194468-36-5

Basic information

• Product Name: F 12158
• Synonyms: 20',20'-Difluoro-3',4'-dihydrovinorelbine Ditartrate;4'-Deoxy-20',20'-difluoro-5'-norvincaleukoblastine Ditartrate;BMS 710485;F 12158;Javlor;Vinflunine Ditartrate;(2β,3β,4β,5α,12β,19α)-4-(Acetyloxy)-6,7-didehydro-15-[(2R,4R,6S,8S)-4-(1,1-difluoroethyl)-1,3,4,5,6,7,8,9-octahydro-8-(Methoxycarbonyl)-2,6-Methano-2H-azecino[4,3-b]indol-8-yl]-3-hydroxy-16-Methoxy-1-MethylaspidosperMidine-3-carboxylic Acid Methyl Ester (2R,3R)-2,3-Dihydroxybutanedioate;Ditartrate
• CAS NO: 194468-36-5
• Molecular Formula: C49H59F2N4O14
• Molecular Weight: 966.0079664
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 194468-36-5.mol
• Article Data: 1

Chemical Properties

• Melting Point: 244-246°C (dec)
• Appearance: /
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: F 12158(CAS DataBase Reference)
• NIST Chemistry Reference: F 12158(194468-36-5)
• EPA Substance Registry System: F 12158(194468-36-5)

Safety Data

• Hazardous Substances Data: 194468-36-5(Hazardous Substances Data)

Usage

Description

F 12158, also known as Glycerol, is a simple polyol compound that is widely used in various industries due to its unique properties. It is a colorless, odorless, viscous liquid with a sweet taste. Glycerol has three hydroxyl groups that allow it to form hydrogen bonds, making it highly soluble in water and compatible with a wide range of substances. Its versatility and compatibility make it a valuable component in numerous applications.

Uses

Used in Pharmaceutical Industry:
F 12158 is used as a solvent for various pharmaceutical formulations, such as elixirs, syrups, and injectable solutions. Its ability to dissolve a wide range of substances, including active pharmaceutical ingredients, makes it an ideal choice for drug delivery systems.
Used in Cosmetics and Personal Care Industry:
F 12158 is used as a humectant in cosmetics and personal care products, such as lotions, creams, and toothpaste. Its hygroscopic nature helps to retain moisture, providing hydration and improving the texture and feel of these products.
Used in Food and Beverage Industry:
F 12158 is used as a humectant, emulsifier, and sweetener in the food and beverage industry. It helps to maintain the moisture content in foods, improve the texture of baked goods, and enhance the taste of various products.
Used in Industrial Applications:
F 12158 is used as a component in the manufacturing of various products, such as antifreeze, lubricants, and explosives. Its compatibility with different substances and ability to form hydrogen bonds make it a valuable additive in these applications.
Used in Energy Storage:
F 12158 is used as a component in the production of biodiesel and as a solvent in the manufacturing of lithium-ion batteries. Its ability to dissolve various substances and improve the efficiency of these energy storage systems makes it a valuable resource in the renewable energy sector.

Clinical Use

Vinflunine ditartrate is a second generation difluorinated analog of the naturally-occuring substance vinorelbine and it is approved for the treatment of non-small cell lung cancer, metastatic breast cancer and ovarian cancer. Vinflunine, a tubulin polymerization inhibitor, belongs to the vinca alkaloid class of anti-cancer agents. Introduction of the difluoro group of vinflunine dramatically improved antitumor activity of the parent vinorelbine structure. Vinflunine was discovered by Pierre Fabre Laboratories and in 2004 was licensed to Bristol-Myers Squibb for development and commercialization. In 2007, the rights to venflunine were returned to Pierre Fabre which completed its development.

Synthesis

Vinflunine can be prepared directly from vinorelbine (155) through the use of superacid chemistry. Reaction of 155 with antimony pentaflouride in hydrofluoric acid and Nbromosuccinimide followed by treatment with two equivalents of tartaric acid produced vinflunine ditartrate (XV) in 25% yield. An alternative synthesis of vinflunine was realized through reaction of vinblastine or 3’,4’-dihydrovinblastine (156) with antimony pentaflouride and hydrofluoric acid in chloroform to give the difluoro alkaloid 157 in 40% yield Ring contraction was effected by reaction with trifluoroacetic acid and N-bromosuccinimide followed by aqueous sodium bicarbonate and silver tetrafluoroborate to give vinflunine in 88% yield. Vinflunine ditartrate (XV) was prepared by treating a solution of vinflunine in toluene with two equivalents of tartaric acid.

Relevant articles and documents

CRYSTALLINE FORM OF VINFLUNINE DITARTRATE

The present invention relates to a novel crystalline form of vinflunine, to a process for preparing it, and to its uses in the therapeutic field, in particular for treating cancer.