T7402

Paclitaxel

From Taxus brevifolia, ≥95% (HPLC), anti-neoplastic , powder

• Empirical Formula (Hill Notation): C₄₇H₅₁NO₁₄
• CAS Number: 33069-62-4
• Molecular Weight: 853.91
• NACRES: NA.77
• PubChem Substance ID: 24277878
• UNSPSC Code: 12161501
• MDL number: MFCD00869953
• Beilstein/REAXYS Number: 1420457

Properties

• Product Name: Paclitaxel, from Taxus brevifolia, ≥95% (HPLC), powder
• InChI key: RCINICONZNJXQF-MZXODVADSA-N
• 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
• biological source: Taxus brevifolia
• assay: ≥95% (HPLC)
• form: powder
• color: white
• mp: 213 °C (dec.) (lit.)
• solubility: DMSO: 50 mg/mL (can be stored frozen for several months); methanol: soluble 50 mg/mL, clear, colorless (undergoes transesterification); ethanol: soluble
• antibiotic activity spectrum: viruses
• mode of action: DNA synthesis | interferes
• originator: Bristol-Myers Squibb
• storage temp.: 2-8°C
• Quality Level: 200
• 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)

Description

Application

Paclitaxel has been used as a component of the dechorionation buffer for Gryllus bimaculatus eggs[1]. Paclitaxel has also been used for studying its effect on the movement of all-trans retinoic acid (ATRA) differentiated NB4 cells[2].

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).

Disclaimer

Paclitaxel undergoes transesterification in methanol and hydrolyzes in aqueous solutions.

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.

General description

Chemical structure: taxoide

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Preparation Note

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

Safety Information

• pictograms: GHS08
• signalword: Danger
• hcodes: H341,H360FD,H371,H372
• pcodes: P202 - P260 - P264 - P280 - P308 + P311 - P405
• Hazard Classifications: Muta. 2 - Repr. 1B - STOT RE 1 - STOT SE 2
• target_organs: Central nervous system,Bone marrow,Cardio-vascular system, Eyes,Central nervous system
• Storage Class: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges