U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
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
Immunoglobulin E binding determinants on beta-lactam drugs.
2002 Aug
Comparative efficacy and safety of 5-day cefaclor and 10-day amoxycillin treatment of group A streptococcal pharyngitis in children.
2002 Jul
Effect of a short course of clarithromycin therapy on sputum production in patients with chronic airway hypersecretion.
2002 Jul
[Microbiological and clinical studies of Haemophilus influenzae isolated at Kitakyushu Municipal Medical Center from 1996 through 1999].
2002 Jun
The fecal microflora of 1-3-month-old infants during treatment with eight oral antibiotics.
2002 Jun
beta-Lactam allergenic determinants: fine structural recognition of a cross-reacting determinant on benzylpenicillin and cephalothin.
2002 Nov
Life-threatening infantile diarrhea from fluoroquinolone-resistant Salmonella enterica typhimurium with mutations in both gyrA and parC.
2003 Feb
Reactive metabolites and adverse drug reactions: clinical considerations.
2003 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 Mon Oct 21 22:33:23 UTC 2019 , Edited by admin on Mon Oct 21 22:33:23 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 22:33:23 UTC 2019 , Edited by admin on Mon Oct 21 22:33:23 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 22:33:23 UTC 2019 , Edited by admin on Mon Oct 21 22:33:23 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 22:33:23 UTC 2019 , Edited by admin on Mon Oct 21 22:33:23 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 22:33:23 UTC 2019 , Edited by admin on Mon Oct 21 22:33:23 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 22:33:23 UTC 2019 , Edited by admin on Mon Oct 21 22:33:23 UTC 2019
WHO-ATC J01DC04
Created by admin on Mon Oct 21 22:33:23 UTC 2019 , Edited by admin on Mon Oct 21 22:33:23 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 22:33:23 UTC 2019 , Edited by admin on Mon Oct 21 22:33:23 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 22:33:23 UTC 2019 , Edited by admin on Mon Oct 21 22:33:23 UTC 2019
NCI_THESAURUS C357
Created by admin on Mon Oct 21 22:33:23 UTC 2019 , Edited by admin on Mon Oct 21 22:33:23 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 22:33:23 UTC 2019 , Edited by admin on Mon Oct 21 22:33:23 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 22:33:23 UTC 2019 , Edited by admin on Mon Oct 21 22:33:23 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 22:33:23 UTC 2019 , Edited by admin on Mon Oct 21 22:33:23 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 22:33:23 UTC 2019 , Edited by admin on Mon Oct 21 22:33:23 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 22:33:23 UTC 2019 , Edited by admin on Mon Oct 21 22:33:23 UTC 2019
Code System Code Type Description
CAS
53994-73-3
Created by admin on Mon Oct 21 22:33:23 UTC 2019 , Edited by admin on Mon Oct 21 22:33:23 UTC 2019
PRIMARY
INN
4086
Created by admin on Mon Oct 21 22:33:23 UTC 2019 , Edited by admin on Mon Oct 21 22:33:23 UTC 2019
PRIMARY
NCI_THESAURUS
C76033
Created by admin on Mon Oct 21 22:33:23 UTC 2019 , Edited by admin on Mon Oct 21 22:33:23 UTC 2019
PRIMARY
EVMPD
SUB06163MIG
Created by admin on Mon Oct 21 22:33:23 UTC 2019 , Edited by admin on Mon Oct 21 22:33:23 UTC 2019
PRIMARY
DRUG BANK
DB00833
Created by admin on Mon Oct 21 22:33:23 UTC 2019 , Edited by admin on Mon Oct 21 22:33:23 UTC 2019
PRIMARY
RXCUI
1450910
Created by admin on Mon Oct 21 22:33:23 UTC 2019 , Edited by admin on Mon Oct 21 22:33:23 UTC 2019
PRIMARY RxNorm
LactMed
53994-73-3
Created by admin on Mon Oct 21 22:33:23 UTC 2019 , Edited by admin on Mon Oct 21 22:33:23 UTC 2019
PRIMARY
EPA CompTox
53994-73-3
Created by admin on Mon Oct 21 22:33:23 UTC 2019 , Edited by admin on Mon Oct 21 22:33:23 UTC 2019
PRIMARY
MERCK INDEX
M3184
Created by admin on Mon Oct 21 22:33:23 UTC 2019 , Edited by admin on Mon Oct 21 22:33:23 UTC 2019
PRIMARY Merck Index
ECHA (EC/EINECS)
258-909-5
Created by admin on Mon Oct 21 22:33:23 UTC 2019 , Edited by admin on Mon Oct 21 22:33:23 UTC 2019
PRIMARY
PUBCHEM
51039
Created by admin on Mon Oct 21 22:33:23 UTC 2019 , Edited by admin on Mon Oct 21 22:33:23 UTC 2019
PRIMARY