cefalexin - wikipedia, the free encyclopedia

7/28/2019 Cefalexin - Wikipedia, The Free Encyclopedia

1/3

4/5/13 Cefalexin - Wikipedia, the free encyclopedia

en.wikipedia.org/wiki/Cefalexin

Cefalexin

Systematic (IUPAC) name

(6R,7R)-7-{[(2R)-2-amino-2-phenylacetyl]amino}- 3-methyl

8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene- 2-carboxylic acid

Clinical dataTrade names Keflex

AHFS/Drugs.com monograph

MedlinePlus a682733

Licence data US FDA:link

Pregnancy cat. A (AU) B (US)

Legal status Prescription Only (S4) (AU)

POM(UK)-only (US)

Routes OralPharmacokinetic data

Bioavailability Well absorbed

Protein binding 15%

Metabolism 80% excreted unchanged in

urine within 6 hours of

administration

Half-life For an adult with normal renal

function, the serum half-life is0.5-1.2 hours[1]

Excretion Renal

Identifiers

CAS number 15686-71-2

ATC code J01DB01 QJ51DB01

PubChem CID 2666

DrugBank DB00567

CefalexinFrom 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 antimicrobialspectrum to the intravenous agents cefalotin and cefazolin. Itwas first marketed as Keflex (Lilly), and is marketed underseveral othertrade names.[2]

As of 2008, cefalexin was the most popular cephalosporinantibiotic in the United States, with more than 25 million

prescriptions of its generic versions alone, for US$255 millionin sales (though less popular than two other antibiotics,amoxicillin and azithromycin, each with 50 million

prescriptions per year).[4][5]

Contents

1 Medical uses1.1 Infections1.2 Formulations

2 Adverse effects3 References4 External links

Medical uses

Cefalexin is used to treat a number of infections including:otitis media, streptococcal pharyngitis, bone and jointinfections, pneumonia, cellulitis, and urinary tract infections.[6]

It may be used to prevent bacterial endocarditis.[6]

Infections

In addition to being a rational first-line treatment for cellulitis,it is a useful alternative to penicillins in patients with penicillinhypersensitivity. In patients with mild or questionable historyof penicillin allergy, cephalasporins are now thought to berelatively safe.[7] Caution should always be taken when

prescribing cephalosporins to those with strong history of true
http://en.wikipedia.org/wiki/Bioavailabilityhttp://en.wikipedia.org/wiki/Bioavailabilityhttp://en.wikipedia.org/wiki/Bioavailabilityhttp://en.wikipedia.org/wiki/Regulation_of_therapeutic_goodshttp://en.wikipedia.org/wiki/Standard_for_the_Uniform_Scheduling_of_Drugs_and_Poisons#Schedule_4_Prescription_Only_Medicinehttp://en.wikipedia.org/wiki/Standard_for_the_Uniform_Scheduling_of_Drugs_and_Poisons#Schedule_4_Prescription_Only_Medicinehttp://en.wikipedia.org/wiki/Pregnancy_categoryhttp://en.wikipedia.org/wiki/Australiahttp://en.wikipedia.org/wiki/United_Stateshttp://en.wikipedia.org/wiki/Regulation_of_therapeutic_goodshttp://en.wikipedia.org/wiki/U.S._Food_and_Drug_Administrationhttp://en.wikipedia.org/wiki/Trade_namehttp://en.wikipedia.org/wiki/File:Cefalexin.svghttp://en.wikipedia.org/wiki/File:Cefalexin.svghttp://en.wikipedia.org/wiki/File:Cefalexin.svghttp://en.wikipedia.org/wiki/File:Cefalexin.svghttp://en.wikipedia.org/wiki/File:Cefalexin.svghttp://en.wikipedia.org/wiki/File:Cefalexin.svghttp://en.wikipedia.org/wiki/File:Cefalexin.svghttp://en.wikipedia.org/wiki/File:Cefalexin.svghttp://en.wikipedia.org/wiki/Hypersensitivityhttp://en.wikipedia.org/wiki/Hypersensitivityhttp://en.wikipedia.org/wiki/Penicillinhttp://en.wikipedia.org/wiki/CAS_registry_numberhttp://en.wikipedia.org/wiki/First-line_treatmenthttp://en.wikipedia.org/wiki/Cellulitishttp://en.wikipedia.org/wiki/Excretionhttp://en.wikipedia.org/wiki/Bacterial_endocarditishttp://en.wikipedia.org/wiki/Bacterial_endocarditishttp://en.wikipedia.org/wiki/Cefalexin#cite_note-AHFS-6http://en.wikipedia.org/wiki/Pneumoniahttp://en.wikipedia.org/wiki/Cellulitishttp://en.wikipedia.org/wiki/Cellulitishttp://en.wikipedia.org/wiki/Infectionhttp://en.wikipedia.org/wiki/Plasma_protein_bindinghttp://en.wikipedia.org/wiki/Cefalexin#External_linkshttp://en.wikipedia.org/wiki/Cefalexin#Referenceshttp://en.wikipedia.org/wiki/Cefalexin#Medical_useshttp://en.wikipedia.org/wiki/Amoxicillinhttp://en.wikipedia.org/wiki/Azithromycinhttp://en.wikipedia.org/wiki/Antibiotichttp://en.wikipedia.org/wiki/Eli_Lilly_and_Companyhttp://en.wikipedia.org/wiki/Cefalexin#cite_note-Martindale-2http://en.wikipedia.org/wiki/Cefalexin#cite_note-Sneader-3http://en.wikipedia.org/wiki/Help:IPA_for_Englishhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_Englishhttp://en.wikipedia.org/wiki/Cephalosporinhttp://en.wikipedia.org/wiki/International_Nonproprietary_Namehttp://en.wikipedia.org/wiki/Cefalexin#cite_note-7http://en.wikipedia.org/wiki/Hypersensitivityhttp://en.wikipedia.org/wiki/Penicillinhttp://en.wikipedia.org/wiki/Cellulitishttp://en.wikipedia.org/wiki/First-line_treatmenthttp://en.wikipedia.org/wiki/Cefalexin#cite_note-AHFS-6http://en.wikipedia.org/wiki/Bacterial_endocarditishttp://en.wikipedia.org/wiki/Cefalexin#cite_note-AHFS-6http://en.wikipedia.org/wiki/Urinary_tract_infectionhttp://en.wikipedia.org/wiki/Cellulitishttp://en.wikipedia.org/wiki/Pneumoniahttp://en.wikipedia.org/wiki/Streptococcal_pharyngitishttp://en.wikipedia.org/wiki/Otitis_mediahttp://en.wikipedia.org/wiki/Infectionhttp://en.wikipedia.org/wiki/Cefalexin#External_linkshttp://en.wikipedia.org/wiki/Cefalexin#Referenceshttp://en.wikipedia.org/wiki/Cefalexin#Adverse_effectshttp://en.wikipedia.org/wiki/Cefalexin#Formulationshttp://en.wikipedia.org/wiki/Cefalexin#Infectionshttp://en.wikipedia.org/wiki/Cefalexin#Medical_useshttp://en.wikipedia.org/wiki/Cefalexin#cite_note-5http://en.wikipedia.org/wiki/Cefalexin#cite_note-4http://en.wikipedia.org/wiki/Azithromycinhttp://en.wikipedia.org/wiki/Amoxicillinhttp://en.wikipedia.org/wiki/Cefalexin#cite_note-Martindale-2http://en.wikipedia.org/wiki/Cefazolinhttp://en.wikipedia.org/wiki/Cefalotinhttp://en.wikipedia.org/wiki/Cefalexin#cite_note-Sneader-3http://en.wikipedia.org/wiki/Cefalexin#cite_note-Martindale-2http://en.wikipedia.org/wiki/Eli_Lilly_and_Companyhttp://en.wikipedia.org/wiki/Antibiotichttp://en.wikipedia.org/wiki/Cephalosporinhttp://en.wikipedia.org/wiki/Help:IPA_for_Englishhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_Englishhttp://en.wikipedia.org/wiki/International_Nonproprietary_Namehttp://www.drugbank.ca/drugs/DB00567http://en.wikipedia.org/wiki/DrugBankhttp://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=2666http://en.wikipedia.org/wiki/PubChemhttp://www.whocc.no/atcvet/atcvet_index/?code=QJ51DB01http://en.wikipedia.org/wiki/ATCvet_code_QJ51http://www.whocc.no/atc_ddd_index/?code=J01DB01http://en.wikipedia.org/wiki/ATC_code_J01http://en.wikipedia.org/wiki/Anatomical_Therapeutic_Chemical_Classification_Systemhttp://www.nlm.nih.gov/cgi/mesh/2009/MB_cgi?term=15686-71-2&rn=1http://en.wikipedia.org/wiki/CAS_registry_numberhttp://en.wikipedia.org/wiki/Kidneyhttp://en.wikipedia.org/wiki/Excretionhttp://en.wikipedia.org/wiki/Cefalexin#cite_note-1http://en.wikipedia.org/wiki/Biological_half-lifehttp://en.wikipedia.org/wiki/Drug_metabolismhttp://en.wikipedia.org/wiki/Plasma_protein_bindinghttp://en.wikipedia.org/wiki/Bioavailabilityhttp://en.wikipedia.org/wiki/Route_of_administrationhttp://en.wikipedia.org/wiki/United_Stateshttp://en.wikipedia.org/wiki/Prescription_drughttp://en.wikipedia.org/wiki/United_Kingdomhttp://en.wikipedia.org/wiki/Prescription_drughttp://en.wikipedia.org/wiki/Australiahttp://en.wikipedia.org/wiki/Standard_for_the_Uniform_Scheduling_of_Drugs_and_Poisons#Schedule_4_Prescription_Only_Medicinehttp://en.wikipedia.org/wiki/Regulation_of_therapeutic_goodshttp://en.wikipedia.org/wiki/United_Stateshttp://en.wikipedia.org/wiki/Australiahttp://en.wikipedia.org/wiki/Pregnancy_categoryhttp://www.accessdata.fda.gov/scripts/cder/drugsatfda/index.cfm?fuseaction=Search.SearchAction&SearchTerm=Keflex&SearchType=BasicSearchhttp://en.wikipedia.org/wiki/U.S._Food_and_Drug_Administrationhttp://en.wikipedia.org/wiki/Regulation_of_therapeutic_goodshttp://www.nlm.nih.gov/medlineplus/druginfo/meds/a682733.htmlhttp://en.wikipedia.org/wiki/MedlinePlushttp://www.drugs.com/monograph/Cephalexin.htmlhttp://en.wikipedia.org/wiki/Drugs.comhttp://en.wikipedia.org/wiki/American_Society_of_Health-System_Pharmacistshttp://en.wikipedia.org/wiki/Trade_namehttp://en.wikipedia.org/wiki/International_Union_of_Pure_and_Applied_Chemistry_nomenclaturehttp://en.wikipedia.org/wiki/File:Cefalexin.svg


2/3



ChemSpider 25541

UNII 5SFF1W6677

KEGG D00263

ChEBI CHEBI:3534

ChEMBL CHEMBL1727

Chemical data

Formula C16H17N3O4S

Mol. mass 347.39 g/mol

(what is this?) (verify)

penicillin hypersensitivity, however, because cefalexin andother first-generation cephalosporins are known to have amodest cross-allergy in patients with penicillinhypersensitivity.[citation needed]

Cefalexin may not be effective against bacteria thatincorporate a gene for beta-lactamase on their R-plasmid asthe beta-lactam ring is present in the chemical structure ofcephalosporin derivatives.[citation needed]

Formulations

Cefalexin is marketed by generic pharmaceuticalmanufacturers under a wide range of brand names, including:Apo-Cephalex, Biocef, Cefanox, Ceforal, Cephabos,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 isnot 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, andabdominal pain.[6] Others may include dizziness, agitation, headache, joint pain, and tiredness. Symptoms of anallergic reaction include rash, itching, swelling, trouble breathing, or red, blistered, swollen or peeling skin. Overallallergies 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: AmericanSociety of Hospital Pharmacists, Inc., 1995 (Plus Supplements 1995)., p. 166

2. ^ ab 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.

SMILES

InChI
http://www.drugs.com/monograph/cephalexin.htmlhttp://en.wikipedia.org/wiki/International_Chemical_Identifierhttp://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specificationhttp://www.drugs.com/monograph/cephalexin.htmlhttp://en.wikipedia.org/wiki/Cefalexin#cite_ref-AHFS_6-2http://en.wikipedia.org/wiki/Cefalexin#cite_ref-AHFS_6-1http://en.wikipedia.org/wiki/Cefalexin#cite_ref-AHFS_6-0http://drugtopics.modernmedicine.com/drugtopics/data/articlestandard//drugtopics/192009/597086/article.pdfhttp://en.wikipedia.org/wiki/Cefalexin#cite_ref-5http://drugtopics.modernmedicine.com/drugtopics/data/articlestandard//drugtopics/222009/599844/article.pdfhttp://en.wikipedia.org/wiki/Cefalexin#cite_ref-4http://en.wikipedia.org/wiki/Special:BookSources/0-471-89980-1http://en.wikipedia.org/wiki/International_Standard_Book_Numberhttp://books.google.com/books?id=mYQxRY9umjcC&pg=PA324http://en.wikipedia.org/wiki/Cefalexin#cite_ref-Sneader_3-0http://en.wikipedia.org/wiki/Special:BookSources/978-0-85369-840-1http://en.wikipedia.org/wiki/International_Standard_Book_Numberhttp://en.wikipedia.org/wiki/Martindale:_The_complete_drug_referencehttp://en.wikipedia.org/wiki/Cefalexin#cite_ref-Martindale_2-1http://en.wikipedia.org/wiki/Cefalexin#cite_ref-Martindale_2-0http://en.wikipedia.org/wiki/Cefalexin#cite_ref-1http://en.wikipedia.org/wiki/Cefalexin#cite_note-AustriaCodex-10http://en.wikipedia.org/wiki/Penicillin_allergyhttp://en.wikipedia.org/wiki/Cefalexin#cite_note-AHFS-6http://en.wikipedia.org/wiki/Vomitinghttp://en.wikipedia.org/wiki/Nauseahttp://en.wikipedia.org/wiki/Diarrheahttp://en.wikipedia.org/wiki/Cefalexin#cite_note-9http://en.wikipedia.org/wiki/Cefalexin#cite_note-8http://en.wikipedia.org/wiki/Orion_Corporationhttp://en.wikipedia.org/wiki/Wikipedia:Citation_neededhttp://en.wikipedia.org/wiki/Sustained_releasehttp://en.wikipedia.org/wiki/Compliance_(medicine)http://en.wikipedia.org/wiki/Generic_drughttp://en.wikipedia.org/wiki/Wikipedia:Citation_neededhttp://en.wikipedia.org/wiki/Wikipedia:Citation_neededhttp://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=457630940&page2=Cefalexinhttp://en.wikipedia.org/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validationhttp://en.wikipedia.org/wiki/Molecular_masshttp://en.wikipedia.org/wiki/Sulfurhttp://en.wikipedia.org/wiki/Oxygenhttp://en.wikipedia.org/wiki/Nitrogenhttp://en.wikipedia.org/wiki/Hydrogenhttp://en.wikipedia.org/wiki/Carbonhttp://en.wikipedia.org/wiki/Chemical_formulahttps://www.ebi.ac.uk/chembldb/index.php/compound/inspect/CHEMBL1727http://en.wikipedia.org/wiki/ChEMBLhttps://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3534http://en.wikipedia.org/wiki/ChEBIhttp://www.kegg.jp/entry/D00263http://en.wikipedia.org/wiki/KEGGhttp://fdasis.nlm.nih.gov/srs/srsdirect.jsp?regno=5SFF1W6677http://en.wikipedia.org/wiki/Unique_Ingredient_Identifierhttp://www.chemspider.com/Chemical-Structure.25541http://en.wikipedia.org/wiki/ChemSpider


3/3



6. ^ a c "Cephalexin" (http://www.drugs.com/monograph/cephalexin.html) . The American Society of Health-System Pharmacists. Retrieved 3 April 2011.

7. ^ Pichichero ME (March 2007). "Use of selected cephalosporins in penicillin-allergic patients: a paradigm shift".Diagnostic Microbiology and Infectious Disease57 (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) .

8. ^ http://spc.nam.fi/indox/nam/html/nam/humpil/2/244412.pdf.9. ^ http://spc.nam.fi/indox/nam/html/nam/humspc/2/244362.shtml.

10. ^ Haberfeld, H, ed. (2009). Austria-Codex (in German) (2009/2010 ed.). Vienna: sterreichischer ApothekerverlaISBN 3-85200-196-X.

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.
http://www.wikimediafoundation.org/http://wikimediafoundation.org/wiki/Privacy_policyhttp://wikimediafoundation.org/wiki/Terms_of_Usehttp://en.wikipedia.org/wiki/Wikipedia:Text_of_Creative_Commons_Attribution-ShareAlike_3.0_Unported_Licensehttp://en.wikipedia.org/wiki/Help:Categorieshttp://en.wikipedia.org/w/index.php?title=Cefalexin&oldid=540294022http://druginfo.nlm.nih.gov/drugportal/dpdirect.jsp?name=cephalexin+anhydroushttp://en.wikipedia.org/wiki/Special:BookSources/3-85200-196-Xhttp://en.wikipedia.org/wiki/International_Standard_Book_Numberhttp://en.wikipedia.org/wiki/Cefalexin#cite_ref-AustriaCodex_10-0http://spc.nam.fi/indox/nam/html/nam/humspc/2/244362.shtmlhttp://en.wikipedia.org/wiki/Cefalexin#cite_ref-9http://spc.nam.fi/indox/nam/html/nam/humpil/2/244412.pdfhttp://en.wikipedia.org/wiki/Cefalexin#cite_ref-8http://www.ncbi.nlm.nih.gov/pubmed/17349459http://en.wikipedia.org/wiki/PubMed_Identifierhttp://dx.doi.org/10.1016%2Fj.diagmicrobio.2006.12.004http://en.wikipedia.org/wiki/Digital_object_identifierhttp://en.wikipedia.org/wiki/Cefalexin#cite_ref-7http://www.drugs.com/monograph/cephalexin.htmlhttp://en.wikipedia.org/wiki/Cefalexin#cite_ref-AHFS_6-2http://en.wikipedia.org/wiki/Cefalexin#cite_ref-AHFS_6-1http://en.wikipedia.org/wiki/Cefalexin#cite_ref-AHFS_6-0http://en.wikipedia.org/wiki/Category:Enantiopure_drugshttp://en.wikipedia.org/wiki/Category:Eli_Lilly_and_Companyhttp://en.wikipedia.org/wiki/Category:Cephalosporin_antibioticshttp://en.wikipedia.org/wiki/Category:1967_introductions

cefalexin - wikipedia, the free encyclopedia

Documents