ContaminantDB: Nitazoxanide

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 04:18:55 UTC

Update Date

2016-11-09 01:15:35 UTC

Accession Number

CHEM017403

Identification

Common Name

Nitazoxanide

Class

Small Molecule

Description

Nitazoxanide belongs to the class of drugs known as _thiazolides_. Nitazoxanide (NTZ) is a broad-spectrum anti-infective drug that markedly modulates the survival, growth, and proliferation of a range of extracellular and intracellular protozoa, helminths, anaerobic and microaerophilic bacteria, in addition to viruses. This drug is effective in the treatment of gastrointestinal infections including Cryptosporidium parvum or Giardia lamblia in healthy subjects. It is generally well tolerated. Nitazoxanide is a first-line, standard treatment for illness caused by C. parvum or G. lamblia infection in healthy (not immunosuppressed) adults and children and may also be considered in the treatment of illnesses caused by other protozoa or helminths [A31976]. Recently, this drug has been studied as a broad-spectrum antiviral agent due to its ability to inhibit the replication of several RNA and DNA viruses [A31977].

Contaminant Sources

HMDB Contaminants - Urine
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

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

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

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	1	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	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9820000000-92fb5445f11125065e46	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-01b9-1950000000-3d1aca26d9cbdaaab410	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-01b9-1950000000-3d1aca26d9cbdaaab410	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-00di-0900000000-1e121f0a39d98b11856b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0a4i-0229000000-53676b9ef27d67cc1750	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0009000000-2008214409594d8a4aa4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-1069000000-3e719ea5b05adffe4b69	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002e-9210000000-c412f82070045302bd47	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-2109000000-985c0c92983f75acb4b0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9212000000-ebc430c35ab9200dcd18	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9010000000-0ec40f1534d5fe909654	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01b9-0960000000-97c646f778e77a560b20	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0900000000-d727decb3e04530d2177	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-1900000000-dc0087192f244a933bea	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0009000000-880114e27c1b22207ace	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-2009000000-db39e69949f5cad9dc20	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9111000000-1bb86956f101434bfa18	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00507

HMDB ID

HMDB0014649

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Authors unspecified: Parasitic infections. Am J Transplant. 2004 Nov;4 Suppl 10:142-55.

Nitazoxanide (CHEM017403)

Structure for CHEM017403: Nitazoxanide