Metronidazole

Summary

Metronidazole (CHEMBL137) is an approved small-molecule antitrichomonal drug (ATC D06BX01); indicated across 57 conditions including bacterial vaginosis and rosacea.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: D06BX01 (+5 more)
• Indications: 57 conditions
• Clinical trials: 317
• Chemistry: 171.15 Da · C6H9N3O3

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL137
Name	Metronidazole
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	4173
ChEBI	CHEBI:6909
ATC	D06BX01, P01AB51, G01AF01, A01AB17, P01AB01, J01XD01
Molecular formula	C6H9N3O3
Molecular weight	171.15
InChIKey	VAOCPAMSLUNLGC-UHFFFAOYSA-N

SMILES: CC1=NC=C(N1CCO)[N+](=O)[O-]

IUPAC name: 2-(2-methyl-5-nitroimidazol-1-yl)ethanol

ChEBI definition: A member of the class of imidazoles substituted at C-1, -2 and -5 with 2-hydroxyethyl, nitro and methyl groups respectively. It has activity against anaerobic bacteria and protozoa, and has a radiosensitising effect on hypoxic tumour cells. It may be given by mouth in tablets, or as the benzoate in an oral suspension. The hydrochloride salt can be used in intravenous infusions. Metronidazole is a prodrug and is selective for anaerobic bacteria due to their ability to intracellularly reduce the nitro group of metronidazole to give nitroso-containing intermediates. These can covalently bind to DNA, disrupting its helical structure, inducing DNA strand breaks and inhibiting bacterial nucleic acid synthesis, ultimately resulting in bacterial cell death.

Pharmacological roles (ChEBI): antitrichomonal drug, prodrug, antibacterial drug, antimicrobial agent, antiparasitic agent, radiosensitizing agent, antiamoebic agent.

Other ChEBI roles (chemical / environmental): xenobiotic, environmental contaminant.

Also known as: Acea, Anabact, BAY-5360, BAYER 5360, BAYER-5360, Deflamon, Drazifon, Elyzol, Flagyl, Flagyl compak, Flagyl er, Flagyl-400

Parent form; salt/anhydrous children: CHEMBL1200869

Patent coverage: 50,922 distinct patent families (141,757 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Broader ChEMBL bioactivity targets: 5 (assay-derived). Sample: Prelamin-A/C, Thyroid hormone receptor beta, Thyrotropin receptor, Aldehyde dehydrogenase 1A1, Mitogen-activated protein kinase 1.

Bioactivity

ChEMBL activities: 4 potent at pChembl ≥ 5 of 7 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
LMNA	5.6	Potency	2512	nM	CHEMBL_ACT_3637368
THRB	5.15	Potency	7080	nM	CHEMBL_ACT_4019197
ALDH1A1	5.1	Potency	7943	nM	CHEMBL_ACT_4143653
MAPK1	5.05	Potency	8912	nM	CHEMBL_ACT_4737992

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

57 indications (10 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
bacterial vaginosis	4	MONDO:0005316	EFO:0003932
rosacea	4	MONDO:0006604	EFO:1000760
duodenal ulcer	4	MONDO:0005412	EFO:0004607
pneumonia	4	MONDO:0005249	EFO:0003106
bacterial infectious disease	4	MONDO:0005113	EFO:0000771
trichomoniasis	4	MONDO:0002154	DOID:1947
cervicitis	4	MONDO:0002345	MONDO:0003632
amebiasis	4	MONDO:0005644	EFO:0007144
Crohn disease	3	MONDO:0005011	EFO:0000384
periodontitis	3	MONDO:0005076	EFO:0000649
HIV infectious disease	3	MONDO:0005109	EFO:0000764
abscess	3	MONDO:0005227	EFO:0003030
colorectal neoplasm	3	MONDO:0005335	EFO:0004142
non-Hodgkin lymphoma	3	MONDO:0018908	EFO:0005952
Trichomonas vaginitis urogenital infection	3	MONDO:0005993	EFO:0007521
Helicobacter pylori infectious disease	3	MONDO:0006781	EFO:1000961
pelvic inflammatory disease	3	MONDO:0000922	EFO:1001388
skin disorder	3	MONDO:0005093	EFO:0000701
vaginal discharge	3	MONDO:0002770	EFO:0009365
blepharitis	3	MONDO:0004785	EFO:0009536
colorectal adenocarcinoma	3	MONDO:0005008	EFO:0000365
fungal infectious disease	3	MONDO:0002041	MONDO:0002041
vaginitis	3	MONDO:0002234	MONDO:0002234
gingivitis	3	MONDO:0002508	MONDO:0002508
hemorrhoid	3	MONDO:0004872	EFO:0009552
Clostridium difficile colitis	3	MONDO:0000705	EFO:1001314
diarrheal disease	3	MONDO:0001673	HP:0002014
candidiasis	3	MONDO:0002026	MONDO:0002026
hidradenitis suppurativa	3	MONDO:0006559	EFO:1000710
B-cell chronic lymphocytic leukemia	2	MONDO:0004948	EFO:0000095
ulcerative colitis	2	MONDO:0005101	EFO:0000729
cervical carcinoma	2	MONDO:0005131	EFO:0001061
non-small cell lung carcinoma	2	MONDO:0005233	EFO:0003060
appendicitis	2	MONDO:0005649	EFO:0007149
rectal cancer	2	MONDO:0006519	EFO:1000657
Clostridium infectious disease	2	MONDO:0024388	EFO:1000874
lichen planus, oral	2	MONDO:0043923	EFO:0008517
multidrug-resistant tuberculosis	2	MONDO:0005861	EFO:0007381
brain disorder	2	MONDO:0005560	HP:0001298
pilonidal sinus	2	MONDO:0008249	HP:0010769
giardiasis	2	MONDO:0001103	DOID:10718
exocrine pancreatic carcinoma	2	MONDO:0005192	EFO:0002618
periodontal disorder	2	MONDO:0002635	MONDO:0002635
tuberculosis	2	MONDO:0018076	MONDO:0018076
sclerosing cholangitis	1	MONDO:0018646	EFO:0004268
periapical periodontitis	1	MONDO:0004508	EFO:1001391
central serous chorioretinopathy	1	MONDO:0018616	EFO:0009784
pouchitis	1	MONDO:0005312	EFO:0003921
osteomyelitis	0	MONDO:0005246	EFO:0003102

8 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 317.

Phase distribution

Phase	Trials
PHASE4	116
Not specified	63
PHASE2	50
PHASE3	42
PHASE1	18
PHASE2/PHASE3	16
PHASE1/PHASE2	6
EARLY_PHASE1	6

Top trials by phase / activity

NCT	Phase	Status	Title
NCT03663504	PHASE4	ACTIVE_NOT_RECRUITING	Comparing No Mechanical Bowel Preparation With Oral Antibiotics Alone in Patients Undergoing Elective Colon Surgery
NCT04527055	PHASE4	ENROLLING_BY_INVITATION	The Efficacy of 10-day and 14-day Bismuth-based Quadruple Therapy in First-line H. Pylori Eradication
NCT04554693	PHASE4	ACTIVE_NOT_RECRUITING	The Use of Low Dose Metronidazole to Decrease Postoperative Pain After Endometriosis Surgery
NCT05061732	PHASE4	RECRUITING	Helicobacter Pylori Eradication and Follow-up
NCT05784311	PHASE4	RECRUITING	Standard Versus Prolonged Antibiotic Prophylaxis After Pancreatoduodenectomy (SPARROW)
NCT05874570	PHASE4	RECRUITING	Doxycycline for Helicobacter Pylori Rescue Treatment
NCT05929794	PHASE4	ACTIVE_NOT_RECRUITING	Pharmacokinetics of Transdermal Metronidazole
NCT06261840	PHASE4	RECRUITING	Refining Treatment Options for Trichomonas Vaginalis Infection: A Comparative Analysis of Metronidazole and Secnidazole
NCT06349122	PHASE4	NOT_YET_RECRUITING	Screen-and-treat Strategy for Vaginal Flora Abnormalities in Pregnant Women at High Risk of Preterm Birth
NCT06396078	PHASE4	RECRUITING	Improvement of PPROM Management With Prophylactic Antimicrobial Therapy (iPROMPT)
NCT06458543	PHASE4	RECRUITING	Optimization of Bacterial Vaginosis Treatment in Women of Reproductive Age
NCT06509139	PHASE4	ENROLLING_BY_INVITATION	Optimal Duration of Bismuth Quadruple Therapy for Helicobacter Pylori Eradication in Females As Compared with Males
NCT06561698	PHASE4	RECRUITING	High-dose Dual Therapy and Minocycline-cotaining Quadruple Therapy for Helicobacter Pylori Infection
NCT07180615	PHASE4	NOT_YET_RECRUITING	Gut Decolonisation With Neomycin/Metronidazole or Rifaximin Before Colon Surgery
NCT00157898	PHASE4	COMPLETED	A Study to Evaluate Ertapenem Versus It’s Comparator in the Treatment of Complicated Intra-abdominal Infections in Adults (0826-050)(COMPLETED)
NCT00236912	PHASE4	TERMINATED	A Study Comparing Safety and Efficacy of Levofloxacin and Metronidazole Versus Piperacillin/Tazobactam in Treating Complicated Appendicitis
NCT00324818	PHASE4	COMPLETED	Treatment of Bacterial Vaginosis
NCT00331994	PHASE4	COMPLETED	EFESO - EFficacy Enterogermina Small Intestinal Bacterial Overgrowth
NCT00334633	PHASE4	COMPLETED	Treatment of Bacterial Vaginosis (BV) With Tinidazole
NCT00376493	PHASE4	TERMINATED	Prolonged Treatment for Infected Abortion After Hospital Discharge.
NCT00464542	PHASE4	COMPLETED	Asymptomatic Bacterial Vaginosis and Herpes Simplex Virus Type 2 (BV/HSV-2) Shedding Study
NCT00613769	PHASE4	COMPLETED	Orally Administered Trimethoprim-sulfamethoxazole and Metronidazole as Prophylaxis of Infection Following Elective Colorectal Surgery
NCT00707369	PHASE4	COMPLETED	Adjunctive Antimicrobial Therapy of Periodontitis: Long-Term Effects on Disease Progression and Oral Microbiological Colonization
NCT00752947	PHASE4	UNKNOWN	Efficacy and Safety Trial to Assess Moxifloxacin in Treating Community-Acquired Pneumonia (CAP) With Aspiration Factors
NCT00841854	PHASE4	COMPLETED	Comparison of 7-day and 14-day Bismuth Based Quadruple Therapy for Secondary Helicobacter Pylori Eradication
NCT00855595	PHASE4	COMPLETED	Efficacy of Topical Azelaic Acid 15% Gel Plus Anti-inflammatory Dose Doxycycline or Metronidazole Gel 1% Plus Anti-inflammatory Dose Doxycycline in Moderate Papulopustular Rosacea
NCT01018095	PHASE4	COMPLETED	Trichomonas Vaginalis Recurrence Among HIV+ Women
NCT01139008	PHASE4	COMPLETED	Split-Face Tolerability Comparison Between MetroGel® 1% Versus Finacea® 15% in Subjects With Healthy Skin
NCT01139047	PHASE4	COMPLETED	Split-face Tolerability Comparison Between MetroGel® 1% vs Finacea® 15% in Subjects With Healthy Skin
NCT01153958	PHASE4	TERMINATED	Colposeptine for the Treatment of Bacterial Vaginosis
NCT01219764	PHASE4	COMPLETED	A Trial of Standard vs Half Dose Rabeprazole, Clarithromycin, Metronidazole and Amoxicillin in the Treatment of Helicobacter Pylori Infection
NCT01314976	PHASE4	COMPLETED	Treatment Study of Metronidazole to Treat Dientamoebiasis in Children
NCT01318928	PHASE4	UNKNOWN	The Treatment of Periodontal Diseases
NCT01426269	PHASE4	COMPLETED	Evaluation of Relapse, Efficacy and Safety of Long-term Treatment With Oracea® vs Placebo
NCT01506986	PHASE4	COMPLETED	Helicobacter Eradication Aspirin Trial
NCT01521403	PHASE4	UNKNOWN	Is it Effective to Treat Patients With Blastocystis Hominis Infection?
NCT01572597	PHASE4	UNKNOWN	Increased Re-eradication Rate of Helicobacter Pylori by Adding N-acetylcystein or Metronidazole to the Triple Therapy
NCT01596894	PHASE4	COMPLETED	Azithromycin Based Therapy for Induction of Remission in Active Pediatric Crohn’s Disease
NCT01668927	PHASE4	COMPLETED	Empirical Rescue Therapies of Helicobacter Pylori Infection
NCT01742429	PHASE4	COMPLETED	Levofloxacin and Bismuth-containing Therapy Versus Quadruple Therapy as Second-line Treatment of Resistant Helicobacter Pylori Infection

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline, but PharmGKB curates 1 clinical and 2 variant annotation(s) for this drug (gene-keyed; see PharmGKB).

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).