T7191

Paclitaxel

semisynthetic, ≥98%, Apoptosis inducer

• Empirický vzorec (Hillův zápis): C₄₇H₅₁NO₁₄
• Číslo CAS: 33069-62-4
• Molekulová hmotnost: 853.91
• NACRES: NA.77
• PubChem Substance ID: 24900422
• UNSPSC Code: 12161501
• MDL number: MFCD00869953
• Beilstein/REAXYS Number: 1420457
• Assay: ≥98%

Vlastnosti

• Název produktu: Paclitaxel, from semisynthetic, ≥98%
• biological source: semisynthetic
• Quality Segment: 100
• assay: ≥98%
• impurities: natural taxane impurities, none detected (except ≤0.5% paclitaxel degradation products.)
• mp: 213 °C (dec.) (lit.)
• solubility: DMSO: soluble 50 mg/mL, methanol: soluble 50 mg/mL, clear, colorless, H₂O: soluble (hydrolyzes), ethanol: soluble
• antibiotic activity spectrum: neoplastics
• mode of action: DNA synthesis | interferes
• originator: Bristol-Myers Squibb
• storage temp.: −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
• Gene Information: 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)

Popis

General description

Chemical structure: taxoide

Application

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.

Biochem/physiol Actions

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.

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.

Features and Benefits

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.

Preparation Note

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

Disclaimer

Paclitaxel undergoes transesterification in methanol and hydrolyzes in aqueous solutions.

Bezpečnostní informace

• Piktogramy: GHS08
• Výstražné slovo: Danger
• Kódy nebezpečí: H341,H360FD,H372
• Bezpečnostní pokyny: P202 - P260 - P264 - P280 - P308 + P313 - P405
• Hazard Classifications: Muta. 2 - Repr. 1B - STOT RE 1
• Cílové orgány: Central nervous system,Bone marrow,Cardio-vascular system
• Skladovací třída: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• Co se děje?: WGK 3
• Bod vzplanutí (°F): Not applicable
• Bod vzplanutí (°C): Not applicable
• PPE (osobní ochranné prostředky): Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges