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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
Structure of NITAZOXANIDE

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)

HIDE SMILES / InChI

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

Description
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

Curator's Comment:: In rats tizoxanide (the active metabolite of nitazoxanide) does not permeate into the cerebrospinal fluid. Human data not available.

Originator

Curator's Comment:: Dr. Jean-François Rossignol 1993 at Romark Laboratories, L.C.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
ALINIA

Approved Use

Diarrhea 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 Date

1.09036798E12
Primary
Unknown

Approved Use

Unknown
Curative
Unknown

Approved Use

Unknown
Curative
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
1.38 h
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

Funbound

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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...
Other AEs:
Gastrointestinal disorders NEC
Sources: Page: 1
AEs

AEs

AESignificanceDosePopulation
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
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
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 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
Clostridium difficile: recent epidemiologic findings and advances in therapy.
2007 Jul
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
Patents

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
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 Fri Jun 25 21:52:46 UTC 2021
Edited
by admin
on Fri Jun 25 21:52:46 UTC 2021
Record UNII
SOA12P041N
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NITAZOXANIDE
GREEN BOOK   INN   MART.   MI   ORANGE BOOK   USAN   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
NITAZOXANIDE [GREEN BOOK]
Common Name English
ALINIA
Brand Name English
NITAZOXANIDE [VANDF]
Common Name English
NITAZOXANIDE [INN]
Common Name English
NITAZOXANIDE [ORANGE BOOK]
Common Name English
NSC-760057
Code English
NITAZOXANIDE [MI]
Common Name English
NITAZOXANIDE [USP-RS]
Common Name English
PH 5776
Code English
N-(5-NITROTHIAZOL-2-YL)SALICYLAMIDE ACETATE ESTER
Common Name English
NITAZOXANIDE [WHO-DD]
Common Name English
NITAZOXANIDE [USAN]
Common Name English
NSC-697855
Code English
BENZAMIDE, 2-(ACETYLOXY)-N-(5-NITRO-2-THIAZOLYL)-
Systematic Name English
PH-5776
Code English
NITAZOXANIDE [MART.]
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
DRUG BANK
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
INN
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
USP_CATALOG
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
MERCK INDEX
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
NCI_THESAURUS
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
PUBCHEM
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
LACTMED
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
WIKIPEDIA
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
RXCUI
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
MESH
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
ChEMBL
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
EVMPD
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
EPA CompTox
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
FDA UNII
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
CAS
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
DRUG CENTRAL
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
ECHA (EC/EINECS)
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
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