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865-21-4 分子结构
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methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(13S,15S,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0^{4,12}.0^{5,10}]nonadeca-4(12),5,7,9-tetraen-13-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:452
分子式:C46H58N4O9
平均质量:810.97412
单一同位素质量:810.42037946
SMILES和InChIs

SMILES:
c1c2c(cc(c1OC)[C@@]1(c3[nH]c4ccccc4c3CCN3C[C@](C[C@@H](C3)C1)(O)CC)C(=O)OC)[C@@]13CCN4CC=C[C@@]([C@@H]34)(CC)[C@@H](OC(=O)C)[C@@](O)([C@@H]1N2C)C(=O)OC
Canonical SMILES:
COc1cc2N(C)[C@@H]3[C@@]4(c2cc1[C@]1(C[C@@H]2CN(CCc5c1[nH]c1c5cccc1)C[C@](C2)(O)CC)C(=O)OC)CCN1[C@H]4[C@@]([C@H]([C@]3(O)C(=O)OC)OC(=O)C)(CC)C=CC1
InChI:
InChI=1S/C46H58N4O9/c1-8-42(54)23-28-24-45(40(52)57-6,36-30(15-19-49(25-28)26-42)29-13-10-11-14-33(29)47-36)32-21-31-34(22-35(32)56-5)48(4)38-44(31)17-20-50-18-12-16-43(9-2,37(44)50)39(59-27(3)51)46(38,55)41(53)58-7/h10-14,16,21-22,28,37-39,47,54-55H,8-9,15,17-20,23-26H2,1-7H3/t28-,37+,38-,39-,42+,43-,44-,45+,46+/m1/s1
InChIKey:
JXLYSJRDGCGARV-XQKSVPLYSA-N

引用这个纪录

CBID:452 http://www.chembase.cn/molecule-452.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(13S,15S,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0^{4,12}.0^{5,10}]nonadeca-4(12),5,7,9-tetraen-13-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
methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(13S,15S,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraen-13-yl]-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate
IUPAC传统名
vincaleukoblastine
vinblastine
商标名
Nincaluicolflastine
Rozevin
Velban
Velbe
Vinblastin
Vinblastina [Dcit]
Vinblastine Sulfate
Vinblastinum [INN-Latin]
Vincaleucoblastin
Vincaleucoblastine
Vincaleukoblastine
Vincoblastine
别名
Vinblastine
vincaleukoblastine
CAS号
865-21-4
PubChem SID
160963915
46504550
PubChem CID
241903
CHEBI ID
27375
ATC码
L01CA01
CHEMBL
159
Chemspider ID
211446
DrugBank ID
DB00570
KEGG ID
D08675
美国药典/FDA物质标识码
5V9KLZ54CY
维基百科标题
Vinblastine
Medline Plus
a682848

数据来源

数据来源

所有数据来源 商品来源 非商品来源
数据来源 数据ID 价格

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 10.869524  质子受体
质子供体 LogD (pH = 5.5) -1.6706752 
LogD (pH = 7.4) 1.8057727  Log P 4.1831455 
摩尔折射率 222.4206 cm3 极化性 87.76486 Å3
极化表面积 154.1 Å2 可自由旋转的化学键 10 
里宾斯基五规则 false 
Log P 4.22  LOG S -4.68 
溶解度 1.69e-02 g/l 

分子性质

分子性质

理化性质 药理学性质 生物活性(PubChem)
溶解度
Negligible expand 查看数据来源
疏水性(logP)
3.9 expand 查看数据来源
给药途径
Exclusively intravenous expand 查看数据来源
生物利用度
n/a expand 查看数据来源
排泄
Biliary and renal expand 查看数据来源
半衰期
24.8 hours (terminal) expand 查看数据来源
代谢
Hepatic (CYP3A4-mediated) expand 查看数据来源
法定药品分级
POM (UK) expand 查看数据来源
Rx-only (US) expand 查看数据来源
妊娠期药物分类
D (Australia) expand 查看数据来源
D (US) expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank Wikipedia Wikipedia
DrugBank -  DB00570 external link
Item Information
Drug Groups approved
Description Antitumor alkaloid isolated from Vinca rosea. (Merck, 11th ed.)
Indication For treatment of breast cancer, testicular cancer, lymphomas, neuroblastoma, Hodgkin's and non-Hodgkin's lymphomas, mycosis fungoides, histiocytosis, and Kaposi's sarcoma.
Pharmacology Vinblastine is a vinca alkaloid antineoplastic agent. 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. Vinblastine has some immunosuppressant effect. The vinca alkaloids are considered to be cell cycle phase-specific.
Toxicity Oral, mouse: LD50 = 423 mg/kg; Oral, rat: LD50 = 305 mg/kg.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic. Metabolism of vinblastine has been shown to be mediated by hepatic cytochrome P450 3A isoenzymes.
Half Life Triphasic: 35 min, 53 min, and 19 hours
Protein Binding 98-99%
Elimination The major route of excretion may be through the biliary system.
References
Starling D: Two ultrastructurally distinct tubulin paracrystals induced in sea-urchin eggs by vinblastine sulphate. J Cell Sci. 1976 Jan;20(1):79-89. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Starling D: Two ultrastructurally distinct tubulin paracrystals induced in sea-urchin eggs by vinblastine sulphate. J Cell Sci. 1976 Jan;20(1):79-89. Pubmed
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专利

专利

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