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Compound Detail

CHEMBL137

METRONIDAZOLE
💊 Approved Drug
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💊 Approved Drug
Cc1ncc([N+](=O)[O-])n1CCO

Basic Information

ChEMBL ID CHEMBL137
Name METRONIDAZOLE
Phase Approved
Structure Type MOL
InChI Key VAOCPAMSLUNLGC-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Acea Anabact BAY-5360 BAYER 5360 BAYER-5360 Deflamon Drazifon Elyzol Flagyl Flagyl 375 Flagyl compak Flagyl er +18 more
10
Targets
194
Activities
3
Assay Types
29
PK Parameters
20
Publications
30
Known Names
20
Indications
1
Mechanisms

Molecular Properties

171.2
MW (Da)
0.09
ALogP
5
HBA
1
HBD
81.2
PSA (Ų)
0.52
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1963
Availability Prescription
Chirality Achiral

Routes of Administration

Oral Parenteral Topical

Flags

Black Box Warning Natural Product
USAN Stem -nidazole
USAN Year 1962

Extended Properties

Molecular Formula C6H9N3O3
MW 171.16
Aromatic Rings 1
Heavy Atoms 12
NP-Likeness -1.67

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
DNA inhibitor INHIBITOR DNA

Indications

Amebiasis Bacterial Infections Duodenal Ulcer Infections Intraabdominal Infections Pneumonia Rosacea Sepsis Trichomonas Infections Uterine Cervicitis Vaginosis, Bacterial Abscess Blepharitis Candidiasis Colorectal Neoplasms Colorectal Neoplasms Colorectal Neoplasms Crohn Disease Diarrhea Enterocolitis, Pseudomembranous

ATC Classification

A01AB17
metronidazole
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: STOMATOLOGICAL PREPARATIONS
D06BX01
metronidazole
Level 1: DERMATOLOGICALS
Level 2: ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE
G01AF01
metronidazole
Level 1: GENITO URINARY SYSTEM AND SEX HORMONES
Level 2: GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
J01XD01
metronidazole
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIBACTERIALS FOR SYSTEMIC USE
P01AB01
metronidazole
Level 1: ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
Level 2: ANTIPROTOZOALS
P01AB51
metronidazole, combinations
Level 1: ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
Level 2: ANTIPROTOZOALS

Drug Warnings

Black Box Warning
carcinogenicity
Country: United States
Black Box Warning
infectious disease
Country: United States
Black Box Warning
nephrotoxicity
Country: United States

Activity Summary

IC50 173 meas. best 7.17
EC50 19 meas. best 6.1
Ki 2 meas. best 5.48

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Trichomonas vaginalis
CHEMBL612884
IC50 7.17 6.0151 68.0 39
Entamoeba histolytica
CHEMBL612853
IC50 6.7 5.7931 200.0 65
Giardia intestinalis
CHEMBL612652
IC50 6.3 5.734 500.0 52
NON-PROTEIN TARGET
CHEMBL3879801
EC50 6.1 5.3517 794.3 6
Tritrichomonas foetus
CHEMBL4888467
IC50 6.05 6.05 900.0 1
Trichomonas vaginalis
CHEMBL612884
EC50 5.92 5.6567 1200.0 3
Giardia intestinalis
CHEMBL612652
EC50 5.83 5.23 1479.1 7
Entamoeba histolytica
CHEMBL612853
EC50 5.7 5.4333 2000.0 3
Entamoeba invadens
CHEMBL1075346
IC50 5.52 5.52 3000.0 1
Thioredoxin reductase
CHEMBL3879846
Ki 5.48 5.48 3300.0 1
ADMET
CHEMBL612558
IC50 5.27 5.27 5400.0 1
Mycobacterium tuberculosis
CHEMBL360
IC50 4.85 4.645 14000.0 2
Unchecked
CHEMBL612545
Ki 4.37 4.37 42610.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC - - Mus musculus
AUC 35.0 - Cavia porcellus
AUC 595.0 ng.hr.mL-1 Homo sapiens
AUC 962.0 ng.hr.mL-1 Homo sapiens
CL 0.85 mL.min-1.kg-1 Homo sapiens
CL 0.7 mL.min-1.kg-1 Homo sapiens
CL 0.85 mL.min-1.kg-1 Homo sapiens
CL 0.85 mL.min-1.kg-1 Homo sapiens
CL 3.0 uL.min-1.(10^6cells)-1 Rattus norvegicus
CL 3.0 uL.min-1.(10^6cells)-1 Homo sapiens
CL_renal 10.0 mL/min/1.73 m2 Homo sapiens
Cmax - - Mus musculus
Cmax 233699.46 nM Homo sapiens
Cmax 70109.84 nM Homo sapiens
Cmax 35054.92 nM Homo sapiens
Cmax 186.96 nM Homo sapiens
Cmax 560.88 nM Homo sapiens
F 80.0 % Homo sapiens
Fu 0.89 - -
Fu 0.609 - -
Fu 0.89 - Homo sapiens
Fu 0.96 - Homo sapiens
Fu 0.96 - Homo sapiens
MRT 7.8 hr Homo sapiens
T1/2 20.0 hr -
T1/2 7.1 hr Homo sapiens
T1/2 6.0 hr -
Tmax 1.0 hr Homo sapiens
Tmax 6.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Trichomonas vaginalis IC50 = 68.0 nM 7.17 Anti-trichomonas activity against Trichomonas vaginalis JT incubated for 48 hrs ... 33234343
Entamoeba histolytica IC50 = 200.0 nM 6.7 Antiparasitic activity against Entamoeba histolytica HM1-IMSS trophozoites asses... 31063376
Trichomonas vaginalis IC50 = 210.0 nM 6.68 Growth inhibition of mtronidazole-resistant Trichomonas vaginalis after 24 hrs b... 22579483
Trichomonas vaginalis IC50 = 216.0 nM 6.67 Antiprotozoal activity against Trichomonas vaginalis G3 after 48 hrs 20430484
Entamoeba histolytica IC50 = 230.0 nM 6.64 Antiprotozoal activity against Entamoeba histolytica HM-1:IMSS 26517282
Entamoeba histolytica IC50 = 230.0 nM 6.64 Antiprotozoal activity against Entamoeba histolytica HM-1:IMSS 24502360
Trichomonas vaginalis IC50 = 236.0 nM 6.63 Antiparasitic activity against trophozoite stage of Trichomonas vaginalis CNCD 1... 28595066
Trichomonas vaginalis IC50 = 236.0 nM 6.63 Antiprotozoal activity against trophozoite stage of Trichomonas vaginalis GT3 as... 23731944
Trichomonas vaginalis IC50 = 236.0 nM 6.63 Antiprotozoan activity against Trichomonas vaginalis GT3 trophozoites compound t... 22047694
Trichomonas vaginalis IC50 = 236.0 nM 6.63 Antiprotozoal activity against Trichomonas vaginalis GT3 trophozoites after 48 h... 19186059
Trichomonas vaginalis IC50 = 290.0 nM 6.54 Antimicrobial activity against Trichomonas vaginalis GT3 incubated for 48 hrs fo... 24529307
Trichomonas vaginalis IC50 = 286.0 nM 6.54 Antiprotozoal activity against Trichomonas vaginalis 18486471
Trichomonas vaginalis IC50 = 290.0 nM 6.54 Antiparasitic activity against Trichomonas vaginalis GT3 trophozoites after 48 h... 19208443
Trichomonas vaginalis IC50 = 290.0 nM 6.54 Antimicrobial activity against Trichomonas vaginalis GT3 after 48 hrs 20674375
Trichomonas vaginalis IC50 = 290.0 nM 6.54 Antiprotozoan activity against Trichomonas vaginalis GT3 trophozoites after 48 h... 21397502
Trichomonas vaginalis IC50 = 290.0 nM 6.54 Trichomonicidal activity against Trichomonas vaginalis GT3 compound treated for ... 25801157
Trichomonas vaginalis IC50 = 290.0 nM 6.54 Antiprotozoal activity against Trichomonas vaginalis GT3 trophozoites incubated ... 28645659
Trichomonas vaginalis IC50 = 316.23 nM 6.5 Antimicrobial activity against Trichomonas vaginalis GT3 incubated for 48 hrs fo... 24529307
Entamoeba histolytica IC50 = 350.0 nM 6.46 Antiprotozoan activity against Entamoeba histolytica HM1-IMSS trophozoites compo... 22047694
Entamoeba histolytica IC50 = 350.0 nM 6.46 Antiprotozoal activity against Entamoeba histolytica HM-1:IMSS after 48 hrs 20430484

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 439
19581457 10.1128/aac.00908-08 NON-PROTEIN TARGET 108
20100877 10.1128/aac.01788-09 NON-PROTEIN TARGET 68
19805556 10.1128/aac.01003-09 Prevotella bivia 56
19223619 10.1128/aac.01449-08 Helicobacter pylori 40
19805556 10.1128/aac.01003-09 NON-PROTEIN TARGET 34
18955522 10.1128/aac.00595-08 NON-PROTEIN TARGET 31
35175750 10.1021/acs.jmedchem.1c02045 Helicobacter pylori 26
18411326 10.1128/aac.00019-08 NON-PROTEIN TARGET 24
33231455 10.1021/acs.jnatprod.0c00892 Entamoeba histolytica 20
35175750 10.1021/acs.jmedchem.1c02045 Clostridioides difficile 20
- 10.1007/s00044-012-0429-8 Helicobacter pylori 19
24224794 10.1021/np400145u Mycobacterium tuberculosis 19
16472241 10.2174/1570163043334794 Hepatotoxicity 18
32869995 10.1021/acs.jmedchem.0c00910 Giardia intestinalis 17
19223615 10.1128/aac.01557-08 NON-PROTEIN TARGET 17
20585132 10.1128/aac.00481-10 NON-PROTEIN TARGET 16
37732641 10.1021/acs.jmedchem.3c01249 Clostridioides difficile 15
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
18442909 10.1016/j.bmcl.2008.04.033 Helicobacter pylori 13

Data from ChEMBL 36 via Core Engine