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Metronidazole

Metronidazole
Clinical data
Trade namesFlagyl
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
  • 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 Edit this at Wikidata
Chemical and physical data
FormulaC6H9N3O3
Molar mass171.156 g·mol−1
3D model (JSmol)
Melting point159 to 163 °C (318 to 325 °F)
  • OCCn1c(C)ncc1[N+](=O)[O-]
  • InChI=1S/C6H9N3O3/c1-5-7-4-6(9(11)12)8(5)2-3-10/h4,10H,2-3H2,1H3 checkY
  • Key:VAOCPAMSLUNLGC-UHFFFAOYSA-N checkY
  (verify)

Metronidazole, sold under the brand name Flagyl 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] Some state that metronidazole should not be used in early pregnancy, while others state doses for trichomoniasis are safe.[1][weasel words] Metronidazole is generally considered compatible with breastfeeding.[1][12]

Metronidazole began to be commercially used in 1960 in France.[13] It is on the World Health Organization's List of Essential Medicines.[14] It is available in most areas of the world.[15] In 2022, it was the 133rd most commonly prescribed medication in the United States, with more than 4 million prescriptions.[16][17]

  1. ^ a b c "Metronidazole Use During Pregnancy". www.drugs.com. Archived from the original on 1 January 2017. Retrieved 1 January 2017.
  2. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  3. ^ https://www.tga.gov.au/resources/prescription-medicines-registrations/metronidamed-medsurge-pharma-pty-ltd
  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, Flagyl 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.[dead link‍]
  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. ^ "Safety in Lactation: Metronidazole and tinidazole". SPS - Specialist Pharmacy Service. Archived from the original on 21 February 2020. Retrieved 22 February 2020.
  13. ^ 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.
  14. ^ 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.
  15. ^ Schmid G (28 July 2003). "Trichomoniasis treatment in women". Archived from the original on 1 August 2015. Retrieved 1 August 2015.
  16. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  17. ^ "Metronidazole Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.

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