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 6502		4.52 mM [Ki]
Bacterial penicillin-binding protein 218	Inhibitor 6502	Pharyngitis
Canalicular multispecific organic anion transporter 1 11	Inhibitor 6502		1.15 mM [Ki]
Solute carrier family 15 member 2 7	Inhibitor 6502		65.0 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Skin Infections, Staphylococcal 23	Primary	Bacterial penicillin-binding protein	Approved 7817	CEFACLOR
Tonsillitis 36	Primary	Bacterial penicillin-binding protein	Approved 7817	CEFACLOR
Urinary Tract Infections 221	Primary	Bacterial penicillin-binding protein	Approved 7817	CEFACLOR
Pharyngitis 45	Primary	Bacterial penicillin-binding protein	Approved 7817	CEFACLOR
Otitis Media 74	Primary	Bacterial penicillin-binding protein	Approved 7817	CEFACLOR
Respiratory Tract Infections 125	Primary	Bacterial penicillin-binding protein	Approved 7817	CEFACLOR

PubMed

Title	Date	PubMed
Antibiotic susceptibilities among recent clinical isolates of Haemophilus influenzae and Moraxella catarrhalis from fifteen countries.	2001 Jan	11245326
Susceptibility of Canadian isolates of Haemophilus influenzae, Moraxella catarrhalis and Streptococcus pneumoniae to oral antimicrobial agents.	2001 Jun	11397615
What have we learned from pharmacokinetic and pharmacodynamic theories?	2001 Mar 15	11249828
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.	2001 Nov	11792017
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	12218263
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
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
Antimicrobial resistance in Gram-negative bacteria from Intensive Care Units and Urology Services. A nationwide study in The Netherlands 1995-2000.	2003 Jun	12791468
How can we predict bacterial eradication?	2003 Mar	12839703
Surveillance of antibiotic resistance in clinical isolates of Streptococcus pneumoniae collected in Belgium during winter 2000-2001.	2003 Mar-Apr	12836494
[Report of questionnaire survey for methicillin-resistant Staphylococcus aureus and penisillin-resistant Streptococcus pneumoniae between 1998 and 2000 in the Kinki district].	2003 May	12806929
[Hypersensitivity reactions to beta-lactam antibiotics in childhood].	2003 May-Jun	12783760

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