METRONIDAZOLE

Search structure
Trade Names:
Synonyms:
Status: Approved (1963)
Entry Type: Small molecule
Molecule Category: Parent
ATC: A01AB17
UNII: 140QMO216E

Structure
InChI Key VAOCPAMSLUNLGC-UHFFFAOYSA-N
Smile Cc1ncc([N+](=O)[O-])n1CCO
InChI
InChI=1S/C6H9N3O3/c1-5-7-4-6(9(11)12)8(5)2-3-10/h4,10H,2-3H2,1H3

Physicochemical Descriptors

Property Name Value
Molecular Formula C6H9N3O3
Molecular Weight 171.16
AlogP 0.09
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 3.0
Polar Surface Area 81.19
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 12.0

Experimental and Estimated Properties

Property Name Value Unit Method
log P (octanol-water) -0.02 - EXP
Henry's Law Constant 1.69E-11 atm-m3/mole EST
Atmospheric OH Rate Constant 9.30E-12 cm3/molecule-sec EST
Melting Point 160.5 deg C EXP
Water Solubility 9500 mg/L EXP
Vapor Pressure 3.05E-07 mm Hg EST

Pharmacology

Action Mechanism of Action Reference
INHIBITOR DNA inhibitor FDA Wikipedia
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Oxidoreductase
- - - - 17
Enzyme
- - - 3300 17
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 103

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Duodenal Ulcer 4 D004381 ClinicalTrials
Fecal Incontinence 3 D005242 ClinicalTrials
Crohn Disease 3 D003424 ClinicalTrials
Periodontitis 3 D010518 ClinicalTrials
HIV Infections 3 D015658 ClinicalTrials
Abscess 3 D000038 ClinicalTrials
Colorectal Neoplasms 3 D015179 ClinicalTrials
Lymphoma, Non-Hodgkin 3 D008228 ClinicalTrials
Trichomonas Vaginitis 3 D014247 ClinicalTrials
Helicobacter Infections 3 D016481 ClinicalTrials
Pelvic Inflammatory Disease 3 D000292 ClinicalTrials
Skin Diseases 3 D012871 ClinicalTrials
Vaginal Discharge 3 D019522 ClinicalTrials
Blepharitis 3 D001762 ClinicalTrials
Colorectal Neoplasms 3 D015179 ClinicalTrials
Mycoses 3 D009181 ClinicalTrials
Gingivitis 3 D005891 ClinicalTrials
Diarrhea 3 D003967 ClinicalTrials
Candidiasis 3 D002177 ClinicalTrials
Kidney Calculi 3 D007669 ClinicalTrials
Hemorrhoids 3 D006484 ClinicalTrials
Enterocolitis, Pseudomembranous 3 D004761 ClinicalTrials
Carcinoma, Non-Small-Cell Lung 2 D002289 ClinicalTrials
Colitis, Ulcerative 2 D003093 ClinicalTrials
Lichen Planus, Oral 2 D017676 ClinicalTrials
Malnutrition 2 D044342 ClinicalTrials
Clostridium Infections 2 D003015 ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-Cell 2 D015451 ClinicalTrials
Uterine Cervical Neoplasms 2 D002583 ClinicalTrials
Tuberculosis, Multidrug-Resistant 2 D018088 ClinicalTrials
Clostridium Infections 2 D003015 ClinicalTrials
Brain Diseases 2 D001927 ClinicalTrials
Pilonidal Sinus 2 D010864 ClinicalTrials
Rectal Neoplasms 2 D012004 ClinicalTrials
Appendicitis 2 D001064 ClinicalTrials
Cholangitis, Sclerosing 1 D015209 ClinicalTrials
Central Serous Chorioretinopathy 1 D056833 ClinicalTrials
Periapical Periodontitis 1 D010485 ClinicalTrials
Vaginitis 0 D014627 ClinicalTrials
Osteomyelitis 0 D010019 ClinicalTrials

Related Entries

MCS

Salt
Salt
Mixture
Mixture

Side Effects from Label

Side effects Relative Frequency (%) Labels
Infections and infestations Fungal infection 22.0
Skin and subcutaneous tissue disorders Pruritus 19.0
Nervous system disorders Headache 18.0
Gastrointestinal disorders Nausea 18.0
Skin and subcutaneous tissue disorders Pruritus 15.8
Nervous system disorders Headache 15.4
General disorders and administration site conditions Pain 15.2
Infections and infestations Vaginal infection 15.0
Vaginal inflammation 15.0
Infections and infestations Infection 14.8
Infections and infestations Infestation 14.8
Infections and infestations Vaginal infection 14.6
Vaginal inflammation 14.6
Infections and infestations Infection 13.6
Infections and infestations Infestation 13.6
Gastrointestinal disorders Abdominal pain 12.0
Gastrointestinal disorders Constipation 12.0
Infections and infestations Fungal infection 12.0
Reproductive system and breast disorders Vaginal discharge 12.0
Infections and infestations Vaginal infection 12.0
Vaginal inflammation 12.0
Infections and infestations Vaginal infection 11.2
Vaginal inflammation 11.2
Gastrointestinal disorders Nausea 10.5
General disorders and administration site conditions Pain 10.3
Gastrointestinal disorders Diarrhoea 10.0
Cardiac disorders Dizziness 10.0
Gastrointestinal disorders Nausea 10.0
Infections and infestations Vaginal infection 10.0
Vaginal inflammation 10.0
Reproductive system and breast disorders Vulvovaginal pruritus 10.0
Infections and infestations Fungal infection 9.1
Gastrointestinal disorders Dysgeusia 9.0
Reproductive system and breast disorders Pruritus genital 9.0
Reproductive system and breast disorders Pruritus genital 8.77
Gastrointestinal disorders Dysgeusia 8.61
Infections and infestations Fungal infection 8.6
Reproductive system and breast disorders Vaginal discharge 8.2
Infections and infestations Bacterial infection 7.12
General disorders and administration site conditions Influenza like illness 7.02
Gastrointestinal disorders Abdominal discomfort 7.0
Infections and infestations Bacterial infection 7.0
Nervous system disorders Headache 7.0
General disorders and administration site conditions Influenza like illness 7.0
Skin and subcutaneous tissue disorders Skin disorder 6.46
General disorders and administration site conditions Influenza like illness 6.37
Skin and subcutaneous tissue disorders Skin disorder 6.35
Infections and infestations Bacterial infection 6.0
General disorders and administration site conditions Decreased appetite 6.0
General disorders and administration site conditions Influenza like illness 6.0
Skin and subcutaneous tissue disorders Pruritus 6.0
Infections and infestations Urinary tract infection 6.0
Infections and infestations Bacterial infection 5.96
Infections and infestations Urinary tract infection 5.61
Reproductive system and breast disorders Pruritus genital 5.24
Gastrointestinal disorders Abdominal pain 5.0
Gastrointestinal disorders Gastrointestinal pain 5.0
Nervous system disorders Headache 5.0
Reproductive system and breast disorders Pruritus genital 5.0
Gastrointestinal disorders Abdominal discomfort 4.7
Gastrointestinal disorders Abdominal pain 4.56
Gastrointestinal disorders Gastrointestinal pain 4.56
Infections and infestations Rhinitis 4.49
Infections and infestations Nasopharyngitis 4.23
Gastrointestinal disorders Diarrhoea 4.12
Cardiac disorders Dizziness 4.12
Infections and infestations Upper respiratory tract infection 4.12
Gastrointestinal disorders Abdominal pain 4.0
Gastrointestinal disorders Diarrhoea 4.0
Cardiac disorders Dizziness 4.0
Gastrointestinal disorders Gastrointestinal pain 4.0
Nervous system disorders Headache 4.0
Infections and infestations Rhinitis 4.0
Infections and infestations Upper respiratory tract infection 4.0
Gastrointestinal disorders Vomiting 4.0
Respiratory, thoracic and mediastinal disorders Mediastinal disorder 3.95
Gastrointestinal disorders Abdominal pain 3.75
Gastrointestinal disorders Gastrointestinal pain 3.75
Infections and infestations Rhinitis 3.51
Infections and infestations Upper respiratory tract infection 3.51
Musculoskeletal and connective tissue disorders Connective tissue disorder 3.41
Infections and infestations Candida infection 3.37
Reproductive system and breast disorders Dysmenorrhoea 3.37
Musculoskeletal and connective tissue disorders Muscle spasms 3.3
Gastrointestinal disorders Nausea 3.3
Nervous system disorders Nervous system disorder 3.23
Infections and infestations Nasopharyngitis 3.05
Infections and infestations Candida infection 3.0
Reproductive system and breast disorders Dysmenorrhoea 3.0
Gastrointestinal disorders Nausea 3.0
Gastrointestinal disorders Pelvic discomfort 3.0
Gastrointestinal disorders Pharyngitis 3.0
Infections and infestations Sinusitis 3.0
Renal and urinary disorders Urine abnormality 3.0
Investigations Urine analysis abnormal 3.0
Infections and infestations Candida infection 2.81
Gastrointestinal disorders Nausea 2.81
Musculoskeletal and connective tissue disorders Connective tissue disorder 2.65
Respiratory, thoracic and mediastinal disorders Mediastinal disorder 2.65
Infections and infestations Sinusitis 2.62
Renal and urinary disorders Urine abnormality 2.62
Investigations Urine analysis abnormal 2.62
Infections and infestations Upper respiratory tract infection 2.51
Gastrointestinal disorders Diarrhoea 2.5
Reproductive system and breast disorders Vulvovaginal burning sensation 2.5
Reproductive system and breast disorders Dysmenorrhoea 2.46
Infections and infestations Urinary tract infection 2.25
Gastrointestinal disorders Nausea 2.2
Skin and subcutaneous tissue disorders Pruritus
Gastrointestinal disorders Vomiting 2.2
Reproductive system and breast disorders Vulvovaginal burning sensation
Nervous system disorders Headache 2.15
Infections and infestations Upper respiratory tract infection 2.12
Infections and infestations Sinusitis 2.11
Nervous system disorders Headache 2.1
General disorders and administration site conditions Asthenia 2.0
Cardiac disorders Dizziness 2.0
Gastrointestinal disorders Dry mouth 2.0
Skin and subcutaneous tissue disorders Dry skin 2.0
Reproductive system and breast disorders Dysmenorrhoea 2.0
Skin and subcutaneous tissue disorders Erythema 2.0
General disorders and administration site conditions Fatigue 2.0
Immune system disorders Hypersensitivity 2.0
Gastrointestinal disorders Pharyngitis 2.0
Infections and infestations Sinusitis 2.0
Infections and infestations Urinary tract infection 2.0
Reproductive system and breast disorders Vaginal discharge 2.0
Gastrointestinal disorders Pelvic discomfort 1.9
Gastrointestinal disorders Dry mouth 1.87
Skin and subcutaneous tissue disorders Dry skin 1.8
Skin and subcutaneous tissue disorders Erythema 1.8
Cardiac disorders Dizziness 1.7
Gastrointestinal disorders Dysgeusia 1.7
Investigations White blood cell count decreased 1.7
Infections and infestations Fungal infection 1.6
Infections and infestations Bronchitis 1.59
Skin and subcutaneous tissue disorders Dry skin 1.59
Respiratory, thoracic and mediastinal disorders Nasal congestion 1.59
Nervous system disorders Nervous system disorder 1.59
Infections and infestations Sinusitis 1.59
Vascular disorders Angiopathy 1.44
Infections and infestations Influenza 1.44
Infections and infestations Sinusitis 1.44
Skin and subcutaneous tissue disorders Erythema 1.4
Gastrointestinal disorders Pharyngitis 1.4
Skin and subcutaneous tissue disorders Pruritus 1.4
Skin and subcutaneous tissue disorders Rosacea 1.4
Skin and subcutaneous tissue disorders Skin irritation 1.4
Renal and urinary disorders Urine abnormality 1.4
Investigations Urine analysis abnormal 1.4
Immune system disorders Dermatitis contact 1.26
General disorders and administration site conditions Decreased appetite 1.1
Infections and infestations Bronchitis 1.08
Skin and subcutaneous tissue disorders Dry skin 1.08
Vascular disorders Hypertension 1.08
Respiratory, thoracic and mediastinal disorders Nasal congestion 1.08
Infections and infestations Urinary tract infection 1.08
Musculoskeletal and connective tissue disorders Back pain 1.06
Neoplasms benign, malignant and unspecified (incl cysts and polyps) Basal cell carcinoma 1.06
Neoplasms benign, malignant and unspecified (incl cysts and polyps) Neoplasm 1.06
Infections and infestations Vulvovaginal mycotic infection 1.06
Gastrointestinal disorders Diarrhoea 1.05
Cardiac disorders Dizziness 1.05
Reproductive system and breast disorders Breast pain 1.0
General disorders and administration site conditions Burning sensation 1.0
General disorders and administration site conditions Decreased appetite 1.0
Skin and subcutaneous tissue disorders Dermatitis 1.0
Gastrointestinal disorders Diarrhoea 1.0
Cardiac disorders Dizziness 1.0
Gastrointestinal disorders Dry mouth 1.0
Skin and subcutaneous tissue disorders Erythema 1.0
Eye disorders Eye disorder 1.0
Infections and infestations Infection 1.0
Eye disorders Lacrimation increased 1.0
Reproductive system and breast disorders Metrorrhagia 1.0
Musculoskeletal and connective tissue disorders Muscle spasms 1.0
Gastrointestinal disorders Pharyngitis 1.0
Skin and subcutaneous tissue disorders Pruritus 1.0
Skin and subcutaneous tissue disorders Rash 1.0
Skin and subcutaneous tissue disorders Rosacea 1.0
Skin and subcutaneous tissue disorders Skin irritation 1.0
Renal and urinary disorders Urine abnormality 1.0
Investigations Urine analysis abnormal 1.0
General disorders and administration site conditions Burning sensation 0.9
Eye disorders Eye disorder 0.9
Eye disorders Lacrimation increased 0.9
Neoplasms benign, malignant and unspecified (incl cysts and polyps) Neoplasm 0.718
Gastrointestinal disorders Dry mouth 0.702
Musculoskeletal and connective tissue disorders Back pain 0.539
Vascular disorders Angiopathy 0.529
Immune system disorders Dermatitis contact 0.529
Nervous system disorders Headache 0.529
Vascular disorders Hypertension 0.529
Infections and infestations Influenza 0.529
Infections and infestations Urinary tract infection 0.529
Gastrointestinal disorders Dysgeusia 0.351
Neoplasms benign, malignant and unspecified (incl cysts and polyps) Basal cell carcinoma 0.18
Infections and infestations Vulvovaginal mycotic infection 0.18

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Nervous system disorders
16.67
General disorders and administration site conditions
11.95
Immune system disorders
11.02
Gastrointestinal disorders
10.26
Skin and subcutaneous tissue disorders
9.08
Injury, poisoning and procedural complications
5.84
Psychiatric disorders
5.23
Vascular disorders
4.29
Infections and infestations
3.86
Musculoskeletal and connective tissue disorders
3.58
Cardiac disorders
3.3
Respiratory, thoracic and mediastinal disorders
2.7
Investigations
2.24

Cross References

Resources Reference
CAS NUMBER 443-48-1
ChEBI 6909
ChEMBL CHEMBL137
DrugBank DB00916
DrugCentral 1790
EPA CompTox DTXSID2020892
FDA SRS 140QMO216E
Human Metabolome Database HMDB0015052
Guide to Pharmacology 10914
KEGG C07203
PDB 2MN
PharmGKB PA450484
PubChem 4173
SureChEMBL SCHEMBL23042
ZINC ZINC000000113442
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