Merck
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T7191

Sigma-Aldrich

Paclitaxel

from semisynthetic, ≥97%

Empirical Formula (Hill Notation):
C47H51NO14
CAS Number:
Molecular Weight:
853.91
Beilstein:
1420457
Número MDL:
ID de substância PubChem:
NACRES:
NA.77

fonte biológica

semisynthetic

Nível de qualidade

100

teor

≥97%

Impurezas

natural taxane impurities, none detected (except ≤0.5% paclitaxel degradation products.)

pf

213 °C (dec.) (lit.)

solubilidade

DMSO: soluble 50 mg/mL
methanol: soluble 50 mg/mL, clear, colorless
H2O: soluble (hydrolyzes)
ethanol: soluble

espectro de atividade do antibiótico

neoplastics

Modo de ação

DNA synthesis | interferes

originador

Bristol-Myers Squibb

temperatura de armazenamento

−20°C

SMILES string

[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

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Descrição geral

Chemical structure: taxoide

Aplicação

Paclitaxel has been used to study its effects on tumor regression in mouse models of pancreatic ductal adenocarcinoma. Paclitaxel has also been used as an internal standard for chromatographic assays of docetaxel. Furthermore, paclitaxel has been used to analyze its effects on Caenorhabditis elegans embryos.

Embalagem

1, 5, 25 mg in glass insert

Ações bioquímicas/fisiológicas

Paclitaxel is a potent anti-neoplastic and anti-mitotic taxane drug, which binds to the N-terminus of β-tubulin and and stabilizes microtubules arresting the cell cycle at the G2/M phase. The microtubule damage induces apoptosis through a JNK-dependent pathway followed by a JNK-independent pathway, perhaps related to the activation of protein kinase A (PKA) or of Raf-1 kinase, resulting in phosphorylation of Bcl-2. A major metabolite via CYP2CB is 6α-hydroxypaclitaxel (6α-OHP).
Paclitaxel is highly lipophilic. It serves as a substrate for p-glycoprotein, a multi-drug resistance protein. Paclitaxel is thus, less localized to the brain. Apart from its cytocidal action, paclitaxel is known to stimulate tumor invasion process.

Características e benefícios

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.

Atenção

Paclitaxel undergoes transesterification in methanol and hydrolyzes in aqueous solutions.

Nota de preparo

Paclitaxel is soluble in methanol at 50 mg/ml and yields a clear, colorless solution. It is also soluble in ethanol, water and DMSO.

Palavra indicadora

Danger

Classificações de perigo

Eye Dam. 1 - Muta. 1A - Repr. 1A - Resp. Sens. 1 - Skin Irrit. 2 - Skin Sens. 1 - STOT RE 1 - STOT SE 3

Órgãos-alvo

Respiratory system

Código de classe de armazenamento

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Equipamento de proteção individual

Eyeshields, Faceshields, Gloves, type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

Certificate of Analysis

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Certificate of Origin

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