Cefadroxil, a New Broad-Spectrum Cephalosporin

Buck, R. E.; Price, K. E.

doi:10.1128/aac.11.2.324

Cited by 104 publications

(35 citation statements)

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“…Excluding S. epidermidis, most organisms were inhibited by concentrations of antibiotics that could be achieved in serum with oral administration. Buck and Price have reported similar results (3). In addition to these observations, the cefadroxil concentration in urine was maintained well above the MIC of all organisms tested (except for the unusual resistant S. epidermidis isolates) for 12 h and, in most instances, for 18 h. In contrast, 6 h after ingestion, the cephalexin concentration in urine was relatively low.…”

Section: Methodssupporting

confidence: 47%

“…Cefadroxil, the para-hydroxy analog of cephalexin, is a new oral semisynthetic cephalosporin possessing antimicrobial activity against most strains of Streptococcus pneumoniae, Streptococcus pyogenes, Escherichia coli, Klebsiella species, and penicillin-sensitive and -resistant Staphylococcus aureus (3). Below are results of absorption and excretion studies of cefadroxil and cephalexin in human volunteers.…”

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confidence: 99%

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Comparison of Pharmacological and Antimicrobial Properties of Cefadroxil and Cephalexin

Hartstein

Patrick

Jones

et al. 1977

Antimicrob Agents Chemother

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Pharmacological and antimicrobial properties of cefadroxil, a new cephalosporin antibiotic, were compared with cephalexin. Absorption and excretion were studied in 20 healthy men. Peak concentrations of the drugs in serum were similar after ingestion of single 500-mg tablets. The concentration of cefadroxil in serum was more sustained than that of cephalexin. Levels of cefadroxil in serum after a dose of 1,000 mg were approximately twice those after a 500-mg dose through 6 h. Each drug administered in a dose of 500 mg every 6 h for 24 h resulted in concentrations in serum that were similar to a single dose without accumulation. Ninety-three percent of the cefadroxil and 85% of the cephalexin were excreted in urine after ingestions of single 500-mg tablets. The urine concentration of cefadroxil was more sustained than cephalexin. Minimal inhibitory and minimal bactericidal concentrations for clinical isolates were comparable with each drug. Cefadroxil compares favorably with cephalexin in this study. Sustained levels of cefadroxil in serum and urine suggest that this drug may be given at less frequent intervals than cephalexin.

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Section: Methodssupporting

confidence: 47%

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confidence: 99%

Comparison of Pharmacological and Antimicrobial Properties of Cefadroxil and Cephalexin

Hartstein

Patrick

Jones

et al. 1977

Antimicrob Agents Chemother

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“…Cephalexin (4), cefadroxil (7), cefaclor (4,21), cefroxadine (34), and cefatrizine (22) have been widely used for clinical purposes as oral cephalosporins, but their usage is limited because they have relatively narrow spectra against various strains of pathogenic bacteria and are hydrolyzed by 1-lactamases. BK-218, 5-thia-1-azabicyclo [ Fig.…”

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In vitro investigation of BK-218, a new oral and parenteral cephalosporin

Szabó

Barabás

Tar

et al. 1990

Antimicrob Agents Chemother

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The antibacterial activity of BK-218 was similar to that of cefamandole when it was tested against several laboratory strains. The inhibiting effect of BK-218 was greater than that of cephalexin and cefoxitin on penicillin-binding proteins of Escherichia col HB101. This result was in close correlation with the relative inhibition of radiolabeled glucosamine incorporation (greatest with BK-218) and with the lytic effect (most intensive with BK-218). BK-218 proved to be a good inhibitor for all five of the ,-lactamases that were investigated, although two enzymes (Enterobacter cloacae P99 and Pseudomonas aeruginosa Cilote) hydrolyzed it to some extent.Cephalexin (4), cefadroxil (7), cefaclor (4,21), cefroxadine (34), and cefatrizine (22) (Fig. 1.), is a new oral cephalosporin.It is well-known that beta-lactam antibiotics first bind to their targets, the so-called penicillin-binding proteins (PBPs). The inhibition of these enzymes suspends peptidoglycan synthesis, and as a consequence the autolytic enzymes are triggered with a mechanism whose details are not completely understood (16).The purpose of this study was to report the results of preliminary investigations concerning the in vitro activity of BK-218 against a limited number of gram-positive and gramnegative bacteria. The MICs of BK-218 were compared with those of other parenteral (cefuroxime, cefamandole, and cefoxitin) and oral (cephalexin) antibiotics.The in vitro effect on the targets was measured by (i) affinity to PBPs, (ii) incorporation of labeled glucosamine into the cell wall of Escherichia coli, and (iii) release of labeled glucosamine-containing fragments from prelabeled cell wall of E. coli to assess the lysis capability of BK-218.

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“…The mother liquor was concentrated to 10 ml, treated with 20 ml of acetone and allowed to stand overnight in a refrigerator to afford crystalline precipitate, which was collected by filtration and dried in vacuo over P2O5 to give 670 mg of the second crop of 6d as prisms. The total yield of6d was 4.76g (40%): IR *££ cm"1 1750, 1680, 1560, 1520, 1460, 1390, 1350, 1270, 1235; UV^max (pH 7 phosphate buffer) nm (e) 228 (12,300), 279 (9,800); *H NMR (D2O+ NaHCO3) 8 The second fraction from the preparative HPLCwas concentrated to 500 ml. The concentrate was adjusted to pH 3 with dilute HC1 and chromatographed on an Diaion HP-20 column (100 ml) by eluting with 1 liter each of H2Oand 30% MeOH.The latter eluate (about 300 ml) was concentrated to 10 ml and lyophilized to give 290 mg of the crude trans isomer 7d (55% pure).…”

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Synthesis and structure-activity relationships of a new oral cephalosporin, BMY-28100 and related compounds.

et al. 1987

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The synthesis and structure-activity relationships of 7-[D-a-amino-a-(4-hydroxyphenyl)-acetamido]-3-[(Z)-l-propenyl]-3-cephem-4-carboxylic acid (BMY-28100) and its analogs in the 3-and 7-side chains are described. The 3-(substituted-propenyl) groups were introduced by the Wittig reaction of the 3-phosphoniomethyl cephems which were derived from the 3-chloromethyl derivatives. The reaction gave predominantly the cis isomer regarding the 3-side chain. The cis and trans isomers showed characteristic UV and 1H NMRspectra. Most of cephems of this series were well-absorbed orally and more active both in vitro and in vivo than cephalexin and cefaclor against Gram-positive organisms. Their Gram-negative activity varied depending on the 3-and 7-substituents.Compounds with a c/s-propenyl group showed the best Gram-negative activity among the 3-alkenyl analogs prepared, whereas the D-4-hydroxyphenylglycyl and D-4-hydroxy-3-methoxyphenylglycyl substitutions in the 7-side chain were found suitable to improve the Gram-negative activity of 3-cw-propenyl series of cephalosporins to the level favorably compared with that of cefaclor. The 3,4-dihydroxyphenyl analog was found to be metabolized in vivo to the 4-hydroxy-3-methoxyphenyl derivative and, therefore, showed nearly the same in vivo activity as that of the latter. BMY-28100was selected for further evaluation and the results will be reported in the subsequent paper.Since cephaloglycin1'^was launched in 1965, several oral cephalosporins have been developed for clinical use, such as cephalexin3), cephradine4), cefatrizine5) , cefaclor6), cefroxadine70 and cefadroxil8), which have a phenylglycyl (or its congener) or 4-hydroxyphenylglycyl group at the 7 position of cephalosporin nucleus. In our search for new orally active cephalosporins, we found that the 3-alkenyl derivatives of 7-phenylglycyl cephalosporins were well absorbed by oral administration. The representative member of this group is 7-[D-a-amino-a-(4-hydroxyphenyl)acetamido]-3-[(Z)-l-propenyl]-3-cephem-4-carboxylic acid designated as BMY-28100 (Fig.

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Cefadroxil, a New Broad-Spectrum Cephalosporin

Cited by 104 publications

References 6 publications

Comparison of Pharmacological and Antimicrobial Properties of Cefadroxil and Cephalexin

Comparison of Pharmacological and Antimicrobial Properties of Cefadroxil and Cephalexin

In vitro investigation of BK-218, a new oral and parenteral cephalosporin

Synthesis and structure-activity relationships of a new oral cephalosporin, BMY-28100 and related compounds.

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