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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
Structure of NITAZOXANIDE

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)

HIDE SMILES / InChI

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

Description
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

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
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
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
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 Wed Jul 05 23:54:11 UTC 2023
Edited
by admin
on Wed Jul 05 23:54:11 UTC 2023
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 [WHO-DD]
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 [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 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
DRUG BANK
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
DAILYMED
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
INN
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
SMS_ID
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
MERCK INDEX
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
NCI_THESAURUS
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
NSC
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
USAN
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
PUBCHEM
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
LACTMED
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
WIKIPEDIA
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
RXCUI
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
MESH
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
ChEMBL
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
EVMPD
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
EPA CompTox
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
FDA UNII
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
CAS
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
DRUG CENTRAL
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
NSC
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
ECHA (EC/EINECS)
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
RS_ITEM_NUM
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
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