Metronidazole

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

Metronidazole
Clinical data
AHFS/Drugs.comMonograph
MedlinePlusa689011
License data
Pregnancy
category
  • AU: B2
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)
Protein binding20%
MetabolismLiver
MetabolitesHydroxymetronidazole
Elimination half-life8 hours
ExcretionUrine (77%), faeces (14%)
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
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 Y
  • Key:VAOCPAMSLUNLGC-UHFFFAOYSA-N Y
  (verify)

Common side effects include nausea, a metallic taste, loss of appetite, and headaches. Occasionally seizures or allergies to the medication may occur. Some state that metronidazole should not be used in early pregnancy, while others state doses for trichomoniasis are safe. Metronidazole is generally considered compatible with breastfeeding.

Metronidazole began to be commercially used in 1960 in France. It is on the World Health Organization's List of Essential Medicines. It is available in most areas of the world. In 2020, it was the 222nd most commonly prescribed medication in the United States, with more than 2 million prescriptions.

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