(8S,10S)-8-acetyl-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

• ChemBase编号: 576
• 分子式: C27H29NO10
• 平均质量: 527.51986
• 单一同位素质量: 527.17914613
• SMILES: O([C@H]1C[C@@](O)(Cc2c1c(O)c1c(c2O)C(=O)c2c(C1=O)c(OC)ccc2)C(=O)C)[C@@H]1O[C@H]([C@@H](O)[C@@H](N)C1)C
• Canonical SMILES: COc1cccc2c1C(=O)c1c(C2=O)c(O)c2c(c1O)[C@@H](O[C@H]1C[C@H](N)[C@@H]([C@@H](O1)C)O)C[C@](C2)(O)C(=O)C
• InChI: InChI=1S/C27H29NO10/c1-10-22(30)14(28)7-17(37-10)38-16-9-27(35,11(2)29)8-13-19(16)26(34)21-20(24(13)32)23(31)12-5-4-6-15(36-3)18(12)25(21)33/h4-6,10,14,16-17,22,30,32,34-35H,7-9,28H2,1-3H3/t10-,14-,16-,17-,22+,27-/m0/s1
• InChIKey: STQGQHZAVUOBTE-VGBVRHCVSA-N

名称和登记号

名称

• IUPAC标准名: (8S,10S)-8-acetyl-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
• IUPAC传统名: daunorubicin
• 商标名: Acetyladriamycin; Anthracyline; Antibiotics From Streptomyces Coeruleorubidus; Cerubidin; Cerubidine; DM1; Daunamycin; Daunarubicinum; Daunoblastin; Daunomycin; Daunomycin Hydrochloride; Daunomycin, Hydrochloride; Daunorrubicina; Daunorubicin Hcl; Daunorubicin Hydrochloride; Daunorubicin, Hydrochloride; Daunorubicine; Daunorubicinum [INN-Latin]; Daunoxome; Leukaemomycin C; Ondena; Rcra Waste No. U059; Rp 13057 Hydrochloride; Rubidomycin; Rubidomycin Hydrochloride; Rubomycin C
• 别名: Daunorubicin

登记号

• CAS号: 20830-81-3
• PubChem SID: 160964039; 46508433
• PubChem CID: 30323
• CHEBI ID: 41977
• ATC码: L01DB02
• CHEMBL: 178
• Chemspider ID: 28163
• DrugBank ID: DB00694
• KEGG ID: C01907
• 美国药典/FDA物质标识码: ZS7284E0ZP
• 维基百科标题: Daunorubicin
• Medline Plus: a682289

理论计算性质

JChem

• Acid pKa: 9.530939
• 质子受体: 11
• 质子供体: 5
• LogD (pH = 5.5): -0.6256268
• LogD (pH = 7.4): 0.54168487
• Log P: 1.7336931
• 摩尔折射率: 132.8915 cm^3
• 极化性: 52.022972 Å^3
• 极化表面积: 185.84 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: 1.68
• LOG S: -2.93
• 溶解度: 6.27e-01 g/l

分子性质

理化性质

• 溶解度: 39.2 mg/L
• 疏水性(logP): 0.1

药理学性质

• 给药途径: Exclusively intravenous. Causes severe necrosis if administered intramuscularly or subcutaneously
• 排泄: Biliary and urinary
• 半衰期: 26.7 hours (metabolite)
• 代谢: Hepatic
• 法定药品分级: Rx-only (US)
• 妊娠期药物分类: D (U.S.)

详细说明

DrugBank - DB00694

• Drug Groups: approved
• Description: A very toxic anthracycline aminoglycoside antineoplastic isolated from Streptomyces peucetius and others, used in treatment of leukemia and other neoplasms. [PubChem]
• Indication: For remission induction in acute nonlymphocytic leukemia (myelogenous, monocytic, erythroid) of adults and for remission induction in acute lymphocytic leukemia of children and adults.
• Pharmacology: Daunorubicin 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. Daunorubicin may also inhibit polymerase activity, affect regulation of gene expression, and produce free radical damage to DNA. Daunorubicin possesses an antitumor effect against a wide spectrum of tumors, either grafted or spontaneous. The anthracyclines are cell cycle-nonspecific.
• Toxicity: LD₅₀=20 mg/kg (mice, IV); LD₅₀=13 mg/kg (rat, IV)
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Half Life: 18.5 hours
• Protein Binding: 97% binding-albumin
• Elimination: Twenty-five percent of an administered dose of daunorubicin hydrochloride is eliminated in an active form by urinary excretion and an estimated 40% by biliary excretion.
• External Links: Wikipedia; RxList; Drugs.com