T7191

Paclitaxel

from semisynthetic, ≥98%

• Formula empirica (notazione di Hill): C₄₇H₅₁NO₁₄
• Numero CAS: 33069-62-4
• Peso molecolare: 853.91
• Beilstein: 1420457
• Numero MDL: MFCD00869953
• Codice UNSPSC: 12161501
• ID PubChem: 24900422
• NACRES: NA.77

Proprietà

• Origine biologica: semisynthetic
• Saggio: ≥98%
• Impurezze: natural taxane impurities, none detected (except ≤0.5% paclitaxel degradation products.)
• Punto di fusione: 213 °C (dec.) (lit.)
• Solubilità: DMSO: soluble 50 mg/mL; methanol: soluble 50 mg/mL, clear, colorless; H₂O: soluble (hydrolyzes); ethanol: soluble
• Spettro attività antibiotica: neoplastics
• Modalità d’azione: DNA synthesis | interferes
• Ideatore: Bristol-Myers Squibb
• Temperatura di conservazione: −20°C
• Stringa SMILE: [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; RCINICONZNJXQF-MZXODVADSA-N
• Informazioni sul gene: 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)

Descrizione

Descrizione generale

Chemical structure: taxoide

Applicazioni

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.

Azioni biochim/fisiol

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.

Caratteristiche e vantaggi

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.

Avvertenza

Paclitaxel undergoes transesterification in methanol and hydrolyzes in aqueous solutions.

Nota sulla preparazione

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

Informazioni sulla sicurezza

• Pittogrammi: GHS08
• Avvertenze: Danger
• Indicazioni di pericolo: H341,H360FD,H372
• Consigli di prudenza: P202 - P260 - P264 - P280 - P308 + P313 - P405
• Classi di pericolo: Muta. 2 - Repr. 1B - STOT RE 1
• Organi bersaglio: Central nervous system,Bone marrow,Cardio-vascular system
• Codice della classe di stoccaggio: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• Classe di pericolosità dell'acqua (WGK): WGK 3
• Punto d’infiammabilità (°F): Not applicable
• Punto d’infiammabilità (°C): Not applicable
• Dispositivi di protezione individuale: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges