Metronidazole
Identification
- Name
- Metronidazole
- Accession Number
- DB00916
- Description
Metronidazole is a commonly used antibiotic, belonging to the nitroimidazole class of antibiotics.14 It is frequently used to treat gastrointestinal infections as well as trichomoniasis and giardiasis, and amebiasis which are parasitic infections.4 Metronidazole has been used as an antibiotic for several decades15, with added antiparasitic properties that set it apart from many other antibacterial drugs, allowing it to treat a wide variety of infections. It is available in capsule form, tablet form, and topical form, and suppository preparations for the treatment of various infections.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Metronidazole (DB00916)
- Weight
- Average: 171.154
Monoisotopic: 171.064391169 - Chemical Formula
- C6H9N3O3
- Synonyms
- 1-(2-hydroxy-1-ethyl)-2-methyl-5-nitroimidazole
- 1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole
- 1-(β-ethylol)-2-methyl-5-nitro-3-azapyrrole
- 1-(β-hydroxyethyl)-2-methyl-5-nitroimidazole
- 1-(β-oxyethyl)-2-methyl-5-nitroimidazole
- 2-methyl-1-(2-hydroxyethyl)-5-nitroimidazole
- 2-methyl-3-(2-hydroxyethyl)-4-nitroimidazole
- 2-methyl-5-nitroimidazole-1-ethanol
- Metronidazol
- Métronidazole
- Metronidazole
- Metronidazolum
- External IDs
- Bayer 5360
- BAYER-5360
- NSC-50364
- NSC-69587
- RP 8823
- RP-8823
Pharmacology
- Indication
Metronidazole is indicated for the treatment of confirmed trichomoniasis caused by Trichomonas vaginalis (except for in the first trimester of pregnancy) and the patient's sexual partners, bacterial vaginosis16, certain types of amebiasis, and various anaerobic infections.11 The above anaerobic infections may occur on the skin and skin structures, the abdomen, the heart, reproductive organs, central nervous system, and the respiratory system. Some may also be present in the bloodstream in cases of septicemia. Common infections treated by metronidazole are Bacteroides species infections, Clostridium infections, and Fusobacterium infections, as well as Peptococcus and Peptostreptococcus infections.14
It is also used off-label in the treatment of Crohn's disease and rosacea, as a prophylactic agent after surgery5, and in the treatment of Helicobacter pylori infection.7 It has also been studied in the prevention of preterm births and to treat periodontal disease.1,12
- Associated Conditions
- Abscess, Intra-Abdominal
- Acne Rosacea
- Amebiasis
- Anaerobic Infection
- Bacteremia
- Bacterial Endocarditis
- Bacterial Infection Due to Helicobacter Pylori (H. Pylori)
- Bacterial Vaginosis (BV)
- Balantidiasis
- Bloodstream Infections
- Bone and Joint Infections
- Brain abscess
- CNS Infection
- Clostridium Difficile Infection (CDI)
- Empyema
- Endometritis
- Endomyometritis
- Giardiasis
- Gynaecological infection
- Infection, Bacteroides
- Intraabdominal Infections
- Lower Respiratory Infection
- Lower respiratory tract infection bacterial
- Lung Abscess
- Meningitis
- Parasitic infection NOS
- Periodontitis
- Peritonitis bacterial
- Pneumonia
- Postoperative Infections
- Pouchitis
- Septicemia bacterial anaerobic
- Skin and Subcutaneous Tissue Bacterial Infections
- Tetanus
- Tubo-ovarian abscess
- Urethritis
- Asymptomatic Trichomoniasis
- Entamoeba histolytica
- Hepatic abscess
- Refractory Sinusitis
- Skin and skin-structure infections
- Symptomatic Trichomoniasis
- Associated Therapies
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
Metronidazole treats amebiasis, trichomoniasis, and giardiasis, exerting both antibacterial and antiprotozoal activities.16 Metronidazole is an effective treatment for some anaerobic bacterial infections.11 Metronidazole has shown antibacterial activity against the majority of obligate anaerobes, however, during in vitro studies, it does not demonstrate significant action against facultative anaerobes or obligate aerobes.14 The nitro group reduction of metronidazole by anaerobic organisms is likely responsible for the drug's antimicrobial cytotoxic effects, causing DNA strand damage to microbes.5,7
A note on convulsions and neuropathy and carcinogenesis
It is important to be aware of the risk of peripheral neuropathy and convulsions associated with metronidazole, especially at higher doses. If convulsions or numbness of an extremity occur, discontinue the drug immediately.14 Metronidazole has been found to be carcinogenic in mice and rats. The relevance to this effect in humans is unknown. It is advisable to only administer metronidazole when clinically necessary and only for its approved indications.17
- Mechanism of action
The exact mechanism of action of metronidazole has not been fully established, however, it is possible that an intermediate in the reduction of metronidazole which is only made by anaerobic bacteria and protozoa, binds deoxyribonucleic acid and electron-transport proteins of organisms, blocking nucleic acid synthesis.14 After administration, metronidazole enters cells by passive diffusion. Following this, ferredoxin or flavodoxin reduce its nitro group to nitro radicals. The redox potential of the electron transport portions of anaerobic or microaerophilic microorganisms renders metronidazole selective to these organisms, which cause nitro group reduction, leading to the production of toxic metabolites. These include N-(2-hydroxyethyl) oxamic acid and acetamide, which may damage DNA of replicating organisms.5
Target Actions Organism AOxygen-insensitive NADPH nitroreductase potentiatorHelicobacter pylori (strain ATCC 700392 / 26695) UAnaerobic bacterial DNA inhibitorUProtozoal DNA inhibitor- Absorption
After the intravenous infusion of a 1.5g dose, peak concentration was reached within 1 hour and was peak level of 30-40 mg/L.16 When a multiple-dose regimen of 500mg three times a day administered intravenously, steady-state concentrations were achieved within about 3 days and peak concentration was measured at 26 mg/L.16 When administered orally in the tablet form, metronidazole is absorbed entirely absorbed, showing a bioavailability of greater than 90%.7 One resource indicates that Cmax after a single oral dose of 500mg metronidazole ranges from 8 to 13 mg/L, with a Tmax of 25 minutes to 4 hours. The AUC following a single 500mg oral dose of metronidazole was 122 ± 10.3 mg/L • h.7
A note on the absorption of topical preparations
Insignificant percutaneous absorption of metronidazole occurs after the application of 1% metronidazole cream topically. Healthy volunteers applied one 100 mg dose of 14C-labelled metronidazole 2% cream to unbroken skin. After 12 hours, metronidazole was not detected in the plasma. Approximately 0.1% to 1% of the administered metronidazole was measured in the urine and feces.16
- Volume of distribution
Metronidazole is widely distributed throughout the body5 and various body fluids. They include the bile, saliva, breastmilk, cerebrospinal fluid, and the placenta.16 Steady-state volume distribution of metronidazole in adults ranges from 0.51 to 1.1 L/kg. It attains 60 to 100% of plasma concentrations in various tissues, such as the central nervous system, however, is not measured in high concentrations in the placental tissue.7
- Protein binding
Metronidazole is less than 20% bound to plasma proteins.7,16
- Metabolism
Metronidazole undergoes hepatic metabolism via hydroxylation, oxidation, and glucuronidation. The metabolism of metronidazole yields 5 metabolites. The hydroxy metabolite, 1-(2-hydroxy-ethyl)-2-hydroxy methyl-5-nitroimidazole, is considered the major active metabolite.7,13 Unchanged metronidazole is found in the plasma along with small amounts of its 2- hydroxymethyl metabolite. Several metabolites of metronidazole are found in the urine. They are primarily a product of side-chain oxidation in addition to glucuronide conjugation. Only 20% of the dose found in the urine is accounted for by unchanged metronidazole.16 The two main oxidative metabolites of metronidazole are hydroxy and acetic acid metabolites.6,9
Hover over products below to view reaction partners
- Route of elimination
Metronidazole and metabolites are 60 to 80% eliminated in the urine, and 6-15% excreted in the feces.7,14
- Half-life
The elimination half-life of metronidazole is 7.3 ± 1.0 after a single 500mg IV dose in healthy subjects.16 Another resource indicates that the elimination half-life for metronidazole ranges from 6 to 10 hours.7
- Clearance
Dose adjustments may be required in patients with hepatic impairment, as clearance is impaired in these patients.16 The clearance of metronidazole in the kidneys is estimated at 10 mL/min/1.73 m2.14 The total clearance from serum is about 2.1 to 6.4 L/h/kg.7
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
LD50 information
The oral LD50 of metronidazole in rats is 5000 mg/kg 16
Overdose information
Adverse effects that may be exaggerated with an overdose include peripheral neuropathy, central nervous system toxicity, seizures, disulfiram-like effect (if combined with alcohol) dark urine, a metallic taste in the mouth, nausea, epigastric discomfort, and vertigo, in addition to neutropenia.10,16 There is no specific antidote for metronidazole overdose. Symptomatic and supportive treatment should be employed in addition to the administration of activated charcoal to remove the unabsorbed drug from the gastrointestinal tract. In addition to the above measures, contact the local poison control center for updated information on the management of a metronidazole overdose.16
- Affected organisms
- Bacteria and protozoa
- Helicobacter pylori
- Peptoclostridium difficile
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Unlock Additional DataAbatacept The metabolism of Metronidazole can be increased when combined with Abatacept. Abiraterone The metabolism of Abiraterone can be decreased when combined with Metronidazole. Acalabrutinib The metabolism of Metronidazole can be decreased when combined with Acalabrutinib. Acebutolol The risk or severity of QTc prolongation can be increased when Metronidazole is combined with Acebutolol. Acenocoumarol The serum concentration of Acenocoumarol can be increased when it is combined with Metronidazole. Acetaminophen The metabolism of Metronidazole can be decreased when combined with Acetaminophen. Acetazolamide The therapeutic efficacy of Acetazolamide can be decreased when used in combination with Metronidazole. Acetohexamide The metabolism of Acetohexamide can be decreased when combined with Metronidazole. Acetylsalicylic acid The metabolism of Acetylsalicylic acid can be decreased when combined with Metronidazole. Acrivastine The risk or severity of QTc prolongation can be increased when Metronidazole is combined with Acrivastine. Additional Data Available- Extended DescriptionExtended DescriptionAvailable for Purchase
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - SeveritySeverityAvailable for Purchase
A severity rating for each drug interaction, from minor to major.
Learn more - Evidence LevelEvidence LevelAvailable for Purchase
A rating for the strength of the evidence supporting each drug interaction.
Learn more - ActionActionAvailable for Purchase
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Avoid alcohol. Unpleasant symptoms such as nausea, vomiting, and abdominal distress may occur with alcohol.
- Take with or without food. The extended release formulation should, however, be taken without food.
Products
Purchasing individual compounds or compound libraries for your research?
Learn More- Product Ingredients
Ingredient UNII CAS InChI Key Metronidazole hydrochloride 76JC1633UF 69198-10-3 FPTPAIQTXYFGJC-UHFFFAOYSA-N - Product Images
- International/Other Brands
- Anabact (Cambridge Healthcare Supplies) / Arilin / Clont / Deflamon / Efloran / Elyzol / Entizol / Fossyol / Klion / Klont / Metrolyl / Metrotop / Nalox / Nidagel / Novonidazol / Orvagil / Protostat / Takimetol / Trichazole / Trichex / Trichopol / Tricowas B / Trikacide / Trikozol / Vagilen / Vagimid / Vertisal / Zadstat
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataFlagyl Capsule 375 mg/1 Oral Physicians Total Care, Inc. 1995-05-03 2000-09-19 US 
Flagyl Capsule 500 mg Oral Odan Laboratories Ltd 1979-12-31 Not applicable Canada 
Flagyl Tablet, film coated 500 mg/1 Oral Pfizer Laboratories Div Pfizer Inc 1963-07-18 Not applicable US Flagyl Tablet, film coated 250 mg/1 Oral Pfizer Laboratories Div Pfizer Inc 1963-07-18 2019-02-28 US Flagyl Capsule 375 mg/1 Oral G.D. Searle LLC Division of Pfizer Inc 1995-05-03 Not applicable US Flagyl Cream 10 % Vaginal Sanofi Aventis 1970-12-31 Not applicable Canada Flagyl 500 500mg Suppository Vaginal Aventis Pharma Ltd. 1960-12-31 2003-07-22 Canada Flagyl ER Tablet, film coated, extended release 750 mg/1 Oral G.D. Searle LLC Division of Pfizer Inc 1997-11-26 2014-10-31 US Florazole ER Tablet, extended release Oral Ferring Pharmaceuticals 2002-10-10 2012-09-30 Canada MetroCream Cream 7.5 mg/1g Topical Galderma 1995-09-20 Not applicable US Additional Data Available- Application NumberApplication NumberAvailable for Purchase
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct CodeAvailable for Purchase
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataApo-metronidazole Tablet Oral Apotex Corporation Not applicable Not applicable Canada Apo-metronidazole Capsule Oral Apotex Corporation Not applicable Not applicable Canada Apo-metronidazole Capsule Oral Apotex Corporation 2003-11-27 Not applicable Canada Auro-metronidazole Capsule Oral Auro Pharma Inc 2018-04-03 Not applicable Canada Mar-metronidazole Capsule Oral Marcan Pharmaceuticals Inc Not applicable Not applicable Canada Metronidazole Tablet 500 mg/1 Oral Preferred Pharmaceuticals, Inc. 2016-12-01 Not applicable US Metronidazole Gel 7.5 mg/1g Topical Sandoz 2006-07-13 2015-06-30 US Metronidazole Tablet, film coated 250 mg/1 Oral Cadila Pharmaceuticals Limited 2017-12-29 Not applicable US Metronidazole Tablet 500 mg/1 Oral bryant ranch prepack 2017-11-29 Not applicable US Metronidazole Tablet 250 mg/1 Oral Preferred Pharmaceuticals, Inc. 2010-09-01 2019-10-30 US 
Additional Data Available- Application NumberApplication NumberAvailable for Purchase
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct CodeAvailable for Purchase
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Bismuth Subsalicylate/Metronidazole/Tetracycline Hydrochloride Metronidazole (250 mg/1) + Bismuth subsalicylate (262.4 mg/1) + Tetracycline hydrochloride (500 mg/1) Kit Oral Ailex Pharmaceuticals, Llc 2018-11-30 Not applicable US Flagystatin Metronidazole (500 mg) + Nystatin (100000 unit) Suppository Vaginal Sanofi Aventis 1979-12-31 Not applicable Canada Flagystatin Metronidazole (500 mg) + Nystatin (100000 unit) Cream Vaginal Sanofi Aventis 1976-12-31 2017-08-24 Canada Flagystatin Metronidazole (500 mg) + Nystatin (100000 unit) Suppository Vaginal Aventis Pharma Ltd. 1972-12-31 2004-07-30 Canada HELIDAC Therapy Metronidazole (250 mg/1) + Bismuth subsalicylate (262.4 mg/1) + Tetracycline hydrochloride (500 mg/1) Kit Oral Prometheus Laboratories 1996-08-15 2014-02-01 US HELIDAC Therapy Metronidazole (250 mg/1) + Bismuth subsalicylate (262.4 mg/1) + Tetracycline hydrochloride (500 mg/1) Kit Oral Casper Pharma Llc 2020-06-11 Not applicable US Pylera Metronidazole (125 mg) + Bismuth subcitrate potassium monohydrate (40 mg) + Tetracycline hydrochloride (125 mg) Capsule Oral Aptalis Pharma Canada Ulc Not applicable Not applicable Canada Pylera Metronidazole (125 mg/1) + Bismuth subcitrate potassium monohydrate (140 mg/1) + Tetracycline hydrochloride (125 mg/1) Capsule Oral Allergan, Inc. 2013-08-01 Not applicable US Pylera Metronidazole (125 mg/1) + Bismuth subcitrate potassium monohydrate (140 mg/1) + Tetracycline hydrochloride (125 mg/1) Capsule Oral Physicians Total Care, Inc. 2010-08-18 Not applicable US Pylera Metronidazole (125 mg/1) + Bismuth subcitrate potassium monohydrate (140 mg/1) + Tetracycline hydrochloride (125 mg/1) Capsule Oral Axcan Pharma US, Inc. 2007-05-01 2011-06-14 US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image 171083 Ivermectin 1% / Metronidazole 1% / Niacinamide 4% Metronidazole (1 g/100g) + Ivermectin (1 g/100g) + Nicotinamide (4 g/100g) Gel Topical Sincerus Florida, LLC 2020-07-02 Not applicable US Brimonidine Tartrate 0.25% / Ivermectin 1% / Metronidazole 1% / Niacinamide 4% Metronidazole (1 g/100g) + Brimonidine tartrate (0.25 g/100g) + Ivermectin (1 g/100g) + Nicotinamide (4 g/100g) Gel Topical Sincerus Florida, LLC 2019-05-16 Not applicable US Ivermectin 1% / Metronidazole 1% Metronidazole (1 g/100g) + Ivermectin (1 g/100g) Gel Topical Sincerus Florida, LLC 2019-05-01 Not applicable US Ivermectin 1% / Metronidazole 1% / Niacinamide 4% Metronidazole (1 g/100g) + Ivermectin (1 g/100g) + Nicotinamide (4 g/100g) Gel Topical Sincerus Florida, LLC 2019-05-01 Not applicable US Metronidazole Metronidazole (500 mg/100mL) Injection, solution Intravenous Baxter Healthcare Corporation 2017-10-05 2019-10-31 US Metronidazole 1% / Mupirocin 2% Metronidazole (1 g/100g) + Mupirocin (2 g/100g) Ointment Topical Sincerus Florida, LLC 2019-05-15 Not applicable US Metronidazole 1% / Mupirocin 2% Metronidazole (1 g/100g) + Mupirocin (2 g/100g) Ointment Topical Sincerus Florida, LLC 2019-05-15 Not applicable US Metronidazole 1% / Mupirocin 2% / Metronidazole (1 g/100g) + Mupirocin (2 g/100g) Ointment Topical Sincerus Florida, LLC 2019-05-14 Not applicable US Metronidazole 1% / Niacinamide 4% Metronidazole (1 g/100g) + Nicotinamide (4 g/100g) Gel Topical Sincerus Florida, LLC 2019-05-16 Not applicable US Rosaclear System Metronidazole (7.5 mg/1g) Kit Topical OMP, INC. 2012-12-29 Not applicable US
Categories
- ATC Codes
- A02BD11 — Pantoprazole, amoxicillin, clarithromycin and metronidazole
- A02BD — Combinations for eradication of Helicobacter pylori
- A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
- A02 — DRUGS FOR ACID RELATED DISORDERS
- A — ALIMENTARY TRACT AND METABOLISM
- D06BX — Other chemotherapeutics
- D06B — CHEMOTHERAPEUTICS FOR TOPICAL USE
- D06 — ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE
- D — DERMATOLOGICALS
- A02BD — Combinations for eradication of Helicobacter pylori
- A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
- A02 — DRUGS FOR ACID RELATED DISORDERS
- A — ALIMENTARY TRACT AND METABOLISM
- J01XD — Imidazole derivatives
- J01X — OTHER ANTIBACTERIALS
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- J01RA — Combinations of antibacterials
- J01R — COMBINATIONS OF ANTIBACTERIALS
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- A02BD — Combinations for eradication of Helicobacter pylori
- A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
- A02 — DRUGS FOR ACID RELATED DISORDERS
- A — ALIMENTARY TRACT AND METABOLISM
- A02BD — Combinations for eradication of Helicobacter pylori
- A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
- A02 — DRUGS FOR ACID RELATED DISORDERS
- A — ALIMENTARY TRACT AND METABOLISM
- J01RA — Combinations of antibacterials
- J01R — COMBINATIONS OF ANTIBACTERIALS
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- A01AB — Antiinfectives and antiseptics for local oral treatment
- A01A — STOMATOLOGICAL PREPARATIONS
- A01 — STOMATOLOGICAL PREPARATIONS
- A — ALIMENTARY TRACT AND METABOLISM
- G01AF — Imidazole derivatives
- G01A — ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
- G01 — GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- J01RA — Combinations of antibacterials
- J01R — COMBINATIONS OF ANTIBACTERIALS
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- A02BD — Combinations for eradication of Helicobacter pylori
- A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
- A02 — DRUGS FOR ACID RELATED DISORDERS
- A — ALIMENTARY TRACT AND METABOLISM
- A02BD — Combinations for eradication of Helicobacter pylori
- A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
- A02 — DRUGS FOR ACID RELATED DISORDERS
- A — ALIMENTARY TRACT AND METABOLISM
- G01AF — Imidazole derivatives
- G01A — ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
- G01 — GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- P01AB — Nitroimidazole derivatives
- P01A — AGENTS AGAINST AMOEBIASIS AND OTHER PROTOZOAL DISEASES
- P01 — ANTIPROTOZOALS
- P — ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
- A02BD — Combinations for eradication of Helicobacter pylori
- A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
- A02 — DRUGS FOR ACID RELATED DISORDERS
- A — ALIMENTARY TRACT AND METABOLISM
- Drug Categories
- Agents that reduce seizure threshold
- Alimentary Tract and Metabolism
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antiinfectives and Antiseptics for Local Oral Treatment
- Antiinfectives for Systemic Use
- Antiparasitic Agents
- Antiparasitic Products, Insecticides and Repellents
- Antiprotozoals
- Cytochrome P-450 CYP2A6 Substrates
- Cytochrome P-450 CYP2C8 Inhibitors
- Cytochrome P-450 CYP2C8 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2C9 Inhibitors
- Cytochrome P-450 CYP2C9 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A5 Substrates
- Cytochrome P-450 CYP3A7 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Dermatologicals
- Drugs for Acid Related Disorders
- Drugs for Peptic Ulcer and Gastro-Oesophageal Reflux Disease (Gord)
- Genito Urinary System and Sex Hormones
- Gynecological Antiinfectives and Antiseptics
- Imidazole Derivatives
- Imidazoles
- Miscellaneous Antiprotozoals
- Miscellaneous Local Anti-infectives
- Nitro Compounds
- Nitroimidazole Antimicrobial
- Nitroimidazole Derivatives
- Nitroimidazoles
- P-glycoprotein inhibitors
- Potential QTc-Prolonging Agents
- QTc Prolonging Agents
- Stomatological Preparations
- UGT1A1 Substrates
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as nitroimidazoles. These are compounds containing an imidazole ring which bears a nitro group.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Azoles
- Sub Class
- Imidazoles
- Direct Parent
- Nitroimidazoles
- Alternative Parents
- Nitroaromatic compounds / 1,2,5-trisubstituted imidazoles / N-substituted imidazoles / Heteroaromatic compounds / Propargyl-type 1,3-dipolar organic compounds / Organic oxoazanium compounds / Azacyclic compounds / Alkanolamines / Primary alcohols / Organopnictogen compounds show 3 more
- Substituents
- 1,2,5-trisubstituted-imidazole / Alcohol / Alkanolamine / Allyl-type 1,3-dipolar organic compound / Aromatic heteromonocyclic compound / Azacycle / C-nitro compound / Heteroaromatic compound / Hydrocarbon derivative / N-substituted imidazole show 15 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- C-nitro compound, imidazoles, primary alcohol (CHEBI:6909)
Chemical Identifiers
- UNII
- 140QMO216E
- CAS number
- 443-48-1
- InChI Key
- VAOCPAMSLUNLGC-UHFFFAOYSA-N
- InChI
- InChI=1S/C6H9N3O3/c1-5-7-4-6(9(11)12)8(5)2-3-10/h4,10H,2-3H2,1H3
- IUPAC Name
- 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethan-1-ol
- SMILES
- CC1=NC=C(N1CCO)[N+]([O-])=O
References
- Synthesis Reference
- US2944061
- General References
- Shennan A, Crawshaw S, Briley A, Hawken J, Seed P, Jones G, Poston L: A randomised controlled trial of metronidazole for the prevention of preterm birth in women positive for cervicovaginal fetal fibronectin: the PREMET Study. BJOG. 2006 Jan;113(1):65-74. [PubMed:16398774]
- Williams CS, Woodcock KR: Do ethanol and metronidazole interact to produce a disulfiram-like reaction? Ann Pharmacother. 2000 Feb;34(2):255-7. [PubMed:10676835]
- Visapaa JP, Tillonen JS, Kaihovaara PS, Salaspuro MP: Lack of disulfiram-like reaction with metronidazole and ethanol. Ann Pharmacother. 2002 Jun;36(6):971-4. [PubMed:12022894]
- Dingsdag SA, Hunter N: Metronidazole: an update on metabolism, structure-cytotoxicity and resistance mechanisms. J Antimicrob Chemother. 2018 Feb 1;73(2):265-279. doi: 10.1093/jac/dkx351. [PubMed:29077920]
- Hernandez Ceruelos A, Romero-Quezada LC, Ruvalcaba Ledezma JC, Lopez Contreras L: Therapeutic uses of metronidazole and its side effects: an update. Eur Rev Med Pharmacol Sci. 2019 Jan;23(1):397-401. doi: 10.26355/eurrev_201901_16788. [PubMed:30657582]
- Sprandel KA, Schriever CA, Pendland SL, Quinn JP, Gotfried MH, Hackett S, Graham MB, Danziger LH, Rodvold KA: Pharmacokinetics and pharmacodynamics of intravenous levofloxacin at 750 milligrams and various doses of metronidazole in healthy adult subjects. Antimicrob Agents Chemother. 2004 Dec;48(12):4597-605. doi: 10.1128/AAC.48.12.4597-4605.2004. [PubMed:15561831]
- Lamp KC, Freeman CD, Klutman NE, Lacy MK: Pharmacokinetics and pharmacodynamics of the nitroimidazole antimicrobials. Clin Pharmacokinet. 1999 May;36(5):353-73. doi: 10.2165/00003088-199936050-00004. [PubMed:10384859]
- Morales-Leon F, von Plessing-Rossel C, Villa-Zapata L, Fernandez-Rocca P, Sanhueza-Sanhueza C, Bello-Toledo H, Mella-Montecinos S: [Pharmacokinetics/pharmacodinamic (PK/PD) evaluation of a short course of oral administration of metronidazole for the management of infections caused by Bacteroides fragilis]. Rev Chilena Infectol. 2015 Apr;32(2):135-41. doi: 10.4067/S0716-10182015000300001. [PubMed:26065445]
- Lau AH, Lam NP, Piscitelli SC, Wilkes L, Danziger LH: Clinical pharmacokinetics of metronidazole and other nitroimidazole anti-infectives. Clin Pharmacokinet. 1992 Nov;23(5):328-64. doi: 10.2165/00003088-199223050-00002. [PubMed:1478003]
- Kapoor K, Chandra M, Nag D, Paliwal JK, Gupta RC, Saxena RC: Evaluation of metronidazole toxicity: a prospective study. Int J Clin Pharmacol Res. 1999;19(3):83-8. [PubMed:10761537]
- Lofmark S, Edlund C, Nord CE: Metronidazole is still the drug of choice for treatment of anaerobic infections. Clin Infect Dis. 2010 Jan 1;50 Suppl 1:S16-23. doi: 10.1086/647939. [PubMed:20067388]
- Loesche WJ, Schmidt E, Smith BA, Morrison EC, Caffesse R, Hujoel PP: Effects of metronidazole on periodontal treatment needs. J Periodontol. 1991 Apr;62(4):247-57. doi: 10.1902/jop.1991.62.4.247. [PubMed:2037955]
- Pearce RE, Cohen-Wolkowiez M, Sampson MR, Kearns GL: The role of human cytochrome P450 enzymes in the formation of 2-hydroxymetronidazole: CYP2A6 is the high affinity (low Km) catalyst. Drug Metab Dispos. 2013 Sep;41(9):1686-94. doi: 10.1124/dmd.113.052548. Epub 2013 Jun 27. [PubMed:23813797]
- Flagyl (Metronidazole) FDA Label [Link]
- FDA approvals, Metronidazole [Link]
- Canadian monograph, Flagyl [Link]
- Flagyl [Link]
- DailyMed: Flagyl (metronidazole) oral tablets [Link]
- External Links
- Human Metabolome Database
- HMDB0015052
- KEGG Drug
- D00409
- KEGG Compound
- C07203
- PubChem Compound
- 4173
- PubChem Substance
- 46508911
- ChemSpider
- 4029
- BindingDB
- 50375309
- 6922
- ChEBI
- 6909
- ChEMBL
- CHEMBL137
- ZINC
- ZINC000000113442
- Therapeutic Targets Database
- DAP000534
- PharmGKB
- PA450484
- PDBe Ligand
- 2MN
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Metronidazole
- AHFS Codes
- 84:04.04 — Antibiotics
- 08:30.92 — Miscellaneous Antiprotozoals
- 84:04.92 — Miscellaneous Local Anti-infectives
- PDB Entries
- 1w3r
- MSDS
- Download (73.9 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Active Not Recruiting Prevention Surgery, Colorectal 1 4 Active Not Recruiting Treatment Bacterial Infection Due to Helicobacter Pylori (H. Pylori) / Gastrointestinal Ulcer Haemorrhage 1 4 Active Not Recruiting Treatment Blastocystis Hominis Infections 1 4 Active Not Recruiting Treatment Exacerbation of Ulcerative Colitis / Granulomatous Colitis / Ulcerative Colitis, Active Severe 1 4 Active Not Recruiting Treatment Peri-Implantitis 1 4 Active Not Recruiting Treatment Periodontitis, Chronic 2 4 Completed Prevention Infection Prophylaxis in Colo Rectal Surgery 1 4 Completed Prevention Postoperative Wound Infection 1 4 Completed Supportive Care Acne Rosacea 1 4 Completed Supportive Care Amoxicillin / Metronidazole / Ofloxacin / Periodontitis / Root Planing 1
Pharmacoeconomics
- Manufacturers
- Gd searle llc
- Able laboratories inc
- Alembic ltd
- Par pharmaceutical inc
- Galderma laboratories lp
- Altana inc
- G and w laboratories inc
- Sanofi aventis us llc
- Taro pharmaceutical industries ltd
- Tolmar inc
- Graceway pharmaceuticals llc
- Teva pharmaceuticals usa
- Baxter healthcare corp
- B braun medical inc
- Abbott laboratories pharmaceutical products div
- Abraxis pharmaceutical products
- Elkins sinn div ah robins co inc
- International medication systems ltd
- Watson laboratories inc
- Claris lifesciences ltd
- Hospira inc
- Laboratorios aplicaciones farmaceuticas sa de cv
- Halsey drug co inc
- Ivax pharmaceuticals inc sub teva pharmaceuticals usa
- Lnk international inc
- Mutual pharmaceutical co inc
- Pliva inc
- Sandoz inc
- Superpharm corp
- Teva pharmaceuticals usa inc
- World gen llc
- Ortho mcneil pharmaceutical inc
- Savage laboratories inc div altana inc
- Packagers
- Actavis Group
- Advanced Pharmaceutical Services Inc.
- American Pharmaceutical Association
- Ameri-Pac Inc.
- Amerisource Health Services Corp.
- Amneal Pharmaceuticals
- Apace Packaging
- Apotheca Inc.
- A-S Medication Solutions LLC
- Atlantic Biologicals Corporation
- B. Braun Melsungen AG
- Baxter International Inc.
- Ben Venue Laboratories Inc.
- Bryant Ranch Prepack
- Cardinal Health
- Carlisle Laboratories Inc.
- Central Texas Community Health Centers
- Claris Lifesciences Inc.
- Community Action Inc. Community Health Services
- Comprehensive Consultant Services Inc.
- Contract Pharm
- Darby Dental Supply Co. Inc.
- Dept Health Central Pharmacy
- Dermik Labs
- DHHS Program Support Center Supply Service Center
- Direct Dispensing Inc.
- Dispensing Solutions
- Diversified Healthcare Services Inc.
- DPT Laboratories Ltd.
- Dudley Corp.
- E. Fougera and Co.
- G & W Labs
- Galderma Laboratories
- GD Searle LLC
- GlaxoSmithKline Inc.
- Golden State Medical Supply Inc.
- Graceway Pharmaceuticals
- Group Health Cooperative
- H and H Laboratories
- H.J. Harkins Co. Inc.
- Harris Pharmaceutical Inc.
- Hawkins Inc.
- Heartland Repack Services LLC
- Hospira Inc.
- Kaiser Foundation Hospital
- Lake Erie Medical and Surgical Supply
- Liberty Pharmaceuticals
- Major Pharmaceuticals
- Mckesson Corp.
- Medisca Inc.
- Medvantx Inc.
- Mississippi State Dept Health
- Murfreesboro Pharmaceutical Nursing Supply
- Mutual Pharmaceutical Co.
- Nord Ost Corp.
- Nucare Pharmaceuticals Inc.
- Nycomed Inc.
- Obagi Medical Products Inc.
- Palmetto Pharmaceuticals Inc.
- Pangeo Pharma Quebec Inc.
- Par Pharmaceuticals
- Patheon Inc.
- Patient First Corp.
- PCA LLC
- PD-Rx Pharmaceuticals Inc.
- Pfizer Inc.
- Pharmacia Inc.
- Pharmedix
- Pharmpak Inc.
- Physicians Total Care Inc.
- Pliva Inc.
- Prasco Labs
- Preferred Pharmaceuticals Inc.
- Prepackage Specialists
- Prepak Systems Inc.
- Prescription Dispensing Service Inc.
- Qualitest
- Raz Co. Inc.
- Rebel Distributors Corp.
- Redpharm Drug
- Remedy Repack
- Rochester Pharmaceuticals
- Sagent Pharmaceuticals
- Sandhills Packaging Inc.
- Sandoz
- Sanofi-Aventis Inc.
- SCS Pharmaceuticals
- Southwood Pharmaceuticals
- St Mary's Medical Park Pharmacy
- Stat Rx Usa
- Taro Pharmaceuticals USA
- Teva Pharmaceutical Industries Ltd.
- Tolmar Inc.
- UDL Laboratories
- Upsher Smith Laboratories
- Vangard Labs Inc.
- Veratex Corp.
- Watson Pharmaceuticals
- West-Ward Pharmaceuticals
- Dosage Forms
Form Route Strength Liquid Topical 10 mg/1mL Capsule, coated Oral 300 mg Suspension Oral 8.04 g Solution Intravenous 5 mg/ml Tablet, film coated Oral 250 mg Tablet, film coated Oral 500 mg Capsule Vaginal 100 mg Injection, solution Parenteral 500 MG/100ML Tablet 50 mg Tablet Vaginal 750 mg Capsule Oral 375 mg/1 Capsule Oral 500 mg Cream Vaginal 10 % Suppository Vaginal 1 G Tablet Oral 250 MG Tablet Oral; Vaginal 500 MG Tablet, coated Oral 200 mg Suppository Vaginal Cream Vaginal Suppository Vaginal Tablet, extended release Oral Cream Vaginal 2 g Insert Vaginal 750 mg Kit Oral Suspension Oral 8 g Gel Topical Capsule, coated Oral 600 mg Solution Parenteral 0.5 % Suppository Vaginal 750 mg Suppository Vaginal 750 mg/200g Tablet, coated Oral 400 mg Suspension Oral 200 mg/5mL Suspension Oral 5 g Tablet, film coated 1.5 IU Suspension Oral 125 mg/5ml Tablet 200 mg Solution Topical 1 g/100g Capsule, coated Oral 400 mg Cream Topical Gel Topical 10 mg/1g Gel Vaginal 7.5 mg/1g Gel Topical Gel 1 g/100g Injection Intravenous 5 MG/ML Lotion Topical 0.75 % Insert Vaginal 500 mg Suspension Oral 4 g Tablet 400 MG Tablet Vaginal 500 mg Solution Parenteral Tablet 250 mg Solution Parenteral 5 mg/ml Solution Parenteral 500 MG/100ML Tablet Oral 500 mg Tablet, coated Oral 500 mg Capsule, liquid filled Oral 300 mg Cream Topical 10 mg/1g Cream Topical 7.5 mg/1g Gel Topical 7.5 mg/1g Gel Vaginal 13 mg/1g Injection Intravenous Injection, solution Intravenous 500 mg/100mL Lotion Topical 7.5 mg/1mL Lotion Topical 7.5 mg/1g Powder Not applicable 1 g/1g Solution Intravenous 500 mg/100mL Suspension Oral 20 mg/1mL Tablet Oral 250 mg/1 Tablet Oral 500 mg/1 Tablet Vaginal 200 mg Tablet, coated Oral 250 mg Tablet, coated Oral 250 mg/1 Tablet, coated Oral 500 1/1 Tablet, film coated Oral Tablet, film coated Oral 500 mg/1 Tablet, film coated, extended release Oral 750 mg/1 Tablet; tablet, film coated Oral Ointment Topical Solution Intravenous Syrup Tablet Oral Tablet, film coated Oral 250 mg/1 Injection, solution Parenteral 5 MG/ML Injection, solution Intravenous; Parenteral 0.5 G/100ML Injection, solution Parenteral 0.5 G/100ML Injection Intravenous 0.5 % Capsule, liquid filled Oral 500 mg Cream Vaginal 1 g Capsule Oral 200 mg Suppository Vaginal 200 mg Suppository Vaginal 500 mg Gel Vaginal Gel Topical 7.5 mg/g Solution 200 mg/5ml Injection, solution Intravenous 500 mg Cream Topical 1 % Cream Topical 10 mg/60g Gel Topical 65 mg/5g Gel Vaginal 65 mg/5g Capsule Oral Solution Intravenous 0.5 % Capsule Oral Capsule Oral 140 MG Gel 750 mg/100g Kit Topical 7.5 mg/1g Cream Topical Gel Topical 0.75 % Cream Topical 10 mg/g Cream 0.75 % Emulsion 0.75 % Gel 0.75 % Gel Topical 0.75 g Solution Intravenous 500 mg Tablet Capsule Oral 250 MG Insert Vaginal 100 mg - Prices
Unit description Cost Unit MetroLotion 0.75% Lotion 59ml Bottle 292.66USD bottle MetroCream 0.75% Cream 45 gm Tube 281.09USD tube Metrogel 1% Gel 60 gm Tube 200.93USD tube Metrogel 1% Kit Box 200.93USD box Metrogel 1% kit 193.2USD kit Noritate 1% Cream 60 gm Tube 156.44USD tube MetroNIDAZOLE 0.75% Lotion 59ml Bottle 89.86USD bottle MetroNIDAZOLE 0.75% Cream 45 gm Tube 80.87USD tube MetroNIDAZOLE 0.75% Gel 45 gm Tube 74.0USD tube MetroNIDAZOLE 0.75% Gel 70 gm Tube 68.53USD tube Flagyl ER 750 mg 24 Hour tablet 13.2USD tablet Flagyl er 750 mg tablet 12.7USD tablet MetroNIDAZOLE 750 mg 24 Hour tablet 8.07USD tablet Flagyl 500 mg tablet 6.24USD tablet Metrocream 0.75% cream 5.99USD g Danazol 200 mg capsule 5.63USD capsule Flagyl 375 mg capsule 5.45USD capsule Metrolotion topical 0.75% 4.77USD ml Metronidazole benz powder 4.74USD g Flagyl 250 mg tablet 3.49USD tablet Danazol 100 mg capsule 2.98USD capsule Noritate 1% cream 2.51USD g Danazol 50 mg capsule 1.99USD capsule Metronidazole powder 1.65USD g Metronidazole 0.75% cream 1.34USD g Metronidazole vaginal 0.75% gl 0.94USD g Metronidazole 500 mg tablet 0.72USD tablet Metrogel 0.75 % Gel 0.69USD g Metrogel 1 % Gel 0.63USD g Noritate 1 % Cream 0.58USD g Rosasol 1 % Cream 0.57USD g Metrocream 0.75 % Cream 0.52USD g Metrolotion 0.75 % Lotion 0.52USD g Metrogel-vaginal 0.75% gel 0.51USD g Vandazole vaginal 0.75% gel 0.48USD g Metronidazole 250 mg tablet 0.44USD tablet Flagyl 10 % Cream 0.25USD g Apo-Metronidazole 250 mg Tablet 0.06USD tablet Flagyl 5 mg/ml 0.03USD ml Metro iv 500 mg/100 ml 0.03USD ml Metronidazole 5 mg/ml 0.03USD ml Metronidazole 500 mg/100 ml 0.03USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region Unlock Additional DataUS5536743 No 1996-07-16 2013-07-16 US CA2470492 No 2010-02-23 2022-11-07 Canada CA2161737 No 1998-10-20 2015-10-30 Canada US6881726 No 2005-04-19 2022-02-21 US US7348317 No 2008-03-25 2022-02-21 US US7456207 No 2008-11-25 2024-09-22 US US6350468 No 2002-02-26 2018-12-14 US US8946276 No 2015-02-03 2032-06-28 US US8658678 No 2014-02-25 2028-06-27 US US9198858 No 2015-12-01 2032-06-28 US US8877792 No 2014-11-04 2028-02-02 US US7893097 No 2011-02-22 2028-02-19 US US10238634 No 2019-03-26 2032-06-28 US US10596155 No 2012-06-28 2032-06-28 US Additional Data Available- Filed OnFiled OnAvailable for Purchase
The date on which a patent was filed with the relevant government.
Learn more
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 160 http://www.inchem.org/documents/pims/pharm/metronid.htm boiling point (°C) 405.4 http://www.emelcabio.com/metronidazole-41310008.html logP -0.02 http://www.t3db.ca/toxins/T3D4703 logS -1.5 http://www.t3db.ca/toxins/T3D4703 pKa 2.57,15.42 http://www.t3db.ca/toxins/T3D4703 - Predicted Properties
Property Value Source Water Solubility 5.92 mg/mL ALOGPS logP -0.15 ALOGPS logP -0.46 ChemAxon logS -1.5 ALOGPS pKa (Strongest Acidic) 15.44 ChemAxon pKa (Strongest Basic) 3.09 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 83.87 Å2 ChemAxon Rotatable Bond Count 3 ChemAxon Refractivity 41.22 m3·mol-1 ChemAxon Polarizability 15.82 Å3 ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9805 Blood Brain Barrier + 0.9297 Caco-2 permeable - 0.5365 P-glycoprotein substrate Non-substrate 0.5141 P-glycoprotein inhibitor I Non-inhibitor 0.8954 P-glycoprotein inhibitor II Non-inhibitor 0.8755 Renal organic cation transporter Non-inhibitor 0.7762 CYP450 2C9 substrate Non-substrate 0.7318 CYP450 2D6 substrate Non-substrate 0.8815 CYP450 3A4 substrate Non-substrate 0.6767 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9242 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9401 CYP450 3A4 inhibitor Non-inhibitor 0.9242 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8483 Ames test AMES toxic 0.9107 Carcinogenicity Non-carcinogens 0.7471 Biodegradation Not ready biodegradable 0.5941 Rat acute toxicity 2.0422 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.5 hERG inhibition (predictor II) Non-inhibitor 0.8272
Spectra
- Mass Spec (NIST)
- Download (9.68 KB)
- Spectra
Targets
- Kind
- Protein
- Organism
- Helicobacter pylori (strain ATCC 700392 / 26695)
- Pharmacological action
- Yes
- Actions
- Potentiator
- General Function
- Oxidoreductase activity
- Specific Function
- Reduction of a variety of nitroaromatic compounds using NADPH as source of reducing equivalents; two electrons are transferred (By similarity). Capable of reducing metronidazole; inactive RdxA rend...
- Gene Name
- rdxA
- Uniprot ID
- O25608
- Uniprot Name
- Oxygen-insensitive NADPH nitroreductase
- Molecular Weight
- 24067.775 Da
References
- Sisson G, Jeong JY, Goodwin A, Bryden L, Rossler N, Lim-Morrison S, Raudonikiene A, Berg DE, Hoffman PS: Metronidazole activation is mutagenic and causes DNA fragmentation in Helicobacter pylori and in Escherichia coli containing a cloned H. pylori RdxA(+) (Nitroreductase) gene. J Bacteriol. 2000 Sep;182(18):5091-6. [PubMed:10960092]
- Chisholm SA, Owen RJ: Mutations in Helicobacter pylori rdxA gene sequences may not contribute to metronidazole resistance. J Antimicrob Chemother. 2003 Apr;51(4):995-9. Epub 2003 Mar 13. [PubMed:12654749]
- Debets-Ossenkopp YJ, Pot RG, van Westerloo DJ, Goodwin A, Vandenbroucke-Grauls CM, Berg DE, Hoffman PS, Kusters JG: Insertion of mini-IS605 and deletion of adjacent sequences in the nitroreductase (rdxA) gene cause metronidazole resistance in Helicobacter pylori NCTC11637. Antimicrob Agents Chemother. 1999 Nov;43(11):2657-62. [PubMed:10543743]
- Pisharath H, Parsons MJ: Nitroreductase-mediated cell ablation in transgenic zebrafish embryos. Methods Mol Biol. 2009;546:133-43. doi: 10.1007/978-1-60327-977-2_9. [PubMed:19378102]
2. Anaerobic bacterial DNA
Unknown
Inhibitor
References
- Samuelson J: Why metronidazole is active against both bacteria and parasites. Antimicrob Agents Chemother. 1999 Jul;43(7):1533-41. [PubMed:10390199]
- Soule AF, Green SB, Blanchette LM: Clinical efficacy of 12-h metronidazole dosing regimens in patients with anaerobic or mixed anaerobic infections. Ther Adv Infect Dis. 2018 May;5(3):57-62. doi: 10.1177/2049936118766462. Epub 2018 Apr 3. [PubMed:29796265]
- Flagyl (Metronidazole) FDA Label [Link]
3. Protozoal DNA
Unknown
Inhibitor
References
- Uzlikova M, Nohynkova E: The effect of metronidazole on the cell cycle and DNA in metronidazole-susceptible and -resistant Giardia cell lines. Mol Biochem Parasitol. 2014 Dec;198(2):75-81. doi: 10.1016/j.molbiopara.2015.01.005. Epub 2015 Feb 12. [PubMed:25681616]
- Nasirudeen AM, Hian YE, Singh M, Tan KS: Metronidazole induces programmed cell death in the protozoan parasite Blastocystis hominis. Microbiology. 2004 Jan;150(Pt 1):33-43. doi: 10.1099/mic.0.26496-0. [PubMed:14702395]
- Flagyl (Metronidazole) FDA Label [Link]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C9
- Uniprot ID
- P11712
- Uniprot Name
- Cytochrome P450 2C9
- Molecular Weight
- 55627.365 Da
References
- Kudo T, Endo Y, Taguchi R, Yatsu M, Ito K: Metronidazole reduces the expression of cytochrome P450 enzymes in HepaRG cells and cryopreserved human hepatocytes. Xenobiotica. 2015 May;45(5):413-9. doi: 10.3109/00498254.2014.990948. Epub 2014 Dec 3. [PubMed:25470432]
- Hersh EV, Moore PA: Three Serious Drug Interactions that Every Dentist Should Know About. Compend Contin Educ Dent. 2015 Jun;36(6):408-13; quiz 414, 416. [PubMed:26053779]
- Sychev DA, Ashraf GM, Svistunov AA, Maksimov ML, Tarasov VV, Chubarev VN, Otdelenov VA, Denisenko NP, Barreto GE, Aliev G: The cytochrome P450 isoenzyme and some new opportunities for the prediction of negative drug interaction in vivo. Drug Des Devel Ther. 2018 May 8;12:1147-1156. doi: 10.2147/DDDT.S149069. eCollection 2018. [PubMed:29780235]
- CYP table [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Kudo T, Endo Y, Taguchi R, Yatsu M, Ito K: Metronidazole reduces the expression of cytochrome P450 enzymes in HepaRG cells and cryopreserved human hepatocytes. Xenobiotica. 2015 May;45(5):413-9. doi: 10.3109/00498254.2014.990948. Epub 2014 Dec 3. [PubMed:25470432]
- Michalets EL: Update: clinically significant cytochrome P-450 drug interactions. Pharmacotherapy. 1998 Jan-Feb;18(1):84-112. [PubMed:9469685]
- Spina E, Pisani F, Perucca E: Clinically significant pharmacokinetic drug interactions with carbamazepine. An update. Clin Pharmacokinet. 1996 Sep;31(3):198-214. doi: 10.2165/00003088-199631030-00004. [PubMed:8877250]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C8
- Uniprot ID
- P10632
- Uniprot Name
- Cytochrome P450 2C8
- Molecular Weight
- 55824.275 Da
References
- Kudo T, Endo Y, Taguchi R, Yatsu M, Ito K: Metronidazole reduces the expression of cytochrome P450 enzymes in HepaRG cells and cryopreserved human hepatocytes. Xenobiotica. 2015 May;45(5):413-9. doi: 10.3109/00498254.2014.990948. Epub 2014 Dec 3. [PubMed:25470432]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Steroid binding
- Specific Function
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
- Gene Name
- UGT1A1
- Uniprot ID
- P22309
- Uniprot Name
- UDP-glucuronosyltransferase 1-1
- Molecular Weight
- 59590.91 Da
References
- Williams JA, Hyland R, Jones BC, Smith DA, Hurst S, Goosen TC, Peterkin V, Koup JR, Ball SE: Drug-drug interactions for UDP-glucuronosyltransferase substrates: a pharmacokinetic explanation for typically observed low exposure (AUCi/AUC) ratios. Drug Metab Dispos. 2004 Nov;32(11):1201-8. doi: 10.1124/dmd.104.000794. Epub 2004 Aug 10. [PubMed:15304429]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Const...
- Gene Name
- CYP2A6
- Uniprot ID
- P11509
- Uniprot Name
- Cytochrome P450 2A6
- Molecular Weight
- 56501.005 Da
References
- Pearce RE, Cohen-Wolkowiez M, Sampson MR, Kearns GL: The role of human cytochrome P450 enzymes in the formation of 2-hydroxymetronidazole: CYP2A6 is the high affinity (low Km) catalyst. Drug Metab Dispos. 2013 Sep;41(9):1686-94. doi: 10.1124/dmd.113.052548. Epub 2013 Jun 27. [PubMed:23813797]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Oxygen binding
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP3A5
- Uniprot ID
- P20815
- Uniprot Name
- Cytochrome P450 3A5
- Molecular Weight
- 57108.065 Da
References
- Pearce RE, Cohen-Wolkowiez M, Sampson MR, Kearns GL: The role of human cytochrome P450 enzymes in the formation of 2-hydroxymetronidazole: CYP2A6 is the high affinity (low Km) catalyst. Drug Metab Dispos. 2013 Sep;41(9):1686-94. doi: 10.1124/dmd.113.052548. Epub 2013 Jun 27. [PubMed:23813797]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Oxygen binding
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP3A7
- Uniprot ID
- P24462
- Uniprot Name
- Cytochrome P450 3A7
- Molecular Weight
- 57525.03 Da
References
- Pearce RE, Cohen-Wolkowiez M, Sampson MR, Kearns GL: The role of human cytochrome P450 enzymes in the formation of 2-hydroxymetronidazole: CYP2A6 is the high affinity (low Km) catalyst. Drug Metab Dispos. 2013 Sep;41(9):1686-94. doi: 10.1124/dmd.113.052548. Epub 2013 Jun 27. [PubMed:23813797]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- Curator comments
- Evidence regarding this transporter inhibition is conflicting in the literature. Various references have been attached, some of which may provide conflicting evidence.
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- Tan SY, Kan E, Lim WY, Chay G, Law JH, Soo GW, Bukhari NI, Segarra I: Metronidazole leads to enhanced uptake of imatinib in brain, liver and kidney without affecting its plasma pharmacokinetics in mice. J Pharm Pharmacol. 2011 Jul;63(7):918-25. doi: 10.1111/j.2042-7158.2011.01296.x. Epub 2011 May 19. [PubMed:21635257]
- Kim KA, Park JY: Effect of metronidazole on the pharmacokinetics of fexofenadine, a P-glycoprotein substrate, in healthy male volunteers. Eur J Clin Pharmacol. 2010 Jul;66(7):721-5. doi: 10.1007/s00228-010-0797-2. Epub 2010 Mar 20. [PubMed:20306185]
- Page RL 2nd, Klem PM, Rogers C: Potential elevation of tacrolimus trough concentrations with concomitant metronidazole therapy. Ann Pharmacother. 2005 Jun;39(6):1109-13. doi: 10.1345/aph.1E399. Epub 2005 Apr 26. [PubMed:15855244]
Drug created on June 13, 2005 07:24 / Updated on October 31, 2020 10:29
Are you a
new drug developer?
Contact us to learn more about our customized products and solutions.
![]({"CS-Molecular-Health-1.jpg":"/assets/ads/CS-Molecular-Health-1-19e76f023997d5ac198da2cb9976457f7b9ba733f0ea8a780fe21191c759e8fa.jpg","Drug-Dev-2.jpg":"/assets/ads/Drug-Dev-2-7c3039d93245f493c23278efbf759e4f933848a676262d579087d5cc516af179.jpg","Drug-Search-3.jpg":"/assets/ads/Drug-Search-3-7346c33d2133f62b46cbfbbe2b666e78f955c6847e242692c6081fec37c4d10d.jpg","PM-3.jpg":"/assets/ads/PM-3-13494ac4c996d71619127a11f685681418d4280832dec162c0b2c9c8bc2eda50.jpg","OD-Webinar-1.jpg":"/assets/ads/OD-Webinar-1-f9357f6d57fef5e411aa1c0439ef46c86d9151214434659d096eeed6407b799b.jpg","DDI-3.jpg":"/assets/ads/DDI-3-12808cf864d540ad43757b10b08fc52ae93e793b0c6e81345555187b2840ad09.jpg","EMR-2.jpg":"/assets/ads/EMR-2-adacf8de3f42cb06d6676d06fce611c29781db6ad30776cd18b72a7d8e69f0c8.jpg","Covid.jpg":"/assets/ads/Covid-eed8f17668b0308db62ce3c656f5e2f562376e9185ae08dda5ce6ed9ab0bbd1f.jpg","CS-Molecular-Health-2.jpg":"/assets/ads/CS-Molecular-Health-2-22f41f94b3f87e44a1dcaa8f6c03dc411ab69558efd4f3148ff9bb6adaa956dc.jpg","PM-5.jpg":"/assets/ads/PM-5-d0dc031e0fa0d0097d912eff07b7e80b27b867264dd5b055e379a57bfa2a8723.jpg","DDI-4.jpg":"/assets/ads/DDI-4-313b9c374b937fd78bb2ade652b9b030abb9e6cb90efd35833f793e384e8185b.jpg","Discover-1.jpg":"/assets/ads/Discover-1-b48ae6a3872eeb442f4c22a9a1d867428c83a917ec78a8c3ff4e02f84c5d4fef.jpg","Discover-2.jpg":"/assets/ads/Discover-2-6e7759998ee0fdc234cd84eea962f2480f0c7dafadabd785924918420decb102.jpg","Repurpose-1.jpg":"/assets/ads/Repurpose-1-265fbec40f0eac18d51d3ec4f558c10cb623d834ea75e0296259e458b72ee6d4.jpg","Repurpose-2.jpg":"/assets/ads/Repurpose-2-d12bd1d18b92d36eab60e71e6fd59acf04ef60a53783570e11eef397a0e0f4f5.jpg","PM-6.jpg":"/assets/ads/PM-6-3ae66e41f7ae1e851a0910be89141cf2533509b46df6379464efc885d5ee2f07.jpg","Drug-Search-4.jpg":"/assets/ads/Drug-Search-4-2a9102bd41f16e8c40c9d8044d1dcb6f206ff80107cc269aa83d02ea683bc829.jpg","DDI-5.jpg":"/assets/ads/DDI-5-fa1c287946f4044094c723161577cb5ac631f9cd1217446e510dc79ace6cb94e.jpg","TH-1.jpg":"/assets/ads/TH-1-55a9077bb39e8c38a68c67b555b8091d21a9d41b1c21c7daed3fe53e6f9f3c97.jpg","TH-2.jpg":"/assets/ads/TH-2-1d488747fa4af00ab970a48dba0b228b054d166aa22c1760a310e2b72dd22589.jpg"})
Stay in the know!
As part of our commitment to providing the most up-to-date drug information, we will be releasing #DrugBankUpdates with our newly added curated drug pages.
#DrugBankUpdates