Cefuroxime

Cefuroxime
Skeletal formula of cefuroxime
Ball-and-stick model of the cefuroxime molecule
Names
Trade namesZinacef, Ceftin, others
IUPAC name
  • (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
Clinical data
Drug classAntibiotic (2nd-generation cephalosporin)
Main usesPneumonia, meningitis, otitis media, sepsis, urinary tract infections, Lyme disease[1]
Side effectsNausea, diarrhea, allergic reactions, pain at the site of injection[1]
WHO AWaReUnlinkedWikibase error: ⧼unlinkedwikibase-error-statements-entity-not-set⧽
Pregnancy
category
  • B
Routes of
use		Intramuscular, intravenous, by mouth
Defined daily dose500 mg (by mouth)[2]
3,000 mg (by injection)[2]
External links
AHFS/Drugs.comMonograph
MedlinePlusa601206
Legal
License data
Legal status
  • AU: S4 (Prescription only)
  • In general: ℞ (Prescription only)
Pharmacokinetics
Bioavailability37% on an empty stomach, up to 52% if taken after food
Elimination half-life80 minutes
ExcretionUrine 66–100% unchanged
Chemical and physical data
FormulaC16H16N4O8S
Molar mass424.38 g·mol−1
3D model (JSmol)
SMILES
  • O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)C(=N\OC)\c3occc3)COC(=O)N)C(=O)O
InChI
  • 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/s1 checkY
  • Key:JFPVXVDWJQMJEE-SWWZKJRFSA-N checkY

Cefuroxime, sold under the brand name Zinacef among others, is an antibiotic used to treat and prevent a number of bacterial infections.[3] These include pneumonia, meningitis, otitis media, sepsis, urinary tract infections, and Lyme disease.[1] It is used by mouth or by injection into a vein or muscle.[1]

Common side effects include nausea, diarrhea, allergic reactions, and pain at the site of injection.[1] Serious side effects may include Clostridium difficile infection, anaphylaxis, and Stevens–Johnson syndrome.[1] Use in pregnancy and breastfeeding is believed to be safe.[4] It is a second-generation cephalosporin and works by interfering with a bacteria's ability to make a cell wall resulting in its death.[1]

Cefuroxime was patented in 1971, and approved for medical use in 1977.[5] It is on the World Health Organization's List of Essential Medicines.[6] It is available as a generic medication.[3] A week of treatment when taken by mouth in the United Kingdom costs the NHS about £18 as of 2019.[3] In the United States, the wholesale cost of this amount is about US$8.50.[7] In 2017, it was the 342nd most commonly prescribed medication in the United States, with more than 800 thousand prescriptions.[8]

Medical uses

It is in the 'watch' group of the WHO AWaRe Classification.[9]

As with the other cephalosporins, it is susceptible to beta-lactamase, although as a second-generation variety, it is less so. Hence, it may have greater activity against Haemophilus influenzae, Neisseria gonorrhoeae, and Lyme disease. Unlike other second-generation cephalosporins, cefuroxime can cross the blood-brain barrier.[10]

Injecting the eye with cefuroxime after cataract surgery lowers the chance of developing endophthalmitis.[11]

Dosage

The defined daily dose is 500 mg by mouth and 3,000 mg by injection.[2]

Side effects

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 of diarrhea, nausea, vomiting, headaches/migraines, dizziness, and abdominal pain compared to most antibiotics in its class.

Although a widely stated cross-allergic risk of about 10% exists between cephalosporins and penicillin, recent assessments have shown no increased risk for a cross-allergic reaction for cefuroxime and several other second-generation or later cephalosporins.[12]

Chemistry

Cefuroxime axetil is an acetoxyethyl ester prodrug of cefuroxime which is effective when taken by mouth.[13] It is a second-generation cephalosporin.

Society and culture

Cost

In the United States, the wholesale cost of this amount is about US$8.50.[7] In 2017, it was the 342nd most commonly prescribed medication in the United States, with more than 800 thousand prescriptions.[8]. A week of treatment when taken by mouth in the United Kingdom costs the NHS about £18 as of 2019.[3]

  • Cefuroxime costs (US)
    Cefuroxime costs (US)
  • Cephalexin prescriptions (US)
    Cephalexin prescriptions (US)

Trade names

In the U.S. it is marketed as "Zinacef" by Covis Pharmaceuticals since the company acquired the U.S. rights to the product from GSK.[14] GSK had continued marketing a pediatric oral suspension as "Ceftin"; however, this presentation was discontinued as of 24 June 2017.[15]

In Bangladesh, it is available as Rofurox by Radiant, Kilbac by Incepta and Xorimax by Sandoz. In India, it is available as Ceftum in tablet form and Supacef in injection form by GSK.[16] In Poland, it is available as Zamur by Mepha, subsidiary of Teva Pharmaceutical Industries.[17] In Australia, the "first generic" form of Cefuroxime axetil, Pharmacor Cefuroxime (tablets) from Pharmacor Pty Ltd, was registered on 27 March 2017, by the Therapeutic Goods Administration.[18] 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.[19]

References

  1. 1 2 3 4 5 6 7 "Cefuroxime Sodium Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Archived from the original on 22 March 2019. Retrieved 22 March 2019.
  2. 1 2 3 "WHOCC - ATC/DDD Index". www.whocc.no. Archived from the original on 19 July 2021. Retrieved 9 September 2020.
  3. 1 2 3 4 British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 518. ISBN 9780857113382.
  4. ↑ "Cefuroxime Use During Pregnancy". Drugs.com. Archived from the original on 22 March 2019. Retrieved 3 March 2019.
  5. ↑ Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 493. ISBN 9783527607495. Archived from the original on 2 March 2019. Retrieved 2 March 2019.
  6. ↑ 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.
  7. 1 2 "NADAC as of 2019-02-27". Centers for Medicare and Medicaid Services. Archived from the original on 6 March 2019. Retrieved 3 March 2019.
  8. 1 2 "Cefuroxime - Drug Usage Statistics". ClinCalc. Archived from the original on 19 June 2020. Retrieved 11 April 2020.
  9. ↑ Zanichelli, Veronica; Sharland, Michael; Cappello, Bernadette; Moja, Lorenzo; Getahun, Haileyesus; Pessoa-Silva, Carmem; Sati, Hatim; van Weezenbeek, Catharina; Balkhy, Hanan; Simão, Mariângela; Gandra, Sumanth; Huttner, Benedikt (1 April 2023). "The WHO AWaRe (Access, Watch, Reserve) antibiotic book and prevention of antimicrobial resistance". Bulletin of the World Health Organization. 101 (4): 290–296. doi:10.2471/BLT.22.288614. ISSN 0042-9686. Archived from the original on 7 May 2023. Retrieved 17 November 2023.
  10. ↑ Root, Richard K.; Waldvogel, Francis; Corey, Lawrence; Stamm, Walter E. (1999). Clinical Infectious Diseases: A Practical Approach. Oxford University Press. p. 259. ISBN 9780195081039. Archived from the original on 28 August 2021. Retrieved 9 November 2019.
  11. ↑ Gower EW, Lindsley K, Tulenko SE, Nanji AA, Leyngold I, McDonnell PJ (2017). "Perioperative antibiotics for prevention of acute endophthalmitis after cataract surgery". Cochrane Database Syst Rev. 2: CD006364. doi:10.1002/14651858.CD006364.pub3. PMC 5375161. PMID 28192644.
  12. ↑ Pichichero ME (2006). "Cephalosporins can be prescribed safely for penicillin-allergic patients" (PDF). The Journal of family practice. 55 (2): 106–12. PMID 16451776. Archived from the original (PDF) on 24 February 2012.
  13. ↑ Walter Sneader. "Drug Discovery: History".
  14. ↑ "Archive copy" (PDF). Archived from the original (PDF) on 8 August 2014. Retrieved 6 August 2012.{{cite web}}: CS1 maint: archived copy as title (link)
  15. ↑ "FDA Drug Shortages". Food and Drug Administration (FDA). 2018-03-20. Archived from the original on 12 September 2019. Retrieved 11 September 2019.
  16. ↑ "GlaxoSmithKline Pharmaceuticals Limited – Prescription Medicines – Anti-Infective". Gsk-india.com. 26 March 2013. Archived from the original on 22 March 2016. Retrieved 12 March 2012.
  17. ↑ "Charakterystyka produktu lecznicznego" (PDF). Urząd Rejestracji Produktów Leczniczych, Wyrobów Medycznych i Produktów Biobójczych. 12 November 2015. Archived (PDF) from the original on 5 March 2016. Retrieved 12 November 2015.
  18. ↑ "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". TGA. Therapeutic Goods Administration. Archived from the original on 30 July 2018. Retrieved 30 July 2018.
  19. ↑ "ARTG ID 81301". TGA. Therapeutic Goods Administration. Archived from the original on 28 August 2021. Retrieved 30 July 2018.
  • "Cefuroxime". Drug Information Portal. U.S. National Library of Medicine. Archived from the original on 7 May 2021. Retrieved 22 March 2019.
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