Cefalexin
|
|
| Clinical data |
| Pronunciation |
|
| Trade names |
Keflex, Cepol, Ceporex, others[1] |
| AHFS/Drugs.com |
Monograph |
| MedlinePlus |
a682733 |
| License data |
|
Pregnancy
category |
- AU: A
- US: B (No risk in non-human studies)
|
Routes of
administration |
by mouth |
| ATC code |
- J01DB01 (WHO) QJ51DB01 (WHO)
|
| Legal status |
| Legal status |
- AU: S4 (Prescription only)
- UK: POM (Prescription only)
- US: ℞-only
|
| Pharmacokinetic data |
| Bioavailability |
Well absorbed |
| Protein binding |
15% |
| Metabolism |
80% excreted unchanged in urine within 6 hours of administration |
| Biological half-life |
For an adult with normal renal function, the serum half-life is 0.6–1.2 hours[2] |
| Excretion |
Renal |
| 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 |
|
| ECHA InfoCard |
100.036.142 |
| Chemical and physical data |
| Formula |
C16H17N3O4S |
| Molar mass |
347.39 g/mol |
| 3D model (JSmol) |
|
| Melting point |
326.8 °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.[3] It kills gram-positive and some gram-negative bacteria by disrupting the growth of the bacterial cell wall.[3] Cefalexin is a beta-lactam antibiotic within the class of first-generation cephalosporins.[3] It works similarly to other agents within this class, including intravenous cefazolin, but can be taken by mouth.[4]
Cefalexin can treat certain bacterial infections, including those of the middle ear, bone and joint, skin, and urinary tract.[3] It may also be used for certain types of pneumonia, strep throat, and to prevent bacterial endocarditis.[3] Cefalexin is not effective against infections caused by methicillin-resistant Staphylococcus aureus (MRSA), Enterococcus, or Pseudomonas.[3] Like other antibiotics, cefalexin cannot treat viral infections, such as the flu, common cold or acute bronchitis.[3] Cefalexin can be used in those who have mild or moderate allergies to penicillin.[3] However, it is not recommended in those with severe penicillin allergies.[3]
Common side effects include stomach upset and diarrhea.[3] An allergic reaction and infection with Clostridium difficile, a type of diarrhea, is also possible.[3] To date, no evidence of harm to the baby has been found when used during pregnancy[3][5] or breast feeding.[6] It can be used in children and those over 65 years of age.[3] Those with kidney problems may require a decrease in dose.[3]
In 2012, cefalexin was one of the top 100 most prescribed medications in the United States.[7] In Canada, it was the 5th most common antibiotic used in 2013.[8] In Australia, it is one of the top 15 most prescribed medications.[9] Cefalexin was developed in 1967.[10] It was first marketed in 1969 and 1970 under the names Keflex and Ceporex, among others.[1][11] Generic drug versions are available under several other trade names and are inexpensive.[3][12] Cefalexin is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system.[13]
Contents
- 1 Medical uses
- 1.1 Pregnancy and breastfeeding
- 2 Adverse effects
- 3 Interactions
- 4 Mechanism of action
- 5 Society and culture
- 6 References
- 7 External links
Medical uses
A course of cefalexin capsules, commonly prescribed for infections
Cefalexin can treat a number of bacterial infections including: otitis media, streptococcal pharyngitis, bone and joint infections, pneumonia, cellulitis, and urinary tract infections.[3] It may be used to prevent bacterial endocarditis.[3] It can also be used for the prevention of recurrent urinary-tract infections.[14]
Cefalexin does not treat methicillin-resistant Staphylococcus aureus infections.[14]
Cefalexin is a useful alternative to penicillins in patients with penicillin intolerance. For example, penicillin is the treatment of choice for respiratory tract infections caused by Streptococcus, but cefalexin may be used as an alternative in penicillin-intolerant patients.[15] Caution must be exercised when administering cephalosporin antibiotics to penicillin-sensitive patients, because cross sensitivity with beta-lactam antibiotics has been documented in up to 10% of patients with a documented penicillin allergy.[16]
Pregnancy and breastfeeding
It is pregnancy category B in the United States and category A in Australia, meaning that no evidence of harm has been found after being taken by many pregnant women.[3][5] Use during breast feeding is generally safe.[6]
Adverse effects
The most common adverse effects of cefalexin, like other oral cephalosporins, are gastrointestinal (stomach area) disturbances and hypersensitivity reactions. Gastrointestinal disturbances include nausea, vomiting, and diarrhea, diarrhea being most common.[17] Hypersensitivity reactions include skin rashes, urticaria, fever, and anaphylaxis.[18] Pseudomembranous colitis and Clostridium difficile have been reported with use of cefalexin.[18]
Signs and symptoms of an allergic reaction include rash, itching, swelling, trouble breathing, or red, blistered, swollen, or peeling skin. Overall, cefalexin allergy occurs in less than 0.1% of patients, but it is seen in 1% to 10% of patients with a penicillin allergy.[19]
Interactions
Like other β-lactam antibiotics, renal excretion of cefalexin is delayed by probenecid.[20] Alcohol consumption reduces the rate at which it is absorbed.[21] Cefalexin also interacts with metformin, an antidiabetic drug,[18] and this can lead to higher concentrations of metformin in the body.[18][22]
Mechanism of action
Cefalexin is a beta-lactam antibiotic of the cephalosporin family.[23] It is bactericidal and acts by inhibiting synthesis of the peptidoglycan layer of the bacterial cell wall.[24] As cefalexin closely resembles d-alanyl-d-alanine, an amino acid ending on the peptidoglycan layer of the cell wall, it is able to irreversibly bind to the active site of PBP, which is essential for the synthesis of the cell wall.[24] It is most active against gram-positive cocci, and has moderate activity against some gram-negative bacilli.[25] However, some bacterial cells have the enzyme β-lactamase, which hydrolyzes the beta-lactam ring, rendering the drug inactive. This contributes to antibacterial resistance towards cephalexin.[26]
Society and culture
Cefalexin is on the World Health Organization's List of Essential Medicines, the most important medications needed in a health system.[27] The World Health Organization classifies cephalexin as a highly important antimicrobial in their list of Critically Important Antimicrobials for Human Medicine.[28]
Names
Cefalexin is the INN and BAN while cephalexin is the USAN and AAN.
Common brand names for cefalexin include Keflex, Cepol, Ceporexine, Ceporex, Cefadal, Derantel, Mecilex, Medoxine, Sporibest (Bionova), Xahl, and Tokiolexin.[29]
References
- ^ a b McPherson, Edwin M. (2007). Pharmaceutical Manufacturing Encyclopedia (3rd ed.). Burlington: Elsevier. p. 915. ISBN 9780815518563. Archived from the original on 2017-09-08.
- ^ 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
- ^ a b c d e f g h i j k l m n o p q r "Cephalexin". The American Society of Health-System Pharmacists. Archived from the original on 2014-05-01. Retrieved Apr 21, 2014.
- ^ Brunton, Laurence L. (2011). "53, Penicillins, Cephalosporins, and Other β-Lactam Antibiotics". Goodman & Gilman's pharmacological basis of therapeutics (12th ed.). New York: McGraw-Hill. ISBN 978-0071624428.
- ^ a b "Prescribing medicines in pregnancy database". Australian Government. 3 March 2014. Archived from the original on 8 April 2014. Retrieved 22 April 2014.
- ^ a b Wendy Jones (2013). Breastfeeding and Medication. Routledge. p. 227. ISBN 9781136178153. Archived from the original on 2017-09-08.
- ^ Bartholow, Michael. "Top 200 Drugs of 2012". Pharmacy Times. Archived from the original on 17 May 2014. Retrieved 22 April 2014.
- ^ "Human Antimicrobial Drug Use Report 2012/2013" (PDF). Public Health Agency of Canada (PHAC). November 2014. Archived (PDF) from the original on March 21, 2015. Retrieved February 24, 2015.
- ^ Australia's Health 2012: The Thirteenth Biennial Health Report of the Australian Institute of Health and Welfare. Australian Institute of Health and Welfare. 2012. p. 408. ISBN 9781742493053. Archived from the original on 2017-09-08.
- ^ Hey, Edmund, 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 2017-09-08.
- ^ Ravina, Enrique (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 2017-09-08.
- ^ Hanlon, Geoffrey; Hodges, Norman (2012). Essential Microbiology for Pharmacy and Pharmaceutical Science. Hoboken: Wiley. p. 140. ISBN 9781118432433. Archived from the original on 2017-09-08.
- ^ "WHO Model List of Essential Medicines (19th List)" (PDF). World Health Organization. April 2015. Archived (PDF) from the original on 13 December 2016. Retrieved 8 December 2016.
- ^ a b "Lexicomp: Cefalexin". Archived from the original on 2016-12-21. (Subscription required (help)).
- ^ "Lexicomp: Antibacterials". Archived from the original on 2016-12-21. (Subscription required (help)).
- ^ "FDA Cephalexin drug label" (PDF). Archived (PDF) from the original on 18 April 2014. Retrieved 18 April 2014.
- ^ "Cephalexin Side Effects". Drugs.com. Archived from the original on 8 February 2015. Retrieved 9 February 2015.
- ^ a b c d "Cefalexin". Lexicomp. Archived from the original on 21 December 2016. Retrieved 18 April 2014. (Subscription required (help)).
- ^ Haberfeld, H, ed. (2009). Austria-Codex (in German) (2009/2010 ed.). Vienna: Österreichischer Apothekerverlag. ISBN 3-85200-196-X.
- ^ "Cefalexin". Lexicomp. Archived from the original on 21 December 2016. Retrieved 17 April 2014. (Subscription required (help)).
- ^ Barrio Lera JP, Alvarez AI, Prieto JG (Jun 1991). "Effects of ethanol on the pharmacokinetics of cephalexin and cefadroxil in the rat". Journal of Pharmaceutical Sciences. 80 (6): 511–6. doi:10.1002/jps.2600800602. PMID 1941538.
- ^ Jayasagar G, Krishna Kumar M, Chandrasekhar K, Madhusudan Rao C, Madhusudan Rao Y (2002). "Effect of cephalexin on the pharmacokinetics of metformin in healthy human volunteers". Drug Metabolism and Drug Interactions. 19 (1): 41–8. doi:10.1515/dmdi.2002.19.1.41. PMID 12222753.
- ^ Bothara SS, Kadam KR, Mahadik KG (2006). "Antibiotics". Principles of Medicinal Chemistry. 1 (14th ed.). Pune: Nirali Prakashan. p. 81. ISBN 8185790043.
- ^ a b Fisher JF, Meroueh SO, Mobashery S (Feb 2005). "Bacterial resistance to beta-lactam antibiotics: compelling opportunism, compelling opportunity". Chemical Reviews. 105 (2): 395–424. doi:10.1021/cr030102i. PMID 15700950.
- ^ "Cefalexin". Lexicomp. Archived from the original on 21 December 2016. Retrieved 17 April 2014. (Subscription required (help)).
- ^ Drawz SM, Bonomo RA (Jan 2010). "Three decades of beta-lactamase inhibitors". Clinical Microbiology Reviews. 23 (1): 160–201. doi:10.1128/CMR.00037-09. PMC 2806661 . PMID 20065329.
- ^ "WHO Model List of EssentialMedicines" (PDF). World Health Organization. October 2013. p. 6. Archived (PDF) from the original on 23 April 2014. Retrieved 22 April 2014.
- ^ "Critically Important Medicines for Human Medicine, 3rd Revision 2011" (PDF). World Health Organization. Archived (PDF) from the original on 13 April 2015. Retrieved 24 February 2015.
- ^ "SciFinder". scifinder.cas.org. Retrieved 2016-02-20. (Subscription required (help)).
External links
- U.S. National Library of Medicine: Drug Information Portal — Cephalexin
|
Antibiotics active on the cell wall and envelope (J01C-J01D)
|
| Intracellular |
- Inhibit peptidoglycan subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin)
- DADAL/AR inhibitors (Cycloserine)
- bactoprenol inhibitors (Bacitracin)
|
| Glycopeptide |
- Inhibit PG chain elongation: Vancomycin# (Oritavancin
- Telavancin)
- Teicoplanin (Dalbavancin)
- Ramoplanin
|
β-lactams/
(inhibit PBP
cross-links) |
|
| Other |
- polymyxins/detergent
- depolarizing
- Hydrolyze NAM-NAG
- Tyrothricin
- Isoniazid#
- Teixobactin
|
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
|
