6-Methoxy-2-naphthylacetic acid

C18H20O4 101743-90-2) see Methallenestril 6-methoxy-2-naphthylacetic acid (C13H12OJ 23981-47-7) see Naproxen... 

L. K. Wadhwa, P. D. Sharma, Glycolamide Esters of 6-Methoxy-2-naphthylacetic Acid as Potential Prodrugs-Physicochemical Properties, Chemical Stability and Enzymatic Hydrolysis , Int. J. Pharm. 1995, 118, 31-39. 

Nabumetone selectively inhibits COX-2. It is metabolised into 6-methoxy-2-naphthylacetic acid (MNA), that is a potent inhibitor of COX-2. It has no inhibitory effect on COX-1 which is responsible for prostaglandin synthesis in gastric mucosa, thereby minimising the risk of problems like ulcers and hypertension. After oral administration 80% of dose is excreted in the urine. Peak plasma concentration is reached after 2.5 to 4 hours. 

Nabumetone. Nabumetone. 4-(6-mcthoxy-2-naphthyl)-2-butanone (Relafen), serves os a pmdnig to its aetive metabolite. 6-methoxy-2-naphthylacetic acid. Like the other aryla-cetic acid drugs, it is used in short- ur long-term management of RA and OA. It is available as tablets (500 and 750 mg), with a recommended. single daily dose of 1.000 mg. 

Carboxylic acids have also been masked as ketones and alcohols, which would require oxidation to convert to the active acid drugs. Nabumetone (61) is a nonaci-dic nonsteroidal anti-inflammatory prodrug (NSAID).39 After absorption, nabumetone undergoes extensive metabolism, the main circulating active form is 6-methoxy-2-naphthylacetic acid (62), a potent COX-2 inhibitor (Scheme 8). Since... 

All compounds of the test dataset are nonsteroidal anti-inflammatory drugs (NSAIDs) and are thus relatively similar in terms of their pharmacological properties (Fig. 18). The compounds are 1, acetylsalicylic acid 2, diclofenac 3, flufe-namic acid 4, flubiprofen 5, ibuprofen 6, indometacin 7, ketoprofen 8, meclofe-namic acid 9, mefenamic acid 10, naproxen 11, piroxicam 12, sulindac sulfide (active metabolite of sulindac) 13, tenoxicam 14, meloxicam 15, cgp 28238 16, DuP-697 17, L-745-337 18, 6-methoxy-2-naphthylacetic acid (active metabolite of nabumeton) 19, NS-389 20, SC 58125. 

Bosca, F., Canudas, N., Marin, M.L., and Miranda, M.A. (2002) A photophysical and photochemical study of 6-methoxy-2-naphthylacetic acid, the major metabolite of the phototoxic non-steroidal antiinflammatory drug nabumetone, Photochem. Photobiol., 71, 173-177. 

Nabumetone is absorbed rapidly and is converted in the liver to one or more active metabohtes, principally 6-methoxy-2-naphthylacetic acid, a potent nonselective inhibitor of COX. This metabolite, inactivated by (9-demethylation in the liver, is then conjugated before exaetion, and is eliminated with a half-life of about 24 hours. 

Mikami, E. Goto, T. Ohno, T. Matsumoto, H. Nishida, M. Simultaneous analysis of naproxen, nabumetone and its major metabolite 6-methoxy-2-naphthylacetic acid in pharmaceuticals and human urine by high-performance liquid chromatography. J. Pharm. Biomed. Anal. 2000,23 (5), 917-925. 

Turpeinen M, Hofmann U, Klein K, Murdter T, Schwab M, Zanger UM (2009) A predominate role of CYP1A2 for the metabolism of nabumetone to the active metabolite, 6-methoxy-2-naphthylacetic acid, in human liver microsomes. Drug Metab Dispos 37 1017-1024... 

In this context, laser flash photolysis studies have provided clear evidence for the generation of naphthalene radical cations (X ,3x of 380 and 600 nm). Addition of increasing amounts of CCI4 in the photolysis of 6-methoxy-2-naphthylacetic acid results in fluorescence quenching, together with enhanced generation of the radical cation and a higher efficiency of the photodecarboxylation process. ... 

On the other hand, 2-arylpropionic acids with electron-rich aryl rings, such as naproxen, its demethyl analog 6-methoxy-2-naphthylacetic, carprofen, or its dechlorinated photoproduct, have a very low photodecarboxylation efficiency, both from the free acids and the carboxylate forms. " In the case of the naphthalene derivatives, decarboxylation is enhanced in the presence of oxygen and appears to proceed by photoionization of their singlet excited states (Scheme 6). 

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