nitazoxanide 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |

Stem definitionDrug idCAS RN
antiparasitics, salicylanilides and analogues 1943 55981-09-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • nitazoxanide
  • nitazode
  • nitazoxanida
  • nizonide
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. It was investigated as a potential treatment for COVID-19 based on its broad antiviral activity, including in vitro activity against SARS-CoV-2 and MERS-CoV; however, there are no data to support the use of nitazoxanide in the treatment of COVID-19.
  • Molecular weight: 307.28
  • Formula: C12H9N3O5S
  • CLOGP: 1.25
  • LIPINSKI: 0
  • HAC: 8
  • HDO: 1
  • TPSA: 114.11
  • ALOGS: -4.61
  • ROTB: 5
  • Status: OFP
    • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
1 g O

ADMET properties:

PropertyValueReference
MRTD (Maximum Recommended Therapeutic Daily Dose) 46.49 µM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 70 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
S (Water solubility) 0.01 mg/mL Bocci G, Oprea TI, Benet LZ
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Bocci G, Oprea TI, Benet LZ

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 1.312 Moderate 0.69
caco2-efflux Caco-2 efflux ratio (BA/AB) 0.638 Moderate 0.69
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 43.251 10^-6 cm/s Moderate 0.69
dh-clint Dog hepatocyte intrinsic clearance 86.497 uL/min/10^6 cells Moderate 0.69
dppb Dog plasma protein binding (% unbound) 6.400 % Moderate 0.69
fcs-ppb Fetal calf serum protein binding (% unbound) 3.980 % Moderate 0.69
herg hERG pIC50 4.470 pIC50 Moderate 0.69
hh-clint Human hepatocyte intrinsic clearance 1042.317 uL/min/10^6 cells Moderate 0.69
hlm-clint Human liver microsomal intrinsic clearance 268.534 uL/min/mg protein Moderate 0.69
hppb Human plasma protein binding (% unbound) 2.010 % Moderate 0.69
kinase-safety-class ACVR2A,ACVR2B,ACVRL1,AKT3,ALK,AURKA,AURKB,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK1,CDK19,CDK5,CDK9,CHEK1,CLK4,CSF1R,DDR1,DYRK1A,DYRK1B,EGFR,EIF2AK3,EPHB4,ERBB2,FLT3,GRK2,GRK3,GSK3A,GSK3B,IKBKB,IRAK1,ITK,JAK1,JAK2,KIT,MAP2K6,MAP3K1,MAP3K10,MAP3K11,MAP3K21,MAP3K7,MAP4K1,MAP4K3,MAPK10,MAPK12,MAPK7,MAPK9,MAPKAPK2,MARK4,MELK,MET,MTOR,NTRK2,PAK4,PDK1,PDK2,PDK4,PDPK1,PIK3CA,PIK3CB,PIK3CD,PIK3CG,PIM2,PRKCD,PRKDC,SGK1,SIK2,SIK3,STK33,SYK,TEK,TTK,ULK1,ULK2 76
kinase-selectivity-class ACVR2A,AXL,BRAF,CAMK2B,CAMK2D,CDK1,CDK9,DDR1,DYRK1B,GRK2,GSK3A,GSK3B,IRAK1,MAP2K6,MAP3K21,MAPK7,MTOR,PDK4,PRKDC,SIK2,STK33,TEK,TTK,ULK1 24
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 2.143 Moderate 0.69
mh-clint Mouse hepatocyte intrinsic clearance 306.902 Moderate 0.69
mppb Mouse plasma protein binding (% unbound) 9.020 Moderate 0.69
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 1.945 Moderate 0.69
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pppb Pig plasma protein binding (% unbound) 7.660 % Moderate 0.69
rh-clint Rat hepatocyte intrinsic clearance 283.139 uL/min/10^6 cells Moderate 0.69
rh-fuinc Rat hepatocyte fraction unbound in incubation 86.700 % Moderate 0.69
rppb Rat plasma protein binding (% unbound) 3.980 % Moderate 0.69
solubility-dd Solubility at pH 7.4 in DMSO 401.791 uM Moderate 0.69

Approvals:

DateAgencyCompanyOrphan
Nov. 22, 2002 FDA ROMARK

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Anticholinergic syndrome 60.12 46.13 11 561 2732 90625143
Chromaturia 57.60 46.13 15 557 19172 90608703
Diarrhoea 51.44 46.13 44 528 939146 89688729

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Parasitic gastroenteritis 58.83 52.79 8 489 155 42620683

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Chromaturia 95.19 37.57 27 1100 29333 110558839
Diarrhoea 68.92 37.57 70 1057 1139435 109448737
Parasitic gastroenteritis 56.54 37.57 8 1119 239 110587933
Anticholinergic syndrome 49.93 37.57 11 1116 4269 110583903
Cryptosporidiosis infection 37.82 37.57 7 1120 1136 110587036

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC J01RA17 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
COMBINATIONS OF ANTIBACTERIALS
Combinations of antibacterials
ATC P01AX11 ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
ANTIPROTOZOALS
AGENTS AGAINST AMOEBIASIS AND OTHER PROTOZOAL DISEASES
Other agents against amoebiasis and other protozoal diseases
FDA EPC N0000175485 Antiprotozoal
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000977 Antiparasitic Agents

Related Drugs by ATC class:

J01RA Combinations of antibacterials 18 drugs
amikacinazithromycincefepimecefiximecefuroximeciprofloxacinfluconazolelevofloxacinmetronidazolenorfloxacinnystatinofloxacin show all 18 →
P01AX Other agents against amoebiasis and other protozoal diseases 9 drugs
atovaquonechiniofondihydroemetineemetinefumagillinmepacrinephanquinonetenonitrozoletrimetrexate

Drug Use | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
Giardiasis indication 58265007 DOID:10718
Infection by Cryptosporidium indication 58777003
Coronavirus infection off-label use 186747009
Diabetes mellitus contraindication 73211009 DOID:9351
Kidney disease contraindication 90708001 DOID:557
Disease of liver contraindication 235856003 DOID:409




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 6.29 acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])		Mechanism
action		Bioact sourceMoA source
Anoctamin-1 Ion channel IC50 6.37 CHEMBL
Signal transducer and activator of transcription 3 Transcription factor IC50 5.01 CHEMBL
Aldose reductase Enzyme IC50 5.09 CHEMBL
Histone deacetylase 6 Enzyme IC50 6 CHEMBL
Pyruvate:ferredoxin oxidoreductase Enzyme INHIBITOR CHEMBL CHEMBL
Pyruvate dehydrogenase [NADP(+)] Enzyme INHIBITOR DRUGBANK CHEMBL
Replicase polyprotein 1ab Enzyme IC50 5.01 CHEMBL
Pyruvate-flavodoxin oxidoreductase Enzyme Ki 4.98 CHEMBL
Trehalose-binding lipoprotein LpqY Transporter Kd 4.07 CHEMBL

External reference:

IDSource
4021365 VUID
N0000148784 NUI
D02486 KEGG_DRUG
4021365 VANDF
C0068788 UMLSCUI
CHEBI:94807 CHEBI
CHEMBL1401 ChEMBL_ID
DB00507 DRUGBANK_ID
C041747 MESH_SUPPLEMENTAL_RECORD_UI
41684 PUBCHEM_CID
5007 INN_ID
SOA12P041N UNII
31819 RXNORM
17040 MMSL
189467 MMSL
399984 MMSL
d04826 MMSL
006303 NDDF
407148001 SNOMEDCT_US
407149009 SNOMEDCT_US
NTI PDB_CHEM_ID
SOA12P041N INXIGHT DRUGS

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Nitazoxanide HUMAN PRESCRIPTION DRUG LABEL 1 13517-135 TABLET 500 mg ORAL ANDA 24 sections
Alinia HUMAN PRESCRIPTION DRUG LABEL 1 27437-106 POWDER, FOR SUSPENSION 100 mg ORAL NDA 24 sections
Nitazoxanide HUMAN PRESCRIPTION DRUG LABEL 1 31722-100 TABLET, FILM COATED 500 mg ORAL ANDA 23 sections
Nitazoxanide Human Prescription Drug Label 1 64980-526 TABLET, FILM COATED 500 mg ORAL ANDA 26 sections
Nitazoxanide Human Prescription Drug Label 1 64980-526 TABLET, FILM COATED 500 mg ORAL ANDA 26 sections
Nitazoxanide Human Prescription Drug Label 1 70954-934 TABLET 500 mg ORAL ANDA 24 sections