VOL. 20 NO. 5 CHEMOTHERAPY Methoxy-4-sulfanilamidopyrimidine (OS-3376) Sulfadimethoxine (SDM) Table 1. In vitro antibacterial activities of OS-3
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1 VOL. 20 NO. 5 CHEMOTHERAPY Methoxy-4-sulfanilamidopyrimidine (OS-3376) Sulfadimethoxine (SDM) Table 1. In vitro antibacterial activities of OS-3376, SDM, SIZ and SMZ against Gram-positive and negative organisms Sulfamonomethoxine
2 654 CHEMOTHERAPY SEPT Fig.1 Blood and urinary concentrations of OS-3376, of 100 mg/kg to mice (Bioassay) Fig.2 Blood and urinary concentiations of OS-3376, and SMM SEZ after single intramuscular administriation of 100 mg/kg to mice (Bioassay) Blood Blood Urine Urine
3 VOL. 20 NO. 5 CHEMOTHERAPY 655 Table 2. Tissue concentrations of OS-3376, SMM and SMZ following single oral administration of 250 mg/kg to mice
4 656 CHEMOTHERAPY SEPT Table 3. Acetylations and inactivations of OS- 3376, SMM and SMZ in tissue following single oral administration of 250 mg/kg to mice Fig.3 Blood concentrations of OS-3376, SMM and SMZ after single. oral administration of 50 mg/kg to rabbits Chemical assay Bioassay
5 VOL. 20 NO. 5 CHEMOTHERAPY 657 Fig.4 Urinary excretion of OS-3376, SMM and SMZ after a single oral administration of 50mg/kg to rabbits SMM SMZ 1st experiment 37.9 *(52.2)** 26.9 *** 19.5 (86.6) (41.9) nd experiment 3rd experiment Bioassay of samples of 3rd experiment was not performed Table 4. Acetylations of OS-3376, SMM and SMZ in blood following single oral administration of 50 mg/kg to rabbits Acetylation= (Total-Free) /Total ~ 100
6 658 CHEMOTHERAPY SEPT Fig.5 Therapeutic effects of OS-3376,SMM, SDM and on eperimental infection with S. pyogenes Effect of single oral treatment. at 2 hr after infection Fig.6 Therapeutic effects of OS-3376 in rabbit infected with S. pyogenes (single oral administration of 25 mg/kg) 1) Changes of body weight, body temperature and leucocyte count Body weight Effect of a series of five treatmeats started 2 hr after infection Leucocyte count Mice were inoculated intraperitoneally. with 5 ~103 cells (500 MLD) of S. pyogenes strain (G 36 M5), Rabbits were inoculated intraperitoneally with 2.5 ~106 of S. pyogenes strain (G36 M5). was given at 1 hour after inoculation. Table 5. Therapeutic effects of OS-3376 in rabbit infected with S. pyogenes (single oral administration of 25 mg/kg) (Recovery of hemolytic cocci from rabbits) Number of cocci/g (organ), ml (blood)
7 VOL. 20 NO. 5 CHEMOTHERAPY 659 Fig. 7 Therapeutic effects of OS-3376 and SMM on experimental. with various strains of S. aureus in mice 1) Changes of body weight S. aureus EQR-3 S. aureus R-3 S. aureus R-4 were inoculated intravenously with 1.5 `2.2 ~108 of S. aureus strains (EQP-3, R-4, R-3 and R-7). Treatments were started orally at 1 hr after infection with 400 mg/kg divided 4 times (OS-3376) or 200 mg/kg divided 2 times (SMM) in a day and continued for 6 days. Fig. 8 Therapeutic effects of OS-3376 and SMM on experimental infection with varioustrains of S. aureus in mice 2) Abscess and viable cell count in kidneys S. aureus EQP-3 S. aureus R-3 S. aureus R-4 S. aureus R-7 Mice were inoculated intravenously with 1.5 `2.2 ~108 of S. aureus strains (EQP-3, R-4, and R-7). R-3, Treatments were started orally at 1hr after infection with 400 divided time (OS-3376) or 200 mg/kg mg/kg 4 divided 2 times (SMM) in a day and continued for 6 days. Mice were sacrificed day after last dose.
8 660 CHEMOTHERAPY SEPT. 1972
9 VOL. 20 NO. 5 CHEMOTHERAPY 661 1) NITTA, Y. ; K. OKUI & K. ITO : Pyrimidine derivatives. I. Synthesis of a new series of sulfanilamides having dialkylamino groups in the pyrimidine nucleus. Chem. Pharm. Bull. 13 : 557 `567, ) NITTA, Y. ; K. OKUI, K. ITO & M. TOGO : Pyrimidine derivatives. II. Synthesis of 2- alkoxy-4-sulfanilamido-pyrimidine. Pharm. Bull. 13 : 568 `573, 1965 Chem. 3) NITTA, Y. ; T. MIYAMOTO, T. NEHASHI & F. YONEDA : Pyrimidine derivatives. III. The preparation and bacteriostatic activity of benzamido pyrimidines. Chem. Pharm. Bull. 13 : 901 `906, ) BELL, P. & R. O. ROBLIN : Studies in chemotherapy. VII. A theory of the relation of structure to activity of sulfanilamide type compounds. J. Am. Chem. Soc. 64 : 2905 `2917, ) NEIPP, L. ; W. SACKMANN & J. TRIPOD : Some new trends in the field of experimental rese- arch on sulfonamides. Antibiotic and Chemotherapy Advances 9 : 18 `82, 1961 BACTERIOLOGICAL STUDIES ON 2-METHOXY-4-SULFANILAMIDOPYRIMIDINE KIYOSHI OKUI, TOSHIYUKI NEHASHI and TAKAO NOTO Research Laboratories, Chugai Pharmaceutical Co., Ltd., Tokyo, Japan 2-Methoxy-4-sulfanilamidopyrimidine (OS-3376), a new sulfanilamide synthesized in our laboratory, has an in vitro antibacterial spectrum similar to sulfadimethoxine, sulfisomezole and sulfamethizole which were used as control drugs, and little difference was observed among them in the antibacterial potency. The concentrations of OS-3376 in blood and tissues or urine after the oral administration in mouse and rabbit were compared with the concentrations of sulfamonomethoxine and sulfamethizole in the experiments under the same conditions. The blood peak level of OS-3376 obtained at 30 minutes (mouse) or 1 hour (rabbit) after administration and its disappearance was later than sulfamethizole but sooner than sulfamonomethoxine in mouse, while in rabbit, it was rather later and comparatively high concentrations were observed. Mouse tissue assays showed kidney had the highest concentration of
10 662 CHEMOTHERAPY SEPT and other organs exhibited the concentrations as follows in order of blood, lung, liver and spleen. The drug was excreted in urine with high concentration and the urinary recovery rate was higher than sulfamonomethoxine. The therapeutic effect of OS-3376 has been shown distinctly in mice infected with Staphylococcus aureus and Streptococcus pyogenes, though this effect was rather slight as comparing with sulfamonomethoxine and sulfadimethoxine.
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