Metronidazole

Metronidazole
Clinical data
Trade namesFlagyl, Metrogyl
AHFS/Drugs.comMonograph
MedlinePlusa689011
License data
Pregnancy
category
Routes of
administration		By mouth, topical, rectal, intravenous, vaginal
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability80% (by mouth), 60–80% (rectal), 20–25% (vaginal)[7][8][9]
Protein binding20%[7][8]
MetabolismLiver[7][8]
MetabolitesHydroxymetronidazole
Elimination half-life8 hours[7][8]
ExcretionUrine (77%), faeces (14%)[7][8]
Identifiers
IUPAC name
  • 2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethanol
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
NIAID ChemDB
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.006.489
Chemical and physical data
FormulaC6H9N3O3
Molar mass171.156 g·mol−1
3D model (JSmol)
Melting point159 to 163 °C (318 to 325 °F)
SMILES
  • OCCn1c(C)ncc1[N+](=O)[O-]
InChI
  • InChI=1S/C6H9N3O3/c1-5-7-4-6(9(11)12)8(5)2-3-10/h4,10H,2-3H2,1H3 Y
  • Key:VAOCPAMSLUNLGC-UHFFFAOYSA-N Y
  (verify)

Metronidazole, sold under the brand name Flagyl and Metrogyl among others, is an antibiotic and antiprotozoal medication.[10] It is used either alone or with other antibiotics to treat pelvic inflammatory disease, endocarditis, and bacterial vaginosis.[10] It is effective for dracunculiasis, giardiasis, trichomoniasis, and amebiasis.[10] It is an option for a first episode of mild-to-moderate Clostridioides difficile colitis if vancomycin or fidaxomicin is unavailable.[10][11] Metronidazole is available orally (by mouth), as a cream or gel, and by slow intravenous infusion (injection into a vein).[10][4]

Common side effects include nausea, a metallic taste, loss of appetite, and headaches.[10] Occasionally seizures or allergies to the medication may occur.[10]

Metronidazole began to be commercially used in 1960 in France.[12] It is on the World Health Organization's List of Essential Medicines.[13] It is available in most areas of the world.[14] In 2022, it was the 133rd most commonly prescribed medication in the United States, with more than 4 million prescriptions.[15][16]

  1. ^ Cite error: The named reference Preg2017 was invoked but never defined (see the help page).
  2. ^ "METRONIDAMED (Medsurge Pharma Pty LTD) | Therapeutic Goods Administration (TGA)". Archived from the original on 15 September 2024. Retrieved 15 September 2024.
  3. ^ "Flagyl Product information". health-products.canada.ca. 15 May 2024. Retrieved 17 February 2025.
  4. ^ a b "Metronidazole injection, solution". DailyMed. 16 January 2023. Archived from the original on 6 September 2023. Retrieved 5 July 2023.
  5. ^ "Metronidazole tablet". DailyMed. 30 January 2023. Archived from the original on 6 September 2023. Retrieved 5 July 2023.
  6. ^ "Metronidazole Vaginal Gel, 0.75%- metronidazole gel". DailyMed. 17 June 2023. Archived from the original on 6 September 2023. Retrieved 5 July 2023.
  7. ^ a b c d e "Flagyl,Metrogyl, Flagyl ER ,Metrogyl ER (metronidazole) dosing, indications, interactions, adverse effects, and more". Medscape Reference. WebMD. Archived from the original on 7 April 2014. Retrieved 3 April 2014.
  8. ^ a b c d e Brayfield A, ed. (14 January 2014). "Metronidazole". Martindale: The Complete Drug Reference. Pharmaceutical Press. Retrieved 3 April 2014.
  9. ^ Brayfield A, ed. (2017). Martindale: The Complete Drug Reference (39th ed.). London: Pharmaceutical Press. ISBN 978-0-85711-309-2.
  10. ^ a b c d e f g "Metronidazole". The American Society of Health-System Pharmacists. Archived from the original on 6 September 2015. Retrieved 31 July 2015.
  11. ^ McDonald LC, Gerding DN, Johnson S, Bakken JS, Carroll KC, Coffin SE, et al. (March 2018). "Clinical Practice Guidelines for Clostridium difficile Infection in Adults and Children: 2017 Update by the Infectious Diseases Society of America (IDSA) and Society for Healthcare Epidemiology of America (SHEA)". Clinical Infectious Diseases. 66 (7): e1 – e48. doi:10.1093/cid/cix1085. PMC 6018983. PMID 29462280.
  12. ^ Corey EJ (2013). Drug discovery practices, processes, and perspectives. Hoboken, N.J.: John Wiley & Sons. p. 27. ISBN 978-1-118-35446-9. Archived from the original on 8 September 2017.
  13. ^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
  14. ^ Schmid G (28 July 2003). "Trichomoniasis treatment in women". Archived from the original on 1 August 2015. Retrieved 1 August 2015.
  15. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  16. ^ "Metronidazole Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Archived from the original on 6 December 2024. Retrieved 30 August 2024.
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