CEFACLOR ANHYDROUS

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 Search

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

Targets

Primary Target	Pharmacology	Condition	Potency
Oligopeptide transporter small intestine isoform 5	Inhibitor 7468		4.52 mM [Ki]
Bacterial penicillin-binding protein 223	Inhibitor 7468	Pharyngitis
Canalicular multispecific organic anion transporter 1 19	Inhibitor 7468		1.15 mM [Ki]
Solute carrier family 15 member 2 7	Inhibitor 7468		65.0 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Skin Infections, Staphylococcal 23	Primary	Bacterial penicillin-binding protein	Approved 7883	CEFACLOR
Tonsillitis 37	Primary	Bacterial penicillin-binding protein	Approved 7883	CEFACLOR
Urinary Tract Infections 227	Primary	Bacterial penicillin-binding protein	Approved 7883	CEFACLOR
Pharyngitis 45	Primary	Bacterial penicillin-binding protein	Approved 7883	CEFACLOR
Otitis Media 77	Primary	Bacterial penicillin-binding protein	Approved 7883	CEFACLOR
Respiratory Tract Infections 127	Primary	Bacterial penicillin-binding protein	Approved 7883	CEFACLOR

PubMed

Title	Date	PubMed
Oral pharmacokinetics of cefaclor in Mexican subjects.	2001	11797648
Encouraging good antimicrobial prescribing practice: a review of antibiotic prescribing policies used in the South East Region of England.	2001	11388888
Cefpodoxime proxetil: a review of its use in the management of bacterial infections in paediatric patients.	2001	11269640
Immunopharmacology of antibiotics: direct and indirect immunomodulation of defence mechanisms.	2001 Apr	11330355
Recurrent temporal petrositis.	2001 Apr	11276339
Desirable and undesirable immunotropic effects of antibiotics: immunomodulating properties of cefaclor.	2001 Dec	11806622
Antibiotic susceptibilities among recent clinical isolates of Haemophilus influenzae and Moraxella catarrhalis from fifteen countries.	2001 Jan	11245326
Spectrophotometric determination of selected cephalosporins in drug formulations using flow injection analysis.	2001 Jul	11377057
Evaluation of oral antimicrobial agent levels in tooth extraction sites.	2001 Jun	11402275
What have we learned from pharmacokinetic and pharmacodynamic theories?	2001 Mar 15	11249828
In vitro and in vivo antibacterial activity and pharmacokinetics of SC-002 and its derivative, SC-004: new oral cephalosporins.	2001 May-Jun	11306784
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.	2001 Nov	11792017
Tolerability of 3-day, once-daily azithromycin suspension versus standard treatments for community-acquired paediatric infectious diseases.	2001 Nov	11711256
Antimicrobial susceptibility of Haemophilus influenzae among children in Beijing, China, 1999-2000.	2002	11951998
Cefdinir: an advanced-generation, broad-spectrum oral cephalosporin.	2002 Apr	12017394
Immunoglobulin E binding determinants on beta-lactam drugs.	2002 Aug	12130943
An unusual abdominal mass in a renal transplant recipient.	2002 Dec	12535266
Determination of antimicrobial activity of Cefaclor on common respiratory tract pathogens in Pakistan.	2002 Jan	11963587
Comparative study of cefaclor AF vs. cefuroxime axetil in acute exacerbations of chronic bronchitis.	2002 Jan	11782685
Foreign drug firm pleads guilty to felony charges.	2002 Jan-Feb	11881596
Antibacterial activity of oral antibiotics against community-acquired respiratory pathogens from three European countries.	2002 Jul	12077154
Susceptibility change to antibiotics of Staphylococcus aureus strains isolated from skin infections between July 1994 and November 2000.	2002 Jun	12111576
Serum sickness-like reactions.	2002 May	12041822
beta-Lactam allergenic determinants: fine structural recognition of a cross-reacting determinant on benzylpenicillin and cephalothin.	2002 Nov	12569987
A case of purpuric drug eruption due to cefaclor.	2002 Nov	12431878
An evaluation of cefaclor in Pakistani children with pharyngotonsillitis.	2002 Oct	12553673
[Antimicrobial susceptibility of Streptococcus pneumoniae and Haemophilus influenzae isolated in major hospitals in Nagano Prefecture].	2002 Oct	12532636
Cefaclor induced serum sickness like reaction.	2002 Oct	12450309
Serotype distribution and antimicrobial resistance patterns in Streptococcus pneumoniae isolates from hospitalized pediatric patients with respiratory infections in Shanghai, China.	2003 Aug	12913778
Modelling and analysing exchangeable binary data with random cluster sizes.	2003 Aug 15	12872298
[In vitro sensitivity to antimicrobial agents of Haemophilus influenzae strains isolated from clinical specimens].	2003 Jan	12838674
[Antibiotic resistance and serotype distribution of Streptococcus pneumoniae strains isolated from patients at Hacettepe University Medical Faculty].	2003 Jan	12838672
Etiology of acute otitis media in childhood and evaluation of two different protocols of antibiotic therapy: 10 days cefaclor vs. 3 days azitromycin.	2003 Jan	12560149
Effect of extended-spectrum beta-lactamases on the susceptibility of Haemophilus influenzae to cephalosporins.	2003 Jan	12493785
Sensitive determination of a beta-lactam antibiotic, cefaclor by liquid chromatography with chemiluminescence detection.	2003 Jan 15	12485718
Determination of cefaclor in human plasma by a sensitive and specific liquid chromatographic-tandem mass spectrometric method.	2003 Jan 25	12504178
Natural antibiotic susceptibility of strains of Serratia marcescens and the S. liquefaciens complex: S. liquefaciens sensu stricto, S. proteamaculans and S. grimesii.	2003 Jul	12842326
How can we predict bacterial eradication?	2003 Mar	12839703
Effect of computerised prescribing on use of antibiotics.	2003 Mar 3	12603183

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