Linezolid

Linezolid
Skeletal formula of linezolid
Clinical data
Pronunciation/lɪˈnɛzəlɪd, -ˈneɪz-/
Trade namesZyvox, Zyvoxam, others
AHFS/Drugs.comMonograph
MedlinePlusa602004
License data
Pregnancy
category
Routes of
administration		Intravenous infusion, by mouth
Drug classOxazolidinone antibiotic
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability~100% (oral)
Protein bindingLow (31%)
MetabolismLiver (50–70%, CYP not involved)
Elimination half-life3–7 hours;[9] longer half-life in CSF than plasma[9]
Excretionnon-kidney, kidney, and fecal[10]
Identifiers
  • (S)-N-({3-[3-fluoro-4-(morpholin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
NIAID ChemDB
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.121.520 Edit this at Wikidata
Chemical and physical data
FormulaC16H20FN3O4
Molar mass337.351 g·mol−1
3D model (JSmol)
  • O=C1O[C@@H](CNC(=O)C)CN1c3cc(F)c(N2CCOCC2)cc3
  • InChI=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 checkY
  • Key:TYZROVQLWOKYKF-ZDUSSCGKSA-N checkY
  (verify)

Linezolid is an antibiotic used for the treatment of infections caused by Gram-positive bacteria that are resistant to other antibiotics.[9][10] Linezolid is active against most Gram-positive bacteria that cause disease, including streptococci, vancomycin-resistant enterococci (VRE), and methicillin-resistant Staphylococcus aureus (MRSA).[9][8] 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.[10][11] It is used either by injection into a vein or by mouth.[10]

When given for short periods, linezolid is a relatively safe antibiotic.[12] It can be used in people of all ages and in people with liver disease or poor kidney function.[10] Common side effects with short-term use include headache, diarrhea, rash, and nausea.[10] Serious side effects may include serotonin syndrome, bone marrow suppression, and high blood lactate levels, particularly when used for more than two weeks.[10][13] If used for longer periods it may cause nerve damage, including optic nerve damage, which may be irreversible.[13]

As a protein synthesis inhibitor, linezolid works by suppressing bacterial protein production.[14] This either stops growth or results in bacterial death.[10] 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.[14] As of 2014, bacterial resistance to linezolid has remained low.[15] Linezolid is a member of the oxazolidinone class of medications.[10]

Linezolid was discovered in the mid-1990s, and was approved for commercial use in 2000.[16][17] It is on the World Health Organization's List of Essential Medicines.[18] The World Health Organization classifies linezolid as critically important for human medicine.[19] Linezolid is available as a generic medication.[10]

  1. ^ "Linezolid (Zyvox) Use During Pregnancy". Drugs.com. 16 April 2018. Archived from the original on 17 March 2020. Retrieved 17 March 2020.
  2. ^ "Linezolid, injection, 600 mg per 300 mL, tablet, 600 mg and powder for oral suspension, 20 mg per mL, Zyvox®". Australian Government Department of Health and Aged Care. 24 September 2001. Archived from the original on 18 November 2022. Retrieved 30 March 2024.
  3. ^ "Public Summary" (PDF). Retrieved 30 March 2024.
  4. ^ "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Archived from the original on 6 July 2023. Retrieved 30 March 2024.
  5. ^ "Product information". health-products.canada.ca. 31 July 2020. Archived from the original on 29 March 2024. Retrieved 29 March 2024.
  6. ^ "Product information". health-products.canada.ca. 7 February 2006. Archived from the original on 29 March 2024. Retrieved 29 March 2024.
  7. ^ Cite error: The named reference Zyvox SPC was invoked but never defined (see the help page).
  8. ^ a b "Zyvox- linezolid injection, solution Zyvox- linezolid tablet, film coated Zyvox- linezolid suspension". DailyMed. 21 February 2020. Archived from the original on 26 April 2021. Retrieved 17 March 2020.
  9. ^ a b c d Roger C, Roberts JA, Muller L (May 2018). "Clinical Pharmacokinetics and Pharmacodynamics of Oxazolidinones". Clinical Pharmacokinetics. 57 (5): 559–575. doi:10.1007/s40262-017-0601-x. PMID 29063519. S2CID 4961324.
  10. ^ a b c d e f g h i j "Linezolid". The American Society of Health-System Pharmacists. Archived from the original on 20 December 2016. Retrieved 8 December 2016.
  11. ^ World Health Organization (2015). 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). Geneva: World Health Organization. pp. 26–33. hdl:10665/189763. ISBN 9789241209946. ISSN 0512-3054. WHO technical report series;994.
  12. ^ Marino PL, Sutin KM (2007). "Antimicrobial therapy". The ICU book. Hagerstown, MD: Lippincott Williams & Wilkins. p. 817. ISBN 978-0-7817-4802-5.
  13. ^ a b "Linezolid Side Effects in Detail". drugs.com. Archived from the original on 20 December 2016. Retrieved 11 December 2016.
  14. ^ a b Swaney SM, Aoki H, Ganoza MC, Shinabarger DL (December 1998). "The oxazolidinone linezolid inhibits initiation of protein synthesis in bacteria". Antimicrobial Agents and Chemotherapy. 42 (12): 3251–5. doi:10.1128/AAC.42.12.3251. PMC 106030. PMID 9835522.
  15. ^ Mendes RE, Deshpande LM, Jones RN (April 2014). "Linezolid update: stable in vitro activity following more than a decade of clinical use and summary of associated resistance mechanisms". Drug Resistance Updates. 17 (1–2): 1–12. doi:10.1016/j.drup.2014.04.002. PMID 24880801. Emergence of resistance has been limited ... It is still uncertain whether the occurrences of such isolates are becoming more prevalent.
  16. ^ Li JJ, Corey EJ (2013). Drug Discovery: Practices, Processes, and Perspectives. John Wiley & Sons. p. 6. ISBN 978-1-118-35446-9. Archived from the original on 10 September 2017.
  17. ^ Torok E, Moran E, Cooke F (2009). "Chapter 2 Antimicrobials". Oxford Handbook of Infectious Diseases and Microbiology. OUP Oxford. ISBN 978-0-19-103962-1. Archived from the original on 8 September 2017.
  18. ^ 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.
  19. ^ World Health Organization (2019). Critically important antimicrobials for human medicine (6th revision ed.). Geneva: World Health Organization. hdl:10665/312266. ISBN 9789241515528.