オレアンドマイシン 化学特性,用途語,生産方法
解説
C35H61NO12(687.86)．Streptomyces antibioticusが産生するマクロライド抗生物質．十四員環ラクトンにL-オレアンドロースとD-デソサミンの糖が結合している．分解点110 ℃ の脂溶性塩基性物質．塩酸塩は白色の針状晶．融点134～135 ℃．[α]25D"－54°(メタノール)，UV(メタノール)λmax 286～289 nm(ε 3400)．アルコール類に易溶，エーテルに不溶．細菌リボソームの50Sサブユニットの23S rRNAに結合して，ペプチド転移反応を抑え，タンパク質合成を阻害する．グラム陽性菌，グラム陰性球菌，マイコプラズマ，リケッチア，クラミジア感染症に有効である．リン酸塩が内服または注射で使用される．LD50 600 mg/kg(マウス，静注)．[CAS 3922-90-5][CAS 6696-47-5:塩酸塩][CAS 7060-74-4:リン酸塩]
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森北出版「化学辞典（第2版）
使用
Antibiotic substance produced by Streptomyces antibioticus no. ATCC 11891. Antibacterial.
応用例（製薬）
A natural 14-membered-ring macrolide produced by Streptomyces antibioticus. It is stable in acid conditions. It is less active than erythromycin A in vitro, but four times more active than spiramycin . Several attempts have been made to improve its potency by chemical modification while retaining its relative acid stability.
It is incompletely absorbed, but an ester, triacetyloleandomycin, gives improved plasma levels. Following doses of 0.5 g, mean peak serum levels around 0.8 mg/L were reached by the base and 2 mg/L by the triacetyl ester. A single oral dose of 1 g of the ester produced a mean plasma oleandomycin concentration of 4 mg/L at 1 h after dosing, with an AUC of 14 mg.h/L. The apparent elimination half-life was 4.2 h. Significant quantities of mostly inactivated compound are eliminated in the bile. About 10% of the dose appears in the urine after administration of the base and about 20% after the ester.
Nausea, vomiting and diarrhea are common. Like erythromycin estolate, triacetyloleandomycin can cause liver damage. Abnormal liver function tests were found in about one-third of patients treated for 2 weeks. Hepatic dysfunction resolved when treatment was discontinued. The action of drugs eliminated via the cytochrome P
450 system may be potentiated.
Its uses are similar to those of erythromycin. It is of restricted availability.
安全性プロファイル
A poison by
intravenous route. Low toxicity by ingestion.
When heated to decomposition it emits
toxic vapors of NOx.
オレアンドマイシン 上流と下流の製品情報
原材料
準備製品