Skip to main content
Free research Free research Free compound review with research home and workspace preview
Quick search ChEMBL 36
Compound Detail

CHEMBL1401

NITAZOXANIDE
💊 Approved Drug
Enter ChEMBL ID:
Free Research Context This compound will appear in recent viewed items on the research home for this browser.
Research home View demo workspace
💊 Approved Drug
CC(=O)Oc1ccccc1C(=O)Nc1ncc([N+](=O)[O-])s1

Basic Information

ChEMBL ID CHEMBL1401
Name NITAZOXANIDE
Phase Approved
Structure Type MOL
InChI Key YQNQNVDNTFHQSW-UHFFFAOYSA-N
Therapeutic ✓ Yes
Active Moiety CHEMBL1545

Known Names

Alinia Nitazoxanida Nitazoxanide NSC-697855 NSC-760057 PH 5776 PH-5776
26
Targets
79
Activities
4
Assay Types
30
PK Parameters
20
Publications
7
Known Names
20
Indications
2
Mechanisms

Molecular Properties

307.3
MW (Da)
2.23
ALogP
7
HBA
1
HBD
111.4
PSA (Ų)
0.40
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2002
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Natural Product Prodrug
USAN Stem -oxanide
USAN Year 2003

Extended Properties

Molecular Formula C12H9N3O5S
MW 307.29
Aromatic Rings 2
Heavy Atoms 21
NP-Likeness -1.77

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Pyruvate:ferredoxin oxidoreductase inhibitor INHIBITOR Pyruvate dehydrogenase [NADP(+)]
Pyruvate:ferredoxin oxidoreductase inhibitor INHIBITOR Pyruvate:ferredoxin oxidoreductase

Indications

Amebiasis Diarrhea Arthritis, Rheumatoid Brain Diseases Clostridium Infections Cryptosporidiosis Dyspepsia Enterocolitis, Pseudomembranous Helicobacter Infections Influenza, Human Peritonitis Respiratory Tract Diseases Severe Acute Respiratory Syndrome Severe Acute Respiratory Syndrome Bronchiolitis Crohn Disease Diabetes Mellitus, Type 2 Gastroenteritis Hepatitis B, Chronic Hepatitis C

ATC Classification

P01AX11
nitazoxanide
Level 1: ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
Level 2: ANTIPROTOZOALS

Activity Summary

IC50 52 meas. best 7.82
EC50 21 meas. best 6.92
Ki 5 meas. best 6.52
Kd 1 meas. best 4.07

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Giardia intestinalis
CHEMBL612652
IC50 7.82 6.5664 15.0 11
Trichomonas vaginalis
CHEMBL612884
IC50 7.17 7.156 68.0 5
Hepatitis B virus
CHEMBL613497
IC50 6.92 6.92 120.0 1
Hepatitis B virus
CHEMBL613497
EC50 6.92 6.7475 120.0 4
Hepatitis C virus
CHEMBL379
EC50 6.89 6.4317 130.0 6
Unchecked
CHEMBL612545
Ki 6.52 5.6325 300.0 4
Anoctamin-1
CHEMBL2046267
IC50 6.37 6.37 424.0 1
Entamoeba histolytica
CHEMBL612853
IC50 6.3 5.855 504.0 2
Histone deacetylase 6
CHEMBL1865
IC50 6.0 6.0 1011.0 1
Vaccinia virus
CHEMBL613493
EC50 5.71 5.71 1950.0 1
Chikungunya virus
CHEMBL4296563
EC50 5.71 5.515 1960.0 4
Cryptosporidium parvum
CHEMBL612855
EC50 5.7 5.5775 2000.0 4
Unchecked
CHEMBL612545
IC50 5.69 4.874 2061.2 5
SARS-CoV-2
CHEMBL4303835
EC50 5.67 5.67 2120.0 1
SARS-CoV-2
CHEMBL4303835
IC50 5.55 4.815 2818.4 2
Cryptosporidium parvum
CHEMBL612855
IC50 5.49 5.455 3250.0 2
Plasmodium berghei
CHEMBL612653
IC50 5.41 5.41 3890.0 1
Leishmania mexicana
CHEMBL612880
IC50 5.21 5.21 6180.0 2
Leishmania amazonensis
CHEMBL612877
IC50 5.14 5.14 7230.0 2
Aldo-keto reductase family 1 member B1
CHEMBL1900
IC50 5.08 5.08 8220.0 1
Signal transducer and activator of transcription 3
CHEMBL4026
IC50 5.01 5.005 9800.0 2
Pyruvate-flavodoxin oxidoreductase
CHEMBL3308992
Ki 4.98 4.98 10500.0 1
Vero
CHEMBL391
IC50 4.97 4.97 10740.0 1
HCT-116
CHEMBL394
IC50 4.95 4.95 11200.0 1
Trypanosoma cruzi
CHEMBL368
IC50 4.73 4.73 18730.0 3
Unchecked
CHEMBL612545
EC50 4.7 4.7 20170.0 1
HL-60
CHEMBL383
IC50 4.7 4.7 20100.0 1
Caco-2
CHEMBL614058
IC50 4.57 4.57 26800.0 1
HeLa
CHEMBL399
IC50 4.46 4.46 35000.0 2
PC-3
CHEMBL390
IC50 4.35 4.35 44700.0 1
Trehalose-binding lipoprotein LpqY
CHEMBL5169230
Kd 4.07 4.07 85400.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 6500.0 ng.hr.mL-1 Rattus norvegicus
AUC 2040.0 ng.hr.mL-1 Rattus norvegicus
AUC 14100.0 ng.hr.mL-1 Rattus norvegicus
AUC 15950.0 ng.hr.mL-1 Rattus norvegicus
AUC 202.3 - Chlorocebus sabaeus
AUC 3200.0 ng.hr.mL-1 Rattus norvegicus
AUC 11200.0 ng.hr.mL-1 Rattus norvegicus
CL 105.0 mL.min-1.kg-1 Rattus norvegicus
CL 8.333 mL.min-1.kg-1 Rattus norvegicus
Cmax 66712.23 nM Rattus norvegicus
Cmax 35959.52 nM Rattus norvegicus
Cmax 2414.66 nM Rattus norvegicus
Cmax 15034.66 nM Rattus norvegicus
Cmax 3254.25 nM Rattus norvegicus
Cmax 9111.91 nM Rattus norvegicus
F 30.0 % Homo sapiens
F 2.8 % Rattus norvegicus
F 5.7 % Rattus norvegicus
T1/2 0.1 hr Homo sapiens
T1/2 0.2 hr Rattus norvegicus
T1/2 0.6 hr Rattus norvegicus
T1/2 0.05 hr Rattus norvegicus
T1/2 0.8 hr Rattus norvegicus
T1/2 0.3 hr Rattus norvegicus
T1/2 7.3 hr -
Tmax 2.1 hr Rattus norvegicus
Tmax 0.7 hr Rattus norvegicus
Tmax 0.4 hr Rattus norvegicus
Tmax 0.7 hr Rattus norvegicus
Tmax 0.08333 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Giardia intestinalis IC50 = 15.0 nM 7.82 Giardicidal activity against Giardia intestinalis IMSS isolate incubated for 48 ... 33360795
Giardia intestinalis IC50 = 17.0 nM 7.77 Giardicidal activity against metronidazole-resistant Giardia intestinalis incuba... 33360795
Giardia intestinalis IC50 = 18.0 nM 7.75 Giardicidal activity against Giardia intestinalis WB ATCC 30957 incubated for 48... 33360795
Giardia intestinalis IC50 = 21.0 nM 7.68 Giardicidal activity against albendazole-resistant Giardia intestinalis incubate... 33360795
Trichomonas vaginalis IC50 = 68.0 nM 7.17 Antiprotozoan activity against Trichomonas vaginalis GT3 trophozoites after 48 h... 21397502
Trichomonas vaginalis IC50 = 68.0 nM 7.17 Antimicrobial activity against Trichomonas vaginalis GT3 incubated for 48 hrs fo... 24529307
Trichomonas vaginalis IC50 = 68.0 nM 7.17 Trichomonicidal activity against Trichomonas vaginalis GT3 compound treated for ... 25801157
Trichomonas vaginalis IC50 = 68.0 nM 7.17 Antiprotozoal activity against Trichomonas vaginalis GT3 trophozoites incubated ... 28645659
Trichomonas vaginalis IC50 = 79.43 nM 7.1 Antimicrobial activity against Trichomonas vaginalis GT3 incubated for 48 hrs fo... 24529307
Hepatitis B virus IC50 = 120.0 nM 6.92 Antiviral activity against HBV infected in human HepG2(2.2.15) cells assessed as... 28383274
Hepatitis B virus EC50 = 120.0 nM 6.92 Inhibition of HBV DNA replication -
Hepatitis B virus EC50 = 120.0 nM 6.92 Antiviral activity against Hepatitis B virus infected in human HepG2(2.2.15) cel... 21553812
Hepatitis B virus EC50 = 120.0 nM 6.92 Antiviral activity against Hepatitis B virus 24549242
Hepatitis C virus EC50 = 130.0 nM 6.89 Antiviral activity against HCV genotype 1a in replicon system 18710916
Hepatitis C virus EC50 = 160.0 nM 6.8 Antiviral activity against HCV genotype 1b in RP7 replicon cell after 4 days by ... 18710916
Hepatitis C virus EC50 = 210.0 nM 6.68 Antiviral activity against HCV genotype 1b infected in Ava5 cells assessed as in... 22059983
Unchecked Ki = 300.0 nM 6.52 Inhibition of Giardia lamblia recombinant nitroreductase 1 (EAA43030.1) expresse... 17438059
Hepatitis C virus EC50 = 330.0 nM 6.48 Antiviral activity against HCV genotype 1a infected in Huh7.5 cells assessed as ... 22059983
Anoctamin-1 IC50 = 424.0 nM 6.37 Inhibition of YFP tagged ANO1 (unknown origin) expressed in FRT cells incubated ... 35512566
Entamoeba histolytica IC50 = 504.0 nM 6.3 Antiprotozoan activity against Entamoeba histolytica HM1-IMSS trophozoites after... 21397502

Literature References

PubMed DOI Target Context # Activities
18955526 10.1128/aac.00441-08 NON-PROTEIN TARGET 168
20404119 10.1128/aac.00901-09 Staphylococcus epidermidis 51
34055214 10.1021/acsmedchemlett.0c00544 HeLa 24
27750149 10.1016/j.ejmech.2016.09.080 Rattus norvegicus 17
34055214 10.1021/acsmedchemlett.0c00544 Signal transducer and activator of transcription 3 15
34055214 10.1021/acsmedchemlett.0c00544 ADMET 13
19736929 10.1021/jm9010719 Mycobacterium tuberculosis 12
17158936 10.1128/aac.01159-06 Unchecked 11
34055214 10.1021/acsmedchemlett.0c00544 Unchecked 8
18710916 10.1128/aac.00078-08 Hepatitis C virus 7
21397502 10.1016/j.bmcl.2011.02.100 Unchecked 6
22096616 10.1021/ml200157f Mycobacterium tuberculosis 5
33360795 10.1016/j.ejmech.2020.113110 Giardia intestinalis 5
- 10.6019/CHEMBL4808148 Histone deacetylase 6 4
28689975 10.1016/j.bmc.2017.06.049 Chikungunya virus 4
22059983 10.1021/jm201264t Hepatitis C virus 4
18591280 10.1128/aac.00207-08 Cryptosporidium parvum 4
17438059 10.1128/aac.01548-06 Giardia intestinalis 4
28689975 10.1016/j.bmc.2017.06.049 Unchecked 4
21553812 10.1021/jm200153p Hepatitis B virus 4

Data from ChEMBL 36 via Core Engine