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Record Information
Version3.6
Creation Date2012-09-06 15:16:50 UTC
Update Date2013-02-09 00:32:00 UTC
HMDB IDHMDB14649
Secondary Accession NumbersNone
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
  1. 2-(Acetolyloxy)-N-(5-nitro-2-thiazolyl)benzamide
  2. 2-Acetyloxy-N-[(5-nitro-2-thiazolyl)]benzamide
  3. Nitazoxanid
  4. Nitazoxanida [INN-Spanish]
  5. Nitazoxanidum [INN-Latin]
  6. Tizoxanide Glucuronide
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 salicylamides. These are carboxamide derivatives of salicylic acid. Salicylic acid is the ortho-hydroxylated derivative of benzoic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentSalicylamides
Alternative Parents
Substituents
  • N-arylamide
  • Salicylamide
  • Phenol ester
  • Benzamide
  • Nitrothiazole
  • Benzoyl
  • 2,5-disubstituted 1,3-thiazole
  • Heteroaromatic compound
  • Acetate salt
  • Thiazole
  • Azole
  • Organic nitro compound
  • Secondary carboxylic acid amide
  • Organic nitrite
  • C-nitro compound
  • Carboxylic acid ester
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic oxoazanium
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organic zwitterion
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Antiparasitic Agents
Application
  • Pharmaceutical
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point202 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility7.55e-03 g/LNot Available
LogP1.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0076 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity73.89 m3·mol-1ChemAxon
Polarizability27.54 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00507
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00507
  • Not Applicable
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
NuGOwiki LinkHMDB14649
Metagene LinkHMDB14649
METLIN IDNot Available
PubChem Compound41684
PDB IDNTI
ChEBI ID438934
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Parasitic infections. Am J Transplant. 2004 Nov;4 Suppl 10:142-55. [15504227 ]