CHEMOTHERAPY MAY Fig. 1 Chemical structure of CS-807 and its analogues CS-807 R-4060 R-3763 R-1073 R-5002 * 14C-labelled position
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1 CHEMOTHERAPY
2 CHEMOTHERAPY MAY Fig. 1 Chemical structure of CS-807 and its analogues CS-807 R-4060 R-3763 R-1073 R-5002 * 14C-labelled position
3 CHEMOTHERAPY Fig. 2 Plasma concentration of radioactivity and R-3763 after oral administration of CS C to rats, dogs and monkeys
4 CHEMOTHERAPY MAY Table 1-A Urinary and fecal excretion of radioactivity after oral and I.V. administration of CS C or R C to rats (13mg/kg, n=3-4) Table-1B Urinary and fecal excretion of radioactivity after oral administration of CS C to Beagle dogs (13mg/kg, n=4) Table 1-C Urinary and fecal excretion of radioactivity after oral administration of CS C to Cynoonolgia monkeys (13mg/kg, n=3) Values represent mean }S.E.
5 VOL.36 S-I CHEMOTHERAPY Table 2 Distribution of radioactivity in gastrointestinal lumen and gastrointestinal walls after oral administration of CS C to rats (13mg/kg, n=2) Table 3 Absorption of CS C from different part of rat digestive tract (Dose;lmg/8cm loop, n=4, 30min) Fig. 3 Hydrolysis of CS-807 in 9000 g supernatants from rat small intestine Concentration of CS-807=130 Đg/ml Values represent mean }S.E.
6 234 CHEMOT MAY. HERAPY 小 腸 中部>胃 の順 で あ り胃か ら も吸 収 が認 め られ る もの propylfluorophosphate)を の十 二 指腸,小 腸 上 部 か らの 吸収 が 最 も大 きい こ とが 示 著 明 に抑 制 され た され た 5. 2) 腸 管 での加 水 分 解 添 加 す る と,加 水 分解 が 門脈 血 中 の吸 収形 態 CS C(1mg/loop)を 1) ホ モ ジネ ー ト中 での 加 水分 解 ラ ッ ト小 腸 上 部 の結 紮 腸 ル ー プ内 に投 与 し,門 脈 血 中 に到 達 した放 射能 の形 消 化 管上 部 か ら吸 収 され たCS-807は,循 環 血 で はR -3763の 形 に な って い た こ とか ら,吸 収 過 程 にお い て, 態 をFig.4にTLCオ CS-807がR--3763el加 ー トラ ジオ グ ラム と して示 した の み で あ り投与 形 で あ るCS-807は 有 意 な放 射性 ス ポ ッ トと して検 出 され た の は,R-3763 水 分 解 され る こ とが 推 察 され た 有 意 に は検 出 されrt そ こで,ラ ッ ト小腸 上 部 の9000G遠 心 上 清 にお け るCS -807(130μg/ml)の 加水 分解 性 を測 定 した Fig.3に か った 本 試験 の 投 与量 は約5mg/kgに 示 した よ うに25%ホ 水 分解 されR-3763と モ ジネ ー ト中で,CS-807は この投 与 量 で はCS-807が 急速 に 加 水 分解 され,ほ ぼ定 量 的 に活 性体 で あ るR-3763が 成 した この結 果 はCS-807が 生 吸収 過 程 に お い て腸 管壁 異 性 体 で あ るR-1073と され た CS-807を1/15Mリ ン酸 緩 衝 液(pH で60分3TCで 速 や か に腸壁 内 に移 行 し,加 して 門脈 血 に吸 収 され る こ とが示 6. 組 織 内濃度 Table4に 異 な る生成 物 が 検 出 され たが,こ れ は標 品 との比 較 か らR-3763の 相 当す る域 され た で 十 分加 水 分解 され うる こ とを示 して い る この加 水分 解 でR-3763と 1988 示 した よ う に消化 管 を除 く組 織 内 濃度 は, 投 与 後 急速 に上昇 し,投 与1時 間 に ピー ク値 に達 した 同定 消化 管壁 以 外 で 最大 濃 度 を示 した の は腎 で あ り,血 蟻 7.4)中 肝,肺 が これ につ ぐ濃度 を示 した 以後 イ ン キ ュベ ー トす る と徐 々 に加 水 分解 さ 血 漿で は,半 減期1.9時 間(ピ ー ク 4時 間 まで)で 減少 し,24時 間 れ2時 間 後 に は15%のR-1073を 生 じた こ とか ら,R -1073の 生 成 は,CS-807の 化 学 的 な分 解 に よ り副 生 し ぼ 血 漿 同様 の 減 少 を示 した Fig.5に た もの と結 論 された また,Fig,3で 2時 間,6時 間 後 の ラ ッ ト全 身 オー トラ ジオ グ ラム を示 には ピー ク時 の1%程 は,腸 ホ モ ジネ ー トに非 特 異 的 エ ス テ ラー ゼ 阻 害 剤 で あ るDFP(Diiso- Fig. 4 In situ absorption 度 に まで低 下 し,他 の組 織 で もほ したが 腎 で最 も高 く,肝,肺,皮 from in portal blood は,投 与30分 膚,な らび に全 身の体
7 CHEMOTHERAPY Table 4 Tissue distribution of radioactivity after oral administration CS C to rat (13mg/kg, n=4) Concentration (ki g/ml or g)a) a) Values represent the mean }S.E. as pg equivalent to R-3763; b) n=3
8 236 CHEMOT Fig. 5 Whole-body autoradiograms Fig. 6 Whole-body autoradiogram MAY. HERAPY of CS C in Wistar-Imamichi rats (13 mg/kg, p.o.) of CS C in squirrel monkey 2hr after oral administration (13 mg/kg) 1988
9 VOL.36 S-1 CHEMOTHERAPY Table 5 Urinary and fecal metabolites 24hr after oral administration of CS-807-HC to rats, dogs and monkeys (13mg/kg) Fig. 7 TLC-Bioautogram of urine, plasma and feces in rats administered with CS-807 (13 mg/kg, p.o.) Plate: Silica gel G (Merck Co.) Solvent: n-butanol: Acetic acid: H204: 1: 1 Test organism: S.aureus 209P
10 CHEMOTHERAPY MAY Table 6 Serum protein binding of R-3763 and other oral antibiotics In vitro,, 90% of serum Incubated for 30min at 37 Ž Ultrafiltration method (25ug/ml)
11 \ VOL. 36 S- 1 CHEMOTHERAPY Fig. 8 Metabolic pathways of CS-807 in rats.
12 CHEMOTHERAPY MAY. I 988 5) SHINDO, H.; K. FUKUDA, K. KAWAI & K. TANAKA: Studies on intestinal absorption of pivampicillin and species difference in the intestinal esterase activity. J. Pharm. Dyn. 1: 310 `323, ) SHINDO, H.; K. KAWAI, T. IKEDA, I. IGARASHI & S. SUGAWARA: Absorption, Distribution, Excretion and Metabolism of C,efmetazole in Cynomo4lucl, Monkeys. J. Antibiotics 35 : 742 `754, 1982 ABSORPTION, DISTRIBUTION, METABOLISM AND EXCRETION OF CS-807, A NEW ORAL CEPHEM ANTIBIOTIC, IN EXPERIMENTAL ANIMALS TORU KOMAI, KENJI KAWAI, HIDEMI TSUBAKI, TARO TOKUI, TAKESHI KINOSHITA and MINORU TANAKA Analytical and Metabolic Research Laboratories, Sankyo Co., Ltd., Tokyo Absorption, distribution, excretion and biotransformation of "C-labeled CS-807 was studied after oral administration to Wistar-Imamichi rats, beagle dogs and Cynomolgus monkeys, at the dose of 13mg/kg. CS-807-"C was mainly absorbed from the upper part of the small intestine and the absorption rate was approximately 70% in rats. During absorption, CS-807 was rapidly hydrolyzed to its active form, R-3763, by non-specific esterase in the intestinal epithelium, and transferred to the circulatory blood. The plasma concentration of radioactivity was the highest in dogs(23.4pg/m1), followed by rats(8.4pg/m1)and monkeys (3. 9 gem1). R-3763 was mainly excreted to the urine after being distributed to the kidney, liver, lung, skin or extracellular space in the whole body. Approximately 3% of the dose was excreted in the bile as the active acid. Bioautography showed that R-3763 was the only active substance in the plasma and urine. Serum protein binding ratio in the human was approximately 40% and was lower than those in the experimental animals.
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