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
Thumb
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
Associated Therapies
Contraindications & Blackbox Warnings
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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

TargetActionsOrganism
AOxygen-insensitive NADPH nitroreductase
potentiator
Helicobacter pylori (strain ATCC 700392 / 26695)
UAnaerobic bacterial DNA
inhibitor
UProtozoal 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

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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
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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.
DrugInteraction
AbataceptThe metabolism of Metronidazole can be increased when combined with Abatacept.
AbirateroneThe metabolism of Abiraterone can be decreased when combined with Metronidazole.
AcalabrutinibThe metabolism of Metronidazole can be decreased when combined with Acalabrutinib.
AcebutololThe risk or severity of QTc prolongation can be increased when Metronidazole is combined with Acebutolol.
AcenocoumarolThe serum concentration of Acenocoumarol can be increased when it is combined with Metronidazole.
AcetaminophenThe metabolism of Metronidazole can be decreased when combined with Acetaminophen.
AcetazolamideThe therapeutic efficacy of Acetazolamide can be decreased when used in combination with Metronidazole.
AcetohexamideThe metabolism of Acetohexamide can be decreased when combined with Metronidazole.
Acetylsalicylic acidThe metabolism of Acetylsalicylic acid can be decreased when combined with Metronidazole.
AcrivastineThe risk or severity of QTc prolongation can be increased when Metronidazole is combined with Acrivastine.
Additional Data Available
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  • Evidence Level
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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

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Product Ingredients
IngredientUNIICASInChI Key
Metronidazole hydrochloride76JC1633UF69198-10-3FPTPAIQTXYFGJC-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
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
FlagylCapsule375 mg/1OralPhysicians Total Care, Inc.1995-05-032000-09-19US flag
FlagylCapsule500 mgOralOdan Laboratories Ltd1979-12-31Not applicableCanada flag
FlagylTablet, film coated500 mg/1OralPfizer Laboratories Div Pfizer Inc1963-07-18Not applicableUS flag
FlagylTablet, film coated250 mg/1OralPfizer Laboratories Div Pfizer Inc1963-07-182019-02-28US flag
FlagylCapsule375 mg/1OralG.D. Searle LLC Division of Pfizer Inc1995-05-03Not applicableUS flag
FlagylCream10 %VaginalSanofi Aventis1970-12-31Not applicableCanada flag
Flagyl 500 500mgSuppositoryVaginalAventis Pharma Ltd.1960-12-312003-07-22Canada flag
Flagyl ERTablet, film coated, extended release750 mg/1OralG.D. Searle LLC Division of Pfizer Inc1997-11-262014-10-31US flag
Florazole ERTablet, extended releaseOralFerring Pharmaceuticals2002-10-102012-09-30Canada flag
MetroCreamCream7.5 mg/1gTopicalGalderma1995-09-20Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code
    Available for Purchase

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo-metronidazoleTabletOralApotex CorporationNot applicableNot applicableCanada flag
Apo-metronidazoleCapsuleOralApotex CorporationNot applicableNot applicableCanada flag
Apo-metronidazoleCapsuleOralApotex Corporation2003-11-27Not applicableCanada flag
Auro-metronidazoleCapsuleOralAuro Pharma Inc2018-04-03Not applicableCanada flag
Mar-metronidazoleCapsuleOralMarcan Pharmaceuticals IncNot applicableNot applicableCanada flag
MetronidazoleTablet500 mg/1OralPreferred Pharmaceuticals, Inc.2016-12-01Not applicableUS flag
MetronidazoleGel7.5 mg/1gTopicalSandoz2006-07-132015-06-30US flag
MetronidazoleTablet, film coated250 mg/1OralCadila Pharmaceuticals Limited2017-12-29Not applicableUS flag
MetronidazoleTablet500 mg/1Oralbryant ranch prepack2017-11-29Not applicableUS flag
MetronidazoleTablet250 mg/1OralPreferred Pharmaceuticals, Inc.2010-09-012019-10-30US flag68788 908220180907 15195 1b7pehc
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code
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    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Bismuth Subsalicylate/Metronidazole/Tetracycline HydrochlorideMetronidazole (250 mg/1) + Bismuth subsalicylate (262.4 mg/1) + Tetracycline hydrochloride (500 mg/1)KitOralAilex Pharmaceuticals, Llc2018-11-30Not applicableUS flag
FlagystatinMetronidazole (500 mg) + Nystatin (100000 unit)SuppositoryVaginalSanofi Aventis1979-12-31Not applicableCanada flag
FlagystatinMetronidazole (500 mg) + Nystatin (100000 unit)CreamVaginalSanofi Aventis1976-12-312017-08-24Canada flag
FlagystatinMetronidazole (500 mg) + Nystatin (100000 unit)SuppositoryVaginalAventis Pharma Ltd.1972-12-312004-07-30Canada flag
HELIDAC TherapyMetronidazole (250 mg/1) + Bismuth subsalicylate (262.4 mg/1) + Tetracycline hydrochloride (500 mg/1)KitOralPrometheus Laboratories1996-08-152014-02-01US flag
HELIDAC TherapyMetronidazole (250 mg/1) + Bismuth subsalicylate (262.4 mg/1) + Tetracycline hydrochloride (500 mg/1)KitOralCasper Pharma Llc2020-06-11Not applicableUS flag
PyleraMetronidazole (125 mg) + Bismuth subcitrate potassium monohydrate (40 mg) + Tetracycline hydrochloride (125 mg)CapsuleOralAptalis Pharma Canada UlcNot applicableNot applicableCanada flag
PyleraMetronidazole (125 mg/1) + Bismuth subcitrate potassium monohydrate (140 mg/1) + Tetracycline hydrochloride (125 mg/1)CapsuleOralAllergan, Inc.2013-08-01Not applicableUS flag
PyleraMetronidazole (125 mg/1) + Bismuth subcitrate potassium monohydrate (140 mg/1) + Tetracycline hydrochloride (125 mg/1)CapsuleOralPhysicians Total Care, Inc.2010-08-18Not applicableUS flag
PyleraMetronidazole (125 mg/1) + Bismuth subcitrate potassium monohydrate (140 mg/1) + Tetracycline hydrochloride (125 mg/1)CapsuleOralAxcan Pharma US, Inc.2007-05-012011-06-14US flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
171083 Ivermectin 1% / Metronidazole 1% / Niacinamide 4%Metronidazole (1 g/100g) + Ivermectin (1 g/100g) + Nicotinamide (4 g/100g)GelTopicalSincerus Florida, LLC2020-07-02Not applicableUS flag
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)GelTopicalSincerus Florida, LLC2019-05-16Not applicableUS flag
Ivermectin 1% / Metronidazole 1%Metronidazole (1 g/100g) + Ivermectin (1 g/100g)GelTopicalSincerus Florida, LLC2019-05-01Not applicableUS flag
Ivermectin 1% / Metronidazole 1% / Niacinamide 4%Metronidazole (1 g/100g) + Ivermectin (1 g/100g) + Nicotinamide (4 g/100g)GelTopicalSincerus Florida, LLC2019-05-01Not applicableUS flag
MetronidazoleMetronidazole (500 mg/100mL)Injection, solutionIntravenousBaxter Healthcare Corporation2017-10-052019-10-31US flag
Metronidazole 1% / Mupirocin 2%Metronidazole (1 g/100g) + Mupirocin (2 g/100g)OintmentTopicalSincerus Florida, LLC2019-05-15Not applicableUS flag
Metronidazole 1% / Mupirocin 2%Metronidazole (1 g/100g) + Mupirocin (2 g/100g)OintmentTopicalSincerus Florida, LLC2019-05-15Not applicableUS flag
Metronidazole 1% / Mupirocin 2% /Metronidazole (1 g/100g) + Mupirocin (2 g/100g)OintmentTopicalSincerus Florida, LLC2019-05-14Not applicableUS flag
Metronidazole 1% / Niacinamide 4%Metronidazole (1 g/100g) + Nicotinamide (4 g/100g)GelTopicalSincerus Florida, LLC2019-05-16Not applicableUS flag
Rosaclear SystemMetronidazole (7.5 mg/1g)KitTopicalOMP, INC.2012-12-29Not applicableUS flag

Categories

ATC Codes
A02BD11 — Pantoprazole, amoxicillin, clarithromycin and metronidazoleD06BX01 — MetronidazoleA02BD03 — Lansoprazole, amoxicillin and metronidazoleJ01XD01 — MetronidazoleJ01RA04 — Spiramycin and metronidazoleA02BD01 — Omeprazole, amoxicillin and metronidazoleA02BD15 — Vonoprazan, amoxicillin and metronidazoleJ01RA03 — Cefuroxime and metronidazoleA01AB17 — MetronidazoleG01AF20 — Combinations of imidazole derivativesJ01RA10 — Ciprofloxacin and metronidazoleA02BD02 — Lansoprazole, tetracycline and metronidazoleA02BD13 — Rabeprazole, amoxicillin and metronidazoleG01AF01 — MetronidazoleP01AB51 — Metronidazole, combinationsA02BD08 — Bismuth subcitrate, tetracycline and metronidazoleP01AB01 — Metronidazole
Drug Categories
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
  1. 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]
  2. 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]
  3. 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]
  4. 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]
  5. 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]
  6. 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]
  7. 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]
  8. 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]
  9. 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]
  10. 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]
  11. 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]
  12. 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]
  13. 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]
  14. Flagyl (Metronidazole) FDA Label [Link]
  15. FDA approvals, Metronidazole [Link]
  16. Canadian monograph, Flagyl [Link]
  17. Flagyl [Link]
  18. DailyMed: Flagyl (metronidazole) oral tablets [Link]
Human Metabolome Database
HMDB0015052
KEGG Drug
D00409
KEGG Compound
C07203
PubChem Compound
4173
PubChem Substance
46508911
ChemSpider
4029
BindingDB
50375309
RxNav
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
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Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingPreventionSurgery, Colorectal1
4Active Not RecruitingTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori) / Gastrointestinal Ulcer Haemorrhage1
4Active Not RecruitingTreatmentBlastocystis Hominis Infections1
4Active Not RecruitingTreatmentExacerbation of Ulcerative Colitis / Granulomatous Colitis / Ulcerative Colitis, Active Severe1
4Active Not RecruitingTreatmentPeri-Implantitis1
4Active Not RecruitingTreatmentPeriodontitis, Chronic2
4CompletedPreventionInfection Prophylaxis in Colo Rectal Surgery1
4CompletedPreventionPostoperative Wound Infection1
4CompletedSupportive CareAcne Rosacea1
4CompletedSupportive CareAmoxicillin / Metronidazole / Ofloxacin / Periodontitis / Root Planing1

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
FormRouteStrength
LiquidTopical10 mg/1mL
Capsule, coatedOral300 mg
SuspensionOral8.04 g
SolutionIntravenous5 mg/ml
Tablet, film coatedOral250 mg
Tablet, film coatedOral500 mg
CapsuleVaginal100 mg
Injection, solutionParenteral500 MG/100ML
Tablet50 mg
TabletVaginal750 mg
CapsuleOral375 mg/1
CapsuleOral500 mg
CreamVaginal10 %
SuppositoryVaginal1 G
TabletOral250 MG
TabletOral; Vaginal500 MG
Tablet, coatedOral200 mg
SuppositoryVaginal
CreamVaginal
SuppositoryVaginal
Tablet, extended releaseOral
CreamVaginal2 g
InsertVaginal750 mg
KitOral
SuspensionOral8 g
GelTopical
Capsule, coatedOral600 mg
SolutionParenteral0.5 %
SuppositoryVaginal750 mg
SuppositoryVaginal750 mg/200g
Tablet, coatedOral400 mg
SuspensionOral200 mg/5mL
SuspensionOral5 g
Tablet, film coated1.5 IU
SuspensionOral125 mg/5ml
Tablet200 mg
SolutionTopical1 g/100g
Capsule, coatedOral400 mg
CreamTopical
GelTopical10 mg/1g
GelVaginal7.5 mg/1g
GelTopical
Gel1 g/100g
InjectionIntravenous5 MG/ML
LotionTopical0.75 %
InsertVaginal500 mg
SuspensionOral4 g
Tablet400 MG
TabletVaginal500 mg
SolutionParenteral
Tablet250 mg
SolutionParenteral5 mg/ml
SolutionParenteral500 MG/100ML
TabletOral500 mg
Tablet, coatedOral500 mg
Capsule, liquid filledOral300 mg
CreamTopical10 mg/1g
CreamTopical7.5 mg/1g
GelTopical7.5 mg/1g
GelVaginal13 mg/1g
InjectionIntravenous
Injection, solutionIntravenous500 mg/100mL
LotionTopical7.5 mg/1mL
LotionTopical7.5 mg/1g
PowderNot applicable1 g/1g
SolutionIntravenous500 mg/100mL
SuspensionOral20 mg/1mL
TabletOral250 mg/1
TabletOral500 mg/1
TabletVaginal200 mg
Tablet, coatedOral250 mg
Tablet, coatedOral250 mg/1
Tablet, coatedOral500 1/1
Tablet, film coatedOral
Tablet, film coatedOral500 mg/1
Tablet, film coated, extended releaseOral750 mg/1
Tablet; tablet, film coatedOral
OintmentTopical
SolutionIntravenous
Syrup
TabletOral
Tablet, film coatedOral250 mg/1
Injection, solutionParenteral5 MG/ML
Injection, solutionIntravenous; Parenteral0.5 G/100ML
Injection, solutionParenteral0.5 G/100ML
InjectionIntravenous0.5 %
Capsule, liquid filledOral500 mg
CreamVaginal1 g
CapsuleOral200 mg
SuppositoryVaginal200 mg
SuppositoryVaginal500 mg
GelVaginal
GelTopical7.5 mg/g
Solution200 mg/5ml
Injection, solutionIntravenous500 mg
CreamTopical1 %
CreamTopical10 mg/60g
GelTopical65 mg/5g
GelVaginal65 mg/5g
CapsuleOral
SolutionIntravenous0.5 %
CapsuleOral
CapsuleOral140 MG
Gel750 mg/100g
KitTopical7.5 mg/1g
CreamTopical
GelTopical0.75 %
CreamTopical10 mg/g
Cream0.75 %
Emulsion0.75 %
Gel0.75 %
GelTopical0.75 g
SolutionIntravenous500 mg
Tablet
CapsuleOral250 MG
InsertVaginal100 mg
Prices
Unit descriptionCostUnit
MetroLotion 0.75% Lotion 59ml Bottle292.66USD bottle
MetroCream 0.75% Cream 45 gm Tube281.09USD tube
Metrogel 1% Gel 60 gm Tube200.93USD tube
Metrogel 1% Kit Box200.93USD box
Metrogel 1% kit193.2USD kit
Noritate 1% Cream 60 gm Tube156.44USD tube
MetroNIDAZOLE 0.75% Lotion 59ml Bottle89.86USD bottle
MetroNIDAZOLE 0.75% Cream 45 gm Tube80.87USD tube
MetroNIDAZOLE 0.75% Gel 45 gm Tube74.0USD tube
MetroNIDAZOLE 0.75% Gel 70 gm Tube68.53USD tube
Flagyl ER 750 mg 24 Hour tablet13.2USD tablet
Flagyl er 750 mg tablet12.7USD tablet
MetroNIDAZOLE 750 mg 24 Hour tablet8.07USD tablet
Flagyl 500 mg tablet6.24USD tablet
Metrocream 0.75% cream5.99USD g
Danazol 200 mg capsule5.63USD capsule
Flagyl 375 mg capsule5.45USD capsule
Metrolotion topical 0.75%4.77USD ml
Metronidazole benz powder4.74USD g
Flagyl 250 mg tablet3.49USD tablet
Danazol 100 mg capsule2.98USD capsule
Noritate 1% cream2.51USD g
Danazol 50 mg capsule1.99USD capsule
Metronidazole powder1.65USD g
Metronidazole 0.75% cream1.34USD g
Metronidazole vaginal 0.75% gl0.94USD g
Metronidazole 500 mg tablet0.72USD tablet
Metrogel 0.75 % Gel0.69USD g
Metrogel 1 % Gel0.63USD g
Noritate 1 % Cream0.58USD g
Rosasol 1 % Cream0.57USD g
Metrocream 0.75 % Cream0.52USD g
Metrolotion 0.75 % Lotion0.52USD g
Metrogel-vaginal 0.75% gel0.51USD g
Vandazole vaginal 0.75% gel0.48USD g
Metronidazole 250 mg tablet0.44USD tablet
Flagyl 10 % Cream0.25USD g
Apo-Metronidazole 250 mg Tablet0.06USD tablet
Flagyl 5 mg/ml0.03USD ml
Metro iv 500 mg/100 ml0.03USD ml
Metronidazole 5 mg/ml0.03USD ml
Metronidazole 500 mg/100 ml0.03USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5536743No1996-07-162013-07-16US flag
CA2470492No2010-02-232022-11-07Canada flag
CA2161737No1998-10-202015-10-30Canada flag
US6881726No2005-04-192022-02-21US flag
US7348317No2008-03-252022-02-21US flag
US7456207No2008-11-252024-09-22US flag
US6350468No2002-02-262018-12-14US flag
US8946276No2015-02-032032-06-28US flag
US8658678No2014-02-252028-06-27US flag
US9198858No2015-12-012032-06-28US flag
US8877792No2014-11-042028-02-02US flag
US7893097No2011-02-222028-02-19US flag
US10238634No2019-03-262032-06-28US flag
US10596155No2012-06-282032-06-28US flag
Additional Data Available
  • Filed On
    Filed On
    Available for Purchase

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)160http://www.inchem.org/documents/pims/pharm/metronid.htm
boiling point (°C)405.4http://www.emelcabio.com/metronidazole-41310008.html
logP-0.02http://www.t3db.ca/toxins/T3D4703
logS-1.5http://www.t3db.ca/toxins/T3D4703
pKa2.57,15.42http://www.t3db.ca/toxins/T3D4703
Predicted Properties
PropertyValueSource
Water Solubility5.92 mg/mLALOGPS
logP-0.15ALOGPS
logP-0.46ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)15.44ChemAxon
pKa (Strongest Basic)3.09ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area83.87 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity41.22 m3·mol-1ChemAxon
Polarizability15.82 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9805
Blood Brain Barrier+0.9297
Caco-2 permeable-0.5365
P-glycoprotein substrateNon-substrate0.5141
P-glycoprotein inhibitor INon-inhibitor0.8954
P-glycoprotein inhibitor IINon-inhibitor0.8755
Renal organic cation transporterNon-inhibitor0.7762
CYP450 2C9 substrateNon-substrate0.7318
CYP450 2D6 substrateNon-substrate0.8815
CYP450 3A4 substrateNon-substrate0.6767
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9242
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9401
CYP450 3A4 inhibitorNon-inhibitor0.9242
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8483
Ames testAMES toxic0.9107
CarcinogenicityNon-carcinogens0.7471
BiodegradationNot ready biodegradable0.5941
Rat acute toxicity2.0422 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.5
hERG inhibition (predictor II)Non-inhibitor0.8272
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (9.68 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-0ul0-9300000000-2268b08f47fed3f6d263
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-004i-1900000000-659f2bbb83f8ef5a85d1
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0900000000-50c7cfe79eb17c4440a8
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0900000000-b06d808767cc01c0d494
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00fr-0900000000-e9c07cc448b8fb519022
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0900000000-8ad03b44aa7557127e34
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0900000000-ed7ba5c872a6309a31d4
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-2900000000-e0ead4b0eec72b9c44b6
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-5900000000-2da8a7b45537f9063220
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0900000000-24d94f1704e577b05eb7
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00fr-0900000000-fbb1c4e8457cd3d799b9
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0900000000-fd6166313a17f944f530
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0900000000-5ebb32a580e1f5d00170
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-2900000000-811a6e7e45b7ea1a6184
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-5900000000-082e6de6c0fa3f382d84
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0900000000-baf9e195c01d875e77b5
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-0900000000-ec181c008a10dac8040b
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-004i-1900000000-2a218e19a8fadb9c66d6
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-003r-9500000000-ed02acd36b190c189cc9
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-9000000000-71ea79659ccd75c64bef
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-9000000000-3f7795597c6629540426
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

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
  1. 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]
  2. 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]
  3. 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]
  4. 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
Kind
Group
Organism
Not Available
Pharmacological action
Unknown
Actions
Inhibitor
This group represents the DNA of various anaerobic bacteria as a drug target.
References
  1. Samuelson J: Why metronidazole is active against both bacteria and parasites. Antimicrob Agents Chemother. 1999 Jul;43(7):1533-41. [PubMed:10390199]
  2. 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]
  3. Flagyl (Metronidazole) FDA Label [Link]
3. Protozoal DNA
Kind
Group
Organism
Not Available
Pharmacological action
Unknown
Actions
Inhibitor
This group is created to include the DNA of various protozoans.
References
  1. 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]
  2. 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]
  3. 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
  1. 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]
  2. 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]
  3. 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]
  4. 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
  1. 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]
  2. Michalets EL: Update: clinically significant cytochrome P-450 drug interactions. Pharmacotherapy. 1998 Jan-Feb;18(1):84-112. [PubMed:9469685]
  3. 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
  1. 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
  1. 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
  1. 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
  1. 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
  1. 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
  1. 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]
  2. 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]
  3. 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

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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