General
Preferred name
NITAZOXANIDE
Synonyms
CPD000466367 ()
Nitazoxanide D4 ()
NTZ D4 ()
NSC-697855 D4 ()
NSC 697855 ()
NTZ ()
Nitazoxanide (NSC 697855) ()
NTZ, NSC 697855 ()
Alinia ()
NSC-697855 ()
PH 5776 ()
PH-5776 ()
NSC-760057 ()
P&D ID
PD000850
CAS
55981-09-4
Tags
available
prodrug
drug
Approved by
FDA
First approval
2002
Drug Status
investigational
approved
vet_approved
Drug indication
Diarrhea
Max Phase
Phase 4
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
INDICATION For the treatment of diarrhea in adults and children caused by the protozoa Giardia lamblia, and for the treatment of diarrhea in children caused by the protozoan, Cryptosporidium parvum [FDA label].; ; Nitazoxanide has not been shown to be superior to placebo medication for the management of diarrhea caused by Cryptosporidium parvum in patients with HIV/immunodeficiency [FDA label, A31973, A31976].
METABOLISM The active metabolite of this drug is tizoxanide (desacetyl-nitazoxanide). The initial reaction in the metabolic pathway of Nitazoxanide is hydrolysis to tizoxanide, followed by conjugation, primarily by glucuronidation to tizoxanide glucuronide.; ; The oral suspension bioavailability of this drug is not equivalent to that of the oral tablets. Compared to the to the tablet, the bioavailability of the suspension was 70% [FDA label].; ; When administered with food, the AUCt of tizoxanide and tizoxanide glucuronide in plasma is increased to almost two-fold and the maximum concentration is increased by almost 50% compared to when ingested without food [FDA label].; ; When the oral suspension was ingested with food, the AUC of tizoxanide and tizoxanide glucuronide increased by approximately 50% and the Cmax increased by less than 10% [FDA label].
DESCPRITION a 5-nitrothiazolyl derivative used for a broad range of intestinal parasitic infections including CRYPTOSPORIDIUM and GIARDIA; it is a redox-active nitrothiazolyl-salicylamide prodrug; structure given in first source
TOXICITY Data on nitazoxanide overdosage is not available [FDA label]. In studies in rodents and dogs, the oral LD50 was higher than 10,000 mg/kg. One-time oral doses of up to 4000 mg nitazoxanide have been given to healthy adult volunteers without severe adverse effects. Gastric lavage may be appropriate soon after oral administration if overdose occurs. Supportive and symptomatic treatment should also be administered [FDA label].; ; ; According to previous studies [FDA label], less than 1% of the patients age 12 years and older participating in clinical trials with NTZ suffered from the following adverse effects:; Systemic: asthenia, fever, pain, allergic reaction, pelvic pain, back pain, chills, fever, flu-like syndrome.; Central Nervous System: dizziness, somnolence, insomnia, tremor, hypesthesia.; Gastrointestinal System: vomiting, dyspepsia, anorexia, flatulence, constipation, dry mouth, thirst. ; Urogenital System: discolored urine, dysuria, amenorrhea, metrorrhagia, kidney pain, edema labia. ; Metabolic & Nutrition: increased SGPT.; Hemic & Lymphatic Systems: anemia, leukocytosis.; Skin: rash, pruritus.; Special Senses: eye discoloration, ear ache.; Respiratory System: epistaxis, lung disease, pharyngitis.; Cardiovascular System: tachycardia, syncope, hypertension.; Muscular System: myalgia, leg cramps, spontaneous bone fracture.; ;
DESCRIPTION Coronavirus PLpro inhibitor (Tocris Bioactive Compound Library)
Cell lines
6
Organisms
13
Compound Sets
26
Bioprocess diversity set
Cayman Chemical Bioactives
13692
CeMM library of unique drugs (CLOUD)
ChEMBL Approved Drugs
CHEMBL1401
ChEMBL Drugs
CHEMBL1401
Drug Repurposing Hub
DrugBank
DB00507
DrugBank Approved Drugs
DB00507
DrugCentral
1943
DrugCentral Approved Drugs
1943
DrugMAP
DMOWLVG
DrugMAP Approved Drugs
DMOWLVG
Enamine BioReference Compounds
LSP-MoA library (Laboratory of Systems Pharmacology)
CHEMBL1401
MedChem Express Bioactive Compound Library
HY-B0217
NIH Clinical Collections (NCC)
NPC Screening Collection
Other bioactive compounds
Pandemic Response Box
Prestwick Chemical Library
ReFrame library
Selleckchem Bioactive Compound Library
Nitazoxanide(Alinia)
TargetMol Bioactive Compound Library
T1546
The Pathogen Box
The Spectrum Collection
Tocris Bioactive Compound Library
7234
External IDs
38
Properties
(calculated by RDKit )
Molecular Weight
307.03
Hydrogen Bond Acceptors
7
Hydrogen Bond Donors
1
Rotatable Bonds
4
Ring Count
2
Aromatic Ring Count
2
cLogP
2.23
TPSA
111.43
Fraction CSP3
0.08
Chiral centers
0.0
Largest ring
6.0
QED
0.4
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Target
Influenza Virus
Pyruvate:ferredoxin oxidoreductase
PFOR
Parasite
Autophagy,Influenza Virus,mTOR,Serotonin Transporter
Biological process
Resipration, oxidative phosphorylation, & mitochondrial targeting
Disease
REFERENCE COMPOUNDS
Pathway
Anti-infection
Autophagy
MOA
protozoal pyruvate ferredoxin oxidoreductase substrate
Inhibitor
pyruvate ferredoxin oxidoreductase inhibitor
Primary Target
Other Oxygenases/Oxidases
Indication
diarrhea
Therapeutic Class
Antiparasitic Agents
Source data