Human Metabolome Database Version 3.5

Showing metabocard for Nitazoxanide (HMDB14649)

Record Information
Version 3.5
Creation Date 2012-09-06 09:16:50 -0600
Update Date 2013-02-08 17:32:00 -0700
HMDB ID HMDB14649
Secondary Accession Numbers None
Metabolite Identification
Common Name Nitazoxanide
Description Nitazoxanide, 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
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Display: 2D Structure | 3D Structure
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 Formula C12H9N3O5S
Average Molecular Weight 307.282
Monoisotopic Molecular Weight 307.026291103
IUPAC Name 2-[(5-nitro-1,3-thiazol-2-yl)carbamoyl]phenyl acetate
Traditional IUPAC Name nitazoxanide
CAS Registry Number 55981-09-4
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 Key YQNQNVDNTFHQSW-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Phenylacetic Acid Derivatives
Sub Class N/A
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Benzamides
Substituents
  • Benzoyl
  • Carboxamide Group
  • Carboxylic Acid Ester
  • Nitro Compound
  • Nitrothiazole
  • Organic Oxoazanium
  • Secondary Carboxylic Acid Amide
  • Thiazole
Direct Parent Phenylacetic Acid Derivatives
Ontology
Status Expected and Not Quantified
Origin
  • Drug
Biofunction
  • Antiparasitic Agents
Application
  • Pharmaceutical
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 202 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 7.55e-03 g/L Not Available
LogP 1.2 Not Available
Predicted Properties
Property Value Source
Water Solubility 0.0076 g/L ALOGPS
LogP 2.14 ALOGPS
LogP 2.12 ChemAxon
LogS -4.61 ALOGPS
pKa (strongest acidic) 8.3 ChemAxon
pKa (strongest basic) -4.2 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 114.11 A2 ChemAxon
Rotatable Bond Count 5 ChemAxon
Refractivity 73.89 ChemAxon
Polarizability 27.54 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB00507
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB00507
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB00507 Link_out
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID Not Available
KNApSAcK ID Not Available
Chemspider ID 38037 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Nitazoxanide Link_out
NuGOwiki Link HMDB14649 Link_out
Metagene Link HMDB14649 Link_out
METLIN ID Not Available
PubChem Compound 41684 Link_out
PDB ID NTI Link_out
ChEBI ID 438934 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References
  1. Parasitic infections. Am J Transplant. 2004 Nov;4 Suppl 10:142-55. Pubmed: 15504227 Link_out