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Cefalexin - Wikipedia, the free encyclopedia

Cefalexin
From Wikipedia, the free encyclopedia

Cefalexin (INN) or more commonly cephalexin (pron.: /sflksn/) is a first-generation cephalosporin antibiotic introduced in 1967 by Eli Lilly and Company.[2][3] It is an orally administered agent with a similar antimicrobial spectrum to the intravenous agents cefalotin and cefazolin. It was first marketed as Keflex (Lilly), and is marketed under several other trade names.[2] As of 2008, cefalexin was the most popular cephalosporin antibiotic in the United States, with more than 25 million prescriptions of its generic versions alone, for US$255 million in sales (though less popular than two other antibiotics, amoxicillin and azithromycin, each with 50 million prescriptions per year).[4][5]

Cefalexin

Systematic (IUPAC) name

(6 R,7 R)-7-{[(2 R)-2-amino-2-phenylacetyl]amino}- 3-methyl8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene- 2-carboxylic acid

Clinical data Trade names Keflex a682733 US FDA:link A (AU) B (US) Prescription Only (S4) (AU) POM (UK) -only (US) Routes Bioavailability Oral Pharmacokinetic data Well absorbed 15% 80% excreted unchanged in urine within 6 hours of administration For an adult with normal renal function, the serum half-life is 0.5-1.2 hours [1] Renal Identifiers CAS number ATC code PubChem DrugBank 15686-71-2 J01DB01 QJ51DB01 CID 2666 DB00567
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Contents
1 Medical uses 1.1 Infections 1.2 Formulations 2 Adverse effects 3 References 4 External links

AHFS/Drugs.com monograph MedlinePlus Licence data Pregnancy cat. Legal status

Medical uses
Cefalexin is used to treat a number of infections including: otitis media, streptococcal pharyngitis, bone and joint infections, pneumonia, cellulitis, and urinary tract infections.[6] It may be used to prevent bacterial endocarditis.[6]

Protein binding Metabolism

Half-life

Infections
In addition to being a rational first-line treatment for cellulitis, it is a useful alternative to penicillins in patients with penicillin hypersensitivity. In patients with mild or questionable history of penicillin allergy, cephalasporins are now thought to be relatively safe.[7] Caution should always be taken when prescribing cephalosporins to those with strong history of true
en.wikipedia.org/wiki/Cefalexin

Excretion

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Cefalexin - Wikipedia, the free encyclopedia

penicillin hypersensitivity, however, because cefalexin and other first-generation cephalosporins are known to have a modest cross-allergy in patients with penicillin hypersensitivity.[citation needed ] Cefalexin may not be effective against bacteria that incorporate a gene for beta-lactamase on their R-plasmid as the beta-lactam ring is present in the chemical structure of cephalosporin derivatives.[citation needed ]

ChemSpider UNII KEGG ChEBI ChEMBL Formula Mol. mass SMILES

25541 5SFF1W6677 D00263 CHEBI:3534 CHEMBL1727 Chemical data C16H17N3O4S 347.39 g/mol

Formulations

Cefalexin is marketed by generic pharmaceutical InChI manufacturers under a wide range of brand names, including: Apo-Cephalex, Biocef, Cefanox, Ceforal, Cephabos, (what is this?) (verify) Cephalexin, Cephorum, Ceporex, Cilex, Ialex, Ibilex, Kefexin, Keflet, Keflex, Rekosporin, Keforal, Keftab, Keftal, Lopilexin, Larixin, Novo-Lexin, Ospexin, Tenkorex, Zephalexin, Panixine Disperdose, Rancef, Sialexin, Sporidex and Ulexin. A version of Keflex 750 mg capsules is marketed for twice-daily dosage, to improve compliance. However, it is not a sustained release formulation, and since it is more expensive than the older strengths, some physicians prescribe three 250 mg capsules to be taken twice daily, as a less expensive alternative.[citation needed ] In Finland, cefalexin is marketed under several names. Orion markets Kefexin.[8][9]

Adverse effects
Common adverse effects include gastrointestinal upset such as diarrhea, nausea, vomiting, indigestion, and abdominal pain.[6] Others may include dizziness, agitation, headache, joint pain, and tiredness. Symptoms of an allergic reaction include rash, itching, swelling, trouble breathing, or red, blistered, swollen or peeling skin. Overall, allergies occur in less than 0.1% of patients; they are seen in about 1% to 10% of patients with penicillin allergy.[10]

References
1. ^ McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 95. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1995 (Plus Supplements 1995)., p. 166 2. ^ a b Sweetman, Sean C., ed. (2009). "Antibacterials". Martindale: The complete drug reference (36th ed.). London: Pharmaceutical Press. pp. 2189. ISBN 978-0-85369-840-1. 3. ^ Sneader, Walter (2005). "Cephalosporin analogues" (http://books.google.com/books? id=mYQxRY9umjcC&pg=PA324) . Drug discovery: a history. New York: Wiley. p. 324. ISBN 0-471-89980-1. Retrieved 2009-06-26. 4. ^ "2008 Top 200 generic drugs by total prescriptions" (http://drugtopics.modernmedicine.com/drugtopics/data/articlestandard//drugtopics/222009/599844/article.pdf) PDF (332.8 KB). Drug Topics (May 26, 2009). Retrieved on July 24, 2009. 5. ^ "2008 Top 200 generic drugs by retail dollars" (http://drugtopics.modernmedicine.com/drugtopics/data/articlestandard//drugtopics/192009/597086/article.pdf) PDF (399.4 KB). Drug Topics (May 26, 2009). Retrieved on July 24, 2009. 6. ^ a b c "Cephalexin" (http://www.drugs.com/monograph/cephalexin.html) . The American Society of Healthen.wikipedia.org/wiki/Cefalexin

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Cefalexin - Wikipedia, the free encyclopedia

6. ^ a b c "Cephalexin" (http://www.drugs.com/monograph/cephalexin.html) . The American Society of Health7. System Pharmacists. Retrieved 3 April 2011. ^ Pichichero ME (March 2007). "Use of selected cephalosporins in penicillin-allergic patients: a paradigm shift". Diagnostic Microbiology and Infectious Disease 57 (3 Suppl): 13S18S. doi:10.1016/j.diagmicrobio.2006.12.004 (http://dx.doi.org/10.1016%2Fj.diagmicrobio.2006.12.004) . PMID 17349459 (//www.ncbi.nlm.nih.gov/pubmed/17349459) . ^ http://spc.nam.fi/indox/nam/html/nam/humpil/2/244412.pdf. ^ http://spc.nam.fi/indox/nam/html/nam/humspc/2/244362.shtml. ^ Haberfeld, H, ed. (2009). Austria-Codex (in German) (2009/2010 ed.). Vienna: sterreichischer Apothekerverlag. ISBN 3-85200-196-X.

8. 9. 10.

External links
U.S. National Library of Medicine: Drug Information Portal - Cephalexin (http://druginfo.nlm.nih.gov/drugportal/dpdirect.jsp?name=cephalexin+anhydrous) Retrieved from "http://en.wikipedia.org/w/index.php?title=Cefalexin&oldid=540294022" Categories: 1967 introductions Cephalosporin antibiotics Eli Lilly and Company Enantiopure drugs This page was last modified on 25 February 2013 at 16:48. Text is available under the Creative Commons Attribution-ShareAlike License; additional terms may apply. By using this site, you agree to the Terms of Use and Privacy Policy. Wikipedia is a registered trademark of the Wikimedia Foundation, Inc., a non-profit organization.

en.wikipedia.org/wiki/Cefalexin

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