VOL. 36 S-3 CHEMOTHERAPY 239

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1 238 CHEMOTHERAPY JULY 1988 Fig. 1 Chemical structure of 14C-TE-031 * : Labelled position

2 VOL. 36 S-3 CHEMOTHERAPY 239

3 240 CHEMOTHERAPY JULY 1988 Table 1 Tissue levels of radioactivity in 12th and 19th day gestating rats after oral administration of 14C-TE-031 (5mg/kg) Each value represents the mean }S.E. of five or four(a) animals

4 VOL.36 CHEMOT S-3 Fig. 2 HERAPY Autoradiograms showing the distribution of radioactivity in gestating rats after oral administration of14c-te-031 (20mg/kg) 241

5 242 CHEMOTHERAPY JULY 1988 Table 2 Radioactivity in the milk and maternal blood of mursing rats after oral administration of 14C-TE-031 (5mg/kg) N.D. : Not detected Each value represents the mean }S.E. of six animals Fig. 3 Blood levels of radioactivity during and after repeated oral administration of 14C-TE-031 (5mg/kg/day) to rats D. L. : Detectable limit (background X 2 ; 40dpm) Each point represents the mean }S. E. of five animals

6 VOL. 36 S-3 CHEMOTHERAPY 243 Table 3 Tissue levels of radioactivity in rats after repeated oral administration of C-TE-031 (5mg/kg/day for 14 days) 14 Each value represents the mean }S.E. of36_five animals

7 244 CHEMOT 動 的 拡 散 の 様 式 を と る と さ れ て お り6),乳 汁 のpHは 液 の そ れ よ り若 干 酸性 側 に 片寄 っ て い る ため,エ 血 HERAPY 以 上,14C-TE'-031の JULY 1988 胎 盤 通 過 性 お よ び 乳 汁 中 へ の移 リスロ 行 に関 す る試 験 成 績 は,本 薬 物 の ラ ッ トに お け る器 官形 マ イ シ ンの よ うな 弱塩 基 性 薬 物 は血 液 中濃 度 か そ れ 以 上 成 期 投 与 試 験 あ るい は 周 産 期,授 乳 期投 与 試験 に おいて で 乳 汁 中 へ 移 行 す る もの と考 え ら れ て い る TE5031の 特 記 す べ き毒 性 所 見 が 認 め ら れ て い な い9,こ と を支 持す pkaは8.48で る もの と考 え る NC-TE-0315mg/kgを あ り,脂 溶 性 も高 く また血 漿 蛋 白結 合率 が 比 較 的 低 い こ とか ら,エ リス ロマ イ シ ン と同 様 に乳 汁 中 ラ ッ トに1日1回14日 間反復 へ の 移 行 が 認 め られ た もの と推 察 され る しか し,乳 汁 経 口投 与 し,蓄 積 性 あ る い は代 謝 的 変 動 につ い て検 討 し 中 の 放 射 能 は 血 液 中 濃度 とほ ぼ平 行 して 推 移 し,投 与 後 た 24時 間 に お い て は検 出 限 界以 下 まで 減 衰 した こ とか ら, 乳 汁 中 へ の 残 留性 は 少 な い もの と考 え られ た Fig. 4 各 回投 与 後 の 血 液 中 放 射 能 濃 度 お よ び初 回投 与 と最終 投 与 後 の 血 中 濃 度 曲 線 下 面 積(AUC)に は,有 意 な差 は Autoradiograms showing the distribution of radioactivity in male rats after repeated oral administration of 14C-TE-031 (5mg/kg/day for 14 days)

8 VOL. 36 S-3 CHEMOTHERAPY 245 Fig. 5 Cumulative excretion of radioactivity in urine and feces of rats during and after repeated oral administration of "C-TE-031 (5mg/kg/day) Table 4 Composition of metabolites in urine and feces of rats after repeated oral administration of 4C-TE-031 (5mg/kg/day) M-1 : N-Demethyl TE-031 M-2 : N,N-Didemethyl TE-031 M-3 TE-031 N-oxide M-4 : Decladinosyl TE-031 M-5 (14R)-14-Hydroxy TE-031 : 0-24 hours after the 1st administration O-24 hours after the 14th administration Each value represents the mean of three animals

9 246 CHEMOTHERAPY JULY ) RASMUSSEN F.: Mammary excretion of benzylpenicillin, erythromycin and penethamate hydroiodide. Acta. Pharmacol. et Toxicol., 16: 194 `200, ) MORIMOTO S. ; T. ADACHI, Y. TAKAHASHI, T. AsAKA, M. KASHIMURA, Y. WATANABE, S. OMURA & K. SOTA : A new macrolide antibiotic, TE-031. Synthesis and biological properties. 26th Interscience Conference on Antimicrobial Agents and Chemotherapy Abstracts No. 409, New orleans, La., ) DANAN G.; V. DESCATOIVE & D. PESSAYRE: Selfinduction by erythromycin of its own transformation into a metabolite forming an inactive complex with reduced cytochrome P-450. Exp. Ther., 218: , 1981 J. Pharmacol.

10 VOL. 36 S-3 CHEMOTHERAPY 247 METABOLIC FATE OF TE-031 (A-56268)(V) Feto-placental transfer, excretion into milk and repeated administration of C-TE-031 in rats TOSHIO SUWA, HIDEO YOSHIDA, SACHIYO YOSHITOMI, KATSUJI OHTA & YOSHIRO KOHNO Research Center, Taisho Pharmaceutical Co. Ltd., Saitama Feto-placental transfer and excretion into milk of(6-0-methyl-14c)te-031 and its metabolic fate after repeated administration were studied in rats. The results obtained were as follows. After oral administration of 14C- TE- 031 (5 mg/ kg) to gestating rats on days 12 and 19, favorable distribution of radioactivity was observed in tissues as in normal female rats, and the radioactivity in uterus, ovary and placenta was almost the same as in muscle, whereas the level in amniotic fluid, about one-tenth that of plasma, was very low. The fetal level of radioactivity on day 12 of gestation was 0.05ƒÊeq./ml, which accounted for about one-fourth that in maternal plasma, and the percentage distribution of radioactivity in the fetus was less than % of the administered dose. On day 19 of gestation, the fetal level of radioactivity was similar to that on day 12, which suggests that transport of TE-031 and its metabolites to the fetus was strongly limited by the blood-placental barrier. Radioactivity in milk was 0.27ƒÊg eq./m1 at 1 hour after dosing, amounting to 2.5 times that in blood, and thereafter declined parallel with that in blood. During repeated oral administration of 14C-TE-031 (5 mg/kg)once daily for 14 days, blood levels of radioactivity did not change significantly. After the final administration, radioactivity in most tissues(including lung and liver, but not the central nervous system)was considerably higher than in plasma and was similar to that after single dosing, indicating no significant accumulation in the specific tissues when administered repeatedly. A slight decrease in urinary excretion and increase in feces were observed, but both were almost constant after the 7th day of the repeated administration. Within 5 days after the final administration, 18.78% and 75.13% of the dose were recovered in urine and feces, respectively. In 24 hour urine after the repeated administration, unchanged TE-031, N-demethyl TE-031(M-1)and decladinosyl TE-031 (M-4)accounted for % of the radioactivity excreted in urine, and M-1 was found as the main metabolite in feces. This metabolite composition was similar to that in the 24 hour urine and feces after the initial administration. These data indicate that no significant changes occured in the metabolic fate after repeated administration of TE-031 at the dose of 5 mg/kg.

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