Cefuroxime

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Cefuroxime
Cefuroxime.svg
Cefuroxime-3D-spacefill.png
Clinical data
Trade names Zinacef, others
AHFS/Drugs.com Monograph
MedlinePlus a601206
License data
Routes of
administration 		Intramuscular, intravenous, by mouth
Drug class Second-generation cephalosporin
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability 37% on an empty stomach, up to 52% if taken after food
Elimination half-life 80 minutes
Excretion Urine 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
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.054.127 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C16H16N4O8S
Molar mass 424.38 g·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/s1 Yes check.svgY
  • Key:JFPVXVDWJQMJEE-SWWZKJRFSA-N Yes check.svgY
   (verify)

Cefuroxime, sold under the brand name Zinacef among others, is a second-generation cephalosporin [3] antibiotic used to treat and prevent a number of bacterial infections. [4] These include pneumonia, meningitis, otitis media, sepsis, urinary tract infections, and Lyme disease. [5] It is used by mouth or by injection into a vein or muscle. [5]

Contents

Common side effects include nausea, diarrhea, allergic reactions, and pain at the site of injection. [5] Serious side effects may include Clostridioides difficile infection, anaphylaxis, and Stevens–Johnson syndrome. [5] Use in pregnancy and breastfeeding is believed to be safe. [6] It is a second-generation cephalosporin and works by interfering with a bacteria's ability to make a cell wall resulting in its death. [5]

Cefuroxime was patented in 1971 and approved for medical use in 1977. [7] It is on the World Health Organization's List of Essential Medicines. [8] In 2022, it was the 283rd most commonly prescribed medication in the United States, with more than 600,000 prescriptions. [9] [10]

Medical uses

Cefuroxime is active against many bacteria including susceptible strains of Staphylococci and Streptococci, as well as a range of gram negative organisms. [11] 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. [12]

A systematic review found high quality evidence that injecting the eye with cefuroxime after cataract surgery will lower the chance of developing endophthalmitis after surgery. [13]

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.[ medical citation needed ]

Although a widely stated cross-allergic risk of about 10% exists between cephalosporins and penicillin, an assessment in 2006 have shown no increased risk for a cross-allergic reaction for cefuroxime and several other second-generation or later cephalosporins. [14]

Cefuroxime axetil is an acetoxyethyl ester prodrug of cefuroxime which is effective when taken by mouth. [15] It is a second-generation cephalosporin. [16]

Trade names

In the US it is marketed as Zinacef by Covis Pharmaceuticals since the company acquired the U.S. rights to the product from GSK. [17] GSK had continued marketing a pediatric oral suspension as Ceftin; however, this presentation was discontinued as of 24 June 2017. [18]

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. [19] In Poland, it is available as Zamur by Mepha, subsidiary of Teva Pharmaceutical Industries. [20] 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. [21] Cefuroxime axetil is sold in tablet form in Turkey inder the brand names Aksef  [22] and Cefaks. [23] 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. [24]

Related Research Articles

<span class="mw-page-title-main">Cephalosporin</span> Class of pharmaceutical drugs

The cephalosporins are a class of β-lactam antibiotics originally derived from the fungus Acremonium, which was previously known as Cephalosporium.

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<span class="mw-page-title-main">Esomeprazole</span> Medication which reduces stomach acid

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<span class="mw-page-title-main">Cefazolin</span> Antibiotic medication

Cefazolin, also known as cefazoline and cephazolin, is a first-generation cephalosporin antibiotic used for the treatment of a number of bacterial infections. Specifically it is used to treat cellulitis, urinary tract infections, pneumonia, endocarditis, joint infection, and biliary tract infections. It is also used to prevent group B streptococcal disease around the time of delivery and before surgery. It is typically given by injection into a muscle or vein.

<span class="mw-page-title-main">Bumetanide</span> A loop diuretic

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<span class="mw-page-title-main">Ceftriaxone</span> Antibiotic medication

Ceftriaxone, sold under the brand name Rocephin, is a third-generation cephalosporin antibiotic used for the treatment of a number of bacterial infections. These include middle ear infections, endocarditis, meningitis, pneumonia, bone and joint infections, intra-abdominal infections, skin infections, urinary tract infections, gonorrhea, and pelvic inflammatory disease. It is also sometimes used before surgery and following a bite wound to try to prevent infection. Ceftriaxone can be given by injection into a vein or into a muscle.

<span class="mw-page-title-main">Amoxicillin/clavulanic acid</span> Combination antibiotic medication

Amoxicillin/clavulanic acid, also known as co-amoxiclav or amox-clav, sold under the brand name Augmentin, among others, is an antibiotic medication used for the treatment of a number of bacterial infections. It is a combination consisting of amoxicillin, a β-lactam antibiotic, and potassium clavulanate, a β-lactamase inhibitor. It is specifically used for otitis media, streptococcal pharyngitis, pneumonia, cellulitis, urinary tract infections, and animal bites. It is taken by mouth or by injection into a vein.

<span class="mw-page-title-main">Cefalexin</span> Beta-lactam antibiotic

Cefalexin, also spelled cephalexin, is an antibiotic that can treat a number of bacterial infections. It kills gram-positive and some gram-negative bacteria by disrupting the growth of the bacterial cell wall. Cefalexin is a β-lactam antibiotic within the class of first-generation cephalosporins. It works similarly to other agents within this class, including intravenous cefazolin, but can be taken by mouth.

<span class="mw-page-title-main">Ranitidine</span> Medication that decreases stomach acid

Ranitidine, previously sold under the brand name Zantac among others, is a medication used to decrease stomach acid production. It was commonly used in treatment of peptic ulcer disease, gastroesophageal reflux disease, and Zollinger–Ellison syndrome. It can be given by mouth, injection into a muscle, or injection into a vein.

<span class="mw-page-title-main">Ofloxacin</span> Antibiotic to treat bacterial infections

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<span class="mw-page-title-main">Cefixime</span> A third generation cephalosporin antibiotic

Cefixime, sold under the brand name Suprax among others, is an antibiotic medication used to treat a number of bacterial infections. These infections include otitis media, strep throat, pneumonia, urinary tract infections, gonorrhea, and Lyme disease. For gonorrhea typically only one dose is required. In the United States it is a second-line treatment to ceftriaxone for gonorrhea. It is taken by mouth.

<span class="mw-page-title-main">Cefuroxime axetil</span> Chemical compound

Cefuroxime axetil, sold under the brand name Ceftin among others, is a second generation oral cephalosporin antibiotic.

<span class="mw-page-title-main">Ceftazidime</span> Antibiotic medication

Ceftazidime, sold under the brand name Fortaz among others, is a third-generation cephalosporin antibiotic useful for the treatment of a number of bacterial infections. Specifically it is used for joint infections, meningitis, pneumonia, sepsis, urinary tract infections, malignant otitis externa, Pseudomonas aeruginosa infection, and vibrio infection. It is given by injection into a vein, muscle, or eye.

<span class="mw-page-title-main">Piperacillin/tazobactam</span> Combination antibiotic medication

Piperacillin/tazobactam, sold under the brand name Tazocin among others, is a combination medication containing the antibiotic piperacillin and the β-lactamase inhibitor tazobactam. The combination has activity against many Gram-positive and Gram-negative bacteria including Pseudomonas aeruginosa. It is used to treat pelvic inflammatory disease, intra-abdominal infection, pneumonia, cellulitis, and sepsis. It is given by injection into a vein.

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<span class="mw-page-title-main">Flucloxacillin</span> Penicillin

Flucloxacillin, also known as floxacillin, is an antibiotic used to treat skin infections, external ear infections, infections of leg ulcers, diabetic foot infections, and infection of bone. It may be used together with other medications to treat pneumonia, and endocarditis. It may also be used prior to surgery to prevent Staphylococcus infections. It is not effective against methicillin-resistant Staphylococcus aureus (MRSA). It is taken by mouth or given by injection into a vein or muscle.

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References

  1. ↑ "Product monograph brand safety updates". Health Canada . 7 July 2016. Retrieved 13 July 2024.
  2. ↑ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA . Retrieved 22 October 2023.
  3. ↑ Katzung B (2018). Basic & Clinical Pharmacology. McGraw Hill. p. 803.
  4. ↑ British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 518. ISBN   9780857113382.
  5. 1 2 3 4 5 "Cefuroxime Sodium Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 22 March 2019.
  6. ↑ "Cefuroxime Use During Pregnancy". Drugs.com. Retrieved 3 March 2019.
  7. ↑ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 493. ISBN   9783527607495.
  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. ↑ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  10. ↑ "Cefuroxime Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
  11. ↑ "Appendix 5 – Antibiotic overview". Wellington ICU Drug Manual. Retrieved 7 April 2023.
  12. ↑ Root RK, Waldvogel F, Corey L, Stamm WE (1999). Clinical Infectious Diseases: A Practical Approach. Oxford University Press. p. 259. ISBN   9780195081039.
  13. ↑ 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. PMC   5375161 . PMID   28192644.
  14. ↑ Pichichero ME (February 2006). "Cephalosporins can be prescribed safely for penicillin-allergic patients" (PDF). The Journal of Family Practice. 55 (2): 106–112. PMID   16451776. Archived from the original (PDF) on 24 February 2012.
  15. ↑ Sneader W (23 June 2005). Drug Discovery: History. John Wiley & Sons. ISBN   9780471899792.
  16. ↑ 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. ISSN   8750-2836. PMID   3081544.
  17. ↑ "Covis Pharma to Acquire U.S. Rights from GlaxoSmithKline for Fortaz®, Zinacef®, Lanoxin®, Parnate®, and Zantac® Injection". Covis-pharma-sarl (Press release). Retrieved 6 August 2012.
  18. ↑ "FDA Drug Shortages". Food and Drug Administration (FDA). 20 March 2018.
  19. ↑ "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.
  20. ↑ "Charakterystyka produktu lecznicznego" (PDF). Urząd Rejestracji Produktów Leczniczych, Wyrobów Medycznych i Produktów Biobójczych. 12 November 2015.
  21. ↑ "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". TGA. Therapeutic Goods Administration. 26 March 2018. Retrieved 30 July 2018.
  22. ↑ "Aksef 500mg 20 Tablet". Nobel İlaç Sanayii ve Ticaret A.Ş. Retrieved 26 April 2023.
  23. ↑ "Antiinfectives and antiparasitic products for systemic use". DEVA Holding. Retrieved 3 May 2023.
  24. ↑ "ARTG ID 81301". TGA. Therapeutic Goods Administration. Archived from the original on 28 August 2021. Retrieved 30 July 2018.
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