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targets (2) transporters (2)
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Identification
Name Cefaclor
Accession Number DB00833 (APRD00243)
Type small molecule
Groups approved
Description

Semisynthetic, broad-spectrum antibiotic derivative of cephalexin. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • CCL
  • Cefaclor anhydrous
  • Cefaclorum [INN-Latin]
  • Cephaclor
Brand names
  • Alenfral
  • Alfacet
  • Alfatil
  • Ceclor
  • Ceclor CD
  • Distaclor
  • Kefral
  • Panacef
  • Panoral
  • Raniclor
Brand name mixtures Not Available
Categories
  • Anti-Bacterial Agents
  • Cephalosporins
CAS number 53994-73-3
Weight Average: 367.807
Monoisotopic: 367.039354348
Chemical Formula C15H14ClN3O4S
InChI Key InChIKey=QYIYFLOTGYLRGG-WUMONGPASA-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
Plain Text
IUPAC Name
(6R,7R)-7-(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(N)C1=CC=CC=C1)C(O)=O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Phenethylamines
  • Cephalosporins
Substructures
  • Hydroxy Compounds
  • Acetates
  • Amino Ketones
  • Carboxylic Acids and Derivatives
  • Aliphatic and Aryl Amines
  • Halogen Derivatives
  • Benzene and Derivatives
  • Beta Lactams
  • Phenethylamines
  • Heterocyclic compounds
  • Aromatic compounds
  • Carboxamides and Derivatives
  • Cephalosporins
  • Lactams
  • Azetidines
Pharmacology
Indication For the treatment of certain infections caused by bacteria such as pneumonia and ear, lung, skin, throat, and urinary tract infections.
Pharmacodynamics Cefaclor 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 action Cefaclor, 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.
Absorption Well absorbed after oral administration, independent of food intake.
Volume of distribution Not Available
Protein binding 23.5%
Metabolism

No appreciable biotransformation in liver (approximately 60% to 85% of the drug is excreted unchanged in the urine within 8 hours).
Route of elimination Approximately 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 life 0.6-0.9 hour
Clearance Not Available
Toxicity Symptoms of overdose include diarrhea, nausea, stomach upset, and vomiting.
Affected organisms
  • Enteric bacteria and other eubacteria
Pathways Not Available
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
Form Route Strength
Capsule Oral
Powder Oral
Powder, for solution Oral
Powder, for suspension Oral
Suspension Oral
Prices
Unit description Cost Unit
Ceclor 15 500 mg capsule Bottle 70.0 USD bottle
Ceclor 375 mg/5ml Suspension 100ml Bottle 59.99 USD bottle
Ceclor 250 mg/5ml Suspension 150ml Bottle 58.98 USD bottle
Cefaclor 250 mg/5ml Suspension 150ml Bottle 53.87 USD bottle
Cefaclor 375 mg/5ml Suspension 100ml Bottle 53.87 USD bottle
Ceclor 15 250 mg capsule Bottle 38.0 USD bottle
Ceclor 125 mg/5ml Suspension 150ml Bottle 34.99 USD bottle
Ceclor 187 mg/5ml Suspension 100ml Bottle 34.99 USD bottle
Ceclor 250 mg/5ml Suspension 75ml Bottle 31.99 USD bottle
Cefaclor 125 mg/5ml Suspension 150ml Bottle 29.41 USD bottle
Cefaclor 250 mg/5ml Suspension 75ml Bottle 29.37 USD bottle
Cefaclor 187 mg/5ml Suspension 100ml Bottle 29.26 USD bottle
Cefaclor 375 mg/5ml Suspension 50ml Bottle 27.44 USD bottle
Cefaclor 187 mg/5ml Suspension 50ml Bottle 14.92 USD bottle
Cefaclor 125 mg/5ml Suspension 75ml Bottle 14.7 USD bottle
Ceclor 500 mg pulvule 5.69 USD each
Cefaclor 500 mg capsule 4.05 USD capsule
Cefaclor CR 500 mg 12 Hour tablet 3.79 USD tablet
Ceclor 250 mg pulvule 3.28 USD each
Raniclor 375 mg chewable tablet 2.98 USD tablet
Cefaclor 250 mg capsule 2.07 USD capsule
Raniclor 250 mg chewable tablet 1.99 USD tablet
Patents Not Available
Properties
State solid
Melting point 327 oC
Experimental Properties
Property Value Source
water solubility 8.6 mg/mL PhysProp
logP 0.4 PhysProp
Predicted Properties
Property Value Source
water solubility 2.10e-01 g/l ALOGPS
logP 0.85 ALOGPS
logP -3.88 ChemAxon Molconvert
logS -3.24 ALOGPS
pKa 11.26 ChemAxon Molconvert
hydrogen acceptor count 5 ChemAxon Molconvert
hydrogen donor count 3 ChemAxon Molconvert
polar surface area 112.73 ChemAxon Molconvert
rotatable bond count 4 ChemAxon Molconvert
refractivity 89.56 ChemAxon Molconvert
polarizability 34.29 ChemAxon Molconvert
References
Synthesis Reference Not Available
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
Resource Link
KEGG Drug D00256 Link_out
KEGG Compound C06877 Link_out
PubChem Compound 40958 Link_out
PubChem Substance 46507693 Link_out
ChemSpider 37396 Link_out
ChEBI 3478 Link_out
ChEMBL 3478 Link_out
Therapeutic Targets Database DAP000442 Link_out
PharmGKB PA448833 Link_out
Drug Product Database 2237730 Link_out
RxList http://www.rxlist.com/cgi/generic/cefaclor.htm Link_out
Drugs.com http://www.drugs.com/cdi/cefaclor.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Cefaclor Link_out
ATC Codes
  • J01DC04
AHFS Codes
  • 08:12.06.08
PDB Entries Not Available
FDA label show (186.3 KB)
MSDS show (43.9 KB)
Interactions
Drug Interactions Not Available
Food Interactions
  • Preferably on an empty stomach, not really problematic.
Targets

1. Penicillin-binding protein 3

Pharmacological action: yes
Actions: inhibitor
UniProt ID: Q75Y35 Link_out
Gene: pbp3
SNPs: SNPJam Report Link_out

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 proteins 1A/1B

Pharmacological action: yes
Actions: inhibitor
Organism class: bacterial
UniProt ID: Q8XJ01 Link_out
Gene: pbpA
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Transporters

1. Oligopeptide transporter, small intestine isoform

Actions: inhibitor

Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products

UniProt ID: P46059 Link_out
Gene: SLC15A1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

2. Oligopeptide transporter, kidney isoform

Actions: inhibitor

Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides

UniProt ID: Q16348 Link_out
Gene: SLC15A2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Comments
Drug created on June 13, 2005 07:24 / Updated on April 19, 2011 15:06

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.