Cefalexin

Cefalexin
Clinical data
Pronunciation/ˌsɛfəˈlɛksɪn/
Trade namesKeflex, others
Other namesCephalexin (former BAN UK and current USAN US)
AHFS/Drugs.comMonograph
MedlinePlusa682733
License data
Pregnancy
category
Routes of
administration		By mouth
Drug classFirst-generation cephalosporin
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityWell absorbed
Protein binding15%
Metabolism80% excreted unchanged in urine within 6 hours of administration
Elimination half-life0.6–1.2 hours[3]
ExcretionKidney
Identifiers
IUPAC name
  • (7R)-3-methyl-7-(α-D-phenylglycylamino)-3-cephem-4-carboxylic acid monohydrate
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.036.142
Chemical and physical data
FormulaC16H17N3O4S
Molar mass347.39 g·mol−1
3D model (JSmol)
Melting point326.8 °C (620.2 °F)
SMILES
  • O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)[C@@H](c3ccccc3)N)C)C(=O)O
InChI
  • InChI=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 Y
  • Key:ZAIPMKNFIOOWCQ-UEKVPHQBSA-N Y
  (verify)

Cefalexin, also spelled cephalexin, is an antibiotic that can treat a number of bacterial infections.[4] It kills gram-positive and some gram-negative bacteria by disrupting the growth of the bacterial cell wall.[4] Cefalexin is a β-lactam antibiotic within the class of first-generation cephalosporins.[4] It works similarly to other agents within this class, including intravenous cefazolin, but can be taken by mouth.[5]

Cefalexin can treat certain bacterial infections, including those of the middle ear, bone and joint, skin, and urinary tract.[4] It may also be used for certain types of pneumonia and strep throat and to prevent bacterial endocarditis.[4] Cefalexin is not effective against infections caused by methicillin-resistant Staphylococcus aureus (MRSA), most Enterococcus, or Pseudomonas.[4] Like other antibiotics, cefalexin cannot treat viral infections, such as the flu, common cold or acute bronchitis.[4] Cefalexin can be used in those who have mild or moderate allergies to penicillin.[4] However, it is not recommended in those with severe penicillin allergies.[4]

Common side effects include stomach upset and diarrhea.[4] Allergic reactions or infections with Clostridioides difficile, a cause of diarrhea, are also possible.[4] Use during pregnancy or breastfeeding does not appear to be harmful to the fetus.[4][6][7] It can be used in children and those over 65 years of age.[4] Those with kidney problems may require a decrease in dose.[4]

Cefalexin was developed in 1967.[8][9][10] It was first marketed in 1969 under the brand name Keflex.[11][12] It is available as a generic medication.[4][13] It is on the World Health Organization's List of Essential Medicines.[14] In 2022, it was the 101st most commonly prescribed medication in the United States, with more than 6 million prescriptions.[15][16] In Canada, it was the fifth most common antibiotic used in 2013.[17] In Australia, it was one of the top 10 most prescribed medications between 2017 and 2023.[18]

  1. ^ "Cephalexin Use During Pregnancy". Drugs.com. 28 December 2018. Archived from the original on 7 February 2020. Retrieved 7 February 2020.
  2. ^ Cite error: The named reference Lexylan PI was invoked but never defined (see the help page).
  3. ^ 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
  4. ^ a b c d e f g h i j k l m n o "Cephalexin". The American Society of Health-System Pharmacists. Archived from the original on 1 May 2014. Retrieved 21 April 2014.
  5. ^ Brunton LL (2011). "Chapter 53: Penicillins, Cephalosporins, and Other β-Lactam Antibiotics". Goodman & Gilman's pharmacological basis of therapeutics (12th ed.). New York: McGraw-Hill. ISBN 978-0071624428.
  6. ^ "Prescribing medicines in pregnancy database". Australian Government. 3 March 2014. Archived from the original on 8 April 2014. Retrieved 22 April 2014.
  7. ^ Jones W (2013). Breastfeeding and Medication. Routledge. p. 227. ISBN 9781136178153. Archived from the original on 8 September 2017.
  8. ^ Hey E, ed. (2007). Neonatal formulary 5 drug use in pregnancy and the first year of life (5th ed.). Blackwell. p. 67. ISBN 9780470750353. Archived from the original on 8 September 2017.>
  9. ^ US patent 3275626, Morin RB, Jackson BG, "Penicillin conversion via sulfoxide", published 27 September 1966, issued 27 September 1966, assigned to Eli Lilly and Co  Archived 25 September 2022 at the Wayback Machine
  10. ^ US patent 3507861, Morin RB, Jackson BG, "Certain 3-methyl-cephalosporin compounds", published 21 April 1970, issued 21 April 1970, assigned to Eli Lilly and Co  Archived 25 September 2022 at the Wayback Machine
  11. ^ McPherson EM (2007). "Cefalexin". Pharmaceutical Manufacturing Encyclopedia (3rd ed.). Burlington: Elsevier. p. 915. ISBN 9780815518563. Archived from the original on 8 September 2017.
  12. ^ Ravina E (2011). The evolution of drug discovery : from traditional medicines to modern drugs (1. Aufl. ed.). Weinheim: Wiley-VCH. p. 267. ISBN 9783527326693. Archived from the original on 8 September 2017.
  13. ^ Hanlon G, Hodges N (2012). Essential Microbiology for Pharmacy and Pharmaceutical Science. Hoboken: Wiley. p. 140. ISBN 9781118432433. Archived from the original on 8 September 2017.
  14. ^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
  15. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  16. ^ "Cephalexin Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
  17. ^ "Human Antimicrobial Drug Use Report 2012/2013" (PDF). Public Health Agency of Canada (PHAC). November 2014. Archived (PDF) from the original on 21 March 2015. Retrieved 24 February 2015.
  18. ^ "Medicines in the health system". Australian Institute of Health and Welfare. 2 July 2024. Retrieved 30 September 2024.
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