2-oxo-2-[(2S,4S)-2,5,12-trihydroxy-4-{[5-hydroxy-6-methyl-4-(trifluoroacetamido)oxan-2-yl]oxy}-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-2-yl]ethyl pentanoate

• ChemBase编号: 269
• 分子式: C34H36F3NO13
• 平均质量: 723.6437496
• 单一同位素质量: 723.21387488
• SMILES: FC(F)(F)C(=O)NC1CC(O[C@H]2C[C@@](O)(Cc3c2c(O)c2c(c3O)C(=O)c3c(C2=O)c(OC)ccc3)C(=O)COC(=O)CCCC)OC(C1O)C
• Canonical SMILES: CCCCC(=O)OCC(=O)[C@@]1(O)C[C@H](OC2CC(NC(=O)C(F)(F)F)C(C(O2)C)O)c2c(C1)c(O)c1c(c2O)C(=O)c2c(C1=O)cccc2OC
• InChI: InChI=1S/C34H36F3NO13/c1-4-5-9-21(40)49-13-20(39)33(47)11-16-24(19(12-33)51-22-10-17(27(41)14(2)50-22)38-32(46)34(35,36)37)31(45)26-25(29(16)43)28(42)15-7-6-8-18(48-3)23(15)30(26)44/h6-8,14,17,19,22,27,41,43,45,47H,4-5,9-13H2,1-3H3,(H,38,46)/t14?,17?,19-,22?,27?,33-/m0/s1
• InChIKey: ZOCKGBMQLCSHFP-ZQUOIQDWSA-N

名称和登记号

名称

• IUPAC标准名: 2-oxo-2-[(2S,4S)-2,5,12-trihydroxy-4-{[5-hydroxy-6-methyl-4-(trifluoroacetamido)oxan-2-yl]oxy}-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-2-yl]ethyl pentanoate
• IUPAC传统名: valtaxin
• 商标名: Valstar; Valstar Preservative Free
• 别名: Antibiotic Ad 32; Valrubicin

登记号

• CAS号: 56124-62-0
• PubChem SID: 160963732; 46506642
• PubChem CID: 41744

理论计算性质

JChem

• Acid pKa: 5.3934793
• 质子受体: 12
• 质子供体: 5
• LogD (pH = 5.5): 4.1876435
• LogD (pH = 7.4): 3.5702426
• Log P: 4.486147
• 摩尔折射率: 168.0281 cm^3
• 极化性: 64.89921 Å^3
• 极化表面积: 215.22 Å^2
• 可自由旋转的化学键: 12
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: 2.67
• LOG S: -4.35
• 溶解度: 3.25e-02 g/l

分子性质

理化性质

• 溶解度: insoluble
• 疏水性(logP): 2.2

详细说明

DrugBank - DB00385

• Drug Groups: approved
• Description: Valrubicin (N-trifluoroacetyladriamycin-14-valerate, Valstar®) is a chemotherapy drug used to treat bladder cancer. Valrubicin is a semisynthetic analog of the anthracycline doxorubicin, and is administered by infusion directly into the bladder. [Wikipedia]
• Indication: For the treatment of cancer of the bladder.
• Pharmacology: Valrubicin is a semisynthetic analog of the anthracycline doxorubicin, and is administered by infusion directly into the bladder.
• Toxicity: The primary anticipated complications of overdosage associated with intravesical administration would be consistent with irritable bladder symptoms. Myelosuppression is possible if valrubicin is inadvertently administered systemically or if significant systemic exposure occurs following intravesical administration (e.g., in patients with bladder/rupture perforation). The maximum tolerated dose in humans by either intraperitoneal or intravenous administration is 600 mg/m^2.
• Affected Organisms: Humans and other mammals
• Biotransformation: Valrubicin is metabolized to two primary metabolites: N-trifluoroacetyladriamycin and N-trifluoroacetyladriamycinol.
• Protein Binding: >99%
• External Links: Wikipedia; RxList; Drugs.com