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| 化学名: | エピルビシン·塩酸塩 | | 英語化学名: | Epirubicin hydrochloride | | 别名: | 4’-epi-adriamycinhydrochloride;5,12-naphthacenedione,10-((3-amino-2,3,6-trideoxy-alpha-l-arabino-hexopyranosy;8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-l)oxy)-hyd;EPIRUBICIN HYDROCHLORIDE EP STANDARD;EpirubicinHc,LEp5,;Adrial;(8S,10S)-10-[(3-amino-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,12-naphthacenedione, hydrochloride (1:1);5,12-Naphthacenedione, 10-[(3-amino-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-, hydrochloride (1:1), (8S,10S)- | | CAS番号: | 56390-09-1 | | 分子式: | C27H30ClNO11 | | 分子量: | 579.9802 | | EINECS: | 260-145-2 | | カテゴリ情報: | Anti-cancer&immunity;API;Antineoplastic;Intermediates & Fine Chemicals;Pharmaceuticals;Antibiotics;11;56390-09-1 | | Mol File: | 56390-09-1.mol |  |
| 融点 | 185°C dec. | | 比旋光度 | D20 +274° (c = 0.01 in methanol) | | RTECS 番号 | QI9295750 | | 闪点 | 443.8℃ | | 貯蔵温度 | Inert atmosphere,Store in freezer, under -20°C | | 溶解性 | Soluble in DMSO to 100mM, or in ethanol to 10mM | | 外見 | powder | | 色 | red to deep red | | 安定性： | Stable for 2 years from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20° for up to 3 months. | | InChIKey | MWWSFMDVAYGXBV-UAOJCOQHSA-N | | SMILES | C12=C(O)C3=C(C(=O)C4=C(C3=O)C=CC=C4OC)C(O)=C1[C@@]([H])(O[C@H]1O[C@@H](C)[C@H](O)[C@@H](N)C1)C[C@](O)(C(=O)CO)C2.Cl |
| | エピルビシン·塩酸塩 Usage And Synthesis |
| 外観 | 黄赤色～赤褐色, 結晶性粉末～粉末 | | 溶解性 | 水及びメタノールにやや溶けやすく、エタノール(95)に溶けにくく、アセトニトリルにほとんど溶けない。 | | 用途 | アントラサイクリン系抗生物
質です。がん細胞の DNA と結合し、DNA ポ
リメラーゼ、RNA ポリメラーゼ反応を阻害す
ることにより核酸の生合成を阻害し、細胞分
裂抑制作用を示します。 | | 用途 | アントラサイクリン系抗生物
質です。ドキソルビシン塩酸塩の 4' 位 OH 基
が反転した立体異性体です。DNA ポリメラー
ゼ、RNA ポリメラーゼ反応を阻害することに
より核酸の生合成を阻害し、細胞分裂を抑制
します。 | | 効能 | 抗悪性腫瘍薬, トポイソメラーゼII阻害薬 | | 商品名 | ファルモルビシン (ファイザー); ファルモルビシン (ファイザー) | | 説明 | Epirubicin hydrochloride is an antitumor antibiotic which is epimeric with
doxorubicin a t the 4’-position of the amino sugar moiety. It has shown utility in
the treatment of mammary, gastric, colorectal, pulmonary and ovarian carcinomas,
as well as malignant lymphoma and melanoma and soft tissue sarcoma. It is
reported to be less sardiotoxic than doxorubicin. | | 説明 | Epirubicin is a stereoisomer of the antitumor anthracycline doxorubicin that undergoes β-glucuronidation, which partially detoxifies the dose-limiting side effects that are present with doxorubicin. Compared to doxorubicin, epirubicin is equally cytotoxic to HeLa cells (ID50s = 9 μM). When used either alone or in combination therapies, epirubicin has been shown to demonstrate high rates of complete or partial remission in various cancers including advanced ovary, lymphomas, breast, pancreas, gastric, hepatocellular carcinoma, head and neck tumors, and colorectal. | | 化学的特性 | Orange-Red Crystalline Solid | | Originator | Erbamont (Italy) | | 使用 | Cell-permeable anthracycline anti-tumor antibiotic | | 使用 | Used as an antineoplastic | | brand name | Ellence(Pfizer);FARMORUBICIN. | | 生物学の機能 | This stereoisomer of doxorubicin has the 4′-hydroxy group of the daunosamine sugar oriented in the β-position . Epirubicin will be slowly reduced to the active C13 alcohol (epirubicinol), giving it a 30- to 38-hour half life, which is similar to that of doxorubicin. Unlike doxorubicinol, however, which was equally active with doxorubicin, epirubicinol has only one-tenth the activity of its parent drug and is not believed to contribute significantly to the therapeutic action of this agent. | | 生物活性 | Antibiotic antitumor agent. Inhibits the synthesis and function of DNA (IC 50 = 62.7 μ M in rat glioblastoma cell lines) and inhibits the relaxing property of topoisomerase II. | | 臨床応用 | Epirubicin is indicated for use in breast cancer, and the starting dose is 100 to 120 mg/m2 (compared to a starting dose of 60–75 mg/m2 for doxorubicin). | | 副作用 | The side effects and precautions are as outlined previously for doxorubicin, although there is a lower risk of serious myocardial toxicity or myelotoxicity. | | 薬物相互作用 | Potentially hazardous interactions with other drugsAntipsychotics: avoid with clozapine - increased risk
of agranulocytosis.Ciclosporin: increased risk of neurotoxicityCytotoxics: possible increased risk of cardiotoxicity
with trastuzumab - avoid for up to 28 weeks after
stopping trastuzumab.Ulcer-healing drugs: concentration increased by
cimetidine. Vaccines: avoid with live vaccines | | 代謝 | Cleavage of the epimerized sugar will occur before excretion, generating an aglycone that is indistinguishable from that generated by doxorubicin. Although excretion is primarily biliary, dosage reduction in severe renal impairment, as well as in hepatic dysfunction, is warranted. | | 貯蔵 | +4°C | | 参考文献 | 1) Cersosimo?et al. (1986),?Epirubicin: a review of the pharmacology, clinical activity, and adverse effects of an adriamycin analogue; J. Clin. Oncol.,?4?425
2) Spadari?et al. (1986),?DNA polymerases and DNA topoisomerases as targets for the development of anticancer drugs; Anticancer Res.,?6?935
3) Minotti?et al. (2004),?Anthracyclines: molecular advances and pharmacologic developments in antitumor activity and cardiotoxicity; Pharmacol. Rev.,?56?185
4) Mercuro?et al. (2007),?Early epirubicin-induced myocardial dysfunction revealed by serial tissue Doppler echocardiography: correlation with inflammatory and oxidative stress markers; Oncologist,?12?1124 |
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