Cefuroxime

Last updated

Cefuroxime
Cefuroxime.svg
Cefuroxime-3D-spacefill.png
Clinical data
Trade names Zinacef, Ceftin, Furacia, others
AHFS/Drugs.com Monograph
MedlinePlus a601206
License data
Pregnancy
category
  • B
Routes of
administration 		Intramuscular, intravenous, by mouth
Drug class Second-generation cephalosporin
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • In general: ℞ (Prescription only)
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 [1] antibiotic used to treat and prevent a number of bacterial infections. [2] These include pneumonia, meningitis, otitis media, sepsis, urinary tract infections, and Lyme disease. [3] It is used by mouth or by injection into a vein or muscle. [3]

Contents

Common side effects include nausea, diarrhea, allergic reactions, and pain at the site of injection. [3] Serious side effects may include Clostridium difficile infection, anaphylaxis, and Stevens–Johnson syndrome. [3] 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. [3]

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] In 2020, it was the 325th most commonly prescribed medication in the United States, with more than 800 thousand prescriptions. [7]

Medical uses

Cefuroxime is active against many bacteria including susceptible strains of Staphylococci and Streptococci, as well as a range of gram negative organisms. [8] 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. [9]

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. [10]

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, recent[ when? ] assessments have shown no increased risk for a cross-allergic reaction for cefuroxime and several other second-generation or later cephalosporins. [11]

Chemistry

Cefuroxime axetil is an acetoxyethyl ester prodrug of cefuroxime which is effective when taken by mouth. [12] It is a second-generation cephalosporin.[ citation needed ]

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. [13] GSK had continued marketing a pediatric oral suspension as Ceftin; however, this presentation was discontinued as of 24 June 2017. [14]

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. [15] In Poland, it is available as Zamur by Mepha, subsidiary of Teva Pharmaceutical Industries. [16] 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. [17] Cefuroxime axetil is sold in tablet form in Turkey inder the brand names Aksef  [18] and Cefaks. [19] 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. [20]

Related Research Articles

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

Ampicillin is an antibiotic belonging to the aminopenicillin class of the penicillin family. The drug is used to prevent and treat a number of bacterial infections, such as respiratory tract infections, urinary tract infections, meningitis, salmonellosis, and endocarditis. It may also be used to prevent group B streptococcal infection in newborns. It is used by mouth, by injection into a muscle, or intravenously.

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

Amoxicillin is an antibiotic medication belonging to the aminopenicillin class of the penicillin family. The drug is used to treat bacterial infections such as middle ear infection, strep throat, pneumonia, skin infections, odontogenic infections, and urinary tract infections. It is taken by mouth, or less commonly by injection.

<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.

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

Aztreonam, sold under the brand name Azactam among others, is an antibiotic used primarily to treat infections caused by gram-negative bacteria such as Pseudomonas aeruginosa. This may include bone infections, endometritis, intra abdominal infections, pneumonia, urinary tract infections, and sepsis. It is given by intravenous or intramuscular injection or by inhalation.

<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">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">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">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">Imipenem/cilastatin</span> Combination antibiotic medication

Imipenem/cilastatin, sold under the brand name Primaxin among others, is an antibiotic useful for the treatment of a number of bacterial infections. It is made from a combination of imipenem and cilastatin. Specifically it is used for pneumonia, sepsis, endocarditis, joint infections, intra-abdominal infections, and urinary tract infections. It is given by injection into a vein or muscle.

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

Cefotaxime is an antibiotic used to treat a number of bacterial infections in human, other animals and plant tissue culture. Specifically in humans it is used to treat joint infections, pelvic inflammatory disease, meningitis, pneumonia, urinary tract infections, sepsis, gonorrhea, and cellulitis. It is given either by injection into a vein or muscle.

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

Cefdinir, sold under the brand name Omnicef among others, is an antibiotic used to treat pneumonia, otitis media, strep throat, and cellulitis. It is a less preferred option for pneumonia, otitis media, and strep throat which may be used in those with a severe allergy to penicillin. It is taken by mouth.

<span class="mw-page-title-main">Endophthalmitis</span> Medical condition

Endophthalmitis, or endophthalmia, is inflammation of the interior cavity of the eye, usually caused by an infection. It is a possible complication of all intraocular surgeries, particularly cataract surgery, and can result in loss of vision or loss of the eye itself. Infection can be caused by bacteria or fungi, and is classified as exogenous, or endogenous. Other non-infectious causes include toxins, allergic reactions, and retained intraocular foreign bodies. Intravitreal injections are a rare cause, with an incidence rate usually less than 0.05%.

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

Cefoxitin is a second-generation cephamycin antibiotic developed by Merck & Co., Inc. from Cephamycin C in the year following its discovery, 1972. It was synthesized in order to create an antibiotic with a broader spectrum. It is often grouped with the second-generation cephalosporins. Cefoxitin requires a prescription and as of 2010 is sold under the brand name Mefoxin by Bioniche Pharma, LLC. The generic version of cefoxitin is known as cefoxitin sodium.

<span class="mw-page-title-main">Cephalosporin C</span> Chemical compound

Cephalosporin C is an antibiotic of the cephalosporin class. It was isolated from a fungus of the genus Acremonium and first characterized in 1961. Although not a very active antibiotic itself, synthetic analogs of cephalosporin C, such as cefalotin, became some of the first marketed cephalosporin antibiotic drugs.

<span class="mw-page-title-main">Intracameral injection</span>

An intracameral injection is usually of an antibiotic into the anterior chamber of the eyeball to prevent endophthalmitis caused by an infection of the eye that can occur after cataract surgery. The Food and Drug Administration (FDA) has not approved antibiotics for this use and it is considered 'off-label'. Concerns about this procedure contributing to increasing numbers of antibiotic resistant bacteria have been expressed.

The side effects of penicillin are bodily responses to penicillin and closely related antibiotics that do not relate directly to its effect on bacteria. A side effect is an effect that is not intended with normal dosing. Some of these reactions are visible and some occur in the body's organs or blood. Penicillins are a widely used group of medications that are effective for the treatment of a wide variety of bacterial infections in human adults and children as well as other species. Some side effects are predictable, of which some are common but not serious, some are uncommon and serious and others are rare. The route of administration of penicillin can have an effect on the development of side effects. An example of this is irritation and inflammation that develops at a peripheral infusion site when penicillin is administered intravenously. In addition, penicillin is available in different forms. There are different penicillin medications as well as a number of β-lactam antibiotics derived from penicillin.

<span class="mw-page-title-main">Intravitreal injection</span> Method of administration of drugs into the eye by injection with a fine needle

Intravitreal injection is the method of administration of drugs into the eye by injection with a fine needle. The medication will be directly applied into the vitreous humor. It is used to treat various eye diseases, such as age-related macular degeneration (AMD), diabetic retinopathy, and infections inside the eye such as endophthalmitis. As compared to topical administration, this method is beneficial for a more localized delivery of medications to the targeted site, as the needle can directly pass through the anatomical eye barrier and dynamic barrier. It could also minimize adverse drug effects on other body tissues via the systemic circulation, which could be a possible risk for intravenous injection of medications. Although there are risks of infections or other complications, with suitable precautions throughout the injection process, chances for these complications could be lowered.

References

  1. ↑ Katzung B (2018). Basic & Clinical Pharmacology. McGraw Hill. p. 803.
  2. ↑ British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 518. ISBN   9780857113382.
  3. 1 2 3 4 5 "Cefuroxime Sodium Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 22 March 2019.
  4. ↑ "Cefuroxime Use During Pregnancy". Drugs.com. Retrieved 3 March 2019.
  5. ↑ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 493. ISBN   9783527607495.
  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. ↑ "Cefuroxime – Drug Usage Statistics". ClinCalc. Retrieved 7 October 2022.
  8. ↑ "Appendix 5 – Antibiotic overview". Wellington ICU Drug Manual. Retrieved 7 April 2023.
  9. ↑ Root RK, Waldvogel F, Corey L, Stamm WE (1999). Clinical Infectious Diseases: A Practical Approach. Oxford University Press. p. 259. ISBN   9780195081039.
  10. ↑ 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.
  11. ↑ 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.
  12. ↑ Sneader W (23 June 2005). Drug Discovery: History. ISBN   9780471899792.
  13. ↑ "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.
  14. ↑ "FDA Drug Shortages". Food and Drug Administration (FDA). 20 March 2018.
  15. ↑ "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.
  16. ↑ "Charakterystyka produktu lecznicznego" (PDF). Urząd Rejestracji Produktów Leczniczych, Wyrobów Medycznych i Produktów Biobójczych. 12 November 2015.
  17. ↑ "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". TGA. Therapeutic Goods Administration. 26 March 2018. Retrieved 30 July 2018.
  18. ↑ "Aksef 500mg 20 Tablet". Nobel İlaç Sanayii ve Ticaret A.Ş. Retrieved 26 April 2023.
  19. ↑ "Antiinfectives and antiparasitic products for systemic use". DEVA Holding. Retrieved 3 May 2023.
  20. ↑ "ARTG ID 81301". TGA. Therapeutic Goods Administration. Archived from the original on 28 August 2021. Retrieved 30 July 2018.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.