Editing Metronidazole (section)

{{Short description|Antibiotic and antiprotozoal medication}}
{{Use dmy dates|date=December 2023}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Infobox drug
| Watchedfields = changed
| verifiedrevid = 699169263
| image = Metronidazole.svg
| image_class = skin-invert-image
| width = 160
| alt               =
| image2 = Metronidazole 3D 1w3r.png
| width2 = 160
| alt2              =
| caption           =

<!-- Clinical data -->
| pronounce         =
| tradename         = Flagyl, Metrogyl
| Drugs.com         = {{drugs.com|monograph|metronidazole}}
| MedlinePlus = a689011
| DailyMedID = Metronidazole
| pregnancy_AU = B2
| pregnancy_AU_comment = <ref name="Preg2017" />
| pregnancy_category =
| routes_of_administration = [[Oral administration|By mouth]], [[Topical administration|topical]], [[Rectal administration|rectal]], [[intravenous]], [[Intravaginal administration|vaginal]]
| class             =
| ATC_prefix = A01
| ATC_suffix = AB17
| ATC_supplemental = {{ATC|D06|BX01}}, {{ATC|G01|AF01}}, {{ATC|J01|XD01}}, {{ATC|P01|AB01}}, {{ATCvet|P51|CA01}}

<!-- Legal status -->
| legal_AU = S4
| legal_AU_comment  = <ref>{{Cite web |url=https://www.tga.gov.au/resources/prescription-medicines-registrations/metronidamed-medsurge-pharma-pty-ltd |title=METRONIDAMED (Medsurge Pharma Pty LTD) &#124; Therapeutic Goods Administration (TGA) |access-date=15 September 2024 |archive-date=15 September 2024 |archive-url=https://web.archive.org/web/20240915052402/https://www.tga.gov.au/resources/prescription-medicines-registrations/metronidamed-medsurge-pharma-pty-ltd |url-status=live }}</ref>
| legal_BR          = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F -->
| legal_BR_comment  =
| legal_CA = Rx-only
| legal_CA_comment  = <ref>{{cite web | title=Flagyl Product information | website=health-products.canada.ca | date=15 May 2024 | url=https://health-products.canada.ca/dpd-bdpp/info?lang=eng&code=12221 | access-date=17 February 2025}}</ref>
| legal_DE          = <!-- Anlage I, II, III or Unscheduled -->
| legal_DE_comment  =
| legal_NZ          = <!-- Class A, B, C -->
| legal_NZ_comment  =
| legal_UK = POM
| legal_UK_comment  =
| legal_US = Rx-only
| legal_US_comment  = <ref name="NIH" /><ref name="DailyMed-2023-2">{{cite web | title=Metronidazole tablet | website=DailyMed | date=30 January 2023 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=d7455566-16aa-488a-af2a-93b55a04c02f | access-date=5 July 2023 | archive-date=6 September 2023 | archive-url=https://web.archive.org/web/20230906080325/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=d7455566-16aa-488a-af2a-93b55a04c02f | url-status=live }}</ref><ref name="DailyMed-2023-3">{{cite web | title=Metronidazole Vaginal Gel, 0.75%- metronidazole gel | website=DailyMed | date=17 June 2023 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=63ed1e7e-d264-4e35-af83-ec37fa5b06d1 | access-date=5 July 2023 | archive-date=6 September 2023 | archive-url=https://web.archive.org/web/20230906080325/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=63ed1e7e-d264-4e35-af83-ec37fa5b06d1 | url-status=live }}</ref>
| legal_EU          =
| legal_EU_comment  =
| legal_UN          = <!-- N I, II, III, IV / P I, II, III, IV -->
| legal_UN_comment  =
| legal_status      = <!-- For countries not listed above -->

<!-- Pharmacokinetic data -->
| bioavailability = 80% (by mouth), 60–80% (rectal), 20–25% (vaginal)<ref name=MSR>{{cite web|title=Flagyl, Flagyl ER (metronidazole) dosing, indications, interactions, adverse effects, and more|work=Medscape Reference|publisher=WebMD|access-date=3 April 2014|url=http://reference.medscape.com/drug/flagyl-metronidazole-342566#showall|url-status=live|archive-url=https://web.archive.org/web/20140407080028/http://reference.medscape.com/drug/flagyl-metronidazole-342566#showall|archive-date=7 April 2014 }}</ref><ref name = MD>{{cite web|title=Metronidazole|work=Martindale: The Complete Drug Reference|publisher=Pharmaceutical Press|date=14 January 2014|access-date=3 April 2014|url=http://www.medicinescomplete.com/mc/martindale/current/ms-16893-c.htm| veditors = Brayfield A }}{{dead link|date=September 2019}}</ref><ref name="Pharmaceutical Press-2017">{{cite book | veditors = Brayfield A | title=Martindale: The Complete Drug Reference | edition=39th | year=2017 | publisher=Pharmaceutical Press | location=London | isbn= 978-0-85711-309-2 }}</ref>
| protein_bound = 20%<ref name = MSR/><ref name = MD/>
| metabolism = [[Liver]]<ref name = MSR/><ref name = MD/>
| metabolites = [[Hydroxymetronidazole]]
| onset             =
| elimination_half-life = 8 hours<ref name = MSR/><ref name = MD/>
| duration_of_action =
| excretion = Urine (77%), faeces (14%)<ref name = MSR/><ref name = MD/>

<!-- Identifiers -->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 443-48-1
| CAS_supplemental  =
| PubChem = 4173
| IUPHAR_ligand     =
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00916
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4029
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 140QMO216E
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00409
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 6909
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 137
| NIAID_ChemDB = 007953
| PDB_ligand = 2MN
| synonyms          =

<!-- Chemical and physical data -->
| IUPAC_name = 2-(2-Methyl-5-nitro-1''H''-imidazol-1-yl)ethanol
| C=6 | H=9 | N=3 | O=3
| SMILES = OCCn1c(C)ncc1[N+](=O)[O-]
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C6H9N3O3/c1-5-7-4-6(9(11)12)8(5)2-3-10/h4,10H,2-3H2,1H3
| StdInChI_comment  =
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = VAOCPAMSLUNLGC-UHFFFAOYSA-N
| density           =
| density_notes     =
| melting_point = 159
| melting_high = 163
| melting_notes     =
| boiling_point     =
| boiling_notes     =
| solubility        =
| sol_units         =
| specific_rotation =
}}
<!-- Definition and uses -->
'''Metronidazole''', sold under the brand name '''Flagyl''' among others, is an [[antibiotic]] and [[antiprotozoal medication]].<ref name=AHFS2015/> It is used either alone or with other antibiotics to treat [[pelvic inflammatory disease]], [[endocarditis]], and [[bacterial vaginosis]].<ref name=AHFS2015/> It is effective for [[dracunculiasis]], [[giardiasis]], [[trichomoniasis]], and [[amebiasis]].<ref name=AHFS2015/> It is an option for a first episode of mild-to-moderate [[Clostridioides difficile infection|''Clostridioides difficile'' colitis]] if [[vancomycin]] or [[fidaxomicin]] is unavailable.<ref name=AHFS2015/><ref name="pmid29462280">{{cite journal | vauthors = McDonald LC, Gerding DN, Johnson S, Bakken JS, Carroll KC, Coffin SE, Dubberke ER, Garey KW, Gould CV, Kelly C, Loo V, Shaklee Sammons J, Sandora TJ, Wilcox MH | title = 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) | journal = Clinical Infectious Diseases | volume = 66 | issue = 7 | pages = e1–e48 | date = March 2018 | pmid = 29462280 | pmc = 6018983 | doi = 10.1093/cid/cix1085 }}</ref> Metronidazole is available [[oral administration|orally]] (by mouth), as a cream or gel, and by slow [[intravenous infusion]] (injection into a vein).<ref name="AHFS2015">{{cite web|title=Metronidazole|url=https://www.drugs.com/monograph/metronidazole.html|publisher=The American Society of Health-System Pharmacists|access-date=31 July 2015|url-status=live|archive-url=https://web.archive.org/web/20150906002140/http://www.drugs.com/monograph/metronidazole.html|archive-date=6 September 2015 }}</ref><ref name="NIH">{{cite web | title=Metronidazole injection, solution | website=DailyMed | date=16 January 2023 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=3dc5f411-3312-4add-8198-161eed98132b | access-date=5 July 2023 | archive-date=6 September 2023 | archive-url=https://web.archive.org/web/20230906075601/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=3dc5f411-3312-4add-8198-161eed98132b | url-status=live }}</ref>

<!-- Side effects -->
Common side effects include [[nausea]], [[Dysgeusia|a metallic taste]], [[Anorexia (symptom)|loss of appetite]], and headaches.<ref name=AHFS2015/> Occasionally [[seizure]]s or allergies to the medication may occur.<ref name=AHFS2015/> Some state that metronidazole should not be used in early [[pregnancy]], while others state doses for trichomoniasis are safe.<ref name=Preg2017/>{{Weasel inline|date=July 2023}} Metronidazole is generally considered compatible with [[breastfeeding]].<ref name="Preg2017">{{cite web|title=Metronidazole Use During Pregnancy|url=https://www.drugs.com/pregnancy/metronidazole.html|website=www.drugs.com|access-date=1 January 2017|url-status=live|archive-url=https://web.archive.org/web/20170101163010/https://www.drugs.com/pregnancy/metronidazole.html|archive-date=1 January 2017 }}</ref><ref name="SPS - Specialist Pharmacy Service">{{cite web |title=Safety in Lactation: Metronidazole and tinidazole |url=https://www.sps.nhs.uk/articles/safety-in-lactation-metronidazole-and-tinidazole/ |website=SPS - Specialist Pharmacy Service |access-date=22 February 2020 |archive-date=21 February 2020 |archive-url=https://web.archive.org/web/20200221162641/https://www.sps.nhs.uk/articles/safety-in-lactation-metronidazole-and-tinidazole/ |url-status=live }}</ref>

<!-- History, society and culture -->
Metronidazole began to be commercially used in 1960 in France.<ref name="Corey-2013">{{cite book| vauthors = Corey EJ |title=Drug discovery practices, processes, and perspectives|date=2013|publisher=John Wiley & Sons|location=Hoboken, N.J.|isbn=978-1-118-35446-9|page=27|url=https://books.google.com/books?id=E6Dv5XsXU-IC&pg=PA27|url-status=live|archive-url=https://web.archive.org/web/20170908135757/https://books.google.com/books?id=E6Dv5XsXU-IC&pg=PA27|archive-date=8 September 2017 }}</ref> It is on the [[WHO Model List of Essential Medicines|World Health Organization's List of Essential Medicines]].<ref name="WHO23rd">{{cite book | vauthors = ((World Health Organization)) | title = The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023) | year = 2023 | hdl = 10665/371090 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MHP/HPS/EML/2023.02 | hdl-access=free }}</ref> It is available in most areas of the world.<ref name="Trichomoniasis treatment in women-2003">{{cite web| vauthors = Schmid G |title=Trichomoniasis treatment in women|url=http://apps.who.int/rhl/rti_sti/gscom/en/|access-date=1 August 2015|date=28 July 2003|url-status=dead|archive-url=https://web.archive.org/web/20150801004047/http://apps.who.int/rhl/rti_sti/gscom/en/|archive-date=1 August 2015 }}</ref> In 2022, it was the 133rd most commonly prescribed medication in the United States, with more than 4{{nbsp}}million prescriptions.<ref>{{cite web | title=The Top 300 of 2022 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=30 August 2024 | archive-date=30 August 2024 | archive-url=https://web.archive.org/web/20240830202410/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref>{{cite web | title = Metronidazole Drug Usage Statistics, United States, 2013 - 2022 | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Metronidazole | access-date = 30 August 2024 | archive-date = 6 December 2024 | archive-url = https://web.archive.org/web/20241206124631/https://clincalc.com/DrugStats/Drugs/Metronidazole | url-status = live }}</ref>