Cefuroxime: Difference between revisions

{{Short description|Antibiotic medication}}

{{Use dmy dates|date=July 2024}}

{{cs1 config|name-list-style=vanc|display-authors=6}}

| verifiedrevid = 460025245

| IUPAC_name = (6''R'',7''R'')-3-{[(Aminocarbonyl)oxy]methyl}-7-{[(2''Z'')-2-(2-furyl)-2-(methoxyimino)acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

| image = Cefuroxime.svg

| alt = Skeletal formula of cefuroxime

| image2 = Cefuroxime-3D-spacefill.png

| alt2 = Ball-and-stick model of the cefuroxime molecule

| tradename = Zinacef, others

| Drugs.com = {{drugs.com|monograph|cefuroxime-sodium}}

| DailyMedID = Cefuroxime

| pregnancy_category =

| routes_of_administration = [[Intramuscular]], [[intravenous]], [[by mouth]]

| class = Second-generation [[cephalosporin]]

| ATC_prefix = J01

| ATC_suffix = DC02

| ATC_supplemental = {{ATC|S01|AA27}} {{ATCvet|J51|DC02}}

| legal_AU = S4

| legal_CA = Rx-only

| legal_CA_comment = <ref>{{cite web | title=Product monograph brand safety updates | website=[[Health Canada]] | date=7 July 2016 | url=https://www.canada.ca/en/health-canada/services/drugs-health-products/drug-products/drug-product-database/label-safety-assessment-update/product-monograph-brand-safety-updates.html | access-date=13 July 2024}}</ref>

| legal_status = Rx-only

| bioavailability = 37% on an empty stomach, up to 52% if taken after food

| excretion = Urine 66–100% unchanged

| KEGG_Ref = {{keggcite|correct|kegg}}

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| C=16 | H=16 | N=4 | O=8 | S=1

<!-- Definition and medical uses -->

'''Cefuroxime''', sold under the brand name '''Zinacef''' among others, is a second-generation [[cephalosporin]]<ref>{{Cite book| vauthors = Katzung B |title=Basic & Clinical Pharmacology|publisher=McGraw Hill|year=2018|pages=803}}</ref> [[antibiotic]] used to treat and prevent a number of [[bacterial infections]].<ref name=BNF76>{{cite book|title=British national formulary : BNF 76|date=2018|publisher=Pharmaceutical Press|isbn=9780857113382|pages=518|edition=76}}</ref> These include [[pneumonia]], [[meningitis]], [[otitis media]], [[sepsis]], [[urinary tract infection]]s, and [[Lyme disease]].<ref name=AHFS2019/> It is used by mouth or by [[intravenous|injection into a vein]] or [[intramuscular|muscle]].<ref name=AHFS2019>{{cite web |title=Cefuroxime Sodium Monograph for Professionals |url=https://www.drugs.com/monograph/cefuroxime-sodium.html |website=Drugs.com |publisher=American Society of Health-System Pharmacists |access-date=22 March 2019 }}</ref>

<!-- Side effects and mechanisms -->

Common side effects include nausea, diarrhea, allergic reactions, and pain at the site of injection.<ref name=AHFS2019/> Serious side effects may include [[Clostridium difficile infection|''Clostridium difficile'' infection]], [[anaphylaxis]], and [[Stevens–Johnson syndrome]].<ref name=AHFS2019/> Use in [[pregnancy]] and [[breastfeeding]] is believed to be safe.<ref name=Preg2019>{{cite web |title=Cefuroxime Use During Pregnancy |url=https://www.drugs.com/pregnancy/cefuroxime.html |website=Drugs.com |access-date=3 March 2019 }}</ref> It is a second-generation [[cephalosporin]] and works by interfering with a bacteria's ability to make a [[cell wall]] resulting in its death.<ref name=AHFS2019/>

<!-- Society and culture -->

Cefuroxime was patented in 1971, and approved for medical use in 1977.<ref name=Fis2006>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=493 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA493 }}</ref> It is on the [[WHO Model List of Essential Medicines|World Health Organization's List of Essential Medicines]].<ref name="WHO21st">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 21st list 2019 | year = 2019 | hdl = 10665/325771 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO | hdl-access=free }}</ref> In 2020, it was the 325th most commonly prescribed medication in the United States, with more than 800{{nbsp}}thousand prescriptions.<ref>{{cite web | title = Cefuroxime – Drug Usage Statistics | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Cefuroxime | access-date = 7 October 2022}}</ref>

==Medical uses==

Cefuroxime is active against many bacteria including susceptible strains of [[Staphylococcus|Staphylococci]] and [[Streptococcus|Streptococci]], as well as a range of gram negative organisms.<ref>{{Cite web|title=Appendix 5 – Antibiotic overview|url=https://drug.wellingtonicu.com/appendices/appendix5/|access-date=7 April 2023|website=Wellington ICU Drug Manual|language=en}}</ref> 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]].<ref>{{cite book | vauthors = Root RK, Waldvogel F, Corey L, Stamm WE |title=Clinical Infectious Diseases: A Practical Approach |date=1999 |publisher=Oxford University Press |isbn=9780195081039 |page=259 |url=https://books.google.com/books?id=zvCOpighJggC&pg=PA259 |language=en}}</ref>

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.<ref name="Gower">{{cite journal | vauthors = Gower EW, Lindsley K, Tulenko SE, Nanji AA, Leyngold I, McDonnell PJ | title = Perioperative antibiotics for prevention of acute endophthalmitis after cataract surgery | journal = The Cochrane Database of Systematic Reviews | volume = 2017 | issue = 2 | pages = CD006364 | date = February 2017 | pmid = 28192644 | pmc = 5375161 | doi = 10.1002/14651858.CD006364.pub3 }}</ref>

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/[[migraine]]s, [[dizziness]], and abdominal pain compared to most antibiotics in its class.{{medical citation needed|date=July 2012}}

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.<ref name="pmid16451776">{{cite journal | vauthors = Pichichero ME | title = Cephalosporins can be prescribed safely for penicillin-allergic patients | journal = The Journal of Family Practice | volume = 55 | issue = 2 | pages = 106–112 | date = February 2006 | pmid = 16451776 | url = http://www.jfponline.com/pdf%2F5502%2F5502JFP_AppliedEvidence1.pdf | url-status = dead | archive-url = https://web.archive.org/web/20120224193547/http://www.jfponline.com/pdf%2F5502%2F5502JFP_AppliedEvidence1.pdf | archive-date = 24 February 2012 }}</ref>

==Related compounds==

[[Cefuroxime axetil]] is an {{chem name|acetoxyethyl}} [[ester]] [[prodrug]] of cefuroxime which is effective when taken by mouth.<ref>{{cite book|url=https://books.google.com/books?id=Cb6BOkj9fK4C&pg=PA326 |title=Drug Discovery: History | vauthors = Sneader W |date=23 June 2005 |publisher=John Wiley & Sons |isbn=9780471899792 }}</ref> It is a second-generation [[cephalosporin]].<ref>{{cite journal | last=Glatt | first=A. E. | title=Second-generation cephalosporins | journal=Hospital Practice (Office Ed.) | volume=21 | issue=3 | date=15 March 1986 | issn=8750-2836 | pmid=3081544 | doi=10.1080/21548331.1986.11704945 | pages=158A–158B, 158E, 158H–158L}}</ref>

==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 [[GlaxoSmithKline|GSK]].<ref>{{Cite press release |url=https://www.prnewswire.com/news-releases/covis-pharma-to-acquire-us-rights-from-glaxosmithkline-for-fortaz-zinacef-lanoxin-parnate-and-zantac-injection-136058673.html | title = Covis Pharma to Acquire U.S. Rights from GlaxoSmithKline for Fortaz®, Zinacef®, Lanoxin®, Parnate®, and Zantac® Injection | work = Covis-pharma-sarl |access-date=6 August 2012 }}</ref> GSK had continued marketing a pediatric oral suspension as Ceftin; however, this presentation was discontinued as of 24 June 2017.<ref>{{cite web|url=https://www.accessdata.fda.gov/scripts/drugshortages/dsp_ActiveIngredientDetails.cfm?AI=Cefuroxime+Sodium+%28Zinacef%29+Injection&st=d&tab=tabs-2|title=FDA Drug Shortages|date=20 March 2018|publisher=Food and Drug Administration (FDA)}}</ref>

In Bangladesh, it is available as Kilbac by Incepta, Axim by Aristopharma, Rofurox by Radiant and Xorimax by Sandoz. In India, it is available as Ceftum and Cefuall by Allencia Biosciences in tablet form and Supacef in injection form by GSK.<ref>{{cite web |url=http://www.gsk-india.com/product-antiinfective.html |title=GlaxoSmithKline Pharmaceuticals Limited – Prescription Medicines – Anti-Infective |publisher=Gsk-india.com |date=26 March 2013 |access-date=12 March 2012 |archive-date=22 March 2016 |archive-url=https://web.archive.org/web/20160322131054/http://www.gsk-india.com/product-antiinfective.html |url-status=dead }}</ref> In Poland, it is available as Zamur by [[Mepha]], subsidiary of [[Teva Pharmaceutical Industries]].<ref>

{{cite web|url=http://leki.urpl.gov.pl/files/Zamur_tablpowl_2dawki.pdf |title=Charakterystyka produktu lecznicznego |publisher=Urząd Rejestracji Produktów Leczniczych, Wyrobów Medycznych i Produktów Biobójczych |date=12 November 2015}}</ref> 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]].<ref name="TGA_Pharmacor_Cefuroxime">{{cite web |title=Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017 |url=https://www.tga.gov.au/prescription-medicines-registration-new-generic-medicines-and-biosimilar-medicines-2017 |website=TGA |date=26 March 2018 |publisher=Therapeutic Goods Administration |access-date=30 July 2018}}</ref> Cefuroxime axetil is sold in tablet form in Turkey inder the brand names Aksef&nbsp;<ref>{{cite web |title=Aksef 500mg 20 Tablet |url=https://www.nobel.com.tr/urunler/ilaclar/aksef-500mg-20-tablet |publisher=Nobel İlaç Sanayii ve Ticaret A.Ş. |access-date=26 April 2023}}</ref> and Cefaks.<ref>{{cite web |title=Antiinfectives and antiparasitic products for systemic use |url=https://www.deva.com.tr/en/products/10 |publisher=DEVA Holding |access-date=3 May 2023}}</ref> 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.<ref name="TGA_Zinnat_Cefuroxime">{{cite web |title=ARTG ID 81301 |url=http://search.tga.gov.au/s/search.html?collection=tga-artg&profile=record&meta_i=81301 |website=TGA |publisher=Therapeutic Goods Administration |access-date=30 July 2018 |archive-date=28 August 2021 |archive-url=https://web.archive.org/web/20210828024320/https://search.tga.gov.au/s/search.html?collection=tga-artg&profile=record&meta_i=81301 |url-status=dead }}</ref>

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== References ==

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