156294-36-9

Basic information

• Product Name: Larotaxel
• Synonyms: Larotaxel;PNU 100940
• CAS NO: 156294-36-9
• Molecular Formula: C₄₅H₅₃NO₁₄
• Molecular Weight: 831.90062
• Product Categories: Aromatics;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 156294-36-9.mol

Chemical Properties

• Boiling Point: 889.3±65.0 °C(Predicted)
• Appearance: /
• Density: 1.37
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• PKA: 11.20±0.46(Predicted)
• CAS DataBase Reference: Larotaxel(CAS DataBase Reference)
• NIST Chemistry Reference: Larotaxel(156294-36-9)
• EPA Substance Registry System: Larotaxel(156294-36-9)

Safety Data

• Hazardous Substances Data: 156294-36-9(Hazardous Substances Data)

Usage

Uses

Used in Anticancer Applications:
Larotaxel is used as a chemotherapeutic agent for the treatment of various types of cancer. It demonstrates a broad spectrum of activity, making it effective against a wide range of malignancies. Its unique toxicity profile and potential to overcome resistance mechanisms contribute to its effectiveness in treating cancer.
Used in Drug Delivery Systems:
Larotaxel is also used in the development of novel drug delivery systems to enhance its therapeutic efficacy and bioavailability. These systems aim to improve the delivery of Larotaxel to cancer cells, potentially increasing its effectiveness and reducing side effects. Various organic and metallic nanoparticles have been explored as carriers for Larotaxel delivery, with the goal of optimizing its pharmacokinetics and therapeutic outcomes.
Used in Central Nervous System (CNS) Applications:
Due to its potential to penetrate the CNS, Larotaxel is also being investigated for its use in treating cancers that affect the brain and other components of the central nervous system. This unique property sets it apart from other taxane analogs and may offer new treatment options for patients with CNS malignancies.

Upstream product

• 32981-86-5 10-deacetylbaccatin III 
• 27548-93-2 baccatin III 
• 158811-19-9 10-acetyl-7-trifluoromethanesulfonate baccatin III 
• 156294-33-6 7-deoxy-7β,8β-methanobaccatin III 
• 156294-35-8 (2α,3α,4α,5β,7α,10β,13α)-4,10-bis(acetyloxy)-13-({(2R,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-3-phenylpropanoyl}oxy)-1-hydroxy-9-oxo-5,20-epoxy-7,19-cyclotax-11-en-2-yl benzoate 
• 31077-81-3 7-epi-baccatine III 
• 71629-92-0 10-deacetyl-7-epi-baccatin III 
• 131968-76-8 (+/-)-(3R,4S)-3-acetoxy-N-(4-methoxyphenyl)-4-phenylazetidin-2-one 
• 101067-78-1 (+/-)-(3R,4S)-3-hydroxy-4-phenyl-N-(4-methoxyphenyl)azetidin-2-one 
• 100-52-7 benzaldehyde 

Downstream Products

• 1308398-53-9 larotaxel Cbz-glycinate 
• 1308398-62-0 larotaxel Cbz-aminohexanoate 
• 1308398-64-2 larotaxel aminohexanoate methanosulfonate 
• 1308398-55-1 larotaxel glycinate methansulfonate 
• 1308398-59-5 larotaxel Cbz-aminoethoxyethoxy acetate 
• 1308398-61-9 larotaxel aminoethoxyethoxy acetate methansulfonate 
• 1308398-56-2 larotaxel Cbz-β-alanine glycolate 
• 1321582-53-9 larotaxel MMT-aminoethyldithioethyl carbonate 
• 1308398-58-4 larotaxel β-alanine glycolate 

Relevant articles and documents

A semi-synthetic taxane derivative and its preparation method and application

The invention discloses a semi-synthetic taxane derivative. An anti-tumor effect test shows that the semi-synthetic taxane derivative has relatively good anti-tumor activity on a human lung adenocarcinoma cell line A549, a human breast cancer cell line MCF-7, a human glioblastoma cell line U251, a human pancreatic cancer cell line PANC-1, a human colon cancer cell line HCT116 and a human non-small lung cancer cell line H460. The semi-synthetic taxane derivative can be used for preparing anti-tumor drugs.

Synthesis and biological evaluation of novel larotaxel analogues

Taxoids are a class of successful drugs and have been successfully used in chemotherapy for a variety of cancer types. However, despite the hope and promises that these taxoids have engendered, their utility is hampered by some clinic limitations. Extensive structure-activity relationship (SAR) studies of toxoids have been performed in many different laboratories. Whereas, SAR studies that based on the new-generation toxoid, larotaxel, have not been reported yet. In view of the advantages in preclinical and clinical data of larotaxel over former toxoids, new taxoids that strategicly modified at the C3’/C3′-N and C2 positions of larotaxel were designed, semi-synthesized, and examined for their potency and efficacy in vitro. As a result, it has been shown that the majority of these larotaxel analogues are exceptionally potent against both drug-sensitive tumor cells and tumor cells with drug resistance arising from P-glycoprotein over expression. Further in vivo antitumor efficacies investigations revealed A2 might be a potent antitumor drug candidate for further preclinical evaluation.

PROCESS FOR PREPARING TAXOIDS FROM BACCATIN DERIVATIVES USING LEWIS ACID CATALYST

The present invention relates to a process of preparing a taxoid (X) by reacting a protected baccatin derivative (B) with a β-lactam (C) in the presence of one or more Lewis acids and a base agent. The present invention also relates to a process of preparing the protected baccatin derivative (B) from a baccatin derivative (A) comprising a protection reaction catalyzed by one or more Lewis acids with an optional base agent.