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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
1.8 µM [IC50]
1.2 µM [IC50]
0.716 µM [IC50]
0.211 µM [IC50]
0.15 µM [EC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
ALINIA
Primary
Unknown
Curative
Unknown
Curative
Unknown
Primary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
9.1 μg/mL
500 mg single, oral
TIZOXANIDE plasma
Homo sapiens
6.795 μg/mL
500 mg single, oral
TIZOXANIDE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
39.5 μg × h/mL
500 mg single, oral
TIZOXANIDE plasma
Homo sapiens
27.23 μg × h/mL
500 mg single, oral
TIZOXANIDE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
1.38 h
500 mg single, oral
TIZOXANIDE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
1%
500 mg single, oral
TIZOXANIDE plasma
Homo sapiens

Doses

AEs

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer






Drug as perpetrator​

PubMed

Sample Use Guides

In Vivo Use Guide
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
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
Record UNII
SOA12P041N
Record Status Validated (UNII)
Record Version