T7191

Paclitaxel

from semisynthetic, ≥98%

• Fórmula empírica (notación de Hill): C₄₇H₅₁NO₁₄
• Número de CAS: 33069-62-4
• Peso molecular: 853.91
• Beilstein: 1420457
• Número MDL: MFCD00869953
• Código UNSPSC: 12161501
• ID de la sustancia en PubChem: 24900422
• NACRES: NA.77

Propiedades

• origen biológico: semisynthetic
• Análisis: ≥98%
• impurezas: natural taxane impurities, none detected (except ≤0.5% paclitaxel degradation products.)
• mp: 213 °C (dec.) (lit.)
• solubilidad: DMSO: soluble 50 mg/mL; methanol: soluble 50 mg/mL, clear, colorless; H₂O: soluble (hydrolyzes); ethanol: soluble
• espectro de actividad antibiótica: neoplastics
• Modo de acción: DNA synthesis | interferes
• emisor: Bristol-Myers Squibb
• temp. de almacenamiento: −20°C
• cadena SMILES: [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
• Clave InChI: RCINICONZNJXQF-MZXODVADSA-N
• Información sobre el gen: 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)

Descripción

Descripción general

Chemical structure: taxoide

Aplicación

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.

Acciones bioquímicas o 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 y beneficios

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This compound was developed by Bristol-Myers Squibb. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Precaución

Paclitaxel undergoes transesterification in methanol and hydrolyzes in aqueous solutions.

Nota de preparación

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

Información de seguridad

• Pictogramas: GHS08
• Palabra de señalización: Danger
• Frases de peligro: H341,H360FD,H372
• Consejos de prudencia: P202 - P260 - P264 - P280 - P308 + P313 - P405
• Clasificaciones de peligro: Muta. 2 - Repr. 1B - STOT RE 1
• Órganos de actuación: Central nervous system,Bone marrow,Cardio-vascular system
• Código de clase de almacenamiento: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• Clase de riesgo para el agua (WGK): WGK 3
• Punto de inflamabilidad (°F): Not applicable
• Punto de inflamabilidad (°C): Not applicable
• Equipo de protección personal: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges