Cefalexin
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| 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 data |
| Trade 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 |
Oral |
| Pharmacokinetic 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 is 0.5-1.2 hours[1] |
| Excretion |
Renal |
| Identifiers |
| CAS number |
15686-71-2 Y |
| ATC code |
J01DB01 QJ51DB01 |
| PubChem |
CID 2666 |
| DrugBank |
DB00567 |
| ChemSpider |
25541 Y |
| UNII |
5SFF1W6677 Y |
| KEGG |
D00263 Y |
| ChEBI |
CHEBI:3534 Y |
| ChEMBL |
CHEMBL1727 Y |
| Chemical data |
| Formula |
C16H17N3O4S |
| Mol. mass |
347.39 g/mol |
SMILES
- O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)[C@@H](c3ccccc3)N)C)C(=O)O
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InChI
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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
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Y (what is this?) (verify)
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Cefalexin (INN) or more commonly cephalexin // 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[update], 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]
Contents
- 1 Medical uses
- 1.1 Infections
- 1.2 Formulations
- 2 Adverse effects
- 3 References
- 4 External links
Medical uses[edit source | edit]
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]
Infections[edit source | edit]
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 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]
Formulations[edit source | edit]
Cefalexin is marketed by generic pharmaceutical manufacturers 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 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[edit source | edit]
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[edit source | edit]
- ^ 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 Sweetman, Sean C., ed. (2009). "Antibacterials". Martindale: The complete drug reference (36th ed.). London: Pharmaceutical Press. pp. 218–9. ISBN 978-0-85369-840-1.
- ^ Sneader, Walter (2005). "Cephalosporin analogues". Drug discovery: a history. New York: Wiley. p. 324. ISBN 0-471-89980-1. Retrieved 2009-06-26.
- ^ "2008 Top 200 generic drugs by total prescriptions" PDF (332.8 KB). Drug Topics (May 26, 2009). Retrieved on July 24, 2009.
- ^ "2008 Top 200 generic drugs by retail dollars" PDF (399.4 KB). Drug Topics (May 26, 2009). Retrieved on July 24, 2009.
- ^ a b c "Cephalexin". The American Society of Health-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): 13S–18S. doi:10.1016/j.diagmicrobio.2006.12.004. PMID 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: Österreichischer Apothekerverlag. ISBN 3-85200-196-X.
External links[edit source | edit]
- U.S. National Library of Medicine: Drug Information Portal - Cephalexin
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Antibacterials: cell envelope antibiotics (J01C-J01D)
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| Intracellular |
- inhibit peptidoglycan subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin)
- DADAL/AR inhibitors (Cycloserine)
- bactoprenol inhibitors (Bacitracin)
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| Glycopeptide |
- inhibit PG chain elongation: Vancomycin# (Oritavancin
- Telavancin)
- Teicoplanin (Dalbavancin)
- Ramoplanin
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β-lactams/
(inhibit PBP
cross-links) |
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Penicillins
(penams)
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Extended sp.
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- aminopenicillins: Amoxicillin#
- Ampicillin# (Pivampicillin
- Hetacillin
- Bacampicillin
- Metampicillin
- Talampicillin)
- Epicillin
- carboxypenicillins: Carbenicillin (Carindacillin)
- Ticarcillin
- Temocillin
- ureidopenicillins: Azlocillin
- Piperacillin
- Mezlocillin
- other: Mecillinam (Pivmecillinam)
- Sulbenicillin
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Narrow sp.
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β-lactamase sensitive
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- Benzylpenicillin (G)#: Clometocillin
- Benzathine benzylpenicillin#
- Procaine benzylpenicillin#
- Azidocillin
- Penamecillin
- Phenoxymethylpenicillin (V)#: Propicillin
- Benzathine phenoxymethylpenicillin
- Pheneticillin
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β-lactamase resistant
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- Cloxacillin# (Dicloxacillin
- Flucloxacillin)
- Oxacillin
- Meticillin
- Nafcillin
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Penems
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Carbapenems
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- Biapenem
- Ertapenem
- antipseudomonal (Doripenem
- Imipenem
- Meropenem)
- Panipenem
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Cephalosporins/Cephamycins
(cephems)
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1st (PEcK)
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- Cefazolin#
- Cefacetrile
- Cefadroxil
- Cefalexin
- Cefaloglycin
- Cefalonium
- Cefaloridine
- Cefalotin
- Cefapirin
- Cefatrizine
- Cefazedone
- Cefazaflur
- Cefradine
- Cefroxadine
- Ceftezole
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2nd (HEN)
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- Cefaclor
- Cefamandole
- Cefminox
- Cefonicid
- Ceforanide
- Cefotiam
- Cefprozil
- Cefbuperazone
- Cefuroxime
- Cefuzonam
- cephamycin (Cefoxitin
- Cefotetan
- Cefmetazole)
- carbacephem (Loracarbef)
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3rd
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- Cefixime#
- Ceftriaxone#
- antipseudomonal (Ceftazidime#
- Cefoperazone)
- Cefcapene
- Cefdaloxime
- Cefdinir
- Cefditoren
- Cefetamet
- Cefmenoxime
- Cefodizime
- Cefotaxime
- Cefpimizole
- Cefpiramide
- Cefpodoxime
- Cefsulodin
- Cefteram
- Ceftibuten
- Ceftiolene
- Ceftizoxime
- oxacephem (Flomoxef
- Latamoxef ‡)
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4th (antips-)
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- Cefepime
- Cefozopran
- Cefpirome
- Cefquinome
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5th
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- Ceftobiprole
- Ceftaroline fosamil
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Veterinary
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- Ceftiofur
- Cefquinome
- Cefovecin
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Monobactams
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- Aztreonam
- Tigemonam
- Carumonam
- Nocardicin A
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β-lactamase inh.
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- penam (Sulbactam
- Tazobactam)
- clavam (Clavulanic acid)
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Combinations
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- Amoxicillin/clavulanic acid#
- Imipenem/cilastatin#
- Ampicillin/flucloxacillin
- Ampicillin/sulbactam (Sultamicillin)
- Piperacillin/tazobactam
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| Other |
- polymyxins/detergent (Colistin
- Polymyxin B)
- depolarizing (Daptomycin)
- hydrolyze NAM-NAG (Lysozyme)
- Gramicidin
- Isoniazid
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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gr+f/gr+a (t)/gr-p (c)/gr-o
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drug (J1p, w, n, m, vacc)
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