Chemistry:Cefuroxime axetil
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| Clinical data | |
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| Trade names | Zinnat, Ceftin, Ceftum |
| Other names | Cefuroxime 1-acetoxyethyl ester |
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a601206 |
| Routes of administration | By mouth, intravenous, intramuscular |
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| Pharmacokinetic data | |
| Bioavailability | well absorbed |
| Metabolism | Cefuroxime is not metabolized and excreted as it is in urine, axetil is metabolized to acetaldehyde and acetic acid |
| Excretion | Urine |
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| Chemical and physical data | |
| Formula | C20H22N4O10S |
| Molar mass | 510.47 g·mol−1 |
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Cefuroxime axetil, sold under the brand name Ceftin among others, is a second generation oral cephalosporin antibiotic.
It is an acetoxyethyl ester prodrug of cefuroxime which is effective orally.[1] The activity depends on in vivo hydrolysis and release of cefuroxime tablets.[citation needed]
It was patented in 1976 and approved for medical use in 1987.[2]
Medical uses
Second generation cephalosporins are more effective in treating Gram-negative bacilli compared to first generation cephalosporins, which have a greater coverage for Gram-positive cocci. Also, it has been reported that cefuroxime is resistant to hydrolysis by β-lactamases produced by Gram-negative bacteria.[3]
- Upper respiratory tract infections
- Lower respiratory tract infections
- Urinary tract infections
- Skin and soft tissue infections
- Gonorrhoea
- Early Lyme disease
Bacterial susceptibility
Cefuroxime axetil treats infections against methicillin, oxacillin and penicillin-sensitive bacterial strains.[6] Cefuroxime axetil does not work against enterococci. [4]
Gram-positive aerobic microorganisms
- Staphylococcus aureus (Methicillin-sensitive only)
- Staphylococcus epidermis
- Streptococcus pneumoniae (Penicillin-sensitive only)
Gram-negative aerobic microorganisms
- Haemophilus influenzae
- Moraxella catarrhalis
- Neisseria gonorrhoeae
- Escherichia coli
- Proteus mirabilis
- Klebsiella pneumoniae (variable activity)
Mechanism of action
Cefuroxime axetil is a second generation cephalosporin that, like penicillins antibiotics, contains a β-lactam ring structure. Cephalosporins work as bactericidal antibiotics; that by binding to penicillin-binding proteins (PBPs), inhibit the last step of the bacterial cell wall synthesis. Once the β-lactam ring binds to PBPs, cross-linking between peptidoglycan units is inhibited.[3]
Pharmacokinetics
Absorption: Once consumed, cefuroxime axetil is converted to the active compound cefuroxime by esterases of mucosal cells in the gastrointestinal tract. Cefuroxime is then released for systematic circulation. If cefuroxime axetil is given with food, absorption values can increase by 52% compared to fasting patients.[4]
Distribution: It has been reported that after cefuroxime axetil administration, it can be found in tonsil tissue, sinus tissue, bronchial tissue and middle ear effusion.[4]
Elimination: After cefuroxime production, the body is unable to metabolize the drug, and is eliminated unchanged in the urine.[4]
History
It was discovered by Glaxo (now GlaxoSmithKline) and introduced in 1987.[7] It was approved by FDA on December 28, 1987.[8] It is available by GSK as Ceftin in US[9] and Ceftum in India.[10]
References
- ↑ Drug Discovery: A History. John Wiley, Chichester, UK. 2005-06-23. ISBN 0-471-89979-8. https://books.google.com/books?id=Cb6BOkj9fK4C&pg=PA326.
- ↑ (in en) Analogue-based Drug Discovery. John Wiley & Sons. 2006. p. 494. ISBN 9783527607495. https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA494.
- ↑ 3.0 3.1 "Cephalosporins". StatPearls. StatPearls Publishing. 2020. http://www.ncbi.nlm.nih.gov/books/NBK551517/. Retrieved 2020-04-23.
- ↑ 4.0 4.1 4.2 4.3 4.4 "Cefuroxime axetil. A review of its antibacterial activity, pharmacokinetic properties and therapeutic efficacy". Drugs 52 (1): 125–158. July 1996. doi:10.2165/00003495-199652010-00009. PMID 8799689.
- ↑ "Ceftin (cefuroxime axetil).". GlaxoSmithKline. U.S. Food and Drug Administration. 2015. https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050605s048,050672s034lbl.pdf.
- ↑ "Zinnat SUMMARY OF PRODUCT CHARACTERISTICS - GSKPro for Healthcare Professionals". https://gskpro.com/content/dam/global/hcpportal/en_PH/Pdf/Homepage/elsevier-and-pharmacist/Zinnat%20Tablets.pdf.
- ↑ "Our history - About GSK". GlaxoSmithKline. http://www.gsk.com/about/history.htm.
- ↑ "Cefuroxime Axetil Monograph for Professionals". Drugs.com. https://www.drugs.com/monograph/cefuroxime-axetil.html.
- ↑ "Brands". Gsksource.com. 2018-03-22. https://www.gsksource.com/gskprm/en/US/adirect/gskprm?cmd=ProductsByName#C.
- ↑ "Our products". GlaxoSmithKline. http://www.gsk-india.com/product-antiinfective.html.
External links
"Cefuroxime Injection: MedlinePlus Drug Information". https://medlineplus.gov/druginfo/meds/a684044.html.
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