(7S,9S)-9-acetyl-7-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,9,11-trihydroxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

• ChemBase编号: 1048
• 分子式: C26H27NO9
• 平均质量: 497.49388
• 单一同位素质量: 497.16858145
• SMILES: O([C@H]1C[C@@](O)(Cc2c1c(O)c1c(c2O)C(=O)c2c(C1=O)cccc2)C(=O)C)[C@@H]1O[C@H]([C@@H](O)[C@@H](N)C1)C
• Canonical SMILES: O[C@H]1[C@@H](N)C[C@@H](O[C@H]1C)O[C@H]1C[C@@](O)(Cc2c1c(O)c1c(c2O)C(=O)c2c(C1=O)cccc2)C(=O)C
• InChI: InChI=1S/C26H27NO9/c1-10-21(29)15(27)7-17(35-10)36-16-9-26(34,11(2)28)8-14-18(16)25(33)20-19(24(14)32)22(30)12-5-3-4-6-13(12)23(20)31/h3-6,10,15-17,21,29,32-34H,7-9,27H2,1-2H3/t10-,15-,16-,17-,21+,26-/m0/s1
• InChIKey: XDXDZDZNSLXDNA-TZNDIEGXSA-N

名称和登记号

名称

• IUPAC标准名: (7S,9S)-9-acetyl-7-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,9,11-trihydroxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
• IUPAC传统名: idarubicin
• 商标名: Idamycin; Idamycin PFS; Idarubicin Aglycone; Idarubicin HCl PFS
• 别名: Idarubicin Hcl; Idarubicin Hydrochloride; Idarubicina [INN-Spanish]; Idarubicine [INN-French]; Idarubicinum [INN-Latin]; Idarubicin; (7S-cis)-9-Acetyl-7-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,9,11-trihydroxy-5,12-naphthacenedione; DMDR; IMI-30; Idamycin; Idarubicin hydrochloride

登记号

• CAS号: 57852-57-0; 58957-92-9
• EC号: 260-990-7
• MDL号: MFCD00866457
• PubChem SID: 24278488; 46506973; 160964511
• PubChem CID: 42890

理论计算性质

JChem

• Acid pKa: 9.54545
• 质子受体: 10
• 质子供体: 5
• LogD (pH = 5.5): -0.46867308
• LogD (pH = 7.4): 0.69595975
• Log P: 1.8979983
• 摩尔折射率: 126.4283 cm^3
• 极化性: 49.47403 Å^3
• 极化表面积: 176.61 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.69
• LOG S: -2.81
• 溶解度: 7.72e-01 g/l

分子性质

理化性质

• 外观: solid
• 疏水性(logP): 0.2

安全信息

• RTECS编号: HB7877000
• 欧盟危险性物质标志: 剧毒(Highly toxic) (T+)
• 联合国危险货物编号: 2811
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 2
• 危险公开号: 60-61-28-40
• 安全公开号: 53-45
• GHS危险品标识: GHS06; GHS08
• GHS警示词: Danger
• GHS危险声明: H300-H351-H360
• GHS警示性声明: P201-P264-P281-P301 + P310-P308 + P313
• 个人保护装置: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2
• 保存温度: 2-8°C

产品相关信息

• 运输包装: wet ice
• Empirical Formula (Hill Notation): C26H27NO9 · HCl

详细说明

DrugBank - DB01177

• Drug Groups: approved
• Description: An orally administered anthracycline antineoplastic. The compound has shown activity against breast cancer, lymphomas and leukemias, together with the potential for reduced cardiac toxicity. [PubChem]
• Indication: For the treatment of acute myeloid leukemia (AML) in adults. This includes French-American-British (FAB) classifications M1 through M7.
• Pharmacology: 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.
• Affected Organisms: Humans and other mammals; Bacteria
• Half Life: 22 hours
• Protein Binding: 97%
• Elimination: The drug is eliminated predominately by biliary and to a lesser extent by renal excretion, mostly in the form of idarubicinol.
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - I1656

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Application
Idarubicin is an anthracycline antibiotic that is an anti-leukemia agent with higher DNA binding capacity and greater cytotoxicity than daunorubicin.
Biochem/physiol Actions
Topoisomerase II inhibitor