42771-81-3

Basic information

• Product Name: Flurbiprofen Related Impurity 1
• Synonyms: Flurbiprofen Related Impurity 1;Diethyl 2-[2-fluro-4-biphenyl-4-yl]-2 methylmalonate;Flurbiprofen Impurity 1;Flurbiprofen Impurity I
• CAS NO: 42771-81-3
• Molecular Formula: C₂₀H₂₁FO₄
• Molecular Weight: 344.38
• Mol File: 42771-81-3.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 413.4±40.0 °C(Predicted)
• Appearance: /
• Density: 1.153±0.06 g/cm3(Predicted)
• Solubility: Chloroform, Methanol
• CAS DataBase Reference: Flurbiprofen Related Impurity 1(CAS DataBase Reference)
• NIST Chemistry Reference: Flurbiprofen Related Impurity 1(42771-81-3)
• EPA Substance Registry System: Flurbiprofen Related Impurity 1(42771-81-3)

Safety Data

• Hazardous Substances Data: 42771-81-3(Hazardous Substances Data)

Usage

Description

Flurbiprofen Related Impurity 1, also known as 2-(2-Fluoro[1,1''-biphenyl]-4-yl)-2,3-dimethylbutanedioic Acid Dimethyl Ester, is an intermediate in the synthesis of 2-(2-Fluoro[1,1''-biphenyl]-4-yl)-2,3-dimethylbutanedioic acid. Flurbiprofen Related Impurity 1 is identified as an impurity of Flurbiprofen (F598700), which is an anti-inflammatory drug commonly used as an analgesic.

Uses

Used in Pharmaceutical Industry:
Flurbiprofen Related Impurity 1 is used as an intermediate in the synthesis process for producing Flurbiprofen, an anti-inflammatory drug. Its role is crucial in the development of the final drug product, as it contributes to the overall efficacy and safety of the medication.
Used in Quality Control and Regulatory Compliance:
Flurbiprofen Related Impurity 1 is also used in the quality control and regulatory compliance processes within the pharmaceutical industry. By monitoring and controlling the presence of this impurity, manufacturers can ensure that the final product meets the required safety and efficacy standards, ultimately protecting patients from potential adverse effects.
Used in Research and Development:
In the field of research and development, Flurbiprofen Related Impurity 1 serves as a valuable compound for studying the properties and behavior of Flurbiprofen. This knowledge can be applied to improve the drug's formulation, optimize its delivery methods, and enhance its therapeutic potential.

Upstream product

• 71-43-2 benzene 
• 497-19-8 sodium carbonate 
• 78543-08-5 2-(4-amino-3-fluorophenyl)-2-methylmalonic acid diethyl ester 
• 110-46-3 isopentyl nitrite 
• 149-73-5 trimethyl orthoformate 
• 749917-24-6 2-(3-fluoro-4-iodophenyl)-2-methylmalonic acid diethyl ester 
• 98-80-6 phenylboronic acid 
• 609-08-5 Diethyl methylmalonate 
• 446-35-5 2,4-Difluoronitrobenzene 
• 78543-06-3 diethyl 2-(3-fluoro-4-nitrophenyl)-2-methyl-malonate 

Downstream Products

• 5104-49-4 fluorobiprofen 
• 42771-82-4 2-(2-fluoro-4-biphenylyl)-2-methylmalonic acid 
• 5104-49-4 (S)-(+)-flurbiprofen 
• 5104-49-4 (R)-flurbiprofen 

Relevant articles and documents

Targeted fluorination of a nonsteroidal anti-inflammatory drug to prolong metabolic half-life

In drug design, one way of improving metabolic stability is to introduce fluorine at a metabolically labile site. In the early stages of drug design, identification of such sites is challenging, and a rapid method of assessing the effect of fluorination on a putative drug's metabolic stability would be of clear benefit. One approach to this is to employ micro-organisms that are established as models of drug metabolism in parallel with the synthesis of fluorinated drug analogues. In this study, we have used the filamentous fungus Cunninghamella elegans to identify the metabolically labile site of the nonsteroidal anti-inflammatory drug flurbiprofen, to aid in the design of fluorinated derivatives that were subsequently synthesised. The effect of the additional fluorine substitution on cytochrome P450-catalysed oxidation was then determined via incubation with the fungus, and demonstrated that fluorine substitution at the 4′-position rendered the drug inactive to oxidative transformation, whereas substitution of fluorine at either 2′ or 3′ resulted in slower oxidation compared to the original drug. This approach to modulating the metabolic stability of a drug-like compound is widely applicable and can be used to address metabolic issues of otherwise good lead compounds in drug development. A metabolic stopper: By applying a chemical-microbiological approach to the design of drugs with enhanced metabolic stability, a series of fluorinated derivatives of the nonsteroidal anti-inflammatory drug (NSAID) flurbiprofen was synthesised that were more resistant to cytochrome P450-catalysed transformation than the original drug.

PROCESS FOR PRODUCING BIARYL COMPOUND

A process for producing a biaryl compound, characterized by reacting an arylhydrazine compound, hydrogen peroxide and an aryl compound. When the reaction is conducted in the presence of a given metal or a compound of the metal or in the presence of a metal oxide obtained by reacting the given metal or a compound of the metal with hydrogen peroxide, then the yield of the biaryl compound is improved.

Processes for the preparation of hydratropic acids and esters

The invention concerns the novel compounds dialkyl 2-(3-fluoro-4-nitrophenyl)-2-methylmalonate IIIa and dialkyl 2-(3-fluoro-4-aminophenyl)-2-methylmalonate IVa useful as intermediates in an improved process for making 2-(2-fluoro-4-biphenylyl)propionic acid, known as flurbiprofen, having the formula STR1 and ester thereof. It has anti-inflammatory activity which is about 240 times that of aspirin and analgesic activity which is about 180 times that of aspirin in standard laboratory tests. However, despite this high activity, the toxicity (LD50) is only 1.2 to 2.4 times greater than that of aspirin in standard laboratory tests. Also within the invention is a novel method of making the above intermediates and analogs thereof useful to prepare corresponding biaryl compounds which have pharmaceutical uses.