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安全信息

T1912

Sigma-Aldrich

紫杉醇

from Taxus yannanensis, powder

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About This Item

经验公式（希尔记法）:
C47H51NO14
CAS号:
33069-62-4
分子量:
853.91
Beilstein:
1420457
MDL编号:
MFCD00869953
UNSPSC代码:
12161501
PubChem化学物质编号:
24899998
NACRES:
NA.77

生物来源

Taxus yannanensis

质量水平

200

形式

powder

颜色

white

mp

213 °C (dec.) (lit.)

溶解性

DMSO: 50 mg/mL (can be stored frozen for several months)
acetonitrile: soluble
ethanol: soluble
methanol: soluble (undergoes transesterification)

抗生素抗菌谱

neoplastics

作用机制

DNA synthesis | interferes

创始人

Bristol-Myers Squibb

储存温度

2-8°C

SMILES字符串

[H][C@@]12C[C@H](O)[C@@]3(C)C(=O)[C@H](OC(C)=O)C4=C(C)[C@H](C[C@@](O)([C@@H](OC(=O)c5ccccc5)[C@]3([H])[C@@]1(CO2)OC(C)=O)C4(C)C)OC(=O)[C@H](O)[C@@H](NC(=O)c6ccccc6)c7ccccc7

InChI

1S/C47H51NO14/c1-25-31(60-43(56)36(52)35(28-16-10-7-11-17-28)48-41(54)29-18-12-8-13-19-29)23-47(57)40(61-42(55)30-20-14-9-15-21-30)38-45(6,32(51)22-33-46(38,24-58-33)62-27(3)50)39(53)37(59-26(2)49)34(25)44(47,4)5/h7-21,31-33,35-38,40,51-52,57H,22-24H2,1-6H3,(H,48,54)/t31-,32-,33+,35-,36+,37+,38-,40-,45+,46-,47+/m0/s1

InChI key

RCINICONZNJXQF-MZXODVADSA-N

基因信息

human ... BCL2(596) , TUBA1A(7846) , TUBA1B(10376) , TUBA1C(84790) , TUBA3C(7278) , TUBA3E(112714) , TUBA4A(7277) , TUBB(203068) , TUBB1(81027) , TUBB2A(7280) , TUBB2B(347733) , TUBB3(10381) , TUBB4A(10382) , TUBB4B(10383) , TUBB6(84617) , TUBB8(347688)

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一般描述

Chemical structure: taxoide

应用

Paclitaxel has been used to study PREP2-tubulin interactions using coimmunoprecipitation assays on NIH3T3 cell extracts. This drug has also been used to stabilize tubulin obtained from pig brain.

生化/生理作用

紫杉醇是一种有效的抗肿瘤和抗有丝分裂的紫杉烷类药物，可与 β-微管蛋白的N端结合，并使微管稳定，使细胞周期停滞在G2/M期。微管损伤通过依赖 JNK 的途径诱导细胞凋亡，随后通过不依赖 JNK 的途径诱导细胞凋亡，这可能与蛋白激酶 A（PKA）或 Raf-1 激酶的激活，进而导致 Bcl-2 磷酸化有关。通过 CYP2CB 的主要代谢物是 6α-羟基紫杉醇（6α-OHP）。

特点和优势

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound was developed by Bristol-Myers Squibb. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

注意

紫杉醇可在甲醇中进行酯交换反应，并在水溶液中发生水解。

制备说明

Paclitaxel is soluble in DMSO at 50 mg/ml and can be stored frozen for several months. It is also soluble in methanol (undergoes transesterification), acetonitrile and ethanol. Paclitaxel is rapidly destroyed in weakly alkaline, methanolic solutions and in strongly acidic methanolic solutions (1:1 of methanol:concentrated HCl). It is also soluble in a mixture of 50% Cremophor EL and 50% anhydrous ethanol.

象形图

Health hazard
GHS08

警示用语：

Danger

危险声明

H341,H360FD,H372

危险分类

Muta. 2 - Repr. 1B - STOT RE 1

靶器官

Central nervous system,Bone marrow,Cardio-vascular system

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

法规信息

监管及禁止进口产品

分析证书(COA)

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Akane Furuta et al.
The Journal of biological chemistry, 284(9), 5927-5935 (2009-01-07)
Outer arm dynein (OAD) of cilia and flagella contains two or three distinct heavy chains, each having a motor function. To elucidate their functional difference, we compared the in vitro motile properties of Chlamydomonas wild-type OAD containing the alpha, beta
Makoto Iimori et al.
Nature communications, 7, 11117-11117 (2016-04-01)
Temporal regulation of microtubule dynamics is essential for proper progression of mitosis and control of microtubule plus-end tracking proteins by phosphorylation is an essential component of this regulation. Here we show that Aurora B and CDK1 phosphorylate microtubule end-binding protein
M Onrubia et al.
Current medicinal chemistry, 20(7), 880-891 (2012-12-06)
Taxol (paclitaxel) and its derivatives are microtubule-stabilizing drugs widely used in the treatment of several types of cancer, including mammary, prostate, ovarian and non-small-cell lung carcinoma, as well as AIDS-associated Kaposi's sarcoma and other types of tumor. Taxanes stabilize microtubules
Yoo-Joung Ko et al.
The Lancet. Oncology, 14(8), 769-776 (2013-05-28)
No standard treatment exists for patients with platinum-refractory urothelial cancer. Taxanes and vinflunine are commonly used, but response is less than 20% with no survival benefit. In this phase 2 study, we assessed efficacy and tolerability of nanoparticle albumin-bound (nab)
Zhiping Zhang et al.
Expert opinion on drug delivery, 10(3), 325-340 (2013-01-08)
Paclitaxel (PTX) is one of the most effective broad-spectrum chemotherapeutic agents in the treatment of cancers. However, its clinical application has been limited due to its poor water solubility. Its current clinical administration uses the adjuvant of serious side effects
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