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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
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ceclorcapsule250 mgoralPendopharm Division Of De Pharmascience IncNot AvailableNot AvailableCanada
Ceclorcapsule500 mgoralPendopharm Division Of De Pharmascience IncNot AvailableNot AvailableCanada
Ceclorpowder for suspension375 mgoralPendopharm Division Of De Pharmascience IncNot AvailableNot AvailableCanada
Ceclorpowder for suspension125 mgoralPendopharm Division Of De Pharmascience IncNot AvailableNot AvailableCanada
Ceclorpowder for suspension250 mgoralPendopharm Division Of De Pharmascience IncNot AvailableNot AvailableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Cefaclortablet, film coated, extended release500 mgoralTeva Pharmaceuticals USA Inc2002-09-26Not AvailableUs
Cefaclorcapsule250 mgoralWest ward Pharmaceutical Corp2007-05-01Not AvailableUs
Cefaclorcapsule500 mgoralWest ward Pharmaceutical Corp2007-05-01Not AvailableUs
Cefaclorsuspension125 mg/5mLoralPACK Pharmaceuticals, LLC2012-10-25Not AvailableUs
Cefaclorsuspension250 mg/5mLoralPACK Pharmaceuticals, LLC2012-10-31Not AvailableUs
Cefaclorsuspension375 mg/5mLoralPACK Pharmaceuticals, LLC2012-10-31Not AvailableUs
Cefaclorsuspension250 mg/5mLoralRebel Distributors Corp1997-10-02Not AvailableUs
Cefaclorcapsule500 mgoralPd Rx Pharmaceuticals, Inc.2007-05-01Not AvailableUs
Cefaclorcapsule250 mgoralAlvogen, Inc.2010-01-18Not AvailableUs
Cefaclorcapsule500 mgoralAlvogen, Inc.2010-01-18Not AvailableUs
Cefaclorcapsule250 mgoralA S Medication Solutions Llc2007-05-01Not AvailableUs
Cefaclorcapsule500 mgoralA S Medication Solutions Llc2007-05-01Not AvailableUs
Cefaclorcapsule250 mgoralPhysicians Total Care, Inc.1996-01-24Not AvailableUs
Cefaclorcapsule500 mgoralPhysicians Total Care, Inc.1995-04-05Not AvailableUs
Cefaclorcapsule250 mgoralCarlsbad Technology, Inc.2008-07-31Not AvailableUs
Cefaclorcapsule500 mgoralCarlsbad Technology, Inc.2008-07-31Not AvailableUs
Cefaclorsuspension125 mg/5mLoralCarlsbad Technology, Inc.2012-03-27Not AvailableUs
Cefaclorsuspension187 mg/5mLoralCarlsbad Technology, Inc.2012-03-27Not AvailableUs
Cefaclorsuspension250 mg/5mLoralCarlsbad Technology, Inc.2012-03-27Not AvailableUs
Cefaclorsuspension375 mg/5mLoralCarlsbad Technology, Inc.2012-03-27Not AvailableUs
Cefaclorcapsule250 mgoralbryant ranch prepack2009-11-06Not AvailableUs
Cefaclorcapsule250 mgoralbryant ranch prepack2007-05-01Not AvailableUs
Over the Counter ProductsNot Available
International Brands
NameCompany
AlenfralChoseido Pharmaceutical
AlfacetGalenika
AlfatilDexo
Alfatil LPDexo
Ceclor CDLilly
DistaclorFlynn
KeflorAlphapharm
KefralShionogi Seiyaku
PanacefValeas
PanoralEberth
RaniclorRanbaxy Pharmaceuticals Inc.
Brand mixturesNot Available
SaltsNot 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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 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 moiety or a derivative thereof.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassBeta lactams
Direct ParentCephalosporins
Alternative Parents
Substituents
  • Cephalosporin
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Phenylacetamide
  • Alpha-amino acid or derivatives
  • Aralkylamine
  • Benzenoid
  • Monocyclic benzene moiety
  • Meta-thiazine
  • Vinylogous halide
  • Tertiary carboxylic acid amide
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azetidine
  • Azacycle
  • Chloroalkene
  • Haloalkene
  • Dialkylthioether
  • Vinyl halide
  • Vinyl chloride
  • Hemithioaminal
  • Thioether
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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
PropertyValueProbability
Human Intestinal Absorption-0.8839
Blood Brain Barrier-0.9817
Caco-2 permeable-0.8239
P-glycoprotein substrateSubstrate0.6569
P-glycoprotein inhibitor INon-inhibitor0.9413
P-glycoprotein inhibitor IINon-inhibitor0.9955
Renal organic cation transporterNon-inhibitor0.9369
CYP450 2C9 substrateNon-substrate0.8314
CYP450 2D6 substrateNon-substrate0.8361
CYP450 3A4 substrateNon-substrate0.5597
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 substrateNon-inhibitor0.907
CYP450 2D6 substrateNon-inhibitor0.9236
CYP450 2C19 substrateNon-inhibitor0.9026
CYP450 3A4 substrateNon-inhibitor0.831
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9193
Ames testNon AMES toxic0.6676
CarcinogenicityNon-carcinogens0.8489
BiodegradationNot ready biodegradable1.0
Rat acute toxicity1.2960 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9966
hERG inhibition (predictor II)Non-inhibitor0.85
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
Capsuleoral250 mg
Capsuleoral500 mg
Powder for suspensionoral125 mg
Powder for suspensionoral250 mg
Powder for suspensionoral375 mg
Suspensionoral125 mg/5mL
Suspensionoral187 mg/5mL
Suspensionoral250 mg/5mL
Suspensionoral375 mg/5mL
Tablet, film coated, extended releaseoral500 mg
Prices
Unit descriptionCostUnit
Ceclor 15 500 mg capsule Bottle70.0USD bottle
Ceclor 375 mg/5ml Suspension 100ml Bottle59.99USD bottle
Ceclor 250 mg/5ml Suspension 150ml Bottle58.98USD bottle
Cefaclor 250 mg/5ml Suspension 150ml Bottle53.87USD bottle
Cefaclor 375 mg/5ml Suspension 100ml Bottle53.87USD bottle
Ceclor 15 250 mg capsule Bottle38.0USD bottle
Ceclor 125 mg/5ml Suspension 150ml Bottle34.99USD bottle
Ceclor 187 mg/5ml Suspension 100ml Bottle34.99USD bottle
Ceclor 250 mg/5ml Suspension 75ml Bottle31.99USD bottle
Cefaclor 125 mg/5ml Suspension 150ml Bottle29.41USD bottle
Cefaclor 250 mg/5ml Suspension 75ml Bottle29.37USD bottle
Cefaclor 187 mg/5ml Suspension 100ml Bottle29.26USD bottle
Cefaclor 375 mg/5ml Suspension 50ml Bottle27.44USD bottle
Cefaclor 187 mg/5ml Suspension 50ml Bottle14.92USD bottle
Cefaclor 125 mg/5ml Suspension 75ml Bottle14.7USD bottle
Ceclor 500 mg pulvule5.69USD each
Cefaclor 500 mg capsule4.05USD capsule
Cefaclor CR 500 mg 12 Hour tablet3.79USD tablet
Ceclor 250 mg pulvule3.28USD each
Raniclor 375 mg chewable tablet2.98USD tablet
Cefaclor 250 mg capsule2.07USD capsule
Raniclor 250 mg chewable tablet1.99USD tablet
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 Solubility0.21 mg/mLALOGPS
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 Area112.73 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity89.56 m3·mol-1ChemAxon
Polarizability35.11 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
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
ATC CodesJ01DC04
AHFS Codes
  • 08:12.06.08
PDB EntriesNot Available
FDA labelDownload (186 KB)
MSDSDownload (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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:12