Details
Stereochemistry | ACHIRAL |
Molecular Formula | C12H9N3O5S |
Molecular Weight | 307.2835 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(=O)Oc1ccccc1C(=Nc2ncc(N(=O)=O)s2)O
InChI
InChIKey=YQNQNVDNTFHQSW-UHFFFAOYSA-N
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)
Molecular Formula | C12H9N3O5S |
Molecular Weight | 307.2835 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2005/021818lbl.pdfhttps://www.ncbi.nlm.nih.gov/pubmed/21397502Curator's Comment:: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/25762088
https://www.ncbi.nlm.nih.gov/pubmed/20404119
https://www.ncbi.nlm.nih.gov/pubmed/17888524
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2005/021818lbl.pdfhttps://www.ncbi.nlm.nih.gov/pubmed/21397502
Curator's Comment:: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/25762088
https://www.ncbi.nlm.nih.gov/pubmed/20404119
https://www.ncbi.nlm.nih.gov/pubmed/17888524
Tizoxanide, the primary active metabolite of the FDA approved drug nitazoxanide, an anti-infective that has been approved for the treatment of diarrhea caused by Giardia lamblia. Tizoxanide, an active metabolite of nitazoxanide in humans, is also an antiparasitic drug of the thiazolide class. It has broad-spectrum antiparasitic and broad-spectrum antiviral properties. Besides, it has being found that Tizoxanide exhibits appreciable antagonist activity for both mGluR1 and mGluR5 (IC50 = 1.8 uM and 1.2 uM, respectively).
CNS Activity
Sources: http://www.sciencedirect.com/science/article/pii/S1319016416300974https://www.ncbi.nlm.nih.gov/pubmed/25762088
Curator's Comment:: In rats tizoxanide (the active metabolite of nitazoxanide) does not permeate into the cerebrospinal fluid. Human data not available.
Originator
Sources: http://www.romark.com/about-romark/history
Curator's Comment:: Dr. Jean-François Rossignol 1993 at Romark Laboratories, L.C.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2364027 |
|||
Target ID: CHEMBL360 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27156623 |
|||
Target ID: CHEMBL3772 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25762088 |
1.8 µM [IC50] | ||
Target ID: CHEMBL3227 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25762088 |
1.2 µM [IC50] | ||
Target ID: CHEMBL613722 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23926336 |
|||
Target ID: CHEMBL612652 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21397502 |
0.716 µM [IC50] | ||
Target ID: CHEMBL612884 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21397502 |
0.211 µM [IC50] | ||
Target ID: CHEMBL352 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20404119 |
|||
Target ID: CHEMBL613497 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17888524 |
0.15 µM [EC50] | ||
Target ID: CHEMBL2364026 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | ALINIA Approved UseDiarrhea caused by Giardia lamblia or Cryptosporidium parvum: Alinia for Oral Suspension (patients 1 year of age and older) and Alinia Tablets (patients 12 years and older) are indicated for the treatment of diarrhea caused by Giardia lamblia or Cryptosporidium parvum. Alinia for Oral Suspension and Alinia Tablets have not been shown to be superior to placebo for the treatment of diarrhea caused by Cryptosporidium parvum in HIV-infected or immunodeficient patients (see CLINICAL STUDIES ). Launch Date1.09036798E12 |
|||
Primary | Unknown Approved UseUnknown |
|||
Curative | Unknown Approved UseUnknown |
|||
Curative | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
9.1 μg/mL |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
TIZOXANIDE plasma | Homo sapiens population: UNKNOWN age: ADOLESCENT sex: UNKNOWN food status: FED |
|
6.795 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22533565 |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
TIZOXANIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
39.5 μg × h/mL |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
TIZOXANIDE plasma | Homo sapiens population: UNKNOWN age: ADOLESCENT sex: UNKNOWN food status: FED |
|
27.23 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22533565 |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
TIZOXANIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.38 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22533565 |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
TIZOXANIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1% |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
TIZOXANIDE plasma | Homo sapiens population: UNKNOWN age: ADOLESCENT sex: UNKNOWN food status: FED |
Doses
Dose | Population | Adverse events |
---|---|---|
4 mg 1 times / day steady, oral MTD Dose: 4 mg, 1 times / day Route: oral Route: steady Dose: 4 mg, 1 times / day Sources: Page: 1 |
healthy, adult n = 6 Health Status: healthy Age Group: adult Sex: unknown Population Size: 6 Sources: Page: 1 |
Other AEs: Gastrointestinal disorders NEC... |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Gastrointestinal disorders NEC | 4 mg 1 times / day steady, oral MTD Dose: 4 mg, 1 times / day Route: oral Route: steady Dose: 4 mg, 1 times / day Sources: Page: 1 |
healthy, adult n = 6 Health Status: healthy Age Group: adult Sex: unknown Population Size: 6 Sources: Page: 1 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 8.0 |
no | |||
Page: 8.0 |
no | |||
Page: 16.0 |
no | |||
Page: 8.0 |
no | |||
Page: 8.0 |
no | |||
Page: 16.0 |
no | |||
Page: 16.0 |
no | |||
Page: 8.0 |
weak [IC50 >100 uM] | |||
Page: 8.0 |
weak |
PubMed
Title | Date | PubMed |
---|---|---|
New drugs and treatment for cryptosporidiosis. | 2004 Dec |
|
Evaluation of the in vitro effect of albendazole, metronidazole and nitazoxanide on viability and structure of Giardia lamblia cysts. | 2004 Jul-Oct |
|
Nitazoxanide: a new thiazolide antiparasitic agent. | 2005 Apr 15 |
|
Treatment of cryptosporidiosis in immunocompromised hosts. | 2005 Jul |
|
Use of nitazoxanide as a new therapeutic option for persistent diarrhea: a pediatric perspective. | 2005 Jul |
|
Nitazoxanide for treatment of intestinal parasites in children. | 2005 Jul |
|
Nitazoxanide for persistent diarrhoea in Zambian acquired immune deficiency syndrome patients: a randomized-controlled trial. | 2005 Mar 15 |
|
Nitazoxanide. | 2005 Nov |
|
Effect of nitazoxanide in persistent diarrhea and enteritis associated with Blastocystis hominis. | 2005 Oct |
|
Molecular survival strategies of Echinococcus multilocularis in the murine host. | 2006 |
|
Practical considerations of new drugs: new choices for old problems. | 2006 Apr |
|
[Development of novel antihelminthic therapies]. | 2006 Aug |
|
[Therapeutic alternatives in case of failure of first-line treatment of intestinal helminthiasis in adults]. | 2006 Aug |
|
Current status of anti-diarrheal and anti-secretory drugs in the management of acute childhood diarrhea. | 2006 Aug |
|
Treatment options for the eradication of intestinal protozoa. | 2006 Aug |
|
Nitazoxanide for the treatment of Clostridium difficile colitis. | 2006 Aug 15 |
|
Past, present, and future therapies for Clostridium difficile-associated disease. | 2006 Dec |
|
Emerging therapies in the treatment of Clostridium difficile-associated disease. | 2006 Dec |
|
Efficacy of nitazoxanide and paromomycin in biliary tract cryptosporidiosis in an immunosuppressed gerbil model. | 2006 Feb |
|
14-3-3- and II/3-10-gene expression as molecular markers to address viability and growth activity of Echinococcus multilocularis metacestodes. | 2006 Jan |
|
Effect of nitazoxanide for treatment of severe rotavirus diarrhoea: randomised double-blind placebo-controlled trial. | 2006 Jul 8 |
|
Nitazoxanide for rotavirus diarrhoea? | 2006 Jul 8 |
|
An update on diagnosis, treatment, and prevention of Clostridium difficile-associated disease. | 2006 Jun |
|
Effect of nitazoxanide in diarrhea and enteritis caused by Cryptosporidium species. | 2006 Mar |
|
Use of nitazoxanide for gastrointestinal tract infections: treatment of protozoan parasitic infection and beyond. | 2006 Mar |
|
Nitazoxanide, a broad-spectrum thiazolide anti-infective agent for the treatment of gastrointestinal infections. | 2006 May |
|
Antimicrobial therapy of Clostridium difficile-associated diarrhea. | 2006 Nov |
|
Nitazoxanide in the treatment of viral gastroenteritis: a randomized double-blind placebo-controlled clinical trial. | 2006 Nov 15 |
|
Nitazoxanide in the treatment of acquired immune deficiency syndrome-related cryptosporidiosis: results of the United States compassionate use program in 365 patients. | 2006 Sep 1 |
|
Clostridium difficile colitis that fails conventional metronidazole therapy: response to nitazoxanide. | 2007 Apr |
|
Treatment of cryptosporidiosis in immunocompromised individuals: systematic review and meta-analysis. | 2007 Apr |
|
Characterization of Giardia lamblia WB C6 clones resistant to nitazoxanide and to metronidazole. | 2007 Aug |
|
Induction of tachyzoite egress from cells infected with the protozoan Neospora caninum by nitro- and bromo-thiazolides, a class of broad-spectrum anti-parasitic drugs. | 2007 Aug |
|
Nitazoxanide or CD3+/CD4+ lymphocytes for recovery from severe Cryptosporidium infection after allogeneic bone marrow transplant? | 2007 Feb |
|
Severe cryptosporidiosis in a seven-year-old renal transplant recipient: case report and review of the literature. | 2007 Feb |
|
Structure-activity relationships from in vitro efficacies of the thiazolide series against the intracellular apicomplexan protozoan Neospora caninum. | 2007 Feb |
|
Efficacy of nitazoxanide, tizoxanide and tizoxanide/albendazole sulphoxide combination against Taenia crassiceps cysts. | 2007 Feb |
|
Hymenolepis nana infection: symptoms and response to nitazoxanide in field conditions. | 2007 Feb |
|
Efficacy of nitazoxanide for cyclosporiasis in patients with sulfa allergy. | 2007 Feb 1 |
|
Nitazoxanide versus metronidazole for Clostridium difficile-associated colitis. | 2007 Jan 1 |
|
Prevention and treatment of cryptosporidiosis in immunocompromised patients. | 2007 Jan 24 |
|
[New drugs against parasitic diseases]. | 2007 Jan 31 |
|
In vitro efficacy of nitro- and bromo-thiazolyl-salicylamide compounds (thiazolides) against Besnoitia besnoiti infection in Vero cells. | 2007 Jul |
|
Antibiotic treatment for Clostridium difficile-associated diarrhea in adults. | 2007 Jul 18 |
|
Is nitazoxanide an effective treatment for patients with acquired immune deficiency syndrome-related cryptosporidiosis? | 2007 Mar |
|
Isolated gastric cryptosporidiosis in an immunocompetent patient. | 2007 May |
|
Nitazoxanide in the treatment of amoebiasis. | 2007 Oct |
|
Clostridium difficile: new therapeutic options. | 2007 Oct |
|
Failure of nitazoxanide to cure trichomoniasis in three women. | 2007 Oct |
|
Nitazoxanide in the treatment of Ascaris lumbricoides in a rural zone of Colima, Mexico. | 2007 Sep |
Sample Use Guides
Nitazoxanide treatment of diarrhea caused by Giardia lamblia or Cryptosporidium parvum:
1-3 years old patients: 5 mL of Alinia for Oral Suspension (100 mg nitazoxanide) every 12 hourswith food for 3 days;
4-11 years old patients: 10 mL of Alinia for Oral Suspension (200 mg nitazoxanide) every 12 hours with food for 3 days;
≥12 years old patients: 1 Alinia Tablet (500 mg nitazoxanide) every 12 hours with food or
25 mL of Alinia for Oral Suspension
(500 mg nitazoxanide) every 12 hours
with food for 3 days
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10882689
Nitazoxanide and its metabolites tizoxanide and tizoxanide glucuronide were inhibitory for up to 46 h when added after Cryptosporidium parvum sporozoite invasion in differentiated human enterocytic HCT-8 cells (MIC50 1.2, 22.6 and 2.2 mg/L, respectively).
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Jun 25 21:52:46 UTC 2021
by
admin
on
Fri Jun 25 21:52:46 UTC 2021
|
Record UNII |
SOA12P041N
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
Code | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
NCI_THESAURUS |
C277
Created by
admin on Fri Jun 25 21:52:46 UTC 2021 , Edited by admin on Fri Jun 25 21:52:46 UTC 2021
|
||
|
FDA ORPHAN DRUG |
150501
Created by
admin on Fri Jun 25 21:52:46 UTC 2021 , Edited by admin on Fri Jun 25 21:52:46 UTC 2021
|
||
|
WHO-ATC |
P01AX11
Created by
admin on Fri Jun 25 21:52:46 UTC 2021 , Edited by admin on Fri Jun 25 21:52:46 UTC 2021
|
||
|
FDA ORPHAN DRUG |
91895
Created by
admin on Fri Jun 25 21:52:46 UTC 2021 , Edited by admin on Fri Jun 25 21:52:46 UTC 2021
|
||
|
FDA ORPHAN DRUG |
150401
Created by
admin on Fri Jun 25 21:52:46 UTC 2021 , Edited by admin on Fri Jun 25 21:52:46 UTC 2021
|
||
|
NDF-RT |
N0000175485
Created by
admin on Fri Jun 25 21:52:46 UTC 2021 , Edited by admin on Fri Jun 25 21:52:46 UTC 2021
|
||
|
LIVERTOX |
689
Created by
admin on Fri Jun 25 21:52:46 UTC 2021 , Edited by admin on Fri Jun 25 21:52:46 UTC 2021
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
DB00507
Created by
admin on Fri Jun 25 21:52:46 UTC 2021 , Edited by admin on Fri Jun 25 21:52:46 UTC 2021
|
PRIMARY | |||
|
5007
Created by
admin on Fri Jun 25 21:52:46 UTC 2021 , Edited by admin on Fri Jun 25 21:52:46 UTC 2021
|
PRIMARY | |||
|
1463960
Created by
admin on Fri Jun 25 21:52:46 UTC 2021 , Edited by admin on Fri Jun 25 21:52:46 UTC 2021
|
PRIMARY | USP-RS | ||
|
M7923
Created by
admin on Fri Jun 25 21:52:46 UTC 2021 , Edited by admin on Fri Jun 25 21:52:46 UTC 2021
|
PRIMARY | Merck Index | ||
|
C47637
Created by
admin on Fri Jun 25 21:52:46 UTC 2021 , Edited by admin on Fri Jun 25 21:52:46 UTC 2021
|
PRIMARY | |||
|
41684
Created by
admin on Fri Jun 25 21:52:46 UTC 2021 , Edited by admin on Fri Jun 25 21:52:46 UTC 2021
|
PRIMARY | |||
|
Nitazoxanide
Created by
admin on Fri Jun 25 21:52:46 UTC 2021 , Edited by admin on Fri Jun 25 21:52:46 UTC 2021
|
PRIMARY | |||
|
NITAZOXANIDE
Created by
admin on Fri Jun 25 21:52:46 UTC 2021 , Edited by admin on Fri Jun 25 21:52:46 UTC 2021
|
PRIMARY | |||
|
31819
Created by
admin on Fri Jun 25 21:52:46 UTC 2021 , Edited by admin on Fri Jun 25 21:52:46 UTC 2021
|
PRIMARY | RxNorm | ||
|
C041747
Created by
admin on Fri Jun 25 21:52:46 UTC 2021 , Edited by admin on Fri Jun 25 21:52:46 UTC 2021
|
PRIMARY | |||
|
CHEMBL1401
Created by
admin on Fri Jun 25 21:52:46 UTC 2021 , Edited by admin on Fri Jun 25 21:52:46 UTC 2021
|
PRIMARY | |||
|
SUB09311MIG
Created by
admin on Fri Jun 25 21:52:46 UTC 2021 , Edited by admin on Fri Jun 25 21:52:46 UTC 2021
|
PRIMARY | |||
|
55981-09-4
Created by
admin on Fri Jun 25 21:52:46 UTC 2021 , Edited by admin on Fri Jun 25 21:52:46 UTC 2021
|
PRIMARY | |||
|
SOA12P041N
Created by
admin on Fri Jun 25 21:52:46 UTC 2021 , Edited by admin on Fri Jun 25 21:52:46 UTC 2021
|
PRIMARY | |||
|
55981-09-4
Created by
admin on Fri Jun 25 21:52:46 UTC 2021 , Edited by admin on Fri Jun 25 21:52:46 UTC 2021
|
PRIMARY | |||
|
1943
Created by
admin on Fri Jun 25 21:52:46 UTC 2021 , Edited by admin on Fri Jun 25 21:52:46 UTC 2021
|
PRIMARY | |||
|
259-931-8
Created by
admin on Fri Jun 25 21:52:46 UTC 2021 , Edited by admin on Fri Jun 25 21:52:46 UTC 2021
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
BINDER->LIGAND |
BINDING
|
||
|
TARGET ORGANISM->INHIBITOR |
In Vero E6 cells
EC50
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
METABOLITE ACTIVE -> PARENT | |||
|
METABOLITE ACTIVE -> PRODRUG |
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
---|---|---|---|---|---|---|
Biological Half-life | PHARMACOKINETIC |
|
|
|||