Editing Cefalexin (section)

{{Short description|Beta-lactam antibiotic}}
{{Use dmy dates|date=October 2021}}
{{cs1 config |name-list-style=vanc |display-authors=6}}
{{Drugbox
| Watchedfields = changed
| verifiedrevid = 457630940
| image = Cefalexin.svg
| image_class = skin-invert-image
| alt = 
| image2 = Cefalexin-from-xtal-3D-bs-17.png
| image_class2 = bg-transparent
| alt2 = 

<!-- Clinical data -->
| pronounce  = {{IPAc-en|ˌ|s|ɛ|f|ə|ˈ|l|ɛ|k|s|ᵻ|n}}
| tradename = Keflex, others
| Drugs.com = {{Drugs.com|monograph|cephalexin}} 
| MedlinePlus = a682733
| DailyMedID = Cephalexin
| pregnancy_AU = A
| pregnancy_AU_comment = <ref name="Drugs.com pregnancy">{{cite web | title=Cephalexin Use During Pregnancy | website=Drugs.com | date=28 December 2018 | url=https://www.drugs.com/pregnancy/cephalexin.html | access-date=7 February 2020 | archive-date=7 February 2020 | archive-url=https://web.archive.org/web/20200207073035/https://www.drugs.com/pregnancy/cephalexin.html | url-status=live }}</ref>
| pregnancy_category = 
| routes_of_administration = [[Oral administration|By mouth]]
| class = [[Cephalosporin|First-generation cephalosporin]]
| ATC_prefix = J01
| ATC_suffix = DB01
| ATC_supplemental = {{ATCvet|J51|DB01}}
| synonyms = Cephalexin (former [[British Approved Name|BAN]] {{abbr|<small>UK</small>|United Kingdom}} and current [[United States Adopted Name|USAN]] {{abbr|<small>US</small>|United States}})
| legal_AU = S4
| legal_CA = Rx-only
| legal_CA_comment = 
| legal_UK = POM
| legal_US = Rx-only
| legal_EU = Rx-only
| legal_EU_comment = <ref name="Lexylan PI" />

<!-- Pharmacokinetic data -->
| bioavailability = Well absorbed
| protein_bound = 15%
| metabolism = 80% excreted unchanged in urine within 6 hours of administration
| elimination_half-life = 0.6–1.2 hours<ref>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</ref>
| excretion = [[Kidney]]

<!-- Identifiers -->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 15686-71-2
| PubChem = 2666
| IUPHAR_ligand = 4832
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00567
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 25541
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 5SFF1W6677
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00263
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 3534
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1727

<!-- Chemical data -->
| IUPAC_name = (7''R'')-3-methyl-7-(α-D-phenylglycylamino)-3-cephem-4-carboxylic acid monohydrate
| C=16 | H=17 | N=3 | O=4 | S=1
| smiles = O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)[C@@H](c3ccccc3)N)C)C(=O)O
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C16H17N3O4S/c1-8-7-24-15-11(14(21)19(15)12(8)16(22)23)18-13(20)10(17)9-5-3-2-4-6-9/h2-6,10-11,15H,7,17H2,1H3,(H,18,20)(H,22,23)/t10-,11-,15-/m1/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = ZAIPMKNFIOOWCQ-UEKVPHQBSA-N
| melting_point = 326.8
}} 

<!-- Definition -->
'''Cefalexin''', also spelled '''cephalexin''', is an [[antibiotic]] that can treat a number of [[bacterial infections]].<ref name=AHFS2014/> It kills [[gram-positive bacteria|gram-positive]] and some [[gram-negative bacteria]] by disrupting the growth of the bacterial cell wall.<ref name=AHFS2014/> Cefalexin is a [[beta-lactam antibiotic|β-lactam antibiotic]] within the class of first-generation [[cephalosporin]]s.<ref name=AHFS2014/> It works similarly to other agents within this class, including intravenous [[cefazolin]], but can be taken [[Oral administration|by mouth]].<ref>{{cite book| vauthors = Brunton LL |title=Goodman & Gilman's pharmacological basis of therapeutics.|date=2011|publisher=McGraw-Hill|location=New York|isbn=978-0071624428 |edition=12th |chapter= Chapter 53: Penicillins, Cephalosporins, and Other β-Lactam Antibiotics}}</ref>

<!-- Medical uses -->
Cefalexin can treat certain bacterial infections, including those of the [[otitis media|middle ear]], [[bone infection|bone]] and [[joint infection|joint]], [[Skin infection#Bacterial|skin]], and [[urinary tract infection|urinary tract]].<ref name=AHFS2014/> It may also be used for certain types of [[pneumonia]] and [[streptococcal pharyngitis|strep throat]] and to prevent [[bacterial endocarditis]].<ref name=AHFS2014/> Cefalexin is not effective against infections caused by [[methicillin-resistant Staphylococcus aureus|methicillin-resistant ''Staphylococcus aureus'']] (MRSA), most ''[[Enterococcus]]'', or ''[[Pseudomonas]]''.<ref name=AHFS2014/> Like other antibiotics, cefalexin cannot treat [[viral infection]]s, such as the [[influenza|flu]], [[common cold]] or [[acute bronchitis]].<ref name=AHFS2014/> Cefalexin can be used in those who have mild or moderate allergies to [[penicillin]].<ref name=AHFS2014/> However, it is not recommended in those with severe penicillin allergies.<ref name=AHFS2014/>

<!-- Side effects -->
Common [[side effect]]s include [[dyspepsia|stomach upset]] and [[diarrhea]].<ref name=AHFS2014/> [[Allergy|Allergic reaction]]s or infections with [[Clostridioides difficile infection|'' Clostridioides difficile'']], a cause of diarrhea, are also possible.<ref name=AHFS2014/> Use during [[pregnancy]] or [[breastfeeding]] does not appear to be harmful to the fetus.<ref name=AHFS2014/><ref name=TGA2014>{{cite web|title=Prescribing medicines in pregnancy database|url=http://www.tga.gov.au/hp/medicines-pregnancy.htm|work=Australian Government|access-date=22 April 2014|date=3 March 2014|url-status=live|archive-url=https://web.archive.org/web/20140408040902/http://www.tga.gov.au/hp/medicines-pregnancy.htm#.U1Yw8Bc3tqw|archive-date=8 April 2014}}</ref><ref name=Breast2013>{{cite book|title=Breastfeeding and Medication|date=2013|publisher=Routledge|isbn=9781136178153|page=227|url=https://books.google.com/books?id=0Y8lbCnF1mgC&pg=PA227| vauthors = Jones W |url-status=live|archive-url=https://web.archive.org/web/20170908135050/https://books.google.com/books?id=0Y8lbCnF1mgC&pg=PA227|archive-date=8 September 2017}}</ref> It can be used in children and those over 65 years of age.<ref name=AHFS2014/> Those with [[kidney problems]] may require a decrease in dose.<ref name=AHFS2014>{{cite web|title=Cephalexin|url=https://www.drugs.com/monograph/cephalexin.html|publisher=The American Society of Health-System Pharmacists|access-date=21 April 2014|url-status=live|archive-url=https://web.archive.org/web/20140501202910/http://www.drugs.com/monograph/cephalexin.html|archive-date=1 May 2014}}</ref>

<!-- History, Society and Culture -->
Cefalexin was developed in 1967.<ref>{{cite book | veditors = Hey E |title=Neonatal formulary 5 drug use in pregnancy and the first year of life |date=2007 |publisher=Blackwell |isbn=9780470750353 |page=67 |url=https://books.google.com/books?id=aumIBqHmChwC&pg=PA67 |edition=5th |url-status=live |archive-url=https://web.archive.org/web/20170908135050/https://books.google.com/books?id=aumIBqHmChwC&pg=PA67 |archive-date=8 September 2017 }}></ref><ref>{{cite patent |country=US |number=3275626 |status=patent |title=Penicillin conversion via sulfoxide |pubdate=1966-09-27 |gdate=1966-09-27 |fdate=1962-07-31 |pridate=1962-07-31 |inventor=Morin RB, Jackson BG |assign1=Eli Lilly and Co |url=https://worldwide.espacenet.com/publicationDetails/biblio?CC=US&NR=3275626&KC=&FT=E&locale=en_EP }} {{Webarchive|url=https://web.archive.org/web/20220925035539/https://worldwide.espacenet.com/publicationDetails/biblio?CC=US&NR=3275626&KC=&FT=E&locale=en_EP |date=25 September 2022 }} </ref><ref>{{cite patent |country=US |number=3507861 |status=patent |title=Certain 3-methyl-cephalosporin compounds |pubdate=1970-04-21 |gdate=1970-04-21 |fdate=1966-09-14 |pridate=1966-09-14 |inventor=Morin RB, Jackson BG |assign1=Eli Lilly and Co |url=https://worldwide.espacenet.com/publicationDetails/biblio?CC=US&NR=3507861&KC=&FT=E&locale=en_EP }} {{Webarchive|url=https://web.archive.org/web/20220925035539/https://worldwide.espacenet.com/publicationDetails/biblio?CC=US&NR=3507861&KC=&FT=E&locale=en_EP |date=25 September 2022 }} </ref> It was first marketed in 1969 under the brand name '''Keflex'''.<ref name=McP2007>{{cite book| vauthors = McPherson EM | chapter = Cefalexin |title=Pharmaceutical Manufacturing Encyclopedia.|date=2007|publisher=Elsevier|location=Burlington|isbn=9780815518563|page=915| chapter-url=https://books.google.com/books?id=_J2ti4EkYpkC&pg=PA915|edition=3rd|url-status=live|archive-url=https://web.archive.org/web/20170908135051/https://books.google.com/books?id=_J2ti4EkYpkC&pg=PA915|archive-date=8 September 2017}}</ref><ref>{{cite book|last=Ravina|first=Enrique|title=The evolution of drug discovery : from traditional medicines to modern drugs|date=2011|publisher=Wiley-VCH|location=Weinheim|isbn=9783527326693|page=267|url=https://books.google.com/books?id=iDNy0XxGqT8C&pg=PA267|edition=1. Aufl.|url-status=live|archive-url=https://web.archive.org/web/20170908135051/https://books.google.com/books?id=iDNy0XxGqT8C&pg=PA267|archive-date=8 September 2017}}</ref> It is available as a [[generic medication]].<ref name=AHFS2014/><ref>{{cite book | vauthors = Hanlon G, Hodges N |title =Essential Microbiology for Pharmacy and Pharmaceutical Science |date=2012 |publisher=Wiley |location=Hoboken |isbn=9781118432433 |page=140 |url=https://books.google.com/books?id=P4Ucifn76PUC&pg=PT140 |url-status=live|archive-url=https://web.archive.org/web/20170908135051/https://books.google.com/books?id=P4Ucifn76PUC&pg=PT140|archive-date=8 September 2017}}</ref> It is on the [[WHO Model List of Essential Medicines|World Health Organization's List of Essential Medicines]].<ref name="WHO23rd">{{cite book | vauthors = ((World Health Organization)) | title = The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023) | year = 2023 | hdl = 10665/371090 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MHP/HPS/EML/2023.02 | hdl-access=free }}</ref> In 2022, it was the 101st most commonly prescribed medication in the United States, with more than 6{{nbsp}}million prescriptions.<ref>{{cite web | title=The Top 300 of 2022 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=30 August 2024 | archive-date=30 August 2024 | archive-url=https://web.archive.org/web/20240830202410/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref>{{cite web | title = Cephalexin Drug Usage Statistics, United States, 2013 - 2022 | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Cephalexin | access-date = 30 August 2024 }}</ref> In Canada, it was the fifth most common antibiotic used in 2013.<ref>{{Cite web|url = http://publications.gc.ca/collections/collection_2014/aspc-phac/HP37-20-2013-eng.pdf|title = Human Antimicrobial Drug Use Report 2012/2013|date = November 2014|access-date = 24 February 2015|publisher = Public Health Agency of Canada (PHAC)|url-status = live|archive-url = https://web.archive.org/web/20150321041930/http://publications.gc.ca/collections/collection_2014/aspc-phac/HP37-20-2013-eng.pdf|archive-date = 21 March 2015}}</ref> In Australia, it was one of the top 10 most prescribed medications between 2017 and 2023.<ref>{{cite web | title=Medicines in the health system | website=Australian Institute of Health and Welfare | date=2 July 2024 | url=https://www.aihw.gov.au/reports/medicines/medicines-in-the-health-system | access-date=30 September 2024}}</ref>