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Cefalexin: Difference between revisions

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{{drugbox
{{drugbox
| verifiedrevid = 420030571
| verifiedrevid = 443507819
| IUPAC_name = (6''R'',7''R'')-7-{[(2''R'')-2-amino-2-phenylacetyl]amino}- 3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene- 2-carboxylic acid
| IUPAC_name = (6''R'',7''R'')-7-{[(2''R'')-2-amino-2-phenylacetyl]amino}- 3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene- 2-carboxylic acid
| image = Cefalexin.svg
| image = Cefalexin.svg
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| ATC_suffix = DB01
| ATC_suffix = DB01
| ATC_supplemental = {{ATCvet|J51|DA01}}
| ATC_supplemental = {{ATCvet|J51|DA01}}
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 3534
| ChEBI = 3534
| PubChem = 2666
| PubChem = 2666
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = APRD00250
| DrugBank = APRD00250
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG_Ref = {{keggcite|correct|kegg}}

Revision as of 13:58, 7 August 2011

Cefalexin
Clinical data
Pregnancy
category
  • AU: A
Routes of
administration
Oral
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
Pharmacokinetic data
BioavailabilityWell absorbed
Protein binding15%
Metabolism80% excreted unchanged in urine within 6 hours of administration
Elimination half-lifeFor an adult with normal renal function, the serum half-life is 0.5-1.2 hours[1]
ExcretionRenal
Identifiers
  • (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
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.036.142 Edit this at Wikidata
Chemical and physical data
FormulaC16H17N3O4S
Molar mass347.39 g/mol g·mol−1
3D model (JSmol)
  • O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)[C@@H](c3ccccc3)N)C)C(=O)O
  • 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 checkY
  • Key:ZAIPMKNFIOOWCQ-UEKVPHQBSA-N checkY
  (verify)

Cefalexin (INN) or more commonly cephalexin (/[invalid input: 'icon']ˌsɛfəˈlɛks[invalid input: 'ɨ']n/) 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 now is also sold under several other trade names.[2]

As of 2008, 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.[4][5]

Medical uses

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

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.

Formulations

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, and Sporidex.

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 cheaper alternative.[citation needed]

In Finland, cefalexin is marketed under several names. Orion markets Kefexin.[8] People with renal dysfunction requiring longer periods between doses.[9]

Adverse effects

Adverse effects from cefalexin include diarrhea, dizziness, agitation, headache, indigestion, joint pain, stomach pain (usually mild) and tiredness. The drug can also cause yellowing of the eyes or skin; red, blistered, swollen or peeling skin; unusual bruising or bleeding; decreased urination; severe cramps and confusion. An allergic reaction to this medicine is unlikely. Symptoms of an allergic reaction include rash, itching, swelling, or trouble breathing.

References

  1. ^ 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
  2. ^ 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.
  3. ^ Sneader, Walter (2005). "Cephalosporin analogues". Drug discovery: a history. New York: Wiley. p. 324. ISBN 0-471-89980-1. {{cite book}}: |access-date= requires |url= (help); External link in |chapterurl= (help); Unknown parameter |chapterurl= ignored (|chapter-url= suggested) (help)
  4. ^ Template:PDFlink. Drug Topics (May 26, 2009). Retrieved on July 24, 2009.
  5. ^ Template:PDFlink. Drug Topics (May 26, 2009). Retrieved on July 24, 2009.
  6. ^ a b "Cephalexin". The American Society of Health-System Pharmacists. Retrieved 3 April 2011.
  7. ^ Pichichero ME (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. {{cite journal}}: Unknown parameter |month= ignored (help)
  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.