(10R,11R,15R,16S)-16-{[(4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-(thiophen-2-yl)-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl]oxy}-10-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1(9),2,7-trien-12-one

• ChemBase编号: 327
• 分子式: C32H32O13S
• 平均质量: 656.65368
• 单一同位素质量: 656.15636208
• SMILES: s1c(C2O[C@H]3[C@H](O)[C@@H](O)[C@H](O[C@H]4[C@@H]5[C@@H]([C@@H](c6c4cc4OCOc4c6)c4cc(OC)c(O)c(OC)c4)C(=O)OC5)O[C@@H]3CO2)ccc1
• Canonical SMILES: COc1cc(cc(c1O)OC)[C@H]1[C@H]2C(=O)OC[C@@H]2[C@@H](c2c1cc1OCOc1c2)O[C@@H]1O[C@@H]2COC(O[C@H]2[C@@H]([C@H]1O)O)c1cccs1
• InChI: InChI=1S/C32H32O13S/c1-37-19-6-13(7-20(38-2)25(19)33)23-14-8-17-18(42-12-41-17)9-15(14)28(16-10-39-30(36)24(16)23)44-32-27(35)26(34)29-21(43-32)11-40-31(45-29)22-4-3-5-46-22/h3-9,16,21,23-24,26-29,31-35H,10-12H2,1-2H3/t16-,21+,23+,24-,26+,27+,28+,29+,31?,32-/m0/s1
• InChIKey: NRUKOCRGYNPUPR-PSZSYXFXSA-N

名称和登记号

名称

• IUPAC标准名: (10R,11R,15R,16S)-16-{[(4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-(thiophen-2-yl)-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl]oxy}-10-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1(9),2,7-trien-12-one
• IUPAC传统名: (10R,11R,15R,16S)-16-{[(4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-(thiophen-2-yl)-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl]oxy}-10-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1(9),2,7-trien-12-one
• 商标名: Vee M-26; Veham-Sandoz; Vehem; Vumon
• 别名: Teniposido [INN-Spanish]; Teniposidum [INN-Latin]; Teniposide

登记号

• CAS号: 29767-20-2
• PubChem SID: 46507536; 160963790
• PubChem CID: 34698

理论计算性质

JChem

• Acid pKa: 9.329948
• 质子受体: 12
• 质子供体: 3
• LogD (pH = 5.5): 2.7839653
• LogD (pH = 7.4): 2.7789927
• Log P: 2.7840292
• 摩尔折射率: 155.6095 cm^3
• 极化性: 62.344456 Å^3
• 极化表面积: 160.83 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: 2.78
• LOG S: -4.04
• 溶解度: 5.98e-02 g/l

分子性质

理化性质

• 疏水性(logP): 1.5

详细说明

DrugBank - DB00444

• Drug Groups: approved
• Description: A semisynthetic derivative of podophyllotoxin that exhibits antitumor activity. Teniposide inhibits DNA synthesis by forming a complex with topoisomerase II and DNA. This complex induces breaks in double stranded DNA and prevents repair by topoisomerase II binding. Accumulated breaks in DNA prevent cells from entering into the mitotic phase of the cell cycle, and lead to cell death. Teniposide acts primarily in the G2 and S phases of the cycle. [PubChem]
• Indication: Teniposide is used for the treatment of refractory acute lymphoblastic leukaemia
• Pharmacology: Teniposide is a phase-specific cytotoxic drug, acting in the late S or early G 2 phase of the cell cycle, thus preventing cells from entering mitosis. Teniposide causes dose-dependent single- and double-stranded breaks in DNA and DNA: protein cross-links.
• Affected Organisms: Humans and other mammals
• Half Life: 5 hours
• Elimination: From 4% to 12% of a dose is excreted in urine as parent drug. Fecal excretion of radioactivity within 72 hours after dosing accounted for 0% to 10% of the dose.
• Clearance: * 10.3 mL/min/m2
• External Links: Wikipedia; RxList; Drugs.com