You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameCefaclor
Accession NumberDB00833  (APRD00243)
Typesmall molecule
Groupsapproved
Description

Semisynthetic, broad-spectrum antibiotic derivative of cephalexin. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
3-Chloro-7-D-(2-phenylglycinamido)-3-cephem-4-carboxylic acidNot AvailableNot Available
CCLNot AvailableNot Available
CefaclorGermanINN
CefaclorFrenchINN
CefaclorSpanishINN
Cefaclor anhydrousNot AvailableNot Available
Cefacloro Not AvailableDCIT
CefaclorumLatinINN
Céfeaclor Not AvailableDCF
CephaclorNot AvailableIS
SaltsNot Available
Brand names
NameCompany
AlenfralChoseido Pharmaceutical
AlfacetGalenika
AlfatilDexo
Alfatil LPDexo
CeclorLilly
Ceclor CDLilly
DistaclorFlynn
KeflorAlphapharm
KefralShionogi Seiyaku
PanacefValeas
PanoralEberth
RaniclorRanbaxy Pharmaceuticals Inc.
Brand mixturesNot Available
Categories
CAS number53994-73-3
WeightAverage: 367.807
Monoisotopic: 367.039354348
Chemical FormulaC15H14ClN3O4S
InChI KeyQYIYFLOTGYLRGG-GPCCPHFNSA-N
InChI
InChI=1S/C15H14ClN3O4S/c16-8-6-24-14-10(13(21)19(14)11(8)15(22)23)18-12(20)9(17)7-4-2-1-3-5-7/h1-5,9-10,14H,6,17H2,(H,18,20)(H,22,23)/t9-,10-,14-/m1/s1
IUPAC Name
(6R,7R)-7-[(2R)-2-amino-2-phenylacetamido]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
SMILES
[H][C@]12SCC(Cl)=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; Azetidines; Tertiary Amines; Secondary Carboxylic Acid Amides; Hemiaminals; Thioethers; Carboxylic Acids; Enolates; Polyamines; Aminals; Organochlorides; 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; hemiaminal; carboxamide group; azetidine; tertiary amine; aminal; polyamine; thioether; carboxylic acid derivative; carboxylic acid; enolate; organohalogen; primary aliphatic amine; organochloride; 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 certain infections caused by bacteria such as pneumonia and ear, lung, skin, throat, and urinary tract infections.
PharmacodynamicsCefaclor is a second generation cephalosporin antibiotic with a spectrum resembling first-generation cephalosporins. In vitro tests demonstrate that the bactericidal action of the cephalosporins results from inhibition of cell-wall synthesis. Cefaclor has been shown to be active against most strains of the following microorganisms, both in vitro and in clinical infections: Gram positive aerobes - Staphylococci (including coagulase-positive, coagulase-negative, and penicillinase-producing strains), Streptococcus pneumoniae, and Streptococcus pyogenes (group A ß-hemolytic streptococci). Gram-negative aerobes - Escherichia coli, Haemophilus influenzae (including ß-lactamase-producing ampicillin-resistant strains), Klebsiella sp, and Proteus mirabilis.
Mechanism of actionCefaclor, 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 cefaclor interferes with an autolysin inhibitor.
AbsorptionWell absorbed after oral administration, independent of food intake.
Volume of distributionNot Available
Protein binding23.5%
Metabolism

No appreciable biotransformation in liver (approximately 60% to 85% of the drug is excreted unchanged in the urine within 8 hours).

Route of eliminationApproximately 60% to 85% of the drug is excreted unchanged in the urine within 8 hours, the greater portion being excreted within the first 2 hours.
Half life0.6-0.9 hour
ClearanceNot Available
ToxicitySymptoms of overdose include diarrhea, nausea, stomach upset, and vomiting.
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 - 0.8839
Blood Brain Barrier - 0.9817
Caco-2 permeable - 0.8239
P-glycoprotein substrate Substrate 0.6569
P-glycoprotein inhibitor I Non-inhibitor 0.9413
P-glycoprotein inhibitor II Non-inhibitor 0.9955
Renal organic cation transporter Non-inhibitor 0.9369
CYP450 2C9 substrate Non-substrate 0.8314
CYP450 2D6 substrate Non-substrate 0.8361
CYP450 3A4 substrate Non-substrate 0.5597
CYP450 1A2 substrate Non-inhibitor 0.9046
CYP450 2C9 substrate Non-inhibitor 0.907
CYP450 2D6 substrate Non-inhibitor 0.9236
CYP450 2C19 substrate Non-inhibitor 0.9026
CYP450 3A4 substrate Non-inhibitor 0.831
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9193
Ames test Non AMES toxic 0.6676
Carcinogenicity Non-carcinogens 0.8489
Biodegradation Not ready biodegradable 1.0
Rat acute toxicity 1.2960 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9966
hERG inhibition (predictor II) Non-inhibitor 0.85
Pharmacoeconomics
Manufacturers
  • Eli lilly and co
  • Ceph international corp
  • Clonmel healthcare ltd
  • Hikma pharmaceuticals
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Marsam pharmaceuticals llc
  • Ranbaxy pharmaceuticals inc
  • Teva pharmaceuticals usa inc
  • Yung shin pharmaceutical industrial co ltd
  • Acs dobfar info sa
  • Ranbaxy laboratories ltd
  • World gen llc
Packagers
Dosage forms
FormRouteStrength
CapsuleOral
PowderOral
Powder, for solutionOral
Powder, for suspensionOral
SuspensionOral
Prices
Unit descriptionCostUnit
Ceclor 15 500 mg capsule Bottle70.0USDbottle
Ceclor 375 mg/5ml Suspension 100ml Bottle59.99USDbottle
Ceclor 250 mg/5ml Suspension 150ml Bottle58.98USDbottle
Cefaclor 250 mg/5ml Suspension 150ml Bottle53.87USDbottle
Cefaclor 375 mg/5ml Suspension 100ml Bottle53.87USDbottle
Ceclor 15 250 mg capsule Bottle38.0USDbottle
Ceclor 125 mg/5ml Suspension 150ml Bottle34.99USDbottle
Ceclor 187 mg/5ml Suspension 100ml Bottle34.99USDbottle
Ceclor 250 mg/5ml Suspension 75ml Bottle31.99USDbottle
Cefaclor 125 mg/5ml Suspension 150ml Bottle29.41USDbottle
Cefaclor 250 mg/5ml Suspension 75ml Bottle29.37USDbottle
Cefaclor 187 mg/5ml Suspension 100ml Bottle29.26USDbottle
Cefaclor 375 mg/5ml Suspension 50ml Bottle27.44USDbottle
Cefaclor 187 mg/5ml Suspension 50ml Bottle14.92USDbottle
Cefaclor 125 mg/5ml Suspension 75ml Bottle14.7USDbottle
Ceclor 500 mg pulvule5.69USDeach
Cefaclor 500 mg capsule4.05USDcapsule
Cefaclor CR 500 mg 12 Hour tablet3.79USDtablet
Ceclor 250 mg pulvule3.28USDeach
Raniclor 375 mg chewable tablet2.98USDtablet
Cefaclor 250 mg capsule2.07USDcapsule
Raniclor 250 mg chewable tablet1.99USDtablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point327 °CNot Available
water solubility1E+004 mg/LYALKOWSKY,SH & DANNENFELSER,RM (1992)
logP0.4Not Available
Predicted Properties
PropertyValueSource
water solubility2.10e-01 g/lALOGPS
logP0.85ALOGPS
logP-2.3ChemAxon
logS-3.2ALOGPS
pKa (strongest acidic)3.03ChemAxon
pKa (strongest basic)7.44ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count5ChemAxon
hydrogen donor count3ChemAxon
polar surface area112.73ChemAxon
rotatable bond count4ChemAxon
refractivity89.56ChemAxon
polarizability35.11ChemAxon
number of rings3ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Bing L. Wong, Yong-Qiang Shen, Yung-Pin Chen, “Enzymatic production of cefaclor from cephalexin.” U.S. Patent US5939299, issued November, 1987.

US5939299
General Reference
  1. Hebert AA, Sigman ES, Levy ML: Serum sickness-like reactions from cefaclor in children. J Am Acad Dermatol. 1991 Nov;25(5 Pt 1):805-8. Pubmed
  2. Parra FM, Igea JM, Martin JA, Alonso MD, Lezaun A, Sainz T: Serum sickness-like syndrome associated with cefaclor therapy. Allergy. 1992 Aug;47(4 Pt 2):439-40. Pubmed
External Links
ResourceLink
KEGG DrugD00256
KEGG CompoundC06877
ChEBI3478
ChEMBLCHEMBL680
Therapeutic Targets DatabaseDAP000442
PharmGKBPA164749137
Drug Product Database2237730
RxListhttp://www.rxlist.com/cgi/generic/cefaclor.htm
Drugs.comhttp://www.drugs.com/cdi/cefaclor.html
WikipediaCefaclor
ATC CodesJ01DC04
AHFS Codes
  • 08:12.06.08
PDB EntriesNot Available
FDA labelshow(186 KB)
MSDSshow(43.9 KB)
Interactions
Drug Interactions
Drug
ProbenecidProbenecid may increase the serum level of cefaclor.
Food Interactions
  • Preferably on an empty stomach, not really problematic.

Targets

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. Chambers HF, Miick C: Characterization of penicillin-binding protein 2 of Staphylococcus aureus: deacylation reaction and identification of two penicillin-binding peptides. Antimicrob Agents Chemother. 1992 Mar;36(3):656-61. Pubmed

2. Penicillin-binding protein 1A

Kind: protein

Organism: Clostridium perfringens (strain 13 / Type A)

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Penicillin-binding protein 1A Q8XJ01 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. 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
  3. Chambers HF, Miick C: Characterization of penicillin-binding protein 2 of Staphylococcus aureus: deacylation reaction and identification of two penicillin-binding peptides. Antimicrob Agents Chemother. 1992 Mar;36(3):656-61. Pubmed
  4. Li M, Anderson GD, Phillips BR, Kong W, Shen DD, Wang J: Interactions of amoxicillin and cefaclor with human renal organic anion and peptide transporters. Drug Metab Dispos. 2006 Apr;34(4):547-55. Epub 2006 Jan 24. Pubmed
  5. Li M, Anderson GD, Phillips BR, Kong W, Shen DD, Wang J: Interactions of amoxicillin and cefaclor with human renal organic anion and peptide transporters. Drug Metab Dispos. 2006 Apr;34(4):547-55. Epub 2006 Jan 24. Pubmed
  6. Li M, Anderson GD, Phillips BR, Kong W, Shen DD, Wang J: Interactions of amoxicillin and cefaclor with human renal organic anion and peptide transporters. Drug Metab Dispos. 2006 Apr;34(4):547-55. Epub 2006 Jan 24. Pubmed
  7. Li M, Anderson GD, Phillips BR, Kong W, Shen DD, Wang J: Interactions of amoxicillin and cefaclor with human renal organic anion and peptide transporters. Drug Metab Dispos. 2006 Apr;34(4):547-55. Epub 2006 Jan 24. Pubmed
  8. Li M, Anderson GD, Phillips BR, Kong W, Shen DD, Wang J: Interactions of amoxicillin and cefaclor with human renal organic anion and peptide transporters. Drug Metab Dispos. 2006 Apr;34(4):547-55. Epub 2006 Jan 24. Pubmed
  9. Li M, Anderson GD, Phillips BR, Kong W, Shen DD, Wang J: Interactions of amoxicillin and cefaclor with human renal organic anion and peptide transporters. Drug Metab Dispos. 2006 Apr;34(4):547-55. Epub 2006 Jan 24. Pubmed
  10. Li M, Anderson GD, Phillips BR, Kong W, Shen DD, Wang J: Interactions of amoxicillin and cefaclor with human renal organic anion and peptide transporters. Drug Metab Dispos. 2006 Apr;34(4):547-55. Epub 2006 Jan 24. Pubmed
  11. Li M, Anderson GD, Phillips BR, Kong W, Shen DD, Wang J: Interactions of amoxicillin and cefaclor with human renal organic anion and peptide transporters. Drug Metab Dispos. 2006 Apr;34(4):547-55. Epub 2006 Jan 24. Pubmed
  12. Li M, Anderson GD, Phillips BR, Kong W, Shen DD, Wang J: Interactions of amoxicillin and cefaclor with human renal organic anion and peptide transporters. Drug Metab Dispos. 2006 Apr;34(4):547-55. Epub 2006 Jan 24. Pubmed
  13. Li M, Anderson GD, Phillips BR, Kong W, Shen DD, Wang J: Interactions of amoxicillin and cefaclor with human renal organic anion and peptide transporters. Drug Metab Dispos. 2006 Apr;34(4):547-55. Epub 2006 Jan 24. Pubmed

Enzymes

1. Myeloperoxidase

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inducer

Components

Name UniProt ID Details
Myeloperoxidase P05164 Details

References:

  1. Zuccotti G, Dauria E, Torcoletti M, Lodi F, Bernardo L, Riva E: Clinical and pro-host effects of cefaclor in prophylaxis of recurrent otitis media in HIV-infected children. J Int Med Res. 2001 Jul-Aug;29(4):349-54. Pubmed

Transporters

1. Solute carrier family 15 member 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

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

References:

  1. 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
  2. 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
  3. Li M, Anderson GD, Phillips BR, Kong W, Shen DD, Wang J: Interactions of amoxicillin and cefaclor with human renal organic anion and peptide transporters. Drug Metab Dispos. 2006 Apr;34(4):547-55. Epub 2006 Jan 24. Pubmed

2. 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. 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
    #Li, M. et al. Interactions of amoxicillin and cefaclor with human renal organic anion and peptide transporters. Drug Metab Dispos 34, 547-555 (2006).
    Pubmed

Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:12