Metronidazole

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, 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

Similar Structures

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

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Associated Conditions

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

Target	Actions	Organism
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

Metronidazole
- 2-hydroxymetronidazole

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.

Drug	Interaction
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Abatacept	The metabolism of Metronidazole can be increased when combined with Abatacept.
Abemaciclib	The metabolism of Abemaciclib can be decreased when combined with Metronidazole.
Abrocitinib	The metabolism of Abrocitinib can be decreased when combined with Metronidazole.
Acalabrutinib	The metabolism of Acalabrutinib can be decreased when combined with Metronidazole.
Acenocoumarol	The serum concentration of Acenocoumarol can be increased when it is combined with Metronidazole.
Acetaminophen	The metabolism of Metronidazole can be decreased when combined with Acetaminophen.
Acetazolamide	The therapeutic efficacy of Acetazolamide can be decreased when used in combination with Metronidazole.
Acetohexamide	The metabolism of Acetohexamide can be decreased when combined with Metronidazole.
Acetylsalicylic acid	The metabolism of Acetylsalicylic acid can be decreased when combined with Metronidazole.
Acrivastine	The risk or severity of QTc prolongation can be increased when Metronidazole is combined with Acrivastine.

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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

Ingredient	UNII	CAS	InChI Key
Metronidazole hydrochloride	76JC1633UF	69198-10-3	FPTPAIQTXYFGJC-UHFFFAOYSA-N

Product Images

International/Other Brands

Anabact (Cambridge Healthcare Supplies) / Arilin / Clont / Deflamon / Efloran / Elyzol / Entizol / Fossyol / Klion / Klont / Metrolyl / Metrotop / Nalox / Nidagel / Novonidazol / Orvagil / Protostat / Takimetol / Trichazole / Trichex / Trichopol / Tricowas B / Trikacide / Trikozol / Vagilen / Vagimid / Vertisal / Zadstat

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Flagyl	Capsule	375 mg/1	Oral	Pfizer Laboratories Div Pfizer Inc	1995-05-03	Not applicable
Flagyl	Cream	10 %	Vaginal	Sanofi Aventis	1970-12-31	Not applicable
Flagyl	Capsule	500 mg	Oral	Odan Laboratories Ltd	1979-12-31	Not applicable
Flagyl	Tablet, film coated	500 mg/1	Oral	Pfizer Laboratories Div Pfizer Inc	1963-07-18	2021-10-31
Flagyl	Capsule	375 mg/1	Oral	Physicians Total Care, Inc.	1995-05-03	2000-09-19
Flagyl	Tablet, film coated	500 mg/1	Oral	RedPharm Drug	1963-07-18	Not applicable
Flagyl	Tablet, film coated	250 mg/1	Oral	Pfizer Laboratories Div Pfizer Inc	1963-07-18	2019-02-28
Flagyl 500 500mg	Suppository	500 mg / sup	Vaginal	Aventis Pharma Ltd.	1960-12-31	2003-07-22
Flagyl ER	Tablet, film coated, extended release	750 mg/1	Oral	G.D. Searle LLC Division of Pfizer Inc	1997-11-26	2014-10-31
Florazole ER	Tablet, extended release	750 mg	Oral	Ferring Pharmaceuticals	2002-10-10	2012-09-30

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Apo-metronidazole	Capsule	500 mg	Oral	Apotex Corporation	Not applicable	Not applicable
Apo-metronidazole	Capsule	500 mg	Oral	Apotex Corporation	2003-11-27	Not applicable
Apo-metronidazole	Tablet	250 mg	Oral	Apotex Corporation	Not applicable	Not applicable
Auro-metronidazole	Capsule	500 mg	Oral	Auro Pharma Inc	2018-04-03	Not applicable
Mar-metronidazole	Capsule	500 mg	Oral	Marcan Pharmaceuticals Inc	Not applicable	Not applicable
Metronidazole	Tablet, film coated	500 mg/1	Oral	Unit Dose Services	2014-06-01	Not applicable
Metronidazole	Tablet	500 mg/1	Oral	Mylan Institutional Inc.	2012-10-11	2012-08-24
Metronidazole	Tablet	250 mg/1	Oral	American Health Packaging	2014-01-13	2019-09-30
Metronidazole	Tablet, film coated	500 mg/1	Oral	bryant ranch prepack	2014-06-01	Not applicable
Metronidazole	Tablet, film coated, extended release	750 mg/1	Oral	Alembic Pharmaceuticals Limited	2010-05-07	Not applicable

Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
เมโตรจิล เจล	Gel	1 %w/w	Topical	ห้างหุ้นส่วนจำกัด จีไอเอส ฟาร์มา	2014-06-17	2019-10-21

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
AMEBICOL®	Metronidazole (300 mg) + Nifuroxazide (200 mg)	Capsule, coated	Oral	BIOQUIMICO PHARMAS.A.	2017-05-22	Not applicable
BIOGYNOL® OVULOS	Metronidazole (750 mg) + Miconazole nitrate (200 mg)	Insert	Vaginal	BIOCHEM FARMACEUTICA DE COLOMBIAS.A.	2016-07-08	Not applicable
Bismuth Subsalicylate/Metronidazole/Tetracycline Hydrochloride	Metronidazole (250 mg/1) + Bismuth subsalicylate (262.4 mg/1) + Tetracycline hydrochloride (500 mg/1)	Kit	Oral	Ailex Pharmaceuticals, Llc	2018-11-30	Not applicable
DIARSET NX® M CAPSULAS	Metronidazole (600 mg) + Nifuroxazide (200 mg)	Capsule, coated	Oral	COLOMPACK S.A.	2014-01-10	Not applicable
EXAGYN VAJINAL TABLET, 7 ADET	Metronidazole (750 mg) + Lidocaine hydrochloride (100 mg) + Miconazole nitrate (200 mg)	Tablet	Vaginal	HELBA İLAÇ İÇ VE DIŞ SAN. TİC. LTD. ŞTİ.	2020-08-14	Not applicable
Flagystatin	Metronidazole (500 mg / sup) + Nystatin (100000 unit / sup)	Suppository	Vaginal	Aventis Pharma Ltd.	1972-12-31	2004-07-30
Flagystatin	Metronidazole (500 mg / 4.5 g) + Nystatin (100000 unit / 4.5 g)	Cream	Vaginal	Sanofi Aventis	1976-12-31	2017-08-24
Flagystatin	Metronidazole (500 mg) + Nystatin (100000 unit)	Insert	Vaginal	Sanofi Aventis	1979-12-31	Not applicable
FLAGYSTATIN VAGINAL OVULE	Metronidazole (500 mg) + Nystatin (100000 iu)	Suppository	Vaginal	SANOFI-AVENTIS SINGAPORE PTE. LTD.	1990-02-01	Not applicable
GYNECLOR ®	Metronidazole (10 g) + Clotrimazole (2 g)	Cream	Vaginal	BIOCHEM FARMACEUTICA DE COLOMBIAS.A.	2018-04-13	Not applicable

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
171083 Ivermectin 1% / Metronidazole 1% / Niacinamide 4%	Metronidazole (1 g/100g) + Ivermectin (1 g/100g) + Nicotinamide (4 g/100g)	Gel	Topical	Sincerus Florida, LLC	2020-07-02	Not applicable
Brimonidine Tartrate 0.25% / Ivermectin 1% / Metronidazole 1% / Niacinamide 4%	Metronidazole (1 g/100g) + Brimonidine tartrate (0.25 g/100g) + Ivermectin (1 g/100g) + Nicotinamide (4 g/100g)	Gel	Topical	Sincerus Florida, LLC	2019-05-16	Not applicable
Ivermectin 1% / Metronidazole 1%	Metronidazole (1 g/100g) + Ivermectin (1 g/100g)	Gel	Topical	Sincerus Florida, LLC	2019-05-01	Not applicable
Ivermectin 1% / Metronidazole 1% / Niacinamide 4%	Metronidazole (1 g/100g) + Ivermectin (1 g/100g) + Nicotinamide (4 g/100g)	Gel	Topical	Sincerus Florida, LLC	2019-05-01	Not applicable
Metronidazole	Metronidazole (500 mg/100mL)	Injection, solution	Intravenous	Baxter Healthcare Corporation	2017-10-05	2019-10-31
Metronidazole 1% / Mupirocin 2%	Metronidazole (1 g/100g) + Mupirocin (2 g/100g)	Ointment	Topical	Sincerus Florida, LLC	2019-05-15	Not applicable
Metronidazole 1% / Mupirocin 2%	Metronidazole (1 g/100g) + Mupirocin (2 g/100g)	Ointment	Topical	Sincerus Florida, LLC	2019-05-15	Not applicable
Metronidazole 1% / Mupirocin 2% /	Metronidazole (1 g/100g) + Mupirocin (2 g/100g)	Ointment	Topical	Sincerus Florida, LLC	2019-05-14	Not applicable
Metronidazole 1% / Niacinamide 4%	Metronidazole (1 g/100g) + Nicotinamide (4 g/100g)	Gel	Topical	Sincerus Florida, LLC	2019-05-16	Not applicable
POLGYL %0,5 IV PERFUZYON SOL 100 ML SETLI	Metronidazole (0.5 %)	Solution	Intravenous	POLİFARMA İLAÇ SAN. VE TİC. A.Ş.	2020-08-14	Not applicable

Chemical Identifiers

UNII: 140QMO216E
CAS number: 443-48-1
InChI Key: VAOCPAMSLUNLGC-UHFFFAOYSA-N
InChI: InChI=1S/C6H9N3O3/c1-5-7-4-6(9(11)12)8(5)2-3-10/h4,10H,2-3H2,1H3
IUPAC Name: 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethan-1-ol
SMILES: CC1=NC=C(N1CCO)[N+]([O-])=O

References

Synthesis Reference

US2944061

General References

Shennan A, Crawshaw S, Briley A, Hawken J, Seed P, Jones G, Poston L: A randomised controlled trial of metronidazole for the prevention of preterm birth in women positive for cervicovaginal fetal fibronectin: the PREMET Study. BJOG. 2006 Jan;113(1):65-74. [Article]
Williams CS, Woodcock KR: Do ethanol and metronidazole interact to produce a disulfiram-like reaction? Ann Pharmacother. 2000 Feb;34(2):255-7. [Article]
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]
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]
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]
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]
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]
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]
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]
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]
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]
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]
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]
FDA Approved Drug Products: Flagyl (metronidazole) capsules for oral administration [Link]
FDA approvals, Metronidazole [Link]
Canadian monograph, Flagyl [Link]
Flagyl [Link]
DailyMed: Flagyl (metronidazole) oral tablets [Link]

External Links

Human Metabolome Database: HMDB0015052
KEGG Drug: D00409
KEGG Compound: C07203
PubChem Compound: 4173
PubChem Substance: 46508911
ChemSpider: 4029
BindingDB: 50375309
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

Download (73.9 KB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
4	Active Not Recruiting	Basic Science	Rabies Human	1
4	Active Not Recruiting	Prevention	Surgery, Colorectal	1
4	Active Not Recruiting	Treatment	Antibiotics / Periodontal Disease / Pharmacokinetics	1
4	Active Not Recruiting	Treatment	Blastocystis Hominis Infections	1
4	Active Not Recruiting	Treatment	Chronic Periodontitis (Disorder)	2
4	Completed	Prevention	Infection Prophylaxis in Colo Rectal Surgery	1
4	Completed	Prevention	Postoperative Wound Infection	1
4	Completed	Supportive Care	Amoxicillin / Metronidazole / Ofloxacin / Periodontitis / Root Planing	1
4	Completed	Supportive Care	Generalized Aggressive Periodontitis / Periodontitis, Aggressive	1
4	Completed	Supportive Care	Rosacea	1

Pharmacoeconomics

Manufacturers

Gd searle llc
Able laboratories inc
Alembic ltd
Par pharmaceutical inc
Galderma laboratories lp
Altana inc
G and w laboratories inc
Sanofi aventis us llc
Taro pharmaceutical industries ltd
Tolmar inc
Graceway pharmaceuticals llc
Teva pharmaceuticals usa
Baxter healthcare corp
B braun medical inc
Abbott laboratories pharmaceutical products div
Abraxis pharmaceutical products
Elkins sinn div ah robins co inc
International medication systems ltd
Watson laboratories inc
Claris lifesciences ltd
Hospira inc
Laboratorios aplicaciones farmaceuticas sa de cv
Halsey drug co inc
Ivax pharmaceuticals inc sub teva pharmaceuticals usa
Lnk international inc
Mutual pharmaceutical co inc
Pliva inc
Sandoz inc
Superpharm corp
Teva pharmaceuticals usa inc
World gen llc
Ortho mcneil pharmaceutical inc
Savage laboratories inc div altana inc

Packagers

Actavis Group
Advanced Pharmaceutical Services Inc.
American Pharmaceutical Association
Ameri-Pac Inc.
Amerisource Health Services Corp.
Amneal Pharmaceuticals
Apace Packaging
Apotheca Inc.
A-S Medication Solutions LLC
Atlantic Biologicals Corporation
B. Braun Melsungen AG
Baxter International Inc.
Ben Venue Laboratories Inc.
Bryant Ranch Prepack
Cardinal Health
Carlisle Laboratories Inc.
Central Texas Community Health Centers
Claris Lifesciences Inc.
Community Action Inc. Community Health Services
Comprehensive Consultant Services Inc.
Contract Pharm
Darby Dental Supply Co. Inc.
Dept Health Central Pharmacy
Dermik Labs
DHHS Program Support Center Supply Service Center
Direct Dispensing Inc.
Dispensing Solutions
Diversified Healthcare Services Inc.
DPT Laboratories Ltd.
Dudley Corp.
E. Fougera and Co.
G & W Labs
Galderma Laboratories
GD Searle LLC
GlaxoSmithKline Inc.
Golden State Medical Supply Inc.
Graceway Pharmaceuticals
Group Health Cooperative
H and H Laboratories
H.J. Harkins Co. Inc.
Harris Pharmaceutical Inc.
Hawkins Inc.
Heartland Repack Services LLC
Hospira Inc.
Kaiser Foundation Hospital
Lake Erie Medical and Surgical Supply
Liberty Pharmaceuticals
Major Pharmaceuticals
Mckesson Corp.
Medisca Inc.
Medvantx Inc.
Mississippi State Dept Health
Murfreesboro Pharmaceutical Nursing Supply
Mutual Pharmaceutical Co.
Nord Ost Corp.
Nucare Pharmaceuticals Inc.
Nycomed Inc.
Obagi Medical Products Inc.
Palmetto Pharmaceuticals Inc.
Pangeo Pharma Quebec Inc.
Par Pharmaceuticals
Patheon Inc.
Patient First Corp.
PCA LLC
PD-Rx Pharmaceuticals Inc.
Pfizer Inc.
Pharmacia Inc.
Pharmedix
Pharmpak Inc.
Physicians Total Care Inc.
Pliva Inc.
Prasco Labs
Preferred Pharmaceuticals Inc.
Prepackage Specialists
Prepak Systems Inc.
Prescription Dispensing Service Inc.
Qualitest
Raz Co. Inc.
Rebel Distributors Corp.
Redpharm Drug
Remedy Repack
Rochester Pharmaceuticals
Sagent Pharmaceuticals
Sandhills Packaging Inc.
Sandoz
Sanofi-Aventis Inc.
SCS Pharmaceuticals
Southwood Pharmaceuticals
St Mary's Medical Park Pharmacy
Stat Rx Usa
Taro Pharmaceuticals USA
Teva Pharmaceutical Industries Ltd.
Tolmar Inc.
UDL Laboratories
Upsher Smith Laboratories
Vangard Labs Inc.
Veratex Corp.
Watson Pharmaceuticals
West-Ward Pharmaceuticals

Dosage Forms

Form	Route	Strength
Suspension	Oral	5 g
Tablet	Vaginal	500 mg
Suspension	Oral	8.04 g
Suspension	Oral	4 g
Tablet, film coated	Oral
Solution	Intravenous
Capsule, coated	Oral	400 mg
Tablet	Oral	250 mg
Tablet	Oral	200 mg
Injection, solution		5 mg/1ml
Capsule; kit; tablet	Oral
Capsule	Vaginal
Injection, solution	Parenteral	500 MG/100ML
Suppository	Vaginal	500 mg
Gel	Oral
Tablet	Vaginal
Insert	Vaginal	100 mg
Suppository	Vaginal
Suspension	Oral
Capsule	Oral	375 mg/1
Cream	Vaginal	10 %
Injection	Intravenous	5 mg/ml
Tablet	Oral; Vaginal	500 MG
Tablet, film coated	Oral	400 mg
Suppository	Vaginal	500 mg / sup
Tablet, coated	Oral	500 mg
Injection	Intravenous	0.5 % w/v
Solution	Intravenous	5 mg
Tablet, extended release	Oral	750 mg
Tablet, coated	Oral
Capsule, liquid filled	Vaginal
Gel	Vaginal	0.75 g
Kit	Oral
Suspension	Oral
Gel	Topical
Capsule, coated	Oral
Capsule, coated	Oral	300 mg
Capsule, coated	Oral	600 mg
Cream	Vaginal
Insert	Vaginal
Solution	Vaginal
Tablet, film coated
Cream	Topical	.75 %
Suspension	Oral	4.02 g
Gel	Topical	10 mg/1g
Gel	Vaginal	7.5 mg/1g
Gel	Topical	1 %
Lotion	Topical	0.75 %
Solution	Parenteral
Capsule, liquid filled	Oral	250 mg
Solution	Intravenous	500 mg
Injection, solution	Intravenous
Solution	Intravenous	500 g
Solution	Parenteral	5 MG/ML
Solution	Parenteral	500 MG/100ML
Solution	Intravenous	1.5 g
Solution	Parenteral	500 mg
Solution	Parenteral	5 mg
Tablet, film coated	Oral	500 mg
Tablet	Oral	500 mg
Cream	Topical	10 mg/1g
Cream	Topical	7.5 mg/1g
Gel	Topical	7.5 mg/1g
Gel	Vaginal	13 mg/1g
Injection	Intravenous
Injection	Intravenous	0.5 %
Injection, solution	Intravenous	500 mg/100mL
Lotion	Topical	7.5 mg/1mL
Lotion	Topical	7.5 mg/1g
Powder	Not applicable	1 g/1g
Solution	Intravenous	500 mg/100mL
Tablet	Oral
Tablet	Oral	250 mg/1
Tablet	Oral	500 mg/1
Tablet, coated	Oral	250 mg/1
Tablet, coated	Oral	500 1/1
Tablet, film coated	Oral	500 mg/1
Tablet, film coated, extended release	Oral	750 mg/1
Tablet; tablet, film coated	Oral
Ointment	Topical
Injection	Intravenous	0.5 g/100ml
Injection	Intravenous	500 mg/100ml
Injection, solution	Intravenous	5 mg/1ml
Solution	Intravenous	5 mg / mL
Injection	Intravenous	5.000 g/1000ml
Syrup	Oral	100 MG
Tablet, film coated	Oral	250 mg/1
Tablet	Vaginal
Tablet, film coated	Oral	250 MG
Injection, solution	Parenteral	5 MG/ML
Injection, solution	Intravenous; Parenteral	0.5 G/100ML
Injection, solution	Intravenous; Parenteral	500 MG/100ML
Injection, solution
Injection, solution	Parenteral	0.5 G/100ML
Capsule, liquid filled	Oral
Insert	Vaginal	500 mg
Tablet, film coated	Oral
Capsule, liquid filled	Oral	500 mg
Insert	Vaginal	500 mg
Capsule	Vaginal	500 mg
Suppository	Vaginal	500 mg
Gel	Vaginal	0.75 % w/w
Gel	Topical
Solution
Cream	Topical	1 % w/w
Cream	Topical	10 mg/60g
Tablet
Gel	Topical	65 mg/5g
Gel	Vaginal	65 mg/5g
Injection	Intravenous	500 mg
Injection	Parenteral	500 mg
Tablet, film coated	Oral	200 mg
Tablet	Oral	400 MG
Capsule	Oral	500 mg
Capsule	Oral
Kit	Topical	7.5 mg/1g
Gel; kit	Topical	7.5 mg/1g
Cream	Topical
Cream	Topical
Cream	Oral
Cream	Topical	0.75 %
Emulsion	Topical	0.75 %
Gel	Topical	0.75 g
Gel	Topical	0.75 %
Tablet	Oral
Suppository	Vaginal
Capsule	Oral	250 MG
Gel	Vaginal
Capsule		200 mg
Capsule		250 mg
Tablet		200 mg
Tablet		400 mg
Tablet		250 mg
Solution		5 mg/1ml
Tablet, coated	Oral	200 mg
Gel	Topical	1 %w/w
Tablet, coated	Oral	250 mg
Tablet		500 mg
Tablet, coated	Oral	400 mg

Prices

Unit description	Cost	Unit
MetroLotion 0.75% Lotion 59ml Bottle	292.66USD	bottle
MetroCream 0.75% Cream 45 gm Tube	281.09USD	tube
Metrogel 1% Gel 60 gm Tube	200.93USD	tube
Metrogel 1% Kit Box	200.93USD	box
Metrogel 1% kit	193.2USD	kit
Noritate 1% Cream 60 gm Tube	156.44USD	tube
MetroNIDAZOLE 0.75% Lotion 59ml Bottle	89.86USD	bottle
MetroNIDAZOLE 0.75% Cream 45 gm Tube	80.87USD	tube
MetroNIDAZOLE 0.75% Gel 45 gm Tube	74.0USD	tube
MetroNIDAZOLE 0.75% Gel 70 gm Tube	68.53USD	tube
Flagyl ER 750 mg 24 Hour tablet	13.2USD	tablet
Flagyl er 750 mg tablet	12.7USD	tablet
MetroNIDAZOLE 750 mg 24 Hour tablet	8.07USD	tablet
Flagyl 500 mg tablet	6.24USD	tablet
Metrocream 0.75% cream	5.99USD	g
Danazol 200 mg capsule	5.63USD	capsule
Flagyl 375 mg capsule	5.45USD	capsule
Metrolotion topical 0.75%	4.77USD	ml
Metronidazole benz powder	4.74USD	g
Flagyl 250 mg tablet	3.49USD	tablet
Danazol 100 mg capsule	2.98USD	capsule
Noritate 1% cream	2.51USD	g
Danazol 50 mg capsule	1.99USD	capsule
Metronidazole powder	1.65USD	g
Metronidazole 0.75% cream	1.34USD	g
Metronidazole vaginal 0.75% gl	0.94USD	g
Metronidazole 500 mg tablet	0.72USD	tablet
Metrogel 0.75 % Gel	0.69USD	g
Metrogel 1 % Gel	0.63USD	g
Noritate 1 % Cream	0.58USD	g
Rosasol 1 % Cream	0.57USD	g
Metrocream 0.75 % Cream	0.52USD	g
Metrolotion 0.75 % Lotion	0.52USD	g
Metrogel-vaginal 0.75% gel	0.51USD	g
Vandazole vaginal 0.75% gel	0.48USD	g
Metronidazole 250 mg tablet	0.44USD	tablet
Flagyl 10 % Cream	0.25USD	g
Apo-Metronidazole 250 mg Tablet	0.06USD	tablet
Flagyl 5 mg/ml	0.03USD	ml
Metro iv 500 mg/100 ml	0.03USD	ml
Metronidazole 5 mg/ml	0.03USD	ml
Metronidazole 500 mg/100 ml	0.03USD	ml

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
US5536743	No	1996-07-16	2013-07-16
CA2470492	No	2010-02-23	2022-11-07
CA2161737	No	1998-10-20	2015-10-30
US6881726	No	2005-04-19	2022-02-21
US7348317	No	2008-03-25	2022-02-21
US7456207	No	2008-11-25	2024-09-22
US6350468	No	2002-02-26	2018-12-14
US8946276	No	2015-02-03	2032-06-28
US8658678	No	2014-02-25	2028-06-27
US9198858	No	2015-12-01	2032-06-28
US8877792	No	2014-11-04	2028-02-02
US7893097	No	2011-02-22	2028-02-19
US10238634	No	2019-03-26	2032-06-28
US10596155	No	2020-03-24	2032-06-28

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	160	http://www.inchem.org/documents/pims/pharm/metronid.htm
boiling point (°C)	405.4	http://www.emelcabio.com/metronidazole-41310008.html
logP	-0.02	http://www.t3db.ca/toxins/T3D4703
logS	-1.5	http://www.t3db.ca/toxins/T3D4703
pKa	2.57,15.42	http://www.t3db.ca/toxins/T3D4703

Predicted Properties

Property	Value	Source
Water Solubility	5.92 mg/mL	ALOGPS
logP	-0.15	ALOGPS
logP	-0.46	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	15.41	ChemAxon
pKa (Strongest Basic)	3.03	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	81.19 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	40.22 m³·mol^-1	ChemAxon
Polarizability	15.87 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.9805
Blood Brain Barrier	+	0.9297
Caco-2 permeable	-	0.5365
P-glycoprotein substrate	Non-substrate	0.5141
P-glycoprotein inhibitor I	Non-inhibitor	0.8954
P-glycoprotein inhibitor II	Non-inhibitor	0.8755
Renal organic cation transporter	Non-inhibitor	0.7762
CYP450 2C9 substrate	Non-substrate	0.7318
CYP450 2D6 substrate	Non-substrate	0.8815
CYP450 3A4 substrate	Non-substrate	0.6767
CYP450 1A2 substrate	Non-inhibitor	0.9045
CYP450 2C9 inhibitor	Non-inhibitor	0.9242
CYP450 2D6 inhibitor	Non-inhibitor	0.9231
CYP450 2C19 inhibitor	Non-inhibitor	0.9401
CYP450 3A4 inhibitor	Non-inhibitor	0.9242
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.8483
Ames test	AMES toxic	0.9107
Carcinogenicity	Non-carcinogens	0.7471
Biodegradation	Not ready biodegradable	0.5941
Rat acute toxicity	2.0422 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.5
hERG inhibition (predictor II)	Non-inhibitor	0.8272

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Download (9.68 KB)

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Mass Spectrum (Electron Ionization)	MS	splash10-0ul0-9300000000-2268b08f47fed3f6d263
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-004i-1900000000-659f2bbb83f8ef5a85d1
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-004i-0900000000-50c7cfe79eb17c4440a8
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-00di-0900000000-b06d808767cc01c0d494
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-00fr-0900000000-e9c07cc448b8fb519022
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-004i-0900000000-8ad03b44aa7557127e34
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-004i-0900000000-ed7ba5c872a6309a31d4
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-004i-2900000000-e0ead4b0eec72b9c44b6
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-004i-5900000000-2da8a7b45537f9063220
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-00di-0900000000-24d94f1704e577b05eb7
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-00fr-0900000000-fbb1c4e8457cd3d799b9
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-004i-0900000000-fd6166313a17f944f530
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-004i-0900000000-5ebb32a580e1f5d00170
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-004i-2900000000-811a6e7e45b7ea1a6184
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-004i-5900000000-082e6de6c0fa3f382d84
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-004i-0900000000-baf9e195c01d875e77b5
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-00di-0900000000-ec181c008a10dac8040b
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-004i-1900000000-2a218e19a8fadb9c66d6
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-003r-9500000000-ed02acd36b190c189cc9
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-001i-9000000000-71ea79659ccd75c64bef
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-001i-9000000000-3f7795597c6629540426
1H NMR Spectrum	1D NMR	Not Applicable
13C NMR Spectrum	1D NMR	Not Applicable

Targets

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insights and accelerate drug research.

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Details1. Oxygen-insensitive NADPH nitroreductase

Kind: Protein
Organism: Helicobacter pylori (strain ATCC 700392 / 26695)
Pharmacological action: Yes
Actions: Potentiator

General Function: Oxidoreductase activity
Specific Function: Reduction of a variety of nitroaromatic compounds using NADPH as source of reducing equivalents; two electrons are transferred (By similarity). Capable of reducing metronidazole; inactive RdxA rend...
Gene Name: rdxA
Uniprot ID: O25608
Uniprot Name: Oxygen-insensitive NADPH nitroreductase
Molecular Weight: 24067.775 Da

References

Sisson G, Jeong JY, Goodwin A, Bryden L, Rossler N, Lim-Morrison S, Raudonikiene A, Berg DE, Hoffman PS: Metronidazole activation is mutagenic and causes DNA fragmentation in Helicobacter pylori and in Escherichia coli containing a cloned H. pylori RdxA(+) (Nitroreductase) gene. J Bacteriol. 2000 Sep;182(18):5091-6. [Article]
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]
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]
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

Samuelson J: Why metronidazole is active against both bacteria and parasites. Antimicrob Agents Chemother. 1999 Jul;43(7):1533-41. [Article]
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]
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

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]
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]
FDA Approved Drug Products: Flagyl (metronidazole) capsules for oral administration [Link]

Enzymes

Details1. Cytochrome P450 2C8

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Steroid hydroxylase activity
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name: CYP2C8
Uniprot ID: P10632
Uniprot Name: Cytochrome P450 2C8
Molecular Weight: 55824.275 Da

References

Kudo T, Endo Y, Taguchi R, Yatsu M, Ito K: Metronidazole reduces the expression of cytochrome P450 enzymes in HepaRG cells and cryopreserved human hepatocytes. Xenobiotica. 2015 May;45(5):413-9. doi: 10.3109/00498254.2014.990948. Epub 2014 Dec 3. [Article]

Details2. UDP-glucuronosyltransferase 1-1

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Substrate

General Function: Steroid binding
Specific Function: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
Gene Name: UGT1A1
Uniprot ID: P22309
Uniprot Name: UDP-glucuronosyltransferase 1-1
Molecular Weight: 59590.91 Da

References

Williams JA, Hyland R, Jones BC, Smith DA, Hurst S, Goosen TC, Peterkin V, Koup JR, Ball SE: Drug-drug interactions for UDP-glucuronosyltransferase substrates: a pharmacokinetic explanation for typically observed low exposure (AUCi/AUC) ratios. Drug Metab Dispos. 2004 Nov;32(11):1201-8. doi: 10.1124/dmd.104.000794. Epub 2004 Aug 10. [Article]

Details3. Cytochrome P450 2A6

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Steroid hydroxylase activity
Specific Function: Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Const...
Gene Name: CYP2A6
Uniprot ID: P11509
Uniprot Name: Cytochrome P450 2A6
Molecular Weight: 56501.005 Da

References

Pearce RE, Cohen-Wolkowiez M, Sampson MR, Kearns GL: The role of human cytochrome P450 enzymes in the formation of 2-hydroxymetronidazole: CYP2A6 is the high affinity (low Km) catalyst. Drug Metab Dispos. 2013 Sep;41(9):1686-94. doi: 10.1124/dmd.113.052548. Epub 2013 Jun 27. [Article]

Details4. Cytochrome P450 3A5

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Oxygen binding
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name: CYP3A5
Uniprot ID: P20815
Uniprot Name: Cytochrome P450 3A5
Molecular Weight: 57108.065 Da

References

Pearce RE, Cohen-Wolkowiez M, Sampson MR, Kearns GL: The role of human cytochrome P450 enzymes in the formation of 2-hydroxymetronidazole: CYP2A6 is the high affinity (low Km) catalyst. Drug Metab Dispos. 2013 Sep;41(9):1686-94. doi: 10.1124/dmd.113.052548. Epub 2013 Jun 27. [Article]

Details5. Cytochrome P450 3A7

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Oxygen binding
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name: CYP3A7
Uniprot ID: P24462
Uniprot Name: Cytochrome P450 3A7
Molecular Weight: 57525.03 Da

References

Pearce RE, Cohen-Wolkowiez M, Sampson MR, Kearns GL: The role of human cytochrome P450 enzymes in the formation of 2-hydroxymetronidazole: CYP2A6 is the high affinity (low Km) catalyst. Drug Metab Dispos. 2013 Sep;41(9):1686-94. doi: 10.1124/dmd.113.052548. Epub 2013 Jun 27. [Article]

Details6. Cytochrome P450 2C9

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Steroid hydroxylase activity
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name: CYP2C9
Uniprot ID: P11712
Uniprot Name: Cytochrome P450 2C9
Molecular Weight: 55627.365 Da

References

Kudo T, Endo Y, Taguchi R, Yatsu M, Ito K: Metronidazole reduces the expression of cytochrome P450 enzymes in HepaRG cells and cryopreserved human hepatocytes. Xenobiotica. 2015 May;45(5):413-9. doi: 10.3109/00498254.2014.990948. Epub 2014 Dec 3. [Article]
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]
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]
CYP table [Link]

Details7. Cytochrome P450 3A4

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Vitamin d3 25-hydroxylase activity
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name: CYP3A4
Uniprot ID: P08684
Uniprot Name: Cytochrome P450 3A4
Molecular Weight: 57342.67 Da

References

Kudo T, Endo Y, Taguchi R, Yatsu M, Ito K: Metronidazole reduces the expression of cytochrome P450 enzymes in HepaRG cells and cryopreserved human hepatocytes. Xenobiotica. 2015 May;45(5):413-9. doi: 10.3109/00498254.2014.990948. Epub 2014 Dec 3. [Article]
Michalets EL: Update: clinically significant cytochrome P-450 drug interactions. Pharmacotherapy. 1998 Jan-Feb;18(1):84-112. [Article]
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

Details1. P-glycoprotein 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor
Curator comments: Evidence regarding this transporter inhibition is conflicting in the literature. Various references have been attached, some of which may provide conflicting evidence.

General Function: Xenobiotic-transporting atpase activity
Specific Function: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name: ABCB1
Uniprot ID: P08183
Uniprot Name: Multidrug resistance protein 1
Molecular Weight: 141477.255 Da

References

Tan SY, Kan E, Lim WY, Chay G, Law JH, Soo GW, Bukhari NI, Segarra I: Metronidazole leads to enhanced uptake of imatinib in brain, liver and kidney without affecting its plasma pharmacokinetics in mice. J Pharm Pharmacol. 2011 Jul;63(7):918-25. doi: 10.1111/j.2042-7158.2011.01296.x. Epub 2011 May 19. [Article]
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]
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 August 14, 2022 00:07

Metronidazole

Identification

Structure for Metronidazole (DB00916)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Targets

References

References

References

Enzymes

References

References

References

References

References

References

References

Transporters

References