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Details

Stereochemistry ABSOLUTE
Molecular Formula C15H14ClN3O4S
Molecular Weight 367.807
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CEFACLOR ANHYDROUS

SMILES

N[C@@H](C(=O)N[C@H]1[C@H]2SCC(Cl)=C(N2C1=O)C(O)=O)C3=CC=CC=C3

InChI

InChIKey=QYIYFLOTGYLRGG-GPCCPHFNSA-N
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

HIDE SMILES / InChI

Description

Cefaclor is a semisynthetic cephalosporin antibiotic for oral administration. As with other cephalosporins, the bactericidal action of Cefaclor results from inhibition of cell-wall synthesis. Cefaclor is indicated in the treatment of the following infections when caused by susceptible strains of the designated microorganisms: Otitis media caused by Streptococcus pneumoniae, Haemophilus influenzae, staphylococci, and Streptococcus pyogenes; Lower respiratory tract infections, including pneumonia, caused by Streptococcus pneumoniae, Haemophilus influenzae, and Streptococcus pyogenes; Pharyngitis and Tonsillitis, caused by Streptococcus pyogenes; Urinary tract infections, including pyelonephritis and cystitis, caused by Escherichia coli, Proteus mirabilis, Klebsiella spp., and coagulase-negative staphylococci; Skin and skin structure infections caused by Staphylococcus aureus and Streptococcus pyogenes. Adverse effects considered to be related to therapy with cefaclor are: Hypersensitivity reactions, Rarely, reversible hyperactivity, agitation, nervousness, insomnia, confusion, hypertonia, dizziness, hallucinations, somnolence and diarrhea. Patients receiving Cefaclor may show a false-positive reaction for glucose in the urine with tests that use Benedict's and Fehling's solutions and also with Clinitest® tablets. There have been reports of increased anticoagulant effect when Cefaclor and oral anticoagulants were administered concomitantly.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Antibiotic susceptibilities among recent clinical isolates of Haemophilus influenzae and Moraxella catarrhalis from fifteen countries.
2001 Jan
Susceptibility of Canadian isolates of Haemophilus influenzae, Moraxella catarrhalis and Streptococcus pneumoniae to oral antimicrobial agents.
2001 Jun
What have we learned from pharmacokinetic and pharmacodynamic theories?
2001 Mar 15
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
Antimicrobial action of Nitens mouthwash (cetyltrimethylammonium naproxenate) on multiple isolates of pharyngeal microbes: a controlled study against chlorhexidine, benzydamine, hexetidine, amoxicillin, amoxicillin-clavulanate, clarithromycin, and cefaclor.
2002 Sep
Serotype distribution and antimicrobial resistance patterns in Streptococcus pneumoniae isolates from hospitalized pediatric patients with respiratory infections in Shanghai, China.
2003 Aug
Modelling and analysing exchangeable binary data with random cluster sizes.
2003 Aug 15
[In vitro sensitivity to antimicrobial agents of Haemophilus influenzae strains isolated from clinical specimens].
2003 Jan
[Antibiotic resistance and serotype distribution of Streptococcus pneumoniae strains isolated from patients at Hacettepe University Medical Faculty].
2003 Jan
Natural antibiotic susceptibility of strains of Serratia marcescens and the S. liquefaciens complex: S. liquefaciens sensu stricto, S. proteamaculans and S. grimesii.
2003 Jul
Antimicrobial resistance in Gram-negative bacteria from Intensive Care Units and Urology Services. A nationwide study in The Netherlands 1995-2000.
2003 Jun
How can we predict bacterial eradication?
2003 Mar
Surveillance of antibiotic resistance in clinical isolates of Streptococcus pneumoniae collected in Belgium during winter 2000-2001.
2003 Mar-Apr
[Report of questionnaire survey for methicillin-resistant Staphylococcus aureus and penisillin-resistant Streptococcus pneumoniae between 1998 and 2000 in the Kinki district].
2003 May
[Hypersensitivity reactions to beta-lactam antibiotics in childhood].
2003 May-Jun
Patents

Sample Use Guides

In Vivo Use Guide
The usual adult dosage is 250 mg every 8 hours. For more severe infections (such as pneumonia) or those caused by less susceptible organisms, doses may be doubled.
Route of Administration: Oral
In Vitro Use Guide
Cefaclor inhibits the gram-negative bacteria. At a level of 12.5 ug/ml, 73% of the E. coli, 90% of the Salmonella, 55% of the Shigella, 77% of the Citrobacter, 91% of the Klebsiella, and 75% of the P. mirabilis isolates were inhibited. However, only 18% of the Enterobacter, 3% of the Serratia, 9% of the Proteus morganii, and 16% of the Providencia strains, and less than 10% of the Proteus vulgaris, Proteus rettgeri, and Bacteroides fragilis isolates, were inhibited. All Pseudomonas strains were as resistant to cefaclor as they were to available cephalosporins.
Name Type Language
CEFACLOR ANHYDROUS
Common Name English
CEFACLOR [MI]
Common Name English
CEFACLOR [INN]
Common Name English
CEFACLOR [JAN]
Common Name English
5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-(((2R)-2-AMINO-2-PHENYLACETYL)AMINO)-3-CHLORO-8-OXO-, (6R,7R)-
Common Name English
CEFACLOR [WHO-DD]
Common Name English
(6R,7R)-7-(((2R)-2-AMINO-2-PHENYLACETYL)AMINO)-3-CHLORO-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID
Systematic Name English
Classification Tree Code System Code
NDF-RT N0000175488
Created by admin on Tue Mar 06 11:22:46 UTC 2018 , Edited by admin on Tue Mar 06 11:22:46 UTC 2018
NDF-RT N0000011161
Created by admin on Tue Mar 06 11:22:46 UTC 2018 , Edited by admin on Tue Mar 06 11:22:46 UTC 2018
NDF-RT N0000011161
Created by admin on Tue Mar 06 11:22:46 UTC 2018 , Edited by admin on Tue Mar 06 11:22:46 UTC 2018
NDF-RT N0000011161
Created by admin on Tue Mar 06 11:22:46 UTC 2018 , Edited by admin on Tue Mar 06 11:22:46 UTC 2018
NDF-RT N0000011161
Created by admin on Tue Mar 06 11:22:46 UTC 2018 , Edited by admin on Tue Mar 06 11:22:46 UTC 2018
NDF-RT N0000011161
Created by admin on Tue Mar 06 11:22:46 UTC 2018 , Edited by admin on Tue Mar 06 11:22:46 UTC 2018
WHO-ATC J01DC04
Created by admin on Tue Mar 06 11:22:46 UTC 2018 , Edited by admin on Tue Mar 06 11:22:46 UTC 2018
NDF-RT N0000011161
Created by admin on Tue Mar 06 11:22:46 UTC 2018 , Edited by admin on Tue Mar 06 11:22:46 UTC 2018
NDF-RT N0000011161
Created by admin on Tue Mar 06 11:22:46 UTC 2018 , Edited by admin on Tue Mar 06 11:22:46 UTC 2018
NDF-RT N0000011161
Created by admin on Tue Mar 06 11:22:46 UTC 2018 , Edited by admin on Tue Mar 06 11:22:46 UTC 2018
NDF-RT N0000011161
Created by admin on Tue Mar 06 11:22:46 UTC 2018 , Edited by admin on Tue Mar 06 11:22:46 UTC 2018
NDF-RT N0000011161
Created by admin on Tue Mar 06 11:22:46 UTC 2018 , Edited by admin on Tue Mar 06 11:22:46 UTC 2018
NDF-RT N0000011161
Created by admin on Tue Mar 06 11:22:46 UTC 2018 , Edited by admin on Tue Mar 06 11:22:46 UTC 2018
NDF-RT N0000011161
Created by admin on Tue Mar 06 11:22:46 UTC 2018 , Edited by admin on Tue Mar 06 11:22:46 UTC 2018
Code System Code Type Description
CAS
53994-73-3
Created by admin on Tue Mar 06 11:22:46 UTC 2018 , Edited by admin on Tue Mar 06 11:22:46 UTC 2018
PRIMARY
INN
4086
Created by admin on Tue Mar 06 11:22:46 UTC 2018 , Edited by admin on Tue Mar 06 11:22:46 UTC 2018
PRIMARY
NCI_THESAURUS
C76033
Created by admin on Tue Mar 06 11:22:46 UTC 2018 , Edited by admin on Tue Mar 06 11:22:46 UTC 2018
PRIMARY
EVMPD
SUB06163MIG
Created by admin on Tue Mar 06 11:22:46 UTC 2018 , Edited by admin on Tue Mar 06 11:22:46 UTC 2018
PRIMARY
DRUG BANK
DB00833
Created by admin on Tue Mar 06 11:22:46 UTC 2018 , Edited by admin on Tue Mar 06 11:22:46 UTC 2018
PRIMARY
RXCUI
1450910
Created by admin on Tue Mar 06 11:22:46 UTC 2018 , Edited by admin on Tue Mar 06 11:22:46 UTC 2018
PRIMARY RxNorm
LactMed
53994-73-3
Created by admin on Tue Mar 06 11:22:46 UTC 2018 , Edited by admin on Tue Mar 06 11:22:46 UTC 2018
PRIMARY
EPA CompTox
53994-73-3
Created by admin on Tue Mar 06 11:22:46 UTC 2018 , Edited by admin on Tue Mar 06 11:22:46 UTC 2018
PRIMARY
MERCK INDEX
M3184
Created by admin on Tue Mar 06 11:22:46 UTC 2018 , Edited by admin on Tue Mar 06 11:22:46 UTC 2018
PRIMARY Merck Index
ECHA (EC/EINECS)
258-909-5
Created by admin on Tue Mar 06 11:22:46 UTC 2018 , Edited by admin on Tue Mar 06 11:22:46 UTC 2018
PRIMARY
PUBCHEM
51039
Created by admin on Tue Mar 06 11:22:46 UTC 2018 , Edited by admin on Tue Mar 06 11:22:46 UTC 2018
PRIMARY SWITZERF