Metronidazole

Article Talk

Metronidazole, sold under the brand name

Flagyl among others, is an antibiotic and
antiprotozoal medication.[9] It is used either
alone or with other antibiotics to treat pelvic
inflammatory disease, endocarditis, and
bacterial vaginosis.[9] It is effective for
dracunculiasis, giardiasis, trichomoniasis,
and amebiasis.[9] It is an option for a first
episode of mild-to-moderate Clostridioides
difficile colitis if vancomycin or fidaxomicin
is unavailable.[9][10] Metronidazole is
available orally (by mouth), as a cream or
gel, and by slow intravenous infusion
(injection into a vein).[9][3]

Metronidazole

Clinical data

AHFS/Drugs.com Monograph

MedlinePlus a689011

License US DailyMed: Metronidazole

data
US FDA: Metronidazole

Pregnancy AU: B2[1]

category

Routes of By mouth, topical,

administration
rectal, intravenous,
vaginal

ATC code A01AB17 (WHO )

D06BX01 (WHO ),
G01AF01 (WHO ),
J01XD01 (WHO ),
P01AB01 (WHO ),
QP51CA01 (WHO )

Legal status

Legal status AU: S4 (Prescription

only)
CA: ℞-only
UK: POM
(Prescription only)
US: WARNING [2]Rx-
only[3][4][5]

Pharmacokinetic data

Bioavailability 80% (by mouth),

60–80% (rectal),
20–25% (vaginal)[6]
[7][8]

Protein binding 20%[6][7]

Metabolism Liver[6][7]

Metabolites Hydroxymetronidazole

Elimination half-life 8 hours[6][7]

Excretion Urine (77%), faeces

(14%)[6][7]

Identifiers

IUPAC name
2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethanol

CAS Number 443-48-1

PubChem CID 4173

DrugBank DB00916

ChemSpider 4029

UNII 140QMO216E

KEGG D00409

ChEBI CHEBI:6909

ChEMBL ChEMBL137

NIAID ChemDB 007953

PDB ligand 2MN (PDBe ,

RCSB PDB )

CompTox DTXSID2020892
Dashboard (EPA)

ECHA InfoCard 100.006.489

Chemical and physical data

Formula C6H9N3O3

Molar mass 171.156 g·mol−1

3D model (JSmol) Interactive image

Melting point 159 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
Key:VAOCPAMSLUNLGC-UHFFFAOYSA-N

(verify)

Common side effects include nausea, a

metallic taste, loss of appetite, and
headaches.[9] Occasionally seizures or
allergies to the medication may occur.[9]
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][11]

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 2020, it was the 222nd
most commonly prescribed medication in
the United States, with more than 2 million
prescriptions.[15][16]

Medical uses

Adverse effects

Drug interactions

Pharmacology

Bacterial resistance

History

Brand name

Synthesis

Research

Veterinary use

References

External links

Last edited 12 days ago by Citation …

Content is available under CC BY-SA 4.0

unless otherwise noted.
Terms of Use • Privacy policy • Desktop