Metronidazole

Overview

Description
A medication used to treat a wide variety of infections in the body as well as inflammation and redness of the skin.
Description
A medication used to treat a wide variety of infections in the body as well as inflammation and redness of the skin.
DrugBank ID
DB00916
Type
Small Molecule
US Approved
YES
Other Approved
YES
Clinical Trials
Phase 0
15
Phase 1
39
Phase 2
100
Phase 3
106
Phase 4
205
Therapeutic Categories
  • Anti-Bacterial Agents
  • Nitroimidazole Antimicrobial

Identification

Summary

Metronidazole is a nitroimidazole used to treat trichomoniasis, amebiasis, inflammatory lesions of rosacea, and bacterial infections, as well as prevent postoperative infections.

Brand Names
Flagyl, Flagystatin, Likmez, Metrocream, Metrogel, Metrolotion, Nidagel, Noritate, Nuvessa, Pylera, Rosadan, Vandazole
Generic Name
Metronidazole
DrugBank Accession Number
DB00916
Background

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.4,5 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
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 vaginosis,16,23 certain types of amebiasis, and various anaerobic infections.11,23 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 Topical formulations of metronidazole are indicated for the treatment of inflammatory lesions of rosacea.19

It is also used off-label in the treatment of Crohn's disease, 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

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofAmebiasis••••••••••••••••••••••
Treatment ofAnaerobic bacterial infection•••••••••••••••••••••••••••
Treatment ofAnaerobic bacterial infection•••••••••••••••••••• ••••••••• ••••••
Treatment ofBacterial endocarditis•••••••••••••••••••• ••••••••• ••••••
Treatment ofBacterial septicemia•••••••••••••••••••• ••••••••• ••••••
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

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
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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

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.
AbemaciclibThe serum concentration of Abemaciclib can be increased when it is combined with Metronidazole.
AbrocitinibThe metabolism of Abrocitinib can be decreased when combined with Metronidazole.
AcalabrutinibThe serum concentration of Acalabrutinib can be increased when it is combined with Metronidazole.
AcenocoumarolThe serum concentration of Acenocoumarol can be increased when it is combined with Metronidazole.
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/1OralPfizer Laboratories Div Pfizer Inc1995-05-03Not applicableUS flag
FlagylCapsule500 mgOralSanofi Aventis Deutschland Gmb H1979-12-31Not applicableCanada flag
FlagylTablet, film coated500 mg/1OralPfizer Laboratories Div Pfizer Inc1963-07-182021-10-31US flag
FlagylCapsule375 mg/1OralPhysicians Total Care, Inc.1995-05-032000-09-19US flag
FlagylTablet, film coated500 mg/1OralRedPharm Drug, Inc.1963-07-18Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo-metronidazoleCapsule500 mgOralApotex Corporation2003-11-27Not applicableCanada flag
Apo-metronidazoleTablet250 mgOralApotex CorporationNot applicableNot applicableCanada flag
Apo-metronidazoleCapsule500 mgOralApotex CorporationNot applicableNot applicableCanada flag
Apo-metronidazole TabletsTablet250 mgOralApotex Corporation1982-12-31Not applicableCanada flag
Auro-metronidazoleCapsule500 mgOralAuro Pharma Inc2018-04-03Not applicableCanada flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
เมโตรจิล เจลGel1 %w/wTopicalห้างหุ้นส่วนจำกัด จีไอเอส ฟาร์มา2014-06-172019-10-21Thailand flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
AcnilMetronidazole (8 mg/30mL) + Clindamycin hydrochloride (10 mg/30mL)LinimentTopicalJiangsu Chenpai Bond Pharmaceutical Co.,Ltd.2024-05-01Not applicableUS flag
AMEBICOL®Metronidazole (300 mg) + Nifuroxazide (200 mg)Capsule, coatedOralBIOQUIMICO PHARMAS.A.2017-05-22Not applicableColombia flag
AMZOL FEM®Metronidazole (500 mg) + Clotrimazole (100 mg)InsertVaginal2015-12-022015-12-02Colombia flag
BIOGYNOL® OVULOSMetronidazole (750 mg) + Miconazole nitrate (200 mg)InsertVaginalBIOCHEM FARMACEUTICA DE COLOMBIAS.A.2016-07-08Not applicableColombia flag
Bismuth Subcitrate Potassium, Metronidazole and Tetracycline HydrochlorideMetronidazole (125 mg/1) + Bismuth subcitrate potassium monohydrate (140 mg/1) + Tetracycline hydrochloride (125 mg/1)CapsuleOralPar Pharmaceutical2023-03-07Not applicableUS 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
AcnilMetronidazole (8 mg/30mL) + Clindamycin hydrochloride (10 mg/30mL)LinimentTopicalJiangsu Chenpai Bond Pharmaceutical Co.,Ltd.2024-05-01Not 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

Categories

ATC Codes
A02BD11 — Pantoprazole, amoxicillin, clarithromycin and metronidazoleP01AB52 — Metronidazole and diloxanideD06BX01 — MetronidazoleA02BD03 — Lansoprazole, amoxicillin and metronidazoleJ01XD01 — MetronidazoleJ01RA04 — Spiramycin and metronidazoleA02BD01 — Omeprazole, amoxicillin and metronidazoleJ01RA14 — Norfloxacin 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 and furazolidoneA02BD08 — 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)
Affected organisms
  • Bacteria and protozoa
  • Helicobacter pylori
  • Peptoclostridium difficile

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. [Article]
  2. Williams CS, Woodcock KR: Do ethanol and metronidazole interact to produce a disulfiram-like reaction? Ann Pharmacother. 2000 Feb;34(2):255-7. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  14. FDA Approved Drug Products: Flagyl (metronidazole) capsules for oral administration [Link]
  15. FDA approvals, Metronidazole [Link]
  16. Canadian monograph, Flagyl [Link]
  17. Flagyl [Link]
  18. DailyMed: Flagyl (metronidazole) oral tablets [Link]
  19. FDA Approved Drug Products: Metronidazole gel (January 2023) [Link]
  20. FDA Approved Drug Products: FLAGYL (metronidazole) tablets, for oral use (October 2023) [Link]
  21. DailyMed: Metronidazole Oral Tablet [Link]
  22. DailyMed: Metronidazole Oral Capsule [Link]
  23. FDA Approved Drug Products: LIKMEZ (metronidazole) oral suspension [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
PDB Entries
1w3r
MSDS
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Clinical Trials

Clinical Trials
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PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns
Not AvailableActive Not RecruitingBasic ScienceHelminth Infection / Malnutrition / Tuberculosis (TB)1somestatusstop reasonjust information to hide
Not AvailableActive Not RecruitingTreatmentAppendicitis Acute1somestatusstop reasonjust information to hide
Not AvailableActive Not RecruitingTreatmentPeriimplantitis1somestatusstop reasonjust information to hide
Not AvailableActive Not RecruitingTreatmentPeriodontitis1somestatusstop reasonjust information to hide
Not AvailableActive Not RecruitingTreatmentRevascularization procedures1somestatusstop reasonjust information to hide

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
LinimentTopical
SolutionIntravenous200.000 mg
SuspensionOral5 g
SuspensionOral8.04 g
SolutionIntravenous5 mg/ml
Capsule, coatedOral400 mg
TabletOral250 mg
Tablet, film coatedOral250 mg
Tablet, film coatedOral500 mg
SuspensionOral5.000 g
Injection, solution5 mg/1ml
Capsule; kit; tabletOral
Injection, solutionParenteral500 MG/100ML
SuppositoryVaginal500 mg
GelOral
TabletOral500.000 mg
InsertVaginal500.00 mg
SolutionIntravenous500.000 mg
Injection, solutionIntravenous
CapsuleVaginal
SuspensionOral125 MG/5ML
CapsuleOral375 mg/1
CreamVaginal10 %
SuppositoryVaginal
TabletOral; Vaginal500 MG
Tablet, film coatedOral400 mg
SuppositoryVaginal500 mg / sup
Tablet, coatedOral500 mg
InjectionIntravenous0.5 % w/v
InsertVaginal0.5 g
SolutionIntravenous5 mg
SuppositoryVaginal
Tablet, extended releaseOral750 mg
SuppositoryVaginal250 mg
Tablet, coatedOral
Capsule, liquid filledVaginal
KitOral
Tablet
SuspensionOral
GelTopical
Capsule, coatedOral
TabletOral250.000 mg
InjectionParenteral0.5 %
SuspensionOral100 mg/1mL
CreamVaginal
InsertVaginal
SolutionVaginal
Tablet500.000 mg
Tablet, film coated
SolutionIntravenous5.000 mg
InjectionIntravenous0.5 %
GelVaginal0.75 g
CreamCutaneous0.750 g
CreamTopical.75 %
SuspensionOral4.02 g
GelCutaneous0.750 g
GelTopical10 mg/1g
GelVaginal7.5 mg/1g
GelTopical0.75 %
GelTopical1 %
GelTopical10 mg/g
InjectionIntravenous5 MG/ML
TabletOral400 MG
LotionTopical0.75 %
SolutionParenteral0.5 %
SuspensionOral4 g
Capsule, liquid filledOral250 mg
SolutionIntravenous500 mg
TabletOral50000000 mg
TabletVaginal500 mg
SolutionIntravenous500 g
SolutionParenteral500 mg
SolutionParenteral5 MG/ML
SolutionParenteral500 MG/100ML
SolutionIntravenous1.5 g
SolutionParenteral5 mg
Tablet, film coatedOral
TabletOral500 mg
Capsule, liquid filledOral
CreamTopical10 mg/1g
CreamTopical7.5 mg/1g
GelTopical7.5 mg/1g
GelVaginal13 mg/1g
InjectionIntravenous5 mg
Injection, solutionIntravenous500 mg/100mL
LotionTopical7.5 mg/1mL
LotionTopical7.5 mg/1g
PowderNot applicable1 g/1g
SolutionIntravenous500 mg/100mL
TabletOral
TabletOral250 mg/1
TabletOral500 mg/1
Tablet, coatedOral250 mg/1
Tablet, coatedOral500 mg/1
Tablet, film coatedOral500 mg/1
Tablet, film coated, extended releaseOral750 mg/1
Tablet; tablet, film coatedOral500 MG
OintmentTopical
InjectionIntravenous0.5 g/100ml
InjectionIntravenous500 mg/100ml
Injection, solutionIntravenous5 mg/1ml
SolutionIntravenous5 mg / mL
InjectionIntravenous5.000 g/1000ml
SyrupOral100 MG
Tablet, film coatedOral250 mg/1
TabletVaginal
Injection, solutionParenteral5 MG/ML
Injection, solutionIntravenous; Parenteral0.5 G/100ML
Injection, solutionIntravenous; Parenteral500 MG/100ML
Injection, solution5 MG/ML
Injection, solution
Injection, solutionParenteral0.5 G/100ML
Injection, solution500 MG/100ML
GelTopical
SuspensionOral2.500 g
Tablet, film coatedOral
Capsule, liquid filledOral500 mg
InsertVaginal500 mg
CapsuleVaginal500 mg
GelVaginal0.75 % w/w
GelTopical7.5 mg/g
Solution200 mg/5ml
Injection, solutionIntravenous500 mg
CreamTopical1 % w/w
CreamTopical10 mg/60g
GelTopical65 mg/5g
GelVaginal65 mg/5g
SolutionParenteral200.000 mg
InjectionIntravenous500 mg
InjectionParenteral500 mg
Tablet, film coatedOral200 mg
CapsuleOral500 mg
SolutionIntravenous0.5 %
CapsuleOral
KitTopical7.5 mg/1g
Gel; kitTopical7.5 mg/1g
CreamTopical
CreamOral
CreamTopical
EmulsionTopical0.75 %
GelTopical0.75 g
CreamTopical0.75 %
SolutionIntravenous500.00 mg
TabletOral
SuppositoryVaginal1 G
TabletOral200 mg
SuspensionOral
Injection, powder, for solutionIntramuscular200 mg/200mg
CapsuleOral250 MG
InjectionIntravenous
CapsuleOral400.000 mg
GelVaginal0.75 %
TabletVaginal
Capsule200 mg
Capsule250 mg
Tablet200 mg
Tablet400 mg
Tablet250 mg
Solution5 mg/1ml
Tablet, coatedOral200 mg
GelTopical1 %w/w
Tablet, coatedOral250 mg
Tablet500 mg
Tablet, coatedOral400 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
US10596155No2020-03-242032-06-28US flag
US11541035No2019-10-042039-10-04US flag

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)15.41Chemaxon
pKa (Strongest Basic)3.03Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area81.19 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity40.22 m3·mol-1Chemaxon
Polarizability15.87 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-MSsplash10-0udl-9700000000-f1b60dcdd221dbdf9eaa
Mass Spectrum (Electron Ionization)MSsplash10-0ul0-9300000000-2268b08f47fed3f6d263
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
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-137.19013
predicted
DarkChem Lite v0.1.0
[M-H]-136.93393
predicted
DarkChem Lite v0.1.0
[M-H]-137.37183
predicted
DarkChem Lite v0.1.0
[M-H]-132.8605
predicted
DeepCCS 1.0 (2019)
[M+H]+137.06023
predicted
DarkChem Lite v0.1.0
[M+H]+136.96433
predicted
DarkChem Lite v0.1.0
[M+H]+137.75783
predicted
DarkChem Lite v0.1.0
[M+H]+136.20238
predicted
DeepCCS 1.0 (2019)
[M+Na]+137.42373
predicted
DarkChem Lite v0.1.0
[M+Na]+137.20983
predicted
DarkChem Lite v0.1.0
[M+Na]+137.40463
predicted
DarkChem Lite v0.1.0
[M+Na]+144.92393
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Helicobacter pylori (strain ATCC 700392 / 26695)
Pharmacological action
Yes
Actions
Potentiator
General 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 renders the bacterium resistant to this compound. The reduction of metronidazole generates hydroxylamine, a potent mutagen and bactericide.
Specific Function
oxidoreductase activity
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
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. [Article]
  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. [Article]
  3. FDA Approved Drug Products: Flagyl (metronidazole) capsules for oral administration [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. [Article]
  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. [Article]
  3. FDA Approved Drug Products: Flagyl (metronidazole) capsules for oral administration [Link]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:11093772, PubMed:14559847, PubMed:15766564, PubMed:19965576, PubMed:7574697). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:11093772, PubMed:14559847, PubMed:15766564, PubMed:19965576, PubMed:7574697). Primarily catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) with a preference for the last double bond (PubMed:15766564, PubMed:19965576, PubMed:7574697). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes all trans-retinoic acid toward its 4-hydroxylated form (PubMed:11093772). Displays 16-alpha hydroxylase activity toward estrogen steroid hormones, 17beta-estradiol (E2) and estrone (E1) (PubMed:14559847). Plays a role in the oxidative metabolism of xenobiotics. It is the principal enzyme responsible for the metabolism of the anti-cancer drug paclitaxel (taxol) (PubMed:26427316)
Specific Function
arachidonic acid epoxygenase activity
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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
UDP-glucuronosyltransferase (UGT) that catalyzes phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase the metabolite's water solubility, thereby facilitating excretion into either the urine or bile (PubMed:12181437, PubMed:15472229, PubMed:18004206, PubMed:18004212, PubMed:18719240, PubMed:19830808, PubMed:23288867). Essential for the elimination and detoxification of drugs, xenobiotics and endogenous compounds (PubMed:12181437, PubMed:18004206, PubMed:18004212). Catalyzes the glucuronidation of endogenous estrogen hormones such as estradiol, estrone and estriol (PubMed:15472229, PubMed:18719240, PubMed:23288867). Involved in the glucuronidation of bilirubin, a degradation product occurring in the normal catabolic pathway that breaks down heme in vertebrates (PubMed:17187418, PubMed:18004206, PubMed:19830808, PubMed:24525562). Also catalyzes the glucuronidation the isoflavones genistein, daidzein, glycitein, formononetin, biochanin A and prunetin, which are phytoestrogens with anticancer and cardiovascular properties (PubMed:18052087, PubMed:19545173). Involved in the glucuronidation of the AGTR1 angiotensin receptor antagonist losartan, a drug which can inhibit the effect of angiotensin II (PubMed:18674515). Involved in the biotransformation of 7-ethyl-10-hydroxycamptothecin (SN-38), the pharmacologically active metabolite of the anticancer drug irinotecan (PubMed:12181437, PubMed:18004212, PubMed:20610558)
Specific Function
enzyme binding
Gene Name
UGT1A1
Uniprot ID
P22309
Uniprot Name
UDP-glucuronosyltransferase 1A1
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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General 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. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity
Specific Function
arachidonic acid epoxygenase activity
Gene Name
CYP2A6
Uniprot ID
P11509
Uniprot Name
Cytochrome P450 2A6
Molecular Weight
56517.005 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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
A cytochrome P450 monooxygenase involved in the metabolism of steroid hormones and vitamins (PubMed:10681376, PubMed:11093772, PubMed:12865317, PubMed:2732228). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:10681376, PubMed:11093772, PubMed:12865317, PubMed:2732228). Exhibits high catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes 6beta-hydroxylation of the steroid hormones testosterone, progesterone, and androstenedione (PubMed:2732228). Catalyzes the oxidative conversion of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes all trans-retinoic acid (atRA) to 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Also involved in the oxidative metabolism of xenobiotics, including calcium channel blocking drug nifedipine and immunosuppressive drug cyclosporine (PubMed:2732228)
Specific Function
aromatase activity
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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
A cytochrome P450 monooxygenase involved in the metabolism of steroid hormones and vitamins during embryogenesis (PubMed:11093772, PubMed:12865317, PubMed:14559847, PubMed:17178770, PubMed:9555064). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:11093772, PubMed:12865317, PubMed:14559847, PubMed:17178770, PubMed:9555064). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes 3beta-hydroxyandrost-5-en-17-one (dehydroepiandrosterone, DHEA), a precursor in the biosynthesis of androgen and estrogen steroid hormones (PubMed:17178770, PubMed:9555064). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1), particularly D-ring hydroxylated estrone at the C16-alpha position (PubMed:12865317, PubMed:14559847). Mainly hydroxylates all trans-retinoic acid (atRA) to 4-hydroxyretinoate and may play a role in atRA clearance during fetal development (PubMed:11093772). Also involved in the oxidative metabolism of xenobiotics including anticonvulsants (PubMed:9555064)
Specific Function
all-trans retinoic acid 18-hydroxylase activity
Gene Name
CYP3A7
Uniprot ID
P24462
Uniprot Name
Cytochrome P450 3A7
Molecular Weight
57469.95 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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids and steroids (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:15766564, PubMed:19965576, PubMed:7574697, PubMed:9866708). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Exhibits low catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes bisallylic hydroxylation and hydroxylation with double-bond migration of polyunsaturated fatty acids (PUFA) (PubMed:9435160, PubMed:9866708). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan (PubMed:25994031)
Specific Function
(R)-limonene 6-monooxygenase activity
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. [Article]
  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. [Article]
  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. [Article]
  4. CYP table [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
Specific Function
1,8-cineole 2-exo-monooxygenase activity
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. [Article]
  2. Michalets EL: Update: clinically significant cytochrome P-450 drug interactions. Pharmacotherapy. 1998 Jan-Feb;18(1):84-112. [Article]
  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. [Article]

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
Translocates drugs and phospholipids across the membrane (PubMed:2897240, PubMed:35970996, PubMed:8898203, PubMed:9038218). Catalyzes the flop of phospholipids from the cytoplasmic to the exoplasmic leaflet of the apical membrane. Participates mainly to the flop of phosphatidylcholine, phosphatidylethanolamine, beta-D-glucosylceramides and sphingomyelins (PubMed:8898203). Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells (PubMed:2897240, PubMed:35970996, PubMed:9038218)
Specific Function
ABC-type xenobiotic transporter activity
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
ATP-dependent translocase ABCB1
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. [Article]
  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. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at November 05, 2024 18:59