Details
Stereochemistry | ACHIRAL |
Molecular Formula | C12H9N3O5S |
Molecular Weight | 307.282 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(=O)OC1=C(C=CC=C1)C(=O)NC2=NC=C(S2)[N+]([O-])=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 | 307.282 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/21397502http://www.accessdata.fda.gov/drugsatfda_docs/label/2005/021818lbl.pdfCurator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/15791519
http://www.romark.com/about-romark/history
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21397502http://www.accessdata.fda.gov/drugsatfda_docs/label/2005/021818lbl.pdf
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/15791519
http://www.romark.com/about-romark/history
Nitazoxanide is a new thiazolide antiparasitic agent that shows excellent in vitro activity against a wide variety of protozoa and helminths. In 1993, Dr. Jean-François Rossignol and investor/partner Marc Ayers co-founded Romark Laboratories, L.C., to develop Rossignol's invention, nitazoxanide, as a treatment for Cryptosporidium infection and to discover and develop other new small molecule drugs in the same class called the thiazolides. In 2002, Alinia® (nitazoxanide) suspension was approved by the FDA for treating diarrhea caused by Cryptosporidium parvum and Giardia lamblia in children. Alinia® tablets were approved by the FDA in July 2004. It is given by the oral route with good bioavailability and is well tolerated, with primarily mild gastrointestinal side effects. Following oral administration in humans, nitazoxanide is rapidly hydrolyzed to an active metabolite, tizoxanide (desacetyl-nitazoxanide). Tizoxanide then undergoes conjugation, primarily by glucuronidation. The antiprotozoal 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. Studies have shown that the PFOR enzyme from Giardia lamblia directly reduces nitazoxanide by transfer of electrons in the absence of ferredoxin. The DNA-derived PFOR protein sequence of Cryptosporidium parvum appears to be similar to that of Giardia lamblia. Interference with the PFOR enzyme-dependent electron transfer reaction may not be the only pathway by which nitazoxanide exhibits antiprotozoal activity.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25762088http://www.sciencedirect.com/science/article/pii/S1319016416300974
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 |
---|---|---|
Screening of compounds for antimicrosporidial activity in vitro. | 1998 |
|
In vitro activity of nitazoxanide and related compounds against isolates of Giardia intestinalis, Entamoeba histolytica and Trichomonas vaginalis. | 2002 Jan |
|
Nitazoxanide as a broad-spectrum antiparasitic agent. | 2002 Jun 1 |
|
Nitazoxanide compared with quinfamide and mebendazole in the treatment of helminthic infections and intestinal protozoa in children. | 2002 Mar |
|
Treatment of intestinal parasitic infections: a review of nitazoxanide. | 2002 Mar |
|
Comparative clinical studies of nitazoxanide, albendazole and praziquantel in the treatment of ascariasis, trichuriasis and hymenolepiasis in children from Peru. | 2002 Mar-Apr |
|
In vitro effect of nitazoxanide against Entamoeba histolytica, Giardia intestinalis and Trichomonas vaginalis trophozoites. | 2002 May-Jun |
|
Effect of nitazoxanide on morbidity and mortality in Zambian children with cryptosporidiosis: a randomised controlled trial. | 2002 Nov 2 |
|
Cryptosporidiosis. | 2002 Oct |
|
In-vitro transfer of nitazoxanide across the intestinal epithelial barrier. | 2002 Oct |
|
Nitazoxanide (Alinia)--a new anti-protozoal agent. | 2003 Apr 14 |
|
Double-blind, randomized, placebo-controlled study of nitazoxanide in the treatment of fascioliasis in adults and children from northern Peru. | 2003 Jan |
|
New drugs 04, part 1. | 2004 Feb |
|
[Nitazoxanide vs albendazole against intestinal parasites in a single dose and for three days]. | 2004 Jul-Aug |
|
New drugs of 2003. | 2004 Mar-Apr |
|
Parasitic infections. | 2004 Nov |
|
[Nitazoxanide: adverse effects]. | 2004 Nov-Dec |
|
In vitro effects of nitazoxanide on Echinococcus granulosus protoscoleces and metacestodes. | 2004 Sep |
|
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. | 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 |
|
Past, present, and future therapies for Clostridium difficile-associated disease. | 2006 Dec |
|
Emerging therapies in the treatment of Clostridium difficile-associated disease. | 2006 Dec |
|
Nitazoxanide in the treatment of viral gastroenteritis: a randomized double-blind placebo-controlled clinical trial. | 2006 Nov 15 |
|
Bioequivalence study of a fixed dose combination of nitazoxanide and ofloxacin in Indian healthy volunteers. | 2007 |
|
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 |
|
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 |
|
Characterization of Giardia lamblia WB C6 clones resistant to nitazoxanide and to metronidazole. | 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 |
|
Efficacy of nitazoxanide for cyclosporiasis in patients with sulfa allergy. | 2007 Feb 1 |
|
Prevention and treatment of cryptosporidiosis in immunocompromised patients. | 2007 Jan 24 |
|
[New drugs against parasitic diseases]. | 2007 Jan 31 |
|
Clostridium difficile: recent epidemiologic findings and advances in therapy. | 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 |
|
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 |
|
Neospora caninum: functional inhibition of protein disulfide isomerase by the broad-spectrum anti-parasitic drug nitazoxanide and other thiazolides. | 2008 Jan |
|
Liquid chromatography-tandem mass spectrometry analysis of nitazoxanide and its major metabolites in goat. | 2008 Nov 15 |
|
Nitazoxanide, tizoxanide and a new analogue [4-nitro-N-(5-nitro-1,3-thiazol-2-yl)benzamide; NTB] inhibit the growth of kinetoplastid parasites (Trypanosoma cruzi and Leishmania mexicana) in vitro. | 2009 Jun |
|
Prophylactic and therapeutic efficacy of nitazoxanide against Cryptosporidium parvum in experimentally challenged neonatal calves. | 2009 Mar 9 |
|
Hepatitis C and kidney disease. | 2010 |
|
In Vitro Susceptibility of Canine Influenza A (H3N8) Virus to Nitazoxanide and Tizoxanide. | 2010 Aug 12 |
|
Antiviral treatment of chronic hepatitis B virus (HBV) infections. | 2010 Jun |
|
New treatments for chronic hepatitis C. | 2010 Sep |
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27156623
In mycobacterial growth indicator tube [MGIT] cultures inhibition of Mycobacterium tuberculosis growth occurred at total drug concentrations of ≥16 ug/ml (almost complete inhibition of growth was achieved at 64 ug/ml), whereas in whole blood cultures (albumin concentration = 350 uM), ≥128 ug/ml was required.
Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Jul 05 23:54:11 UTC 2023
by
admin
on
Wed Jul 05 23:54:11 UTC 2023
|
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 | ||
|
Common Name | English | ||
|
Code | 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 Wed Jul 05 23:54:12 UTC 2023 , Edited by admin on Wed Jul 05 23:54:12 UTC 2023
|
||
|
FDA ORPHAN DRUG |
150501
Created by
admin on Wed Jul 05 23:54:12 UTC 2023 , Edited by admin on Wed Jul 05 23:54:12 UTC 2023
|
||
|
WHO-ATC |
P01AX11
Created by
admin on Wed Jul 05 23:54:12 UTC 2023 , Edited by admin on Wed Jul 05 23:54:12 UTC 2023
|
||
|
FDA ORPHAN DRUG |
91895
Created by
admin on Wed Jul 05 23:54:12 UTC 2023 , Edited by admin on Wed Jul 05 23:54:12 UTC 2023
|
||
|
FDA ORPHAN DRUG |
150401
Created by
admin on Wed Jul 05 23:54:12 UTC 2023 , Edited by admin on Wed Jul 05 23:54:12 UTC 2023
|
||
|
NDF-RT |
N0000175485
Created by
admin on Wed Jul 05 23:54:12 UTC 2023 , Edited by admin on Wed Jul 05 23:54:12 UTC 2023
|
||
|
LIVERTOX |
NBK548943
Created by
admin on Wed Jul 05 23:54:12 UTC 2023 , Edited by admin on Wed Jul 05 23:54:12 UTC 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
DB00507
Created by
admin on Wed Jul 05 23:54:12 UTC 2023 , Edited by admin on Wed Jul 05 23:54:12 UTC 2023
|
PRIMARY | |||
|
SOA12P041N
Created by
admin on Wed Jul 05 23:54:12 UTC 2023 , Edited by admin on Wed Jul 05 23:54:12 UTC 2023
|
PRIMARY | |||
|
5007
Created by
admin on Wed Jul 05 23:54:12 UTC 2023 , Edited by admin on Wed Jul 05 23:54:12 UTC 2023
|
PRIMARY | |||
|
100000083891
Created by
admin on Wed Jul 05 23:54:12 UTC 2023 , Edited by admin on Wed Jul 05 23:54:12 UTC 2023
|
PRIMARY | |||
|
M7923
Created by
admin on Wed Jul 05 23:54:12 UTC 2023 , Edited by admin on Wed Jul 05 23:54:12 UTC 2023
|
PRIMARY | Merck Index | ||
|
C47637
Created by
admin on Wed Jul 05 23:54:12 UTC 2023 , Edited by admin on Wed Jul 05 23:54:12 UTC 2023
|
PRIMARY | |||
|
697855
Created by
admin on Wed Jul 05 23:54:12 UTC 2023 , Edited by admin on Wed Jul 05 23:54:12 UTC 2023
|
PRIMARY | |||
|
PP-35
Created by
admin on Wed Jul 05 23:54:12 UTC 2023 , Edited by admin on Wed Jul 05 23:54:12 UTC 2023
|
PRIMARY | |||
|
41684
Created by
admin on Wed Jul 05 23:54:12 UTC 2023 , Edited by admin on Wed Jul 05 23:54:12 UTC 2023
|
PRIMARY | |||
|
Nitazoxanide
Created by
admin on Wed Jul 05 23:54:12 UTC 2023 , Edited by admin on Wed Jul 05 23:54:12 UTC 2023
|
PRIMARY | |||
|
NITAZOXANIDE
Created by
admin on Wed Jul 05 23:54:12 UTC 2023 , Edited by admin on Wed Jul 05 23:54:12 UTC 2023
|
PRIMARY | |||
|
31819
Created by
admin on Wed Jul 05 23:54:12 UTC 2023 , Edited by admin on Wed Jul 05 23:54:12 UTC 2023
|
PRIMARY | RxNorm | ||
|
C041747
Created by
admin on Wed Jul 05 23:54:12 UTC 2023 , Edited by admin on Wed Jul 05 23:54:12 UTC 2023
|
PRIMARY | |||
|
CHEMBL1401
Created by
admin on Wed Jul 05 23:54:12 UTC 2023 , Edited by admin on Wed Jul 05 23:54:12 UTC 2023
|
PRIMARY | |||
|
SUB09311MIG
Created by
admin on Wed Jul 05 23:54:12 UTC 2023 , Edited by admin on Wed Jul 05 23:54:12 UTC 2023
|
PRIMARY | |||
|
DTXSID5033757
Created by
admin on Wed Jul 05 23:54:12 UTC 2023 , Edited by admin on Wed Jul 05 23:54:12 UTC 2023
|
PRIMARY | |||
|
SOA12P041N
Created by
admin on Wed Jul 05 23:54:12 UTC 2023 , Edited by admin on Wed Jul 05 23:54:12 UTC 2023
|
PRIMARY | |||
|
55981-09-4
Created by
admin on Wed Jul 05 23:54:12 UTC 2023 , Edited by admin on Wed Jul 05 23:54:12 UTC 2023
|
PRIMARY | |||
|
1943
Created by
admin on Wed Jul 05 23:54:12 UTC 2023 , Edited by admin on Wed Jul 05 23:54:12 UTC 2023
|
PRIMARY | |||
|
760057
Created by
admin on Wed Jul 05 23:54:12 UTC 2023 , Edited by admin on Wed Jul 05 23:54:12 UTC 2023
|
PRIMARY | |||
|
259-931-8
Created by
admin on Wed Jul 05 23:54:12 UTC 2023 , Edited by admin on Wed Jul 05 23:54:12 UTC 2023
|
PRIMARY | |||
|
1463960
Created by
admin on Wed Jul 05 23:54:12 UTC 2023 , Edited by admin on Wed Jul 05 23:54:12 UTC 2023
|
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 |
|
|
|||