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 6467		4.52 mM [Ki]
Bacterial penicillin-binding protein 217	Inhibitor 6467	Pharyngitis
Canalicular multispecific organic anion transporter 1 11	Inhibitor 6467		1.15 mM [Ki]
Solute carrier family 15 member 2 7	Inhibitor 6467		65.0 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Skin Infections, Staphylococcal 20	Primary	Bacterial penicillin-binding protein	Approved 7678	CEFACLOR
Tonsillitis 36	Primary	Bacterial penicillin-binding protein	Approved 7678	CEFACLOR
Urinary Tract Infections 219	Primary	Bacterial penicillin-binding protein	Approved 7678	CEFACLOR
Pharyngitis 45	Primary	Bacterial penicillin-binding protein	Approved 7678	CEFACLOR
Otitis Media 74	Primary	Bacterial penicillin-binding protein	Approved 7678	CEFACLOR
Respiratory Tract Infections 125	Primary	Bacterial penicillin-binding protein	Approved 7678	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
In vitro antibacterial activities of DQ-113, a potent quinolone, against clinical isolates.	2002 Mar	11850285
beta-Lactam allergenic determinants: fine structural recognition of a cross-reacting determinant on benzylpenicillin and cephalothin.	2002 Nov	12569987
[Antimicrobial susceptibility of Streptococcus pneumoniae and Haemophilus influenzae isolated in major hospitals in Nagano Prefecture].	2002 Oct	12532636
Natural antibiotic susceptibility of Enterobacter amnigenus, Enterobacter cancerogenus, Enterobacter gergoviae and Enterobacter sakazakii strains.	2002 Sep	12427217
Life-threatening infantile diarrhea from fluoroquinolone-resistant Salmonella enterica typhimurium with mutations in both gyrA and parC.	2003 Feb	12604000

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