35853-50-0

Usage

Uses

Used in Pharmaceutical Industry:
Carboxymefloquine is used as an active metabolite for enhancing the efficacy of antimalarial treatments. As a metabolite of Mefloquine, it plays a significant role in the overall effectiveness of the drug against malaria-causing parasites, particularly Plasmodium species.
Used in Research and Development:
In the field of pharmaceutical research and development, Carboxymefloquine is utilized as a subject of study to understand the metabolic pathways and pharmacokinetics of Mefloquine. This knowledge aids in the optimization of drug dosages and the development of more effective antimalarial therapies.
Used in Drug Metabolism Studies:
Carboxymefloquine is also used as a reference compound in drug metabolism studies, helping researchers to comprehend how different individuals metabolize Mefloquine and how this may impact the drug's effectiveness and potential side effects. This information is crucial for personalized medicine and the development of tailored treatment plans for patients with varying metabolic profiles.

InChI:InChI=1/C12H5F6NO2/c13-11(14,15)7-3-1-2-5-6(10(20)21)4-8(12(16,17)18)19-9(5)7/h1-4H,(H,20,21)

Upstream product

• 68682-28-0 mefloquine hydrochloride 
• 35853-45-3 (2,8-bis-trifluoromethyl)-4-bromoquinoline 
• 124-38-9 carbon dioxide 

Downstream Products

• 49752-90-1 (+/-)-mefloquine 
• 35853-55-5 [2,8-bis(trifluoromethyl)-4-quinolinyl]-2-pyridinylmethanone 

Relevant academic research and scientific papers

Base metal-catalyzed benzylic oxidation of (aryl)(heteroaryl)methanes with molecular oxygen

The methylene group of various substituted 2- and 4-benzylpyridines, benzyldiazines and benzyl(iso)quinolines was successfully oxidized to the corresponding benzylic ketones using a copper or iron catalyst and molecular oxygen as the stoichiometric oxidant. Application of the protocol in API synthesis is exemplified by the alternative synthesis of a precursor to the antimalarial drug Mefloquine. The oxidation method can also be used to prepare metabolites of APIs which is illustrated for the natural product papaverine. ICP-MS analysis of the purified reaction products revealed that the base metal impurity was well below the regulatory limit.

Use of (+)mefloquine for the treatment of malaria

Use of (+)-(11R,2′S)-α-2-piperidinyl-2,8-bis(trifluoromethyl)-4-quinolinemethanol or a pharmaceutically acceptable salt thereof substantially free of its (?)-enantiomer in the manufacture of a medicament having reduced side-effect compared to the racemic (±)-(R*,S*)-α-2-piperidinyl-2,8-bis(trifluoromethyl)-4-quinolinemethanol for treating or preventing malaria in a subject. A method of treating or preventing malaria with reduced side-effects comprising administration of (+)-(11R,2′S)-α-2-piperidinyl-2,8-bis(trifluoromethyl)-4-quinolinemethanol or a pharmaceutically acceptable salt thereof substantially free of its (?)-enantiomer.

Photoreactivity of biologically active compounds. XV. Photochemical behaviour of mefloquine in aqueous solution

The photochemical degradation of mefloquine in aqueous solution was studied as a function of pH, oxygen concentration, buffer concentration and ionic strength. The influence of various scavengers on the degradation process was examined. Formation of superoxide was studied and a reaction pathway was proposed. Seven of the main degradation products were isolated and identified. Reaction mechanisms for the formation of the various products were postulated. Photochemical degradation of mefloquine in aqueous solution seems to take place from the neutral form of the molecule by formation of the cation radical from the excited triplet.

Preparation of erythio-αpiperid-2-yl-2,8-bis-trifluoro-methyl)-quinolin-4-yl-methanol

The present invention relates to a simplified process, which avoids organo-lithium intermediates, for the preparation of erythro-α-piperid-2-yl-2,8-bis-(trifluoromethyl)-quinolin-4-yl-methanol, wherein 2,8-bis-(trifluoromethyl)-quinoline-4-carboxylic acid or a salt thereof is reacted with a pyrid-2-yl-magnesium halide to give pyrid-2-yl-2,8-bis-(trifluoromethyl)-quinolin-4-yl ketone in the manner of a Grignard reaction, and this product is hydrogenated, in a conventional manner, to give erythro-α-piperid-2-yl-2,8-bis-(trifluoromethyl)-quinolin-4-yl-methanol.