T7191

Paclitaxel

from semisynthetic, ≥98%

• Wzór empiryczny (zapis Hilla): C₄₇H₅₁NO₁₄
• Numer CAS: 33069-62-4
• Masa cząsteczkowa: 853.91
• Beilstein: 1420457
• Numer MDL: MFCD00869953
• Kod UNSPSC: 12161501
• Identyfikator substancji w PubChem: 24900422
• NACRES: NA.77

Właściwości

• pochodzenie biologiczne: semisynthetic
• Poziom jakości: 100
• Próba: ≥98%
• zanieczyszczenia: natural taxane impurities, none detected (except ≤0.5% paclitaxel degradation products.)
• mp: 213 °C (dec.) (lit.)
• rozpuszczalność: DMSO: soluble 50 mg/mL; methanol: soluble 50 mg/mL, clear, colorless; H₂O: soluble (hydrolyzes); ethanol: soluble
• spektrum działania antybiotyku: neoplastics
• Tryb działania: DNA synthesis | interferes
• inicjator: Bristol-Myers Squibb
• temp. przechowywania: −20°C
• ciąg 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
• Klucz InChI: RCINICONZNJXQF-MZXODVADSA-N
• informacje o genach: 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)

Opis

Opis ogólny

Chemical structure: taxoide

Zastosowanie

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.

Działania biochem./fizjol.

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.

Cechy i korzyści

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.

Przestroga

Paclitaxel undergoes transesterification in methanol and hydrolyzes in aqueous solutions.

Uwaga dotycząca przygotowania

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

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Informacja o środkach bezpieczeństwa

• Piktogramy: GHS08
• Hasło ostrzegawcze: Danger
• Zwroty wskazujące rodzaj zagrożenia: H341,H360FD,H372
• Zwroty wskazujące środki ostrożności: P202 - P260 - P264 - P280 - P308 + P313 - P405
• Klasyfikacja zagrożeń: Muta. 2 - Repr. 1B - STOT RE 1
• Organy docelowe: Central nervous system,Bone marrow,Cardio-vascular system
• Kod klasy składowania: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• Klasa zagrożenia wodnego (WGK): WGK 3
• Temperatura zapłonu (°F): Not applicable
• Temperatura zapłonu (°C): Not applicable
• Środki ochrony indywidualnej: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges