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Identification
NameCephalexin
Accession NumberDB00567  (APRD00250)
Typesmall molecule
Groupsapproved
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]

Structure
Thumb
Synonyms
SynonymLanguageCode
CefalexinNot AvailableINN
CefalexinaSpanishINN
CéfalexineFrenchINN
CefalexinumLatinINN
CéphalexineFrenchNot Available
CEXNot AvailableNot Available
Salts
Name/CAS Structure Properties
Cefalexin Sodium
38932-40-0
Thumb
  • InChI Key: NZDYPHVJLWMLJI-CYJZLJNKSA-M
  • Monoisotopic Mass: 369.07592138
  • Average Mass: 369.371
DBSALT000261
Brand names
NameCompany
AlcephinAlembic
AlexinDabur
AlsporinRenata
CefadinLife
CefalinBioFemme
CeforalTeva
CefovitVitamed
CelexinAtlantic
CephinGeneral Drugs House
CeporexinInvesti
FelexinRemedica
IbilexAlphapharm
KeflexLilly
KeforalSaiph
L-KeflexShionogi Seiyaku
LarixinTaisho Yakuhin
LonflexUnion
MadlexinMeiji
NufexGeneral Pharma
OriphexMaydsm Trading
OspexinSandoz
PalitrexGalenika
PyassanSanofi
SanaxinSandoz
SencephalinTakeda Pharmaceutical
SepexinHetero
ServisporSandoz
SialexinSiam Bheasach
SporicefRanbaxy
SporidexRanbaxy
SynclAsahi Kasei Pharma
TepaxinTakeda
UphalexinCCM
VoxximRoddensers
WinlexWinston
Brand mixturesNot Available
Categories
CAS number15686-71-2
WeightAverage: 347.389
Monoisotopic: 347.093976737
Chemical FormulaC16H17N3O4S
InChI KeyInChIKey=ZAIPMKNFIOOWCQ-UEKVPHQBSA-N
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
IUPAC Name
(6R,7R)-7-[(2R)-2-amino-2-phenylacetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
SMILES
[H][C@]12SCC(C)=C(N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=CC=C1)C(O)=O
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassLactams
SubclassBeta Lactams
Direct parentCephalosporins
Alternative parentsN-acyl-alpha Amino Acids and Derivatives; Alpha Amino Acid Amides; 1,3-Thiazines; Benzene and Substituted Derivatives; Tertiary Carboxylic Acid Amides; Hemiaminals; Azetidines; Secondary Carboxylic Acid Amides; Tertiary Amines; Enamines; Enolates; Polyamines; Thioethers; Aminals; Carboxylic Acids; Monoalkylamines
Substituentsn-acyl-alpha amino acid or derivative; alpha-amino acid amide; alpha-amino acid or derivative; benzene; meta-thiazine; tertiary carboxylic acid amide; secondary carboxylic acid amide; tertiary amine; carboxamide group; hemiaminal; azetidine; enolate; polyamine; aminal; thioether; enamine; carboxylic acid; carboxylic acid derivative; primary aliphatic amine; amine; primary amine; organonitrogen compound
Classification descriptionThis compound belongs to the cephalosporins. These are compounds containing a 1,2-thiazine fused to a 2-azetidinone to for a oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid moeity or a derivative thereof.
Pharmacology
IndicationFor 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.
PharmacodynamicsCephalexin (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 actionCephalexin, 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.
AbsorptionWell absorbed from the gastrointestinal tract
Volume of distributionNot Available
Protein binding14%
Metabolism

No appreciable biotransformation in the liver (90% of the drug is excreted unchanged in the urine).

Route of eliminationCephalexin is excreted in the urine by glomerular filtration and tubular secretion. Studies showed that over 90% of the drug was excreted unchanged in the urine within 8 hours.
Half life1 hour
ClearanceNot Available
ToxicitySymptoms 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.
Affected organisms
  • Enteric bacteria and other eubacteria
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption - 0.7537
Blood Brain Barrier - 0.996
Caco-2 permeable - 0.8956
P-glycoprotein substrate Substrate 0.786
P-glycoprotein inhibitor I Non-inhibitor 0.9033
P-glycoprotein inhibitor II Non-inhibitor 0.9921
Renal organic cation transporter Non-inhibitor 0.9485
CYP450 2C9 substrate Non-substrate 0.8011
CYP450 2D6 substrate Non-substrate 0.8308
CYP450 3A4 substrate Non-substrate 0.5289
CYP450 1A2 substrate Non-inhibitor 0.9242
CYP450 2C9 substrate Non-inhibitor 0.9251
CYP450 2D6 substrate Non-inhibitor 0.9359
CYP450 2C19 substrate Non-inhibitor 0.922
CYP450 3A4 substrate Non-inhibitor 0.831
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9303
Ames test Non AMES toxic 0.6834
Carcinogenicity Non-carcinogens 0.8861
Biodegradation Not ready biodegradable 0.9812
Rat acute toxicity 1.2715 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9971
hERG inhibition (predictor II) Non-inhibitor 0.8686
Pharmacoeconomics
Manufacturers
  • Acs dobfar info sa
  • Apothecon inc div bristol myers squibb
  • Aurobindo pharma ltd inc
  • Barr laboratories inc
  • Belcher pharmaceuticals inc
  • Hikma pharmaceuticals
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Lupin ltd
  • Orchid healthcare
  • Purepac pharmaceutical co
  • Ranbaxy laboratories ltd
  • Jerome stevens pharmaceuticals inc
  • Sun pharmaceutical industries ltd
  • Teva pharmaceuticals usa inc
  • Yoshitomi pharmaceutical industries ltd
  • Yung shin pharmaceutical industrial co ltd
  • Middlebrook pharmaceuticals inc
  • Vitarine pharmaceuticals inc
  • Lex pharmaceuticals inc
  • Eli lilly and co
Packagers
Dosage forms
FormRouteStrength
CapsuleOral
Powder, for solutionOral
Powder, for suspensionOral
SuspensionOral
TabletOral
Prices
Unit descriptionCostUnit
Cephalexin 250 mg/5ml Suspension 200ml Bottle32.76USDbottle
Cephalexin 250 mg/5ml Suspension 100ml Bottle19.66USDbottle
Cephalexin 125 mg/5ml Suspension 200ml Bottle16.39USDbottle
Cephalexin 125 mg/5ml Suspension 100ml Bottle15.99USDbottle
Keflex 500 mg capsule5.75USDcapsule
Keflex 500 mg pulvule4.99USDeach
Keflex 750 mg capsule3.34USDcapsule
Cephalexin 500 mg tablet2.25USDtablet
Keflex 250 mg capsule2.2USDcapsule
Keflex 250 mg pulvule1.85USDeach
Cephalexin 500 mg capsule1.4USDcapsule
Cephalexin 250 mg tablet1.17USDtablet
Cephalexin 250 mg capsule0.72USDcapsule
Apo-Cephalex 500 mg Tablet0.47USDtablet
Novo-Lexin 500 mg Capsule0.47USDcapsule
Novo-Lexin 500 mg Tablet0.47USDtablet
Nu-Cephalex 500 mg Tablet0.47USDtablet
Apo-Cephalex 250 mg Tablet0.24USDtablet
Novo-Lexin 250 mg Capsule0.24USDcapsule
Novo-Lexin 250 mg Tablet0.24USDtablet
Nu-Cephalex 250 mg Tablet0.24USDtablet
Novo-Lexin 50 mg/ml Suspension0.14USDml
Novo-Lexin 25 mg/ml Suspension0.09USDml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point326.8 °CNot Available
water solubility1789 mg/LNot Available
logP0.65HANSCH,C ET AL. (1995)
pKa4.5Not Available
Predicted Properties
PropertyValueSource
water solubility2.97e-01 g/lALOGPS
logP0.55ALOGPS
logP-2.1ChemAxon
logS-3.1ALOGPS
pKa (strongest acidic)3.45ChemAxon
pKa (strongest basic)7.44ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count5ChemAxon
hydrogen donor count3ChemAxon
polar surface area112.73ChemAxon
rotatable bond count4ChemAxon
refractivity88.97ChemAxon
polarizability32.52ChemAxon
number of rings3ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Peter Faarup, “Method of preparing a sparingly soluble complex of cephalexin.” U.S. Patent US4003896, issued May, 1975.

US4003896
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD00263
KEGG CompoundC06895
PubChem Compound27447
PubChem Substance46506749
ChemSpider25541
BindingDB50139896
ChEBI3534
ChEMBLCHEMBL1727
Therapeutic Targets DatabaseDAP000437
PharmGKBPA448883
Drug Product Database828858
RxListhttp://www.rxlist.com/cgi/generic/cephalex.htm
Drugs.comhttp://www.drugs.com/cephalexin.html
PDRhealthhttp://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/kef1213.shtml
WikipediaCephalexin
ATC CodesJ01DB01
AHFS Codes
  • 08:12.06.04
PDB EntriesNot Available
FDA labelshow(2.1 MB)
MSDSshow(93.2 KB)
Interactions
Drug Interactions
Drug
ProbenecidProbenecid may increase the serum level of cephalexin.
Food Interactions
  • Take on empty stomach: 1 hour before or 2 hours after meals.

1. Penicillin-binding protein 3

Kind: protein

Organism: Streptococcus pneumoniae

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Penicillin-binding protein 3 Q75Y35 Details

References:

  1. Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. Pubmed

2. Penicillin-binding protein 2a

Kind: protein

Organism: Streptococcus pneumoniae (strain ATCC BAA-255 / R6)

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Penicillin-binding protein 2a Q8DNB6 Details

References:

  1. Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. Pubmed
  2. Mitsuoka K, Kato Y, Kubo Y, Tsuji A: Functional expression of stereoselective metabolism of cephalexin by exogenous transfection of oligopeptide transporter PEPT1. Drug Metab Dispos. 2007 Mar;35(3):356-62. Epub 2006 Dec 1. Pubmed

3. Penicillin-binding protein 1b

Kind: protein

Organism: Streptococcus pneumoniae (strain ATCC BAA-255 / R6)

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Penicillin-binding protein 1b Q7CRA4 Details

References:

  1. Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. Pubmed

4. Penicillin-binding protein 2B

Kind: protein

Organism: Streptococcus pneumoniae (strain ATCC BAA-255 / R6)

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Penicillin-binding protein 2B P0A3M6 Details

References:

  1. Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. Pubmed

5. Penicillin-binding protein 1A

Kind: protein

Organism: Streptococcus pneumoniae (strain ATCC BAA-255 / R6)

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Penicillin-binding protein 1A Q8DR59 Details

References:

  1. Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. Pubmed

1. Cytochrome P450 2D6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2D6 P10635 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

1. Serum albumin

Kind: protein

Organism: Human

Pharmacological action: no

Actions: other/unknown

Components

Name UniProt ID Details
Serum albumin P02768 Details

References:

  1. Bratlid D, Bergan T: Displacement of albumin-bound antimicrobial agents by bilirubin. Pharmacology. 1976;14(5):464-72. Pubmed

1. Solute carrier family 22 member 5

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 5 O76082 Details

References:

  1. Ganapathy ME, Huang W, Rajan DP, Carter AL, Sugawara M, Iseki K, Leibach FH, Ganapathy V: beta-lactam antibiotics as substrates for OCTN2, an organic cation/carnitine transporter. J Biol Chem. 2000 Jan 21;275(3):1699-707. Pubmed

2. Solute carrier family 15 member 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Solute carrier family 15 member 1 P46059 Details

References:

  1. Liang R, Fei YJ, Prasad PD, Ramamoorthy S, Han H, Yang-Feng TL, Hediger MA, Ganapathy V, Leibach FH: Human intestinal H+/peptide cotransporter. Cloning, functional expression, and chromosomal localization. J Biol Chem. 1995 Mar 24;270(12):6456-63. Pubmed
  2. Wenzel U, Gebert I, Weintraut H, Weber WM, Clauss W, Daniel H: Transport characteristics of differently charged cephalosporin antibiotics in oocytes expressing the cloned intestinal peptide transporter PepT1 and in human intestinal Caco-2 cells. J Pharmacol Exp Ther. 1996 May;277(2):831-9. Pubmed
  3. Covitz KM, Amidon GL, Sadee W: Human dipeptide transporter, hPEPT1, stably transfected into Chinese hamster ovary cells. Pharm Res. 1996 Nov;13(11):1631-4. Pubmed
  4. Han HK, Rhie JK, Oh DM, Saito G, Hsu CP, Stewart BH, Amidon GL: CHO/hPEPT1 cells overexpressing the human peptide transporter (hPEPT1) as an alternative in vitro model for peptidomimetic drugs. J Pharm Sci. 1999 Mar;88(3):347-50. Pubmed
  5. Guo A, Hu P, Balimane PV, Leibach FH, Sinko PJ: Interactions of a nonpeptidic drug, valacyclovir, with the human intestinal peptide transporter (hPEPT1) expressed in a mammalian cell line. J Pharmacol Exp Ther. 1999 Apr;289(1):448-54. Pubmed
  6. Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. Pubmed
  7. Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. Pubmed
  8. Ganapathy ME, Brandsch M, Prasad PD, Ganapathy V, Leibach FH: Differential recognition of beta -lactam antibiotics by intestinal and renal peptide transporters, PEPT 1 and PEPT 2. J Biol Chem. 1995 Oct 27;270(43):25672-7. Pubmed
  9. Tamai I, Nakanishi T, Hayashi K, Terao T, Sai Y, Shiraga T, Miyamoto K, Takeda E, Higashida H, Tsuji A: The predominant contribution of oligopeptide transporter PepT1 to intestinal absorption of beta-lactam antibiotics in the rat small intestine. J Pharm Pharmacol. 1997 Aug;49(8):796-801. Pubmed

3. Solute carrier family 15 member 2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 15 member 2 Q16348 Details

References:

  1. Liu W, Liang R, Ramamoorthy S, Fei YJ, Ganapathy ME, Hediger MA, Ganapathy V, Leibach FH: Molecular cloning of PEPT 2, a new member of the H+/peptide cotransporter family, from human kidney. Biochim Biophys Acta. 1995 May 4;1235(2):461-6. Pubmed
  2. Ganapathy ME, Brandsch M, Prasad PD, Ganapathy V, Leibach FH: Differential recognition of beta -lactam antibiotics by intestinal and renal peptide transporters, PEPT 1 and PEPT 2. J Biol Chem. 1995 Oct 27;270(43):25672-7. Pubmed
  3. Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. Pubmed
  4. Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. Pubmed

4. Solute carrier family 22 member 6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 6 Q4U2R8 Details

References:

  1. Jung KY, Takeda M, Shimoda M, Narikawa S, Tojo A, Kim DK, Chairoungdua A, Choi BK, Kusuhara H, Sugiyama Y, Sekine T, Endou H: Involvement of rat organic anion transporter 3 (rOAT3) in cephaloridine-induced nephrotoxicity: in comparison with rOAT1. Life Sci. 2002 Mar 8;70(16):1861-74. Pubmed
  2. Jariyawat S, Sekine T, Takeda M, Apiwattanakul N, Kanai Y, Sophasan S, Endou H: The interaction and transport of beta-lactam antibiotics with the cloned rat renal organic anion transporter 1. J Pharmacol Exp Ther. 1999 Aug;290(2):672-7. Pubmed
  3. Uwai Y, Saito H, Inui K: Rat renal organic anion transporter rOAT1 mediates transport of urinary-excreted cephalosporins, but not of biliary-excreted cefoperazone. Drug Metab Pharmacokinet. 2002;17(2):125-9. Pubmed

5. Multidrug and toxin extrusion protein 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Multidrug and toxin extrusion protein 1 Q96FL8 Details

References:

  1. Watanabe S, Tsuda M, Terada T, Katsura T, Inui K: Reduced renal clearance of a zwitterionic substrate cephalexin in MATE1-deficient mice. J Pharmacol Exp Ther. 2010 Aug;334(2):651-6. Epub 2010 May 19. Pubmed

6. Solute carrier family 22 member 8

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 8 Q8TCC7 Details

References:

  1. Jung KY, Takeda M, Shimoda M, Narikawa S, Tojo A, Kim DK, Chairoungdua A, Choi BK, Kusuhara H, Sugiyama Y, Sekine T, Endou H: Involvement of rat organic anion transporter 3 (rOAT3) in cephaloridine-induced nephrotoxicity: in comparison with rOAT1. Life Sci. 2002 Mar 8;70(16):1861-74. Pubmed

Comments
Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:11