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55981-09-4 molecular structure
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2-[(5-nitro-1,3-thiazol-2-yl)carbamoyl]phenyl acetate

ChemBase ID: 389
Molecular Formular: C12H9N3O5S
Molecular Mass: 307.28196
Monoisotopic Mass: 307.0262914
SMILES and InChIs

SMILES:
s1c(NC(=O)c2c(OC(=O)C)cccc2)ncc1[N+](=O)[O-]
Canonical SMILES:
CC(=O)Oc1ccccc1C(=O)Nc1ncc(s1)[N+](=O)[O-]
InChI:
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)
InChIKey:
YQNQNVDNTFHQSW-UHFFFAOYSA-N

Cite this record

CBID:389 http://www.chembase.cn/molecule-389.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
2-[(5-nitro-1,3-thiazol-2-yl)carbamoyl]phenyl acetate
IUPAC Traditional name
nitazoxanide
Brand Name
Alinia
Fental
Phavic-1
Synonyms
Nitazoxanida [INN-Spanish]
Nitazoxanid
Nitazoxanidum [INN-Latin]
Tizoxanide Glucuronide
NTZ
2-Acetyloxy-N-[(5-nitro-2-thiazolyl)]benzamide
2-(Acetolyloxy)-N-(5-nitro-2-thiazolyl)benzamide
nitazoxanide
Nitazoxanide
Nitazoxamide
2-(Acetyloxy)-N-(5-nitro-2-thiazolyl)benzamide
Alinia
BRN 1225475
Cryptaz
DRG 0242
N-(5-Nitro-2-thiazolyl)salicylamide Acetate Ester
Nitacure
Nitarid
Nitazoxanida
Nixide
Nixoran
Nizonide
PH 5776
NTZ; 2-(Acetyloxy)-N-(5-nitro-2-thiazolyl)benzamide
Nitazoxanide
CAS Number
55981-09-4
EC Number
259-931-8
MDL Number
MFCD00416599
PubChem SID
46507813
160963852
PubChem CID
41684

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 8.199224  H Acceptors
H Donor LogD (pH = 5.5) 2.1205907 
LogD (pH = 7.4) 2.0608385  Log P 2.1214147 
Molar Refractivity 72.886 cm3 Polarizability 27.28551 Å3
Polar Surface Area 111.43 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.14  LOG S -4.61 
Solubility (Water) 7.55e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
Methanol expand Show data source
Apperance
Off White to Pale Yellow Solid expand Show data source
Melting Point
198-200°C expand Show data source
Hydrophobicity(logP)
1.2 expand Show data source
Storage Condition
-20°C expand Show data source
-20°C Freezer expand Show data source
Storage Warning
IRRITANT expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
22-36/37/38 expand Show data source
Safety Statements
26-36 expand Show data source
TSCA Listed
false expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302-H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P305 + P351 + P338 expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
≥98% (HPLC) expand Show data source
95+% expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Empirical Formula (Hill Notation)
C12H9N3O5S expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00507 external link
Item Information
Drug Groups approved; investigational
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]
Indication For the treatment of diarrhea in adults and children caused by the protozoa Giardia lamblia and for the treatment of diarrhea in children caused by the protozoa Cryptosporidium parvum.
Pharmacology Nitazoxanide is an antifolate containing the pyrrolopyrimidine-based nucleus that exerts its antineoplastic activity by disrupting folate-dependent metabolic processes essential for cell replication. In vitro studies have shown that nitazoxanide inhibits thymidylate synthase (TS), dihydrofolate reductase (DHFR), and glycinamide ribonucleotide formyltransferase (GARFT), all folate-dependent enzymes involved in the de novo biosynthesis of thymidine and purine nucleotides. Nitazoxanide is transported into cells by both the reduced folate carrier and membrane folate binding protein transport systems. Once in the cell, nitazoxanide is converted to polyglutamate forms by the enzyme folylpolyglutamate synthetase. The polyglutamate forms are retained in cells and are inhibitors of TS and GARFT. Polyglutamation is a time- and concentration-dependent process that occurs in tumor cells and, to a lesser extent, in normal tissues. Polyglutamated metabolites have an increased intracellular half-life resulting in prolonged drug action in malignant cells.
Toxicity In acute studies in rodents and dogs, the oral LD50 was higher than 10,000 mg/kg. Single oral doses of up to 4000 mg nitazoxanide have been administered to healthy adult volunteers without significant adverse effects.
Affected Organisms
Protozoa
Biotransformation Rapidly hydrolyzed to an active metabolite, tizoxanide (desacetyl-nitazoxanide), followed by conjugation, primarily by glucuronidation to tizoxanide glucuronide.
Absorption The relative bioavailability of the suspension compared to the tablet was 70%. When administered with food the AUC and Cmax increased by two-fold and 50%, respectively, for the tablet and 45 to 50% and ≤ 10%, respectively, for the oral suspension.
Half Life 3.5 hours in patients with normal renal function
Protein Binding Very High (greater than 99%), bound to proteins. Binding is not affected by degree of renal impairment.
Elimination Tizoxanide is excreted in the urine, bile and feces, and tizoxanide glucuronide is excreted in urine and bile. Approximately two-thirds of the oral dose of nitazoxanide is excreted in the feces and one-third in the urine.
References
Parasitic infections. Am J Transplant. 2004 Nov;4 Suppl 10:142-55. [Pubmed]
External Links
Wikipedia
RxList
PDRhealth
Drugs.com
Selleck Chemicals - S1627 external link
Research Area: Infection
Biological Activity:
Nitazoxanide(Alinia, Annita) is a synthetic nitrothiazolyl-salicylamide derivative and an antiprotozoal agent. (IC50 for canine influenza virus ranges from 0.17 to 0.21 μM) The anti- protozoal activity of nitazoxanide is believed to be due to interference with the pyruvate:ferredoxin oxidoreductase (PFOR) enzyme dependent electron transfer reaction which is essential to anaerobic energy metabolism. [1] It has also been shown to have activity against influenza A virus. Nitazoxanide and tizoxanide inhibited virus replication of all canine influenza virus with 50% and 90% inhibitory concentrations ranging from 0.17 to 0.21 μM and from 0.60 to 0.76 μM, respectively. [2]
Sigma Aldrich - N0290 external link
Biochem/physiol Actions
Nitazoxanide is an inhibitor of pyruvate-ferredoxin oxidoreductase (PFOR); Antimicrobial recently found to kill both non-replicating and replicating mycobacteria. FDA approved anti-parasitic drug (2002). Recent work (C & EN Sept. 14, 2009, p. 28) highlights that NTZ kills non-replicating and replicating TB bacteria and no apparent resistance is detected.
Toronto Research Chemicals - N490100 external link
An anthelmintic (cestodes), antiprotozoal (cryptosporidium). Kills Mycobacterium tuberculosis.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Parasitic infections. Am J Transplant. 2004 Nov;4 Suppl 10:142-55. Pubmed
  • • Cavier, R., et al.: Eur. J. Med. Chem.-Chim. Ther., 13, 539 (1978)
  • • Dubreuil, L., et al.: Antimicrob. Ag. Chemother., 40, 2266 (1978)
  • • Stockis, A., et al.: Int. J. Clin. Pharmacol. Ther., 34, 349 (1978)
  • • Nathan, C., et al.: J. Med. Chem. 52, 5789 (1978)
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PATENTS

PATENTS

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