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Cefuroxime

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Cefuroxime
Skeletal formula of cefuroxime
Ball-and-stick model of the cefuroxime molecule
Clinical data
Trade namesZinacef, others
AHFS/DrugsMonograph
MedlinePlusa601206
License data
Routes of
administration		Intramuscular,intravenous,by mouth
Drug classSecond-generationcephalosporin
ATC code
Legal status
Legal status
Pharmacokineticdata
Bioavailability37% on an empty stomach, up to 52% if taken after food
Eliminationhalf-life80 minutes
ExcretionUrine 66–100% unchanged
Identifiers
  • (6R,7R)-3-{[(Aminocarbonyl)oxy]methyl}-7-{[(2Z)-2-(2-furyl)-2-(methoxyimino)acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
CAS Number
PubChemCID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.054.127Edit this at Wikidata
Chemical and physical data
FormulaC16H16N4O8S
Molar mass424.38g·mol−1
3D model (JSmol)
  • O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)C(=N\OC)\c3occc3)COC(=O)N)C(=O)O
  • InChI=1S/C16H16N4O8S/c1-26-19-9(8-3-2-4-27-8)12(21)18-10-13(22)20-11(15(23)24)7(5-28-16(17)25)6-29-14(10)20/h2-4,10,14H,5-6H2,1H3,(H2,17,25)(H,18,21)(H,23,24)/b19-9+/t10-,14-/m1/s1checkY
  • Key:JFPVXVDWJQMJEE-SWWZKJRFSA-NcheckY
(verify)

Cefuroxime,sold under the brand nameZinacefamong others, is a second-generationcephalosporin[3]antibioticused to treat and prevent a number ofbacterial infections.[4]These includepneumonia,meningitis,otitis media,sepsis,urinary tract infections,andLyme disease.[5]It is used by mouth or byinjection into a veinormuscle.[5]

Common side effects include nausea, diarrhea, allergic reactions, and pain at the site of injection.[5]Serious side effects may includeClostridium difficileinfection,anaphylaxis,andStevens–Johnson syndrome.[5]Use inpregnancyandbreastfeedingis believed to be safe.[6]It is a second-generationcephalosporinand works by interfering with a bacteria's ability to make acell wallresulting in its death.[5]

Cefuroxime was patented in 1971, and approved for medical use in 1977.[7]It is on theWorld Health Organization's List of Essential Medicines.[8]In 2020, it was the 325th most commonly prescribed medication in the United States, with more than 800thousand prescriptions.[9]

Medical uses

[edit]

Cefuroxime is active against many bacteria including susceptible strains ofStaphylococciandStreptococci,as well as a range of gram negative organisms.[10]As with the other cephalosporins, it is susceptible tobeta-lactamase,although as a second-generation variety, it is less so. Hence, it may have greater activity againstHaemophilus influenzae,Neisseria gonorrhoeae,andLyme disease.Unlike other second-generation cephalosporins, cefuroxime can cross theblood–brain barrier.[11]

A systematic review found high quality evidence that injecting the eye with cefuroxime after cataract surgery will lower the chance of developingendophthalmitisafter surgery.[12]

Side effects

[edit]

Cefuroxime is generally well tolerated, and its side effects are usually transient. If ingested after food, this antibiotic is both better absorbed and less likely to cause its most common side effects ofdiarrhea,nausea, vomiting, headaches/migraines,dizziness,and abdominal pain compared to most antibiotics in its class.[medical citation needed]

Although a widely stated cross-allergic risk of about 10% exists between cephalosporins andpenicillin,an assessment in 2006 have shown no increased risk for a cross-allergic reaction for cefuroxime and several other second-generation or later cephalosporins.[13]

[edit]

Cefuroxime axetilis an acetoxyethylesterprodrugof cefuroxime which is effective when taken by mouth.[14]It is a second-generationcephalosporin.[15]

Trade names

[edit]

In the US it is marketed as Zinacef by Covis Pharmaceuticals since the company acquired the U.S. rights to the product fromGSK.[16]GSK had continued marketing a pediatric oral suspension as Ceftin; however, this presentation was discontinued as of 24 June 2017.[17]

In Bangladesh, it is available as Sefur by Opsonin Pharma, Kilbac by Incepta, Axim by Aristopharma, Rofurox by Radiant, Xorimax by Sandoz and Uroxime by EURO Pharma Ltd. In India, it is available as Ceftum and Cefuall by Allencia Biosciences in tablet form and Supacef in injection form by GSK.[18]In Poland, it is available as Zamur byMepha,subsidiary ofTeva Pharmaceutical Industries.[19]In Australia, the "first generic" form of Cefuroxime axetil, Pharmacor Cefuroxime (tablets) from Pharmacor Pty Ltd, was registered on 27 March 2017, by theTherapeutic Goods Administration.[20]Cefuroxime axetil is sold in tablet form in Turkey inder the brand names Aksef[21]and Cefaks.[22]Cefuroxime axetil is also available (in two strengths) as granules for oral suspension from Aspen Pharmacare Australia Pty Ltd under the brand name Zinnat cefuroxime.[23]

References

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  1. ^"FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)".nctr-crs.fda.gov.FDA.Retrieved22 October2023.
  2. ^"Product monograph brand safety updates".Health Canada.7 July 2016.Retrieved13 July2024.
  3. ^Katzung B (2018).Basic & Clinical Pharmacology.McGraw Hill. p. 803.
  4. ^British national formulary: BNF 76(76 ed.). Pharmaceutical Press. 2018. p. 518.ISBN9780857113382.
  5. ^abcde"Cefuroxime Sodium Monograph for Professionals".Drugs.American Society of Health-System Pharmacists.Retrieved22 March2019.
  6. ^"Cefuroxime Use During Pregnancy".Drugs.Retrieved3 March2019.
  7. ^Fischer J, Ganellin CR (2006).Analogue-based Drug Discovery.John Wiley & Sons. p. 493.ISBN9783527607495.
  8. ^World Health Organization(2019).World Health Organization model list of essential medicines: 21st list 2019.Geneva: World Health Organization.hdl:10665/325771.WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  9. ^"Cefuroxime – Drug Usage Statistics".ClinCalc.Retrieved7 October2022.
  10. ^"Appendix 5 – Antibiotic overview".Wellington ICU Drug Manual.Retrieved7 April2023.
  11. ^Root RK, Waldvogel F, Corey L, Stamm WE (1999).Clinical Infectious Diseases: A Practical Approach.Oxford University Press. p. 259.ISBN9780195081039.
  12. ^Gower EW, Lindsley K, Tulenko SE, Nanji AA, Leyngold I, McDonnell PJ (February 2017)."Perioperative antibiotics for prevention of acute endophthalmitis after cataract surgery".The Cochrane Database of Systematic Reviews.2017(2): CD006364.doi:10.1002/14651858.CD006364.pub3.PMC5375161.PMID28192644.
  13. ^Pichichero ME (February 2006)."Cephalosporins can be prescribed safely for penicillin-allergic patients"(PDF).The Journal of Family Practice.55(2): 106–112.PMID16451776.Archived fromthe original(PDF)on 24 February 2012.
  14. ^Sneader W (23 June 2005).Drug Discovery: History.John Wiley & Sons.ISBN9780471899792.
  15. ^Glatt AE (15 March 1986). "Second-generation cephalosporins".Hospital Practice (Office Ed.).21(3): 158A–158B, 158E, 158H–158L.doi:10.1080/21548331.1986.11704945.ISSN8750-2836.PMID3081544.
  16. ^"Covis Pharma to Acquire U.S. Rights from GlaxoSmithKline for Fortaz®, Zinacef®, Lanoxin®, Parnate®, and Zantac® Injection".Covis-pharma-sarl(Press release).Retrieved6 August2012.
  17. ^"FDA Drug Shortages".Food and Drug Administration (FDA). 20 March 2018.
  18. ^"GlaxoSmithKline Pharmaceuticals Limited – Prescription Medicines – Anti-Infective".Gsk-india. 26 March 2013. Archived fromthe originalon 22 March 2016.Retrieved12 March2012.
  19. ^ "Charakterystyka produktu lecznicznego"(PDF).Urząd Rejestracji Produktów Leczniczych, Wyrobów Medycznych i Produktów Biobójczych. 12 November 2015.
  20. ^"Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017".TGA.Therapeutic Goods Administration. 26 March 2018.Retrieved30 July2018.
  21. ^"Aksef 500mg 20 Tablet".Nobel İlaç Sanayii ve Ticaret A.Ş.Retrieved26 April2023.
  22. ^"Antiinfectives and antiparasitic products for systemic use".DEVA Holding.Retrieved3 May2023.
  23. ^"ARTG ID 81301".TGA.Therapeutic Goods Administration. Archived fromthe originalon 28 August 2021.Retrieved30 July2018.
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