Spectrum Cephalosporin with Antipseudomonal Activity
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1 ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, Feb. 1983, p Vol. 23, No /83/020195S06$02.00/0 Copyright C 1983, American Society for Microbiology In Vitro Antibacterial Activity of, a New Broad- Spectrum Cephalosporin with Antipseudomonal Activity M. FUKASAWA,l H. NOGUCHI,' T. OKUDA,'* T. KOMATSU,' AND K. YANO2 Research Laboratory, Pharmaceuticals Division, Sumitomo Chemical Co. Ltd., Takatsukasa, Takarazuka, Hyogo 665,1 and Central Research Institute, Yamanouchi Pharmaceuticals Co. Ltd., Azusawa, Itabashi-ku, Tokyo 174, Japan2 Received 12 July 1982/Accepted 17 November 1982 (sodium 7-[D(-)-a-(4-hydroxy-6-methylpyridine-3-carboxamido)-a-(4- hydroxyphenyl)acetamido] -3- [(l-methyl-1h-tetrazol-5-yl)thiomethyl] -3- cephem- 4-carboxylate) is a new semisynthetic cephalosporin derivative with a broad spectrum of antibacterial activity. Its in vitro activity against gram-positive bacteria was comparable to that of cefazolin. exceeded cefazolin in potency and broadness of antibacterial activity against such Enterobacteriaceae as indole-positive Proteus spp., Enterobacter cloacae, and Serratia marcescens. A remarkable feature of the spectrum of is its high activity against Pseudomonadaceae. Against 200 clinical isolates of Pseudomonas aeruginosa, was significantly more active than cefoperazone, cefotaxime, and sulbenicilhin and as active as cefsulodin. The activities of against Pseudomonas maltophilia and Pseudomonas cepacia were superior to those of cefoperazone, cefotaxime, cefsulodin, sulbenicillin, and gentamicin. was relatively stable to hydrolysis with plasmid-mediated penicillinases and cephalosporinases produced by gram-negative bacteria. Cephalosporin antibiotics are important chemotherapeutic agents because of their broad antibacterial spectra. However, the incidence of infections caused by bacteria resistant to older cephalosporins has increased recently. Therefore, it has been necessary to develop new cephalosporin antibiotics that have more potent antibacterial activities, broader antibacterial spectra and higher effectiveness against resistant bacteria. Therefore, several new cephalosporin derivatives, such as cefotaxime (1) and cefoperazone (4), have been developed in the last few years. These new cephalosporins have higher stability to,-lactamases, broader antibacterial spectra, and more potent antibacterial activities against gram-negative bacteria than those of older cephalosporins. However, their antibacterial activities against Pseudomonas aeruginosa and other Pseudomonas species are moderate ṠM-1652 (sodium 7-[D(-)-a-(4-hydroxy-6- methylpyridine-3-carboxamido)-a-(4-hydroxy- phenyl)acetamido]-3-[(1-methyl-1h4,tetrazol.5- yl)thiomethyl]-3-cephem-4-carboxylate [Fig. 1]), is a new semisynthetic cephalosporin derivative for parenteral use being developed by Sumitomo Chemical Co. Ltd., Osaka, Japan, and Yamanouchi Pharmaceuticals Co. Ltd., Tokyo, Japan. has been shown to have a broad antibacterial spectrum and a potent activity against P. aeruginosa (2). The present report describes the in vitro antibacterial activity of this new cephalosporin and its stability to - lactamases. (Part of this report was presented previously [T. Komatsu, T. Okuda, H. Noguchi, M. Fukasawa, K. Yano, M. Kato, and S. Mitsuhashi, Program Abstr. Intersci. Conf. Antimicrob. Agents Chemother. 19th, Boston, Mass., abstr. no. 565, 1979.) MATERIALS AND METHODS Strains. All of the clinical isolates were collected in 1978 at the Osaka National Hospital and some other hospitals in Kyoto, Japan.,-Lactamase-producing strains were supplied by Gunma University, Maebashi, Japan. Antibiotics. was prepared in the research laboratory of the Pharmaceuticals Division of Sumitomo Chemical Co. Ltd., Osaka, Japan. and cefotaxime were also synthesized in our own research laboratory. The other antibiotics used were commercially available. MIC determinations. Minimal inhibitory concentrations (MICs) were determined by a serial twofold agar dilution method with heart infusion agar (Nissui Seiyaku Co., Ltd., Tokyo). Tryptosoya broth (Nissui) was used for the preparation of seed suspensions. Heart infusion agar and Trypotosoya broth were supplemented with 10%6 defibrinated rabbit blood for streptococci. The inoculum was grown overnight at 37 C (or 30 C when Pseudomonas maltophilia and 195
2 196 FUKASAWA ET AL. OH FIG. 1. Chemical structure of. Pseudomonas cepacia were tested) and diluted in the same broth to a final inoculum of between 106 and 107 CFU/ml. The 5 pl of the diluted broth culture was inoculated onto the apr plates containing the drug tested with a Microplanter (Sakuma Seisakujo, Tokyo). The MICs (expressed in micrograms per mlliliter) were read after 18 h of incubation at 37C (or after 2 days at 30 C for P. maltophilia and P. cepacia). Staily to P-Iatan. The preculture of each strain in brain heart infusion broth (Nissui) was inoculated in the same broth and shaken for 3 h at 37C. For all cephalosporinase-producing strains except Escherichia coli GN5482, the cultures were supplemented with penicillin G as an inducer at one-eighth to onehalf the MIC and incubated for a further 2 h at 37C with shaking. Cells were harvested, washed once with 0.1 M phosphate buffer (ph 7.0), and disrupted by ultrasonic oscillation. The disrupted cells were spun down by centrifugtion, and the supernatant was used as crude enzyme. f-lactamase activity was determined by the spectrophotometric method (9, 10) in a spectrophotometer (model 24; Beckman Instruments, Inc., Fullerton, Calif.) controlled at 30 C. The reaction mixture consisted of 3 ml of a 100 FM substrate solution in 50 mm phosphate buffer (ph 7.0). The decrease in its optical density was recorded after the addition of 50 p1 of crude enzyme. A decomposition product of hydrolyzed by the enzyme was obtained at 275 nm. One unit of enzyme was defined as the activity hydrolyzing 1 pmol of the substrate per min at 30 C. Protein was estimated by the method of Lowry et al. (3). The specific activities of penicillinase and cephalosporinase were expressed as units per miligram of protein when penicillin G and cephaloridine, respectively, were used as substrates. Substrate TABLE 1. ANTIMICROB. AGENTS CHEMOTHER. specificity was expressed as the relative hydrolysis rate of each substrate, taking the absolute rate of penicillin G hydrolysis in penicilhinase and of cephaloridine hydrolysis in cephalosporinase as 100. RESULTS Antibacterial actiity against il isolates. The comparative antibacterial activities of SM and cefazolin (6, 8) against gram-positive bacteria are shown in Table 1. Antibacterial activities of the drugs against all species tested are shown as the concentrations required to inhibit the growth of 50 and 90%o of the total number of strains tested (MIC50 and MIC90, respectively). was as active as, or slightly less active than, cefazolin against grampositive bacteria. The activities of against Staphylococcus aureus, Streptococcus groups A, B, C, and G, and Streptococcus pneumoniae were slightly less than those of cefazolin. was almost as active as cefazolin against Staphylococcus epidermidis and Streptococcus group D. The activities of, cefazolin, cefoperazone (4), and cefotaxime (1) against Enterobacteriaceae are shown in Table 2. Against E. coli, Salmonella spp., Klebsiella pneumoniae, and Proteus mirabilis, was as active as or slightly less active than cefazolin., however, showed 10- to 60-fold higher activity than cefazolin against Proteus vulgaris, Morganella morganii, Enterobacter cloacae, and Serratia spp. The activity of cefoperazone against Enterobacteriaceae was superior to those of and cefazolin, but less active than cefotaxime against most species. Finally, did not exceed cefoperazone and cefotaxime in potency but did exceed cefazolin in potency and broadness of activity against Enterobacteriaceae. The high activity of against Pseudo- Antibacterial activity of against gram-positive bacteria Species (no. of organisms) Antibiotic Range 50% 90% Staphylococcus aureus (100) _ Staphylococcus epidermidis (144) Streptococcus groups A, B, C, and G (104) Streptococcus group D (104) Streptococcus pneumoniae (17) % < s
3 VOL. 23, 1983 Salmonella spp. (50) Kiebsiella pneumoniae (190) Proteus mirabilis (100) Proteus vulgaris (26) Morganella morganii (20) Providencia rettgeri (11) Citrobacterfreundii (21) Enterobacter cloacae (50) Serratia marcescens (89) Serratia liquefaciens (28) IN VITRO ANTIBACTERIAL ACTIVITY OF 197 TABLE 2. Antibacterial activity of against Enterobacteriaceae MIC (>g/m1) Species (no. of organisms) Antibiotic Range 50% 90%/O Escherichia coli (200) S : ! SO.01- ' ' =' =' ' SO.10- ' : monadaceae is the most important feature of its antibacterial activity. was the most active antipseudomonal compounds tested (Table 3). MIC90s of, cefoperazone, cefotaxime, cefsulodin (13), sulbenicillin, and gentamicin against Pseudomonas aeruginosa were 21, 68,, 32,, and 15,ug/ml, respectively. was more active than cefoperazone,
4 198 FUKASAWA ET AL. ANTIMICROB. AGENTS CHEMOTHER. TABLE 3. Antibacterial activity of against Pseudomonadaceae Species (no. of organisms) Antibiotic MIC ( -g/m1) Range 509o 90% Pseudomonas aeruginosa (200) Cefopeazone -' ' Cefsulodin Sulbenicillin Gentamicin ' Pseudomonas maltophilia (82) Cefsulodin Sulbenicillin Gentamicin 9-42 Pseudomonas cepacia (26) Cefsulodin Sulbenicillin Gentamicin ' cefotaxime, and sulbenicillin, slightly less active than gentamicin, and as active as cefsulodin. MIC90s of for Pseudomonas maltophilia and Pseudomonas cepacia were 81 and 20,ug/ml, respectively, and was the most active of the compounds tested. was also effective against Pseudomonas aeruginosa strains resistant to cefsulodin (MIC, 50,ug/ml) and gentamicin (MIC, _12.5,g/ml) (Table 4). The MIC50 of for cefsulodin-resistant Pseudomonas aeruginosa was 21.4 plg/ml; SM was eightfold more active than cefsulodin. However, the activity of against cefsulodin-resistant Pseudomonas aeruginosa was sevenfold less than that against clinical isolates of Pseudomonas aeruginosa (Table 3). The activity of gentamicin against cefsulodin-resistant Pseudomonas aeruginosa was also sixfold less than that against clinical isolates of this species. The MIC90s of and cefsulodin for gentamicin-resistant Pseudomonas aeruginosa were 89 and 1,037,ug/ml, respectively, being 4- and 30-fold less active, respectively, than those against the clinical isolates of Pseudomonas aeruginosa. Stability to,-1actmase. was relatively stable to P-lactamases produced by various species (Table 5). was much more stable than cephaloridine and cefazolin and almost as stable as cefoperazone and cefotaxime to cephalosporinases produced by Escherichia coli GN5482, M. morganii GN926, Citrobacter freundii GN346, and Pseudomonas aeruginosa GN918 (14). also showed a high stability to penicillinase type IV (carbenicillin-hydrolyzing enzyme [7, 11]) and Staphylococcus aure- TABLE 4. Antibacterial activity of against cefsulodin- and gentamicin-resistant Pseudomonas aeruginosaa Pseudomonas MIC (gl/mi) aeruginosa Antibiotic resistance (no. Atboi of organisms) Range 50% 90% Cefsulodin , (21) Cefsulodin 50-> ,600 Gentamicin ' Gentamicin (25) Cefsulodin , ,037 Gentamicin a Cefsulodin MIC, S50,ig/ml; gentamicin MIC, a12.5 &g/ml.
5 VOL. 23, 1983 TABLE 5. IN VITRO ANTIBACTERIAL ACTIVITY OF Stability of to various P-lactamases Enzyme source Type of 0- Sp act (U/mg of Relative rate of hydrolysis (%)b lactamasea protein) CER CEZ CPZ CTX PC-G Escherichia coli GN5482 CSase <1 96 <1 <1 50 Proteus vulgaris GN76 CSase Morganella morganii CSase <1 48 <1 <1 56 GN926 Citrobacterfreundii CSase <1 9 GN346 Pseudomonas CSase <1 109 <1 <1 78 aeruginosa GN918 Pseudomonas PCase type I <1 100 aeruginosa ML4600 RP4+ Escherichia coli ML1410 PCase type II RGN238+ Escherichia coli ML1410 PCase type III <1 100 Rte16+ Pseudomonas PCase type IV <1 <1 <1 100 aeruginosa ML4600 Rms139+ Staphylococcus aureus PCase 0.76 <1 <1 <1 <1 <1 100 MS9408 a CSase, Cephalosporinase; PCase, penicillinase. b CER, Cephaloridine; CEZ, cefazolin; CPZ, cefoperazone; CTX, cefotaxime; PC-G, penicillin G. us penicillinase. However, was partially hydrolyzed by Proteus vulgaris cephalosporinase (cefuroxime-hydrolyzing enzyme [5]) and penicillinases types I (TEM type [12]), II (oxacillin-hydrolyzing enzyme [16]), and III (oxacillin-hydrolyzing enzyme [15]). The stability of to,b-lactamase was almost the same as that of cefoperazone. DISCUSSION is a new parenteral cephalosporin derivative with a broad spectrum of antibacterial activity. This antibiotic has been reported to have potent in vitro and in vivo antibacterial activities against gram-positive and -negative bacteria (2). This paper showed that exceeded cefazolin in potency and broadness of antibacterial spectrum but did not exceed cefoperazone and cefotaxime in potency against Enterobacteriaceae. An interesting feature of the antibacterial activity of is its high activity against Pseudomonadaceae. At a concentration of 12.5,ug/ml, inhibited 87% ofpseudomonas aeruginosa clinical isolates. It was as active as cefsulodin, the only cephalosporin with a selective activity against Pseudomonas aeruginosa. was also effective against cefsulodin- and gentamicin-resistant Pseudomonas aeruginosa, but its activities were 3- to 20-fold less than those against clinical isolates of this species. These diminished activities of may reflect the fact that 48% of the cefsulodinresistant Pseudomonas aeruginosa strains 199 and 40% of the gentamicin-resistant Pseudomonas aeruginosa strains showed resistance to gentamicin and cefsulodin, respectively. was more effective than cefoperazone, cefotaxime, cefsulodin, sulbenicillin, and gentamicin against Pseudomonas maltophilia and Pseudomonas cepacia, the two Pseudomonadaceae species other than Pseudomonas aeruginosa which are important pathogens in opportunistic infections and are in general resistant to the aminoglycosides. was relatively stable to P-lactamases produced by various species. A preliminary report of a study done in humans indicates that the plasma half-lives of SM in intravenous doses of 0.5 and 1 g are 3.9 and 5.1 h, respectively (K. Nakagawa, M. Koyama, N. Nakatsuru, K. Yoshinaga, H. Matsui, C. Ikeda, K. Yano, and T. Noguchi, Program Abstr. Intersci. Conf. Antimicrob. Agents Chemother. 20th, New Orleans, La., abstr. no. 149, 1980). These half-lives of are more prolonged than any others so far reported on cephalosporin derivatives except ceftriaxone (Ro ) (K. Stoeckel, Program Abstr. Intersci. Conf. Antimicrob. Agents Chemother. 21st, Chicago, Ill., abstr. no. 387, 1981). The potent antipseudomonal activity and the broad spectrum of, coupled with its good pharmacokinetics in humans, suggests that it should be an effective therapeutic agent, particularly against Pseudomonas aeruginosa infections.
6 200 FUKASAWA ET AL. ACKNOWLIDGMENTS We thank S. Mitsuhashi of Gunma University for providing us with P-lactamase-producing strains and T. Kamiki of the Osaka National Hospital for supplying clinical isolates. LITERATURE CITED 1. Heymes, R., A. Lutz, and E. Sdrnmer Experimental evaluation of HR-756 a new cephalosporin derivative: pre-clinical study. Infection 5: Komatsu, T., T. Okuda, H. Noguchi, M. Fasawa, K. Yano, M. Kato, and S. Mltnabl , a new parenterally active cephalosporin: microbiological studies, p In J. D. Nelson and C. Grassi (ed.), Current chemotherapy and infectious disease. American Society for Microbiology, Washington, D.C. 3. Lowry, 0. H., N. J. Rasebrogh, A. L. Farr, and R. J. Randadl Protein measurement with the Folin phenol reagent. J. Biol. Chem. 193: Mataba, N., S. Minaml, T. Muraoka, and S. MltuhasL In vitro antibacterial activity of.cefoperazone (T-1551), a new semisynthetic cephalosporin. Antimicrob. Agents Chemother. 16: M bar, N., A. YotsWjl, KK. u, M. lie, ad S. Mltauhashi Purification and some properties of a cephalosporinase from Proteus vulgaris. Antimicrob. Agents Chemother. 19: Motely, M., and S. Shadomy In vitro studies with cefazolin. Antimirob. Agents Chemother. 6: Newsom, S. W. B., R. B. Sykes, and M. H. Rchaon Detection of a P-lactamase markedly active against carbenicillin in a strain of Pseudomonas aeruginosa. J. Bacteriol. 101: Nishda, M., T. Maabara, T. Makawa, Y. Mine, Y. ANTIMICROB. AGENTS CHEMOTHER. Yokota, S. Kuwahra, ad S. Goto In vitro and in vivo evaluation of cefazolin, a new cephalosporin C derivative, p Antimicrob. Agents Chemother Ross, G. W., K. V. Cbatr, A. M. Harris, S. M. K*ry, M. J. Marsa, and C. H. O'Ca Comparison of assay techniques for P-lactamase activity. Anal. Chem. 54: Samn_n, A A direct spectrophotometric assay and determination of Michaelis constants for the f-actamase reaction. Anal. Biochem. 63: Sawada, Y., S. Yaglm, M. Tad, S. Iyobe, and S. Mltsi.hash Plasmid-mediated penicillin B-lactamases in Pseudomonas aeruginosa. Antimicrob. Agents Chemother. 9: Sawal, T., S. Milsuuha--l, and S.Y Drug resistance of enteric bacteria. XIV. Comparison of,- lactamases in gram-negative rod bacteria resistant to a- aminobenzyl-penicillin. Jpn. J. Microbiol. 12: Tschlya, K., M. Koodo, and H. Na SCE- 129, antipseudomonal cephalosporin: in vitro and in vivo antibacterial activities. Antimicrob. Agents Chemother. 13: Yaglnua, S., T. Sawal, H. Ono, S. Yas_, and S. Mltsuhasb Biochemical properties of a cephalosporin f-lactamase from Pseudomonas aeruginosa. Jpn. J. Microbiol. 17: Y a, S., N. Terakad, ad S. MIt Biochemical properties of a penicillin flactamase mediated by R factor from BordeteUa bronchiseptica. Antimicrob. Agents Chemother. 8: Yamagis, S., K. O'Hara, T. Sawal, and S. Mitnadh The purification and properties of penicillin f- lactamases mediated by transmissible R factors in Escherichia coli. J. Biochem. X6: Downloaded from on January 7, 2019 by guest
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