methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(12S)-16-ethyl-12-(methoxycarbonyl)-1,10-diazatetracyclo[12.3.1.0^{3,11}.0^{4,9}]octadeca-3(11),4,6,8,15-pentaen-12-yl]-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2(7),3,5,13-tetraene-10-carboxylate

• ChemBase编号: 245
• 分子式: C45H54N4O8
• 平均质量: 778.93226
• 单一同位素质量: 778.39416471
• SMILES: O([C@@H]1[C@]2([C@@H]3N(CC[C@@]43[C@@H](N(c3c4cc(c(OC)c3)[C@]3(CC4CN(Cc5c3[nH]c3c5cccc3)CC(=C4)CC)C(=O)OC)C)[C@@]1(O)C(=O)OC)CC=C2)CC)C(=O)C
• Canonical SMILES: CCC1=CC2CN(C1)Cc1c3ccccc3[nH]c1[C@@](C2)(C(=O)OC)c1cc2c(cc1OC)N([C@@H]1[C@@]32CCN2[C@H]3[C@@](CC)(C=CC2)[C@H]([C@]1(O)C(=O)OC)OC(=O)C)C
• InChI: InChI=1S/C45H54N4O8/c1-8-27-19-28-22-44(40(51)55-6,36-30(25-48(23-27)24-28)29-13-10-11-14-33(29)46-36)32-20-31-34(21-35(32)54-5)47(4)38-43(31)16-18-49-17-12-15-42(9-2,37(43)49)39(57-26(3)50)45(38,53)41(52)56-7/h10-15,19-21,28,37-39,46,53H,8-9,16-18,22-25H2,1-7H3/t28?,37-,38+,39+,42+,43+,44-,45-/m0/s1
• InChIKey: GBABOYUKABKIAF-BXZSYHTRSA-N

名称和登记号

名称

• IUPAC标准名: methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(12S)-16-ethyl-12-(methoxycarbonyl)-1,10-diazatetracyclo[12.3.1.0^{3,11}.0^{4,9}]octadeca-3(11),4,6,8,15-pentaen-12-yl]-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2(7),3,5,13-tetraene-10-carboxylate
• IUPAC传统名: NVB
• 商标名: Navelbine; Navelbine Base
• 别名: Vinorelbin; Vinorelbina [Spanish]; Vinorelbine Bitartrate; Vinorelbine Ditartarate; Vinorelbine Ditartrate; Vinorelbine Tartrate; Vinorelbinum [Latin]; vinorelbine; Vinorelbine

登记号

• CAS号: 71486-22-1
• PubChem SID: 160963708
• PubChem CID: 60780

理论计算性质

JChem

• Acid pKa: 10.868411
• 质子受体: 8
• 质子供体: 2
• LogD (pH = 5.5): -0.86895776
• LogD (pH = 7.4): 2.6344895
• Log P: 4.6482043
• 摩尔折射率: 216.9875 cm^3
• 极化性: 85.129105 Å^3
• 极化表面积: 133.87 Å^2
• 可自由旋转的化学键: 10
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: 4.39
• LOG S: -4.81
• 溶解度: 1.22e-02 g/l

分子性质

理化性质

• 疏水性(logP): 4

详细说明

DrugBank - DB00361

• Drug Groups: approved; investigational
• Description: Vinorelbine (Navelbine®) is an anti-mitotic chemotherapy drug that is given as a treatment for some types of cancer, including breast cancer and non-small cell lung cancer. [Wikipedia]
• Indication: For the treatment of non-small-cell lung carcinoma.
• Pharmacology: Vinorelbine is a vinca alkaloid antineoplastic agent used as a treatment for various cancers including breast cancer, Hodgkin's disease, Kaposi's sarcoma, and testicular cancer. The vinca alkaloids are structurally similar compounds comprised of 2 multiringed units, vindoline and catharanthine. The vinca alkaloids have become clinically useful since the discovery of their antitumour properties in 1959. Initially, extracts of the periwinkle plant (Catharanthus roseus) were investigated because of putative hypoglycemic properties, but were noted to cause marrow suppression in rats and antileukemic effects in vitro. Vinorelbine binds to the microtubular proteins of the mitotic spindle, leading to crystallization of the microtubule and mitotic arrest or cell death. Vinorelbine has some immunosuppressant effect. The vinca alkaloids are considered to be cell cycle phase-specific.
• Affected Organisms: Humans and other mammals
• Half Life: 27.7-43.6 hours
• Protein Binding: ~27%
• Elimination: Vinorelbine undergoes substantial hepatic elimination in humans, with large amounts recovered in feces after intravenous administration to humans.
• Distribution: * 25.4 to 40.1 L/kg
• Clearance: * 0.97 - 1.26 L/hr/kg
• References: Marty M, Fumoleau P, Adenis A, Rousseau Y, Merrouche Y, Robinet G, Senac I, Puozzo C: Oral vinorelbine pharmacokinetics and absolute bioavailability study in patients with solid tumors. Ann Oncol. 2001 Nov;12(11):1643-9. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

参考文献

• Marty M, Fumoleau P, Adenis A, Rousseau Y, Merrouche Y, Robinet G, Senac I, Puozzo C: Oral vinorelbine pharmacokinetics and absolute bioavailability study in patients with solid tumors. Ann Oncol. 2001 Nov;12(11):1643-9. Pubmed