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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-02-19 16:04:01
Primary Accession Number DB00567
Secondary Accession Number
  • APRD00250
Name Cephalexin
Drug Type
  • Approved
  • Small Molecule
Description A semisynthetic cephalosporin antibiotic with antimicrobial activity similar to that of cephaloridine or cephalothin, but somewhat less potent. It is effective against both gram-positive and gram-negative organisms. [PubChem]
Synonyms
  1. CEX
  2. Cefalessina [DCIT]
  3. Cefalexin
  4. Cefalexin Sodium
  5. Cefalexina [INN-Spanish]
  6. Cefalexine [INN-French]
  7. Cefalexinum [INN-Latin]
  8. Cephalexin 1-hydrate
  9. Cephalexin hydrate
  10. Cephalexin monohydrate
  11. Cephalexine
  12. Cephalexinum
Brand Names
  1. Alcephin
  2. Alexin
  3. Alsporin
  4. Biocef
  5. Carnosporin
  6. Cefa-iskia
  7. Cefablan
  8. Cefadal
  9. Cefadin
  10. Cefadina
  11. Cefaleksin
  12. Cefalin
  13. Cefaloto
  14. Cefaseptin
  15. Cefax
  16. Ceforal
  17. Cefovit
  18. Celexin
  19. Cepastar
  20. Cepexin
  21. Cephacillin
  22. Cephanasten
  23. Cephaxin
  24. Cephin
  25. Cepol
  26. Ceporex
  27. Ceporex Forte
  28. Ceporexin
  29. Ceporexin-E
  30. Ceporexine
  31. Check
  32. Cophalexin
  33. Durantel
  34. Durantel DS
  35. Ed A-Ceph
  36. Erocetin
  37. Factagard
  38. Felexin
  39. Fexin
  40. Ibilex
  41. Ibrexin
  42. Inphalex
  43. Kefalospes
  44. Keflet
  45. Keflex
  46. Kefolan
  47. Keforal
  48. Keftab
  49. Kekrinal
  50. Kidolex
  51. L-Keflex
  52. Lafarine
  53. Larixin
  54. Lenocef
  55. Lexibiotico
  56. Lonflex
  57. Lopilexin
  58. Madlexin
  59. Mamalexin
  60. Mamlexin
  61. Medoxine
  62. Neokef
  63. Neolexina
  64. Novolexin
  65. Nufex
  66. Oracef
  67. Oriphex
  68. Oroxin
  69. Ortisporina
  70. Ospexin
  71. Palitrex
  72. Panixine Disperdose
  73. Pectril
  74. Pyassan
  75. Roceph
  76. Sanaxin
  77. Sartosona
  78. Sencephalin
  79. Sepexin
  80. Servispor
  81. Sialexin
  82. Sinthecillin
  83. Sporicef
  84. Sporidex
  85. Syncl
  86. Syncle
  87. Synecl
  88. Tepaxin
  89. Tokiolexin
  90. Uphalexin
  91. Voxxim
  92. Winlex
  93. Zozarine
Brand Mixtures Not Available
Chemical 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
Chemical Formula C16H17N3O4S
Chemical Structure Structure
CAS Registry Number 15686-71-2
InChI Identifier InChI=1/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/f/h18,22H
InChI Key ZAIPMKNFIOOWCQ-KPHHXKKPDB
KEGG Drug D00263 Link Image
KEGG Compound C06895 Link Image
PubChem Compound 27447 Link Image
PubChem Substance 625390 Link Image
ChEBI ID Not Available
PharmGKB ID PA448883 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] 00828858 Link Image
RxList Link http://www.rxlist.com/cgi/generic/cephalex.htm Link Image
PDRhealth Link http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/kef1213.shtml Link Image
Wikipedia Link http://en.wikipedia.org/wiki/Cephalexin Link Image
FDA Label
Material Safety Data Sheet (MSDS)
Synthesis Reference R. B. Morin, B. G. Jackson, U.S. Pat. 3,275,626,861 (1966,1970)
Average Molecular Weight 347.3890
Monoisotopic Molecular Weight 347.0940
State Solid
Melting Point 326.8oC
Experimental Water Solubility 1789 mg/L Source: PhysProp
Predicted Water Solubility 2.97e-01 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity
Predicted LogP 0.56 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -3.07 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point 4.5
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES CC1=C(N2[C@H](SC1)[C@H](NC(=O)[C@H](N)C1=CC=CC=C1)C2=O)C(O)=O
Canonical SMILES CC1=C(N2C(SC1)C(NC(=O)C(N)C1=CC=CC=C1)C2=O)C(O)=O
Drug Category
  • Anti-Bacterial Agents
  • Cephalosporins
ATC Codes
AHFS Codes
  • 08:12.06.04
Indication For the treatment of respiratory tract infections caused by Streptococcus pneumoniae and Streptococcus pyogenes; otitis media due to Streptococcus pneumoniae, Haemophilus influenzae, Staphylococcus aureus, Streptococcus pyogenes, and Moraxella catarrhalis; skin and skin structure infections caused by Staphylococcus aureus and/or Streptococcus pyogenes; bone infections caused by Staphylococcus aureus and/or Proteus mirabilis; genitourinary tract infections, including acute prostatitis, caused by Escherichia coli, Proteus mirabilis, and Klebsiella pneumoniae.
Pharmacology Cephalexin (also called Cefalexin) is a first generation cephalosporin antibiotic. It is one of the most widely prescribed antibiotics, often used for the treatment of superficial infections that result as complications of minor wounds or lacerations. It is effective against most gram-positive bacteria.
Mechanism of Action Cephalexin, like the penicillins, is a beta-lactam antibiotic. By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, it inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that cephalexin interferes with an autolysin inhibitor.
Absorption Well absorbed from the gastrointestinal tract
Toxicity Symptoms of overdose include blood in the urine, diarrhea, nausea, upper abdominal pain, and vomiting. The oral median lethal dose of cephalexin in rats is >5000 mg/kg.
Protein Binding 14%
Biotransformation No appreciable biotransformation in the liver (90% of the drug is excreted unchanged in the urine).
Half Life 1 hour
Dosage Forms
Form Route
Capsule Oral
Powder, for solution Oral
Powder, for suspension Oral
Suspension Oral
Tablet Oral
Patient Information Show Link Image
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions
Drug Interaction
Probenecid Probenecid increases the antibiotic's level
Food Interactions
  • Take on empty stomach: 1 hour before or 2 hours after meals.
Pathways Not Available
General References
  1. Drugs.com Link Image
  2. Wikipedia Link Image
  3. RxList Link Image
  4. PDRhealth Link Image
Organisms Affected
  • Enteric bacteria and other eubacteria
Targets
  1. Penicillin-binding proteins 1A/1B
Drug Target 1 [top]
Target 1 ID 633
Target 1 Name Penicillin-binding proteins 1A/1B
Target 1 Synonyms Not Available
Target 1 Gene Name pbpA
Target 1 Protein Sequence >Penicillin-binding proteins 1A/1B 
MTERKREHKDRKQNKNSPKNQSKVTKFLKWFFIGILLLGITAVTVVGIYVLSIIRSSPEL
DVQAIQSLNQPSILYDDQGNFMDNVITREQRYVVKSEEIPDNLKKAFVAIEDERFYEHKG
IDIKRIFGVIASNIKGKLSGSNTVQGASTITQQLIKNAVLTNEVSYERKIKEMYLALELE
KHLSKDEILTTYLNTIPMGGYQYGVSAAAQRFFSKNVSDLNLVECAYLGGLTQAPTSYDG
LSEANKENPSRYLNRTKSVLFKMHELGYISSEQYNDAINEIDTNGIKFTPNNKLSKTNFE
WFTRPAITQVKQDLMDKYKYTQEEVDKLIANGGLKIYTSMDRNLQNNVQKVLDDPNNYKA
ITNNPNEKNEDGVYKLQASATIIDYKTGHVKALVGGRGEQPAMSHNRAYYDLKSIGSATK
PLTVYGPAIDLGLGGAGSVVNDSPLSNKELSSTGYKDQPKNEYNSYRGPLTFREAIKISS
NLAAIKVANEVGVSNSIAYGEKLGLVYGPHSRGISTTALGQFQNDPNNPDGGNTYTLASA
FGVFGNNGVKTNAKLYTKVLDSHGNVILDTSTPEETKIFSPQASYIVYDMLKDQVESGSA
KSAKFGNIPVAGKTGTTTGDKDYLFAGLTPYYSAAIWIGYDKPREMRTSSGTVTSPIFGK
IMGLAHKDLQYKEVDNLVE
Target 1 Number of Residues 690
Target 1 Molecular Weight 75178
Target 1 Theoretical pI 9.09
Target 1 GO Classification
Function
binding
drug binding
penicillin binding
transferase activity
transferase activity, transferring glycosyl groups
transferase activity, transferring pentosyl groups
hydrolase activity
peptidase activity
catalytic activity
Process
cellular physiological process
cell organization and biogenesis
external encapsulating structure organization and biogenesis
cell wall organization and biogenesis
cell wall organization and biogenesis (sensu Bacteria)
cell wall biosynthesis (sensu Bacteria)
response to stimulus
response to abiotic stimulus
response to chemical stimulus
response to drug
response to antibiotic
physiological process
metabolism
macromolecule metabolism
carbohydrate metabolism
cellular carbohydrate metabolism
peptidoglycan metabolism
peptidoglycan biosynthesis
Component
cell
external encapsulating structure
cell wall
cell wall (sensu Bacteria)
Target 1 General Function Cell wall/membrane/envelope biogenesis
Target 1 Specific Function Not Available
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • 30-52
Target 1 Essentiality Essential
Target 1 GenBank ID Protein 18145626 Link Image
Target 1 UniProtKB/Swiss-Prot ID Q8XJ01 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name Q8XJ01_CLOPE Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location
  • Cytoplasmic
Target 1 Gene Sequence >2040 bp 
ATGACTGAAAGAAAAAGAGAGCATAAAGATAGAAAGCAGAATAAAAATTCACCTAAAAAT
CAATCGAAAGTAACAAAATTTTTGAAATGGTTCTTTATAGGGATTCTGCTTCTAGGGATA
ACTGCCGTAACAGTAGTTGGAATTTACGTTCTTTCTATTATACGTTCATCTCCAGAGTTA
GATGTTCAGGCAATTCAATCTCTAAATCAGCCATCCATTCTTTACGATGATCAGGGAAAC
TTTATGGATAATGTTATAACTCGTGAACAACGTTATGTAGTTAAATCTGAAGAGATACCT
GATAACTTAAAAAAGGCTTTTGTAGCTATTGAAGACGAAAGATTTTATGAGCATAAAGGA
ATAGACATTAAAAGAATTTTTGGGGTAATAGCTTCTAATATTAAAGGTAAACTTTCAGGA
AGTAATACAGTTCAAGGGGCTTCAACCATAACTCAGCAACTTATAAAAAATGCCGTACTT
ACTAATGAAGTTAGTTATGAAAGAAAAATTAAAGAAATGTACTTAGCTTTGGAATTAGAA
AAGCACCTTTCAAAAGATGAAATCCTTACTACGTATTTAAATACAATTCCTATGGGTGGA
TACCAATATGGGGTTAGCGCAGCTGCTCAAAGATTTTTTAGTAAGAATGTTTCAGATTTG
AATTTAGTTGAGTGCGCTTATTTAGGAGGACTTACTCAAGCACCAACTTCTTATGATGGT
CTTTCAGAAGCAAATAAAGAAAATCCAAGTAGATATTTAAATAGAACTAAATCTGTACTA
TTTAAAATGCATGAACTTGGATATATTTCAAGTGAACAATATAATGACGCAATAAATGAA
ATTGACACAAATGGTATAAAATTCACACCAAATAATAAATTAAGTAAAACTAACTTTGAG
TGGTTCACAAGACCAGCTATAACTCAAGTTAAACAAGACTTAATGGATAAATATAAATAT
ACACAAGAGGAAGTTGACAAACTTATAGCTAATGGTGGATTAAAAATCTATACTTCAATG
GATAGAAATCTTCAAAATAATGTTCAAAAAGTTTTAGATGATCCAAATAACTATAAAGCT
ATAACTAATAATCCTAATGAAAAAAATGAAGATGGTGTTTATAAATTACAAGCATCTGCC
ACAATAATAGACTATAAAACAGGCCATGTTAAGGCTTTAGTTGGAGGAAGAGGGGAACAA
CCTGCTATGTCTCACAATAGAGCTTATTATGATTTAAAATCTATAGGTTCTGCAACAAAA
CCATTAACAGTTTATGGTCCTGCTATTGATTTAGGACTTGGTGGCGCTGGCTCTGTAGTA
AATGATTCTCCATTAAGTAATAAAGAGTTATCTTCTACAGGATATAAAGATCAACCTAAG
AATGAATACAATAGTTATAGAGGCCCTTTAACTTTTAGAGAAGCAATTAAAATCTCTAGT
AACTTAGCAGCCATAAAAGTTGCTAATGAAGTAGGTGTTTCAAACTCTATAGCTTATGGA
GAAAAATTAGGTCTTGTTTATGGACCTCATTCTAGAGGTATTTCCACAACAGCCTTAGGT
CAATTCCAAAATGACCCTAATAATCCTGATGGAGGAAATACTTATACTCTAGCTTCAGCC
TTCGGTGTTTTTGGTAATAACGGTGTTAAAACAAATGCTAAATTATATACAAAGGTATTA
GATTCTCATGGAAATGTAATTCTTGATACAAGTACTCCAGAAGAAACTAAAATATTTAGT
CCTCAAGCGTCTTATATAGTTTATGATATGCTTAAGGATCAAGTAGAAAGTGGCTCTGCA
AAATCTGCTAAATTTGGTAATATTCCTGTGGCGGGTAAAACAGGAACTACTACTGGAGAT
AAAGACTATTTATTTGCAGGATTAACTCCATATTATTCTGCGGCTATTTGGATTGGATAT
GATAAGCCTAGAGAAATGAGAACTAGTAGTGGTACTGTTACCTCTCCTATTTTCGGAAAA
ATAATGGGCTTAGCTCATAAAGACTTACAGTACAAAGAGGTTGACAACCTAGTGGAATAA
Target 1 GenBank Gene ID
Target 1 GeneCard ID Not Available
Target 1 GenAtlas ID Not Available
Target 1 HGNC ID Not Available
Target 1 Chromosome Location Not Available
Target 1 Locus Not Available
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Shimizu T, Ohtani K, Hirakawa H, Ohshima K, Yamashita A, Shiba T, Ogasawara N, Hattori M, Kuhara S, Hayashi H: Complete genome sequence of Clostridium perfringens, an anaerobic flesh-eater. Proc Natl Acad Sci U S A. 2002 Jan 22;99(2):996-1001. Epub 2002 Jan 15. [PubMed Link Image]
Target 1 Drug References
  1. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed Link Image]
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]

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