF nitazoxanide	HMDB
Colufase	HMDB
Daxon	HMDB
Romark brand 2 OF nitazoxanide	HMDB
Taenitaz	HMDB

Chemical Formula

C₁₂H₉N₃O₅S

Average Molecular Mass

307.282 g/mol

Monoisotopic Mass

307.026 g/mol

CAS Registry Number

55981-09-4

IUPAC Name

2-[(5-nitro-1,3-thiazol-2-yl)carbamoyl]phenyl acetate

Traditional Name

nitazoxanide

SMILES

CC(=O)OC1=CC=CC=C1C(=O)NC1=NC=C(S1)[N+]([O-])=O

InChI Identifier

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)

InChI Key

YQNQNVDNTFHQSW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acylsalicylamides. These are o-acylated derivatives of salicylamide.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Acylsalicylamides

Alternative Parents

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

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0076 g/L	ALOGPS
logP	2.14	ALOGPS
logP	2.12	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	8.3	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	114.11 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	73.89 m³·mol⁻¹	ChemAxon
Polarizability	27.54 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-006x-9820000000-92fb5445f11125065e46	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-01b9-1950000000-3d1aca26d9cbdaaab410	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-01b9-1950000000-3d1aca26d9cbdaaab410	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-0900000000-1e121f0a39d98b11856b	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0229000000-53676b9ef27d67cc1750	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0009000000-2008214409594d8a4aa4	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-1069000000-3e719ea5b05adffe4b69	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-002e-9210000000-c412f82070045302bd47	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-2109000000-985c0c92983f75acb4b0	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-9212000000-ebc430c35ab9200dcd18	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-9010000000-0ec40f1534d5fe909654	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01b9-0960000000-97c646f778e77a560b20	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0900000000-d727decb3e04530d2177	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-1900000000-dc0087192f244a933bea	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0009000000-880114e27c1b22207ace	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-2009000000-db39e69949f5cad9dc20	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-052f-9111000000-1bb86956f101434bfa18	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
8677.0	Log mg/kg	[4900:15000]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
346	Combinations of antibacterials	Healthcare, pharmaceuticals & veterinary products	Not Available
385	Antiprotozoals	Healthcare, pharmaceuticals & veterinary products	Not Available
517	Electric Switches	Electrical & Electronic Equipment	Not Available
518	Electrically Stimulated Smoking Devices	Electrical & Electronic Equipment	Not Available
530	Radio Transmission Systems	Electrical & Electronic Equipment	Not Available
547	Preparation Of Malt	Food, food processing & cookware	Not Available
556	Cigar Cigarettes	Household cleaning & consumer products	Not Available
578	Making Cigars	Industrial manufacturing & chemical processing	Not Available
581	Paper Making Machines	Industrial manufacturing & chemical processing	Not Available
584	Buoys	Marine, shipping & aquaculture	Not Available
590	Lifeboat Equipment	Marine, shipping & aquaculture	Not Available
592	Marine Propulsion Or Steering	Marine, shipping & aquaculture	Not Available
598	Fertiliser Distributors	Agriculture & land management	Not Available
601	Lawn Mowers	Agriculture & land management	Not Available
630	Toys	Recreation & sports surfaces	Not Available
650	Purses Luggage Hand Bags	Textiles, leather & furnishings	Not Available
652	Ropes	Textiles, leather & furnishings	Not Available
653	Sewing	Textiles, leather & furnishings	Not Available

Pathways

1 pathway

Nitazoxanide Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Epidermal growth factor receptor	P00533	Humans	Predicted (SEA)	243.123
Click to view 3D structure	Protein deacetylase HDAC6	Q9UBN7	Humans	Predicted (SEA)	84.2329
Click to view 3D structure	Cysteine protease ATG4B	Q9Y4P1	Humans	Predicted (SEA)	1.40129
Click to view 3D structure	Signal transducer and activator of transcription 3	P40763	Humans	Predicted (SEA)	2.41333
Click to view 3D structure	Serine/threonine-protein kinase pim-1	P11309	Humans	Predicted (SEA)	176.562
Click to view 3D structure	Replicase polyprotein 1ab	P0DTD1	SARS-CoV-2	Predicted (SEA)	43.4399
Click to view 3D structure	LIM domain kinase 1	P53667	Humans	Predicted (SEA)	114.283
Click to view 3D structure	Cyclin-dependent kinase 5	Q00535	Humans	Predicted (SEA)	157.489
Click to view 3D structure	Casein kinase I isoform delta	P48730	Humans	Predicted (SEA)	131.098
Click to view 3D structure	Serine/threonine-protein kinase PAK 4	O96013	Humans	Predicted (SEA)	165.819
Click to view 3D structure	Glycogen synthase kinase-3 beta	P49841	Humans	Predicted (SEA)	262.741
Click to view 3D structure	cAMP-dependent protein kinase catalytic subunit alpha	P17612	Humans	Predicted (SEA)	160.914
Click to view 3D structure	Dual specificity tyrosine-phosphorylation-regulated kinase 1A	Q13627	Humans	Predicted (SEA)	191.976
Click to view 3D structure	Ribosomal protein S6 kinase alpha-3	P51812	Humans	Predicted (SEA)	163.483
Click to view 3D structure	Glycogen synthase kinase-3 alpha	P49840	Humans	Predicted (SEA)	165.819
Click to view 3D structure	Rho-associated protein kinase 2	O75116	Humans	Predicted (SEA)	186.994
Click to view 3D structure	Serine/threonine-protein kinase Chk1	O14757	Humans	Predicted (SEA)	183.257
Click to view 3D structure	Cyclin-dependent kinase 2	P24941	Humans	Predicted (SEA)	227.242
Click to view 3D structure	Insulin receptor	P06213	Humans	Predicted (SEA)	196.959
Click to view 3D structure	Rho-associated protein kinase 1	Q13464	Humans	Predicted (SEA)	175.472
Click to view 3D structure	Protein kinase C delta type	Q05655	Humans	Predicted (SEA)	135.302
Click to view 3D structure	RAC-alpha serine/threonine-protein kinase	P31749	Humans	Predicted (SEA)	174.927
Click to view 3D structure	Serine/threonine-protein kinase D2	Q9BZL6	Humans	Predicted (SEA)	131.332
Click to view 3D structure	Mitogen-activated protein kinase 13	O15264	Humans	Predicted (SEA)	118.72
Click to view 3D structure	Aurora kinase B	Q96GD4	Humans	Predicted (SEA)	243.824