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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:41 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
Data?1582753204
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 nitazoxanideHMDB
CryptazHMDB
Columbia brand 1 OF nitazoxanideHMDB
Columbia brand 3 OF nitazoxanideHMDB
HelitonHMDB
NTZHMDB
Romark brand 1 OF nitazoxanideHMDB
ColufaseHMDB
DaxonHMDB
Romark brand 2 OF nitazoxanideHMDB
TaenitazHMDB
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
Description 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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point202 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0076 g/LNot Available
LogP1.2Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+168.63531661259
DarkChem[M-H]-169.37531661259
DeepCCS[M+H]+155.47730932474
DeepCCS[M-H]-152.64130932474
DeepCCS[M-2H]-187.66230932474
DeepCCS[M+Na]+163.70630932474
AllCCS[M+H]+165.232859911
AllCCS[M+H-H2O]+161.932859911
AllCCS[M+NH4]+168.332859911
AllCCS[M+Na]+169.232859911
AllCCS[M-H]-164.532859911
AllCCS[M+Na-2H]-164.032859911
AllCCS[M+HCOO]-163.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
NitazoxanideCC(=O)OC1=CC=CC=C1C(=O)NC1=NC=C(S1)[N+]([O-])=O3721.8Standard polar33892256
NitazoxanideCC(=O)OC1=CC=CC=C1C(=O)NC1=NC=C(S1)[N+]([O-])=O2650.1Standard non polar33892256
NitazoxanideCC(=O)OC1=CC=CC=C1C(=O)NC1=NC=C(S1)[N+]([O-])=O2682.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Nitazoxanide,1TMS,isomer #1CC(=O)OC1=CC=CC=C1C(=O)N(C1=NC=C([N+](=O)[O-])S1)[Si](C)(C)C2497.6Semi standard non polar33892256
Nitazoxanide,1TMS,isomer #1CC(=O)OC1=CC=CC=C1C(=O)N(C1=NC=C([N+](=O)[O-])S1)[Si](C)(C)C2457.8Standard non polar33892256
Nitazoxanide,1TMS,isomer #1CC(=O)OC1=CC=CC=C1C(=O)N(C1=NC=C([N+](=O)[O-])S1)[Si](C)(C)C3563.8Standard polar33892256
Nitazoxanide,1TBDMS,isomer #1CC(=O)OC1=CC=CC=C1C(=O)N(C1=NC=C([N+](=O)[O-])S1)[Si](C)(C)C(C)(C)C2734.3Semi standard non polar33892256
Nitazoxanide,1TBDMS,isomer #1CC(=O)OC1=CC=CC=C1C(=O)N(C1=NC=C([N+](=O)[O-])S1)[Si](C)(C)C(C)(C)C2661.1Standard non polar33892256
Nitazoxanide,1TBDMS,isomer #1CC(=O)OC1=CC=CC=C1C(=O)N(C1=NC=C([N+](=O)[O-])S1)[Si](C)(C)C(C)(C)C3578.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Nitazoxanide GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9820000000-92fb5445f11125065e462017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nitazoxanide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nitazoxanide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Nitazoxanide LC-ESI-qTof , Positive-QTOFsplash10-01b9-1950000000-3d1aca26d9cbdaaab4102017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nitazoxanide , positive-QTOFsplash10-01b9-1950000000-3d1aca26d9cbdaaab4102017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nitazoxanide 35V, Positive-QTOFsplash10-00di-0900000000-1e121f0a39d98b11856b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nitazoxanide 35V, Negative-QTOFsplash10-0a4i-0229000000-53676b9ef27d67cc17502021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nitazoxanide 10V, Positive-QTOFsplash10-0a4i-0009000000-2008214409594d8a4aa42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nitazoxanide 20V, Positive-QTOFsplash10-0a4i-1069000000-3e719ea5b05adffe4b692016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nitazoxanide 40V, Positive-QTOFsplash10-002e-9210000000-c412f82070045302bd472016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nitazoxanide 10V, Negative-QTOFsplash10-0a4i-2109000000-985c0c92983f75acb4b02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nitazoxanide 20V, Negative-QTOFsplash10-0a4i-9212000000-ebc430c35ab9200dcd182016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nitazoxanide 40V, Negative-QTOFsplash10-0a4i-9010000000-0ec40f1534d5fe9096542016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nitazoxanide 10V, Positive-QTOFsplash10-01b9-0960000000-97c646f778e77a560b202021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nitazoxanide 20V, Positive-QTOFsplash10-00di-0900000000-d727decb3e04530d21772021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nitazoxanide 40V, Positive-QTOFsplash10-00di-1900000000-dc0087192f244a933bea2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nitazoxanide 10V, Negative-QTOFsplash10-0a4i-0009000000-880114e27c1b22207ace2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nitazoxanide 20V, Negative-QTOFsplash10-0a4i-2009000000-db39e69949f5cad9dc202021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nitazoxanide 40V, Negative-QTOFsplash10-052f-9111000000-1bb86956f101434bfa182021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00507 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00507 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00507
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]