基本情報
- CAS
58957-92-9- 標準SMILES
CC(=O)[C@]1(O)Cc2c(O)c3c(c(O)c2[C@@H](O[C@H]2C[C@H](N)[C@H](O)[C@H](C)O2)C1)C(=O)c1ccccc1C3=O- InChIKey
XDXDZDZNSLXDNA-TZNDIEGXSA-N- 分子式
- C26H27NO9
- 平均分子量
- 497.5 g/mol
- 単同位体質量
- 497.16858144
概要
Idarubicin is a deoxy hexoside, an anthracycline antibiotic and a monosaccharide derivative. It derives from a hydride of a tetracene.
名称と識別子
- 優先名称
- Idarubicin
- IUPAC
- (7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione
- 現地名
- イダルビシン
- 英語名
- Idarubicin
- 分子式
- C26H27NO9
- 分子量
- 497.49
名称と別名
IDARUBICIN58957-92-94-Demethoxydaunorubicin4-DemethoxydaunomycinIdarubicinaIdarubicineIdarubicinumZavedosZRP63D75JWNSC 256439DTXSID7023142CHEBI:42068
名称をさらに表示
(7S,9S)-9α-アセチル-7β-(3-アミノ-2,3,6-トリデオキシ-α-L-lyxo-ヘキソピラノシルオキシ)-7,8,9,10-テトラヒドロ-6,9β,11-トリヒドロキシ-5,12-ナフタセンジオンデメトキシダウノルビシン4-デメトキシダウノマイシン4-デメトキシダウノルビシン(7S)-7,8,9,10-テトラヒドロ-6,9β,11-トリヒドロキシ-7β-[[(4S)-4α-アミノ-5α-ヒドロキシ-3,4,5,6-テトラヒドロ-6α-メチル-2H-ピラン]-2β-イルオキシ]-9α-アセチルナフタセン-5,12-ジオン(7S)-7β-[(3-アミノ-2,3,6-トリデオキシ-α-L-lyxo-ヘキソピラノシル)オキシ]-9α-アセチル-7,8,9,10-テトラヒドロ-6,9,11-トリヒドロキシナフタセン-5,12-ジオン(7S)-7β-(3-アミノ-2,3,6-トリデオキシ-α-L-lyxo-ヘキソピラノシルオキシ)-9α-アセチル-7,8,9,10-テトラヒドロ-6,9,11-トリヒドロキシナフタセン-5,12-ジオンイダルビシン(7S,9S)-9-アセチル-7-[(3-アミノ-2,3,6-トリデオキシ-α-L-lyxo-ヘキソピラノシル)オキシ]-7,8,9,10-テトラヒドロ-6,9,11-トリヒドロキシ-5,12-ナフタセンジオン(7S)-9-アセチル-7β-[(3-アミノ-2,3,6-トリデオキシ-α-L-lyxo-ヘキソピラノシル)オキシ]-7,8,9,10-テトラヒドロ-6,9β,11-トリヒドロキシ-5,12-ナフタセンジオン
物性
構造計算による物性
- XLogP
- 1.9
- 極性表面積
- 177 Ų
- 水素結合供与体数
- 5
- 水素結合受容体数
- 10
- 回転可能結合数
- 3
- 重原子数
- 36
- 形式電荷
- 0
- 複雑度
- 912
実験および物理化学的性質
Drugs
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Listed in ZINC15
LogP0.2
Solubility7.72e-01 g/L
Human DrugsBreast Feeding; Lactation; Milk, Human; Antineoplastic Agents; Anthracyclines; Antibiotics, Antineoplastic; Topoisomerase II Inhibitors
Physical DescriptionSolid
物理化学的性質
- 沸点
- 589.46 °C · 589.46°C (rough estimate)
- 比重(密度)
- 1.3477 · 1.3477 (rough estimate)
- 屈折率
- 1.6 · 1.6000 (estimate)
- 貯蔵温度
- 2 · Keep in dark place,Sealed in dry,2-8°C
- 外見
- 個体
- 酸解離定数(Pka)
- 4.73 · pKa 4.73± 0.21 (Uncertain)
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
毒性情報
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
idarubicin
DILI Negative
Intravenous
DOI:10.1016/j.drudis.2019.09.022
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
安全データ
- wgk
- 3
- rtecs
- HB7877000
- ridadr
- UN 2811 6.1/PG 2
- risk_code
- 60-61-28-40
- hazard_code
- T+
- safety_code
- 53-45
化学と産業
薬理情報
ATC Code
L01DB06
L - Antineoplastic and immunomodulating agents
QL - Antineoplastic and immunomodulating agents
Protein Binding97%
Pharmacodynamics
Idarubicin is an antineoplastic in the anthracycline class. General properties of drugs in this class include: interaction with DNA in a variety of different ways including intercalation (squeezing between the base pairs), DNA strand breakage and inhibition with the enzyme topoisomerase II. Most of these compounds have been isolated from natural sources and antibiotics. However, they lack the specificity of the antimicrobial antibiotics and thus produce significant toxicity. The anthracyclines are among the most important antitumor drugs available. Doxorubicin is widely used for the treatment of several solid tumors while daunorubicin and idarubicin are used exclusively for the treatment of leukemia. Idarubicin may also inhibit polymerase activity, affect regulation of gene expression, and produce free radical damage to DNA. Idarubicin possesses an antitumor effect against a wide spectrum of tumors, either grafted or spontaneous. The anthracyclines are cell cycle-nonspecific.
Mechanism of Action
Idarubicin has antimitotic and cytotoxic activity through a number of proposed mechanisms of action: Idarubicin forms complexes with DNA by intercalation between base pairs, and it inhibits topoisomerase II activity by stabilizing the DNA-topoisomerase II complex, preventing the religation portion of the ligation-religation reaction that topoisomerase II catalyzes.
Biological Half-Life22 hours
FDA Pharmacological Classification
ZRP63D75JW
IDARUBICIN
Established Pharmacologic Class [EPC] - Anthracycline Topoisomerase Inhibitor
Chemical Structure [CS] - Anthracyclines
Mechanisms of Action [MoA] - Topoisomerase Inhibitors
Idarubicin is an Anthracycline Topoisomerase Inhibitor. The mechanism of action of idarubicin is as a Topoisomerase Inhibitor.
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