Editing Linezolid (section)

{{Short description|Antibiotic medication}}
{{Use dmy dates|date=December 2018}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
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{{Infobox drug
| Verifiedfields = 
| Watchedfields = 
| verifiedrevid = 850189766
| image = Linezolid.svg
| image_class = skin-invert-image
| width             = 
| alt = Skeletal formula of linezolid
| image2 = Linezolid-from-xtal-2008-3D-balls.png
| width2            = 
| alt2              = 
| caption           =

<!-- Clinical data -->
| pronounce   = {{IPAc-en|l|ɪ|ˈ|n|ɛ|z|əl|ɪ|d|,_|-|ˈ|n|eɪ|z|-}}
| tradename = Zyvox, Zyvoxam, others<!-- no generics here, please! -->
| Drugs.com = {{drugs.com|monograph|linezolid}}
| MedlinePlus = a602004
| DailyMedID = Linezolid
| pregnancy_AU = B3
| pregnancy_AU_comment = <ref name="Drugs.com pregnancy">{{cite web | title=Linezolid (Zyvox) Use During Pregnancy | website=Drugs.com | date=16 April 2018 | url=https://www.drugs.com/pregnancy/linezolid.html | access-date=17 March 2020 | archive-date=17 March 2020 | archive-url=https://web.archive.org/web/20200317065515/https://www.drugs.com/pregnancy/linezolid.html | url-status=live }}</ref>
| pregnancy_category= 
| routes_of_administration = [[Intravenous therapy|Intravenous infusion]], [[by mouth]]
| class = [[Oxazolidinone]] antibiotic
| ATC_prefix = J01
| ATC_suffix = XX08
| ATC_supplemental  =

<!-- Legal status -->
| legal_AU = S4
| legal_AU_comment = <ref>{{cite web | title=Linezolid, injection, 600 mg per 300 mL, tablet, 600 mg and powder for oral suspension, 20 mg per mL, Zyvox® | publisher=Australian Government Department of Health and Aged Care | date=24 September 2001 | url=https://www.pbs.gov.au/info/industry/listing/elements/pbac-meetings/psd/2013-07/linezolid | access-date=30 March 2024 | archive-date=18 November 2022 | archive-url=https://web.archive.org/web/20221118203806/https://www.pbs.gov.au/info/industry/listing/elements/pbac-meetings/psd/2013-07/linezolid | url-status=live }}</ref><ref>{{cite web | title=Public Summary | url=https://www.ebs.tga.gov.au/servlet/xmlmillr6?dbid=ebs/PublicHTML/pdfStore.nsf&docid=277696&agid=(PrintDetailsPublic)&actionid=1 | format=PDF | access-date=30 March 2024}}</ref><ref>{{cite web | title=Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017 | website=Therapeutic Goods Administration (TGA) | date=21 June 2022 | url=https://www.tga.gov.au/resources/publication/publications/prescription-medicines-registration-new-generic-medicines-and-biosimilar-medicines-2017 | access-date=30 March 2024 | archive-date=6 July 2023 | archive-url=https://web.archive.org/web/20230706023149/https://www.tga.gov.au/resources/publication/publications/prescription-medicines-registration-new-generic-medicines-and-biosimilar-medicines-2017 | 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=Product information | website=health-products.canada.ca | date=31 July 2020 | url=https://health-products.canada.ca/dpd-bdpp/info?lang=eng&code=67614 | access-date=29 March 2024 | archive-date=29 March 2024 | archive-url=https://web.archive.org/web/20240329202900/https://health-products.canada.ca/dpd-bdpp/info?lang=eng&code=67614 | url-status=live }}</ref><ref>{{cite web | title=Product information | website=health-products.canada.ca | date=7 February 2006 | url=https://health-products.canada.ca/dpd-bdpp/info?lang=eng&code=67615 | access-date=29 March 2024 | archive-date=29 March 2024 | archive-url=https://web.archive.org/web/20240329203402/https://health-products.canada.ca/dpd-bdpp/info?lang=eng&code=67615 | url-status=live }}</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 = <ref name="Zyvox SPC" />
| legal_US = Rx-only
| legal_US_comment = <ref name="Zyvox FDA label" />
| 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 = ~100% (oral)
| protein_bound = Low (31%)
| metabolism = [[Liver]] (50–70%, [[cytochrome P450|CYP]] not&nbsp;involved)
| metabolites       = 
| onset             = 
| elimination_half-life = 3–7&nbsp;hours;<ref name=Roger2018 /> longer half-life in [[Cerebrospinal fluid|CSF]] than [[blood plasma|plasma]]<ref name=Roger2018 />
| duration_of_action = 
| excretion = non-kidney, [[kidney]], and fecal<ref name=AHFS2016/>

<!-- Identifiers -->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 165800-03-3
| CAS_supplemental  = 
| PubChem = 441401
| IUPHAR_ligand     = 
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00601
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 390139
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = ISQ9I6J12J
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00947
| ChEBI_Ref         = 
| ChEBI             = 63607
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 126
| NIAID_ChemDB = 070944
| PDB_ligand        = ZLD
| synonyms          =

<!-- Chemical and physical data -->
| IUPAC_name = (''S'')-''N''-({3-[3-fluoro-4-(morpholin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide
| C=16 | H=20 | F=1 | N=3 | O=4
| SMILES = O=C1O[C@@H](CNC(=O)C)CN1c3cc(F)c(N2CCOCC2)cc3
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C16H20FN3O4/c1-11(21)18-9-13-10-20(16(22)24-13)12-2-3-15(14(17)8-12)19-4-6-23-7-5-19/h2-3,8,13H,4-7,9-10H2,1H3,(H,18,21)/t13-/m0/s1
| StdInChI_comment  = 
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = TYZROVQLWOKYKF-ZDUSSCGKSA-N
| density           = 
| density_notes     = 
| melting_point     = 
| melting_high      = 
| melting_notes     = 
| boiling_point     = 
| boiling_notes     = 
| solubility        = 
| sol_units         = 
| specific_rotation = 
}}

<!-- Definition and uses -->
'''Linezolid''' is an [[antibiotic]] used for the treatment of [[infection]]s caused by [[Gram-positive bacteria]] that are [[antibiotic resistance|resistant]] to other antibiotics.<ref name=Roger2018>{{cite journal | vauthors = Roger C, Roberts JA, Muller L | title = Clinical Pharmacokinetics and Pharmacodynamics of Oxazolidinones | journal = Clinical Pharmacokinetics | volume = 57 | issue = 5 | pages = 559–575 | date = May 2018 | pmid = 29063519 | doi = 10.1007/s40262-017-0601-x | s2cid = 4961324 | doi-access = free }}</ref><ref name=AHFS2016/> Linezolid is active against most Gram-positive bacteria that cause disease, including [[Streptococcus|streptococci]], [[vancomycin-resistant enterococcus|vancomycin-resistant enterococci]] (VRE), and [[methicillin-resistant Staphylococcus aureus|methicillin-resistant ''Staphylococcus aureus'']] (MRSA).<ref name=Roger2018 /><ref name="Zyvox FDA label">{{cite web | title=Zyvox- linezolid injection, solution Zyvox- linezolid tablet, film coated Zyvox- linezolid suspension | website=DailyMed | date=21 February 2020 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=6e70e63b-bfd5-478d-a8ee-8ba22c9efabd | access-date=17 March 2020 | archive-date=26 April 2021 | archive-url=https://web.archive.org/web/20210426030640/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=6e70e63b-bfd5-478d-a8ee-8ba22c9efabd | url-status=live }}</ref> The main uses are infections of the [[skin]] and [[pneumonia]] although it may be used for a variety of other infections including [[drug-resistant tuberculosis]].<ref name=AHFS2016/><ref name=WHO2015Use>{{cite book | vauthors = ((World Health Organization)) | year = 2015 | title = The selection and use of essential medicines. Twentieth report of the WHO Expert Committee 2015 (including 19th WHO Model List of Essential Medicines and 5th WHO Model List of Essential Medicines for Children) | publisher = World Health Organization | location = Geneva | author-link = World Health Organization | hdl = 10665/189763 | id = WHO technical report series;994 | hdl-access=free | isbn = 9789241209946 | issn = 0512-3054 | pages=26–33 }}</ref> It is used either by [[intravenous|injection into a vein]] or [[by mouth]].<ref name=AHFS2016/>

<!-- Side effects -->
When given for short periods, linezolid is a relatively safe antibiotic.<ref name=Marino2007>{{cite book |vauthors=Marino PL, Sutin KM |chapter=Antimicrobial therapy |title=The ICU book |publisher=Lippincott Williams & Wilkins |location=Hagerstown, MD |year=2007 |page=817 |isbn=978-0-7817-4802-5}}</ref> It can be used in people of all ages and in people with [[liver disease]] or [[renal failure|poor kidney function]].<ref name=AHFS2016/> Common side effects with short-term use include [[headache]], [[diarrhea]], rash, and [[nausea]].<ref name=AHFS2016/> Serious side effects may include [[serotonin syndrome]], [[bone marrow suppression]], and [[lactic acidosis|high blood lactate levels]], particularly when used for more than two weeks.<ref name=AHFS2016/><ref name=SFX2016/> If used for longer periods it may cause  [[chemotherapy-induced peripheral neuropathy|nerve damage]], including [[optic neuropathy|optic nerve damage]], which may be irreversible.<ref name=SFX2016>{{cite web|title=Linezolid Side Effects in Detail|url=https://www.drugs.com/sfx/linezolid-side-effects.html|website=drugs.com|access-date=11 December 2016|url-status=live|archive-url=https://web.archive.org/web/20161220233415/https://www.drugs.com/sfx/linezolid-side-effects.html|archive-date=20 December 2016}}</ref>

<!-- Mechanism of action -->
As a [[protein synthesis inhibitor]], linezolid works by suppressing [[bacterial translation|bacterial protein production]].<ref name=Swaney1998/> This either [[bacteriostatic|stops growth]] or results in [[bactericidal|bacterial death]].<ref name=AHFS2016/> Although many antibiotics work this way, the exact [[mechanism of action]] of linezolid appears to be unique in that it blocks the initiation of protein production, rather than one of the later steps.<ref name=Swaney1998>{{cite journal | vauthors = Swaney SM, Aoki H, Ganoza MC, Shinabarger DL | title = The oxazolidinone linezolid inhibits initiation of protein synthesis in bacteria | journal = Antimicrobial Agents and Chemotherapy | volume = 42 | issue = 12 | pages = 3251–5 | date = December 1998 | pmid = 9835522 | pmc = 106030 | url = | doi = 10.1128/AAC.42.12.3251 }}</ref> As of 2014, [[bacterial resistance]] to linezolid has remained low.<ref>{{cite journal | vauthors = Mendes RE, Deshpande LM, Jones RN | title = Linezolid update: stable in vitro activity following more than a decade of clinical use and summary of associated resistance mechanisms | journal = Drug Resistance Updates | volume = 17 | issue = 1–2 | pages = 1–12 | date = April 2014 | pmid = 24880801 | doi = 10.1016/j.drup.2014.04.002 | quote = Emergence of resistance has been limited&nbsp;... It is still uncertain whether the occurrences of such isolates are becoming more prevalent. }}</ref> Linezolid is a member of the [[2-Oxazolidone|oxazolidinone]] class of medications.<ref name=AHFS2016/>

<!-- History and culture -->
Linezolid was discovered in the mid-1990s, and was approved for commercial use in 2000.<ref>{{cite book| vauthors = Li JJ, Corey EJ  |title=Drug Discovery: Practices, Processes, and Perspectives|date=2013|publisher=John Wiley & Sons|isbn=978-1-118-35446-9|page=6|url=https://books.google.com/books?id=mIyxO5cLEAcC&pg=PA6|language=en|url-status=live|archive-url=https://web.archive.org/web/20170910172617/https://books.google.com/books?id=mIyxO5cLEAcC&pg=PA6|archive-date=10 September 2017}}</ref><ref>{{cite book| vauthors = Torok E, Moran E, Cooke F |title=Oxford Handbook of Infectious Diseases and Microbiology|date=2009|publisher=OUP Oxford|isbn=978-0-19-103962-1|chapter-url=https://books.google.com/books?id=5W-WBQAAQBAJ&pg=PT56|language=en|chapter=Chapter 2 Antimicrobials|url-status=live|archive-url=https://web.archive.org/web/20170908143257/https://books.google.com/books?id=5W-WBQAAQBAJ&pg=PT56|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> The World Health Organization classifies linezolid as critically important for human medicine.<ref>{{cite book | vauthors=((World Health Organization)) | year=2019 | title=Critically important antimicrobials for human medicine | edition=6th revision |  author-link = World Health Organization | publisher = World Health Organization | location = Geneva | hdl=10665/312266 | isbn=9789241515528 | hdl-access=free }}</ref> Linezolid is available as a [[generic medication]].<ref name=AHFS2016>{{cite web|title=Linezolid|url=https://www.drugs.com/monograph/linezolid.html|publisher=The American Society of Health-System Pharmacists|access-date=8 December 2016|url-status=live|archive-url=https://web.archive.org/web/20161220231329/https://www.drugs.com/monograph/linezolid.html|archive-date=20 December 2016}}</ref> 
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