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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2017-12-07 02:46:38 UTC
HMDB IDHMDB0014649
Secondary Accession Numbers
  • HMDB14649
Metabolite Identification
Common NameNitazoxanide
DescriptionNitazoxanide, also known by the brand name Alinia, is a synthetic nitrothiazolyl-salicylamide derivative and an anti-protozoal agent. It is approved for treatment of infectious diarrhea caused by Cryptosporidium parvum and Giardia lamblia in patients 1 year of age and older. Following oral administration it is rapidly hydrolyzed to its active metabolite, tizoxanide, which is 99% protein bound. Peak concentrations are observed 1-4 hours after administration. It is excreted in the urine, bile and feces. Untoward effects include abdominal pain, vomiting and diarrhea. [Wikipedia]
Structure
Thumb
Synonyms
ValueSource
AliniaKegg
2-(Acetolyloxy)-N-(5-nitro-2-thiazolyl)benzamideHMDB
2-Acetyloxy-N-[(5-nitro-2-thiazolyl)]benzamideHMDB
NitazoxanidHMDB
Tizoxanide glucuronideHMDB
Columbia brand 2 OF nitazoxanideMeSH
CryptazMeSH
Columbia brand 1 OF nitazoxanideMeSH
Columbia brand 3 OF nitazoxanideMeSH
HelitonMeSH
NTZMeSH
Romark brand 1 OF nitazoxanideMeSH
ColufaseMeSH
DaxonMeSH
Romark brand 2 OF nitazoxanideMeSH
TaenitazMeSH
Chemical FormulaC12H9N3O5S
Average Molecular Weight307.282
Monoisotopic Molecular Weight307.026291103
IUPAC Name2-[(5-nitro-1,3-thiazol-2-yl)carbamoyl]phenyl acetate
Traditional Namenitazoxanide
CAS Registry Number55981-09-4
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 KeyYQNQNVDNTFHQSW-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as acylsalicylamides. These are o-acylated derivatives of salicylamide.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentAcylsalicylamides
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 FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Role

Industrial application:

  Pharmaceutical industry:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point202 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0076 g/LNot Available
LogP1.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0076 g/LALOGPS
logP2.14ALOGPS
logP2.12ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)8.3ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area114.11 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity73.89 m³·mol⁻¹ChemAxon
Polarizability27.54 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9820000000-92fb5445f11125065e46View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-01b9-1950000000-3d1aca26d9cbdaaab410View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-01b9-1950000000-3d1aca26d9cbdaaab410View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0009000000-2008214409594d8a4aa4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1069000000-3e719ea5b05adffe4b69View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002e-9210000000-c412f82070045302bd47View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-2109000000-985c0c92983f75acb4b0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9212000000-ebc430c35ab9200dcd18View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9010000000-0ec40f1534d5fe909654View in MoNA
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00507 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00507 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00507
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID38037
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNitazoxanide
METLIN IDNot Available
PubChem Compound41684
PDB IDNTI
ChEBI ID438934
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Authors unspecified: Parasitic infections. Am J Transplant. 2004 Nov;4 Suppl 10:142-55. [PubMed:15504227 ]