Benorylate

Schmitt, J. U.S. Patent 3,355,463 November 28,1967 assigned to Etablissements Clin-Byla, France 

Chemical Name 2-(acetyloxy)benzoic acid 4-(acetylamino)phenyl ester Common Name Fenasprate p-N-acetamidophenyl acetylsalicylate 

Trade Name Manufacturer Country Year Introduced 

Example 1 65 grams of N-acetyl-p-aminophenol were slurried with 400 ml of water and cooled to 10°C. 125 ml of 20% sodium hydroxide were slowly added to the mixture with 

Example 2 65 grams of sodium N-acetyl-p-aminophenol were slurried with 500 grams of dry benzene and 80 grams of acetyl salicoyl chloride added. The mixture was heated under reflux for four hours and filtered hot. The excess benzene was removed under vacuum and the crude acetyl salicyclic acid ester of N-acetyl-p-aminophenol crystallized from ethanol. 

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Triacort - Triamcinolone acetonide Triaderm Triamcinolone acetonide Triadol Benorylate Triafed Triprolidine Triagen Chlorotrianisene Triaget - Triamcinolone acetonide Trialona Triamcinolone Trielona Triamcinolone acetonide Triamalone Triamcinolone acetonide Triamcin Triamcinolone diacetete Triamcort Triamcinolone Triemetine Triethylenemelemine Triam Forte Triamcinolone diacetete Trieminic Pyrilamine... 

The antirheumatic, benorylate (4), photodegraded at wavelengths above 300 nm under glass, but more rapidly and with the same product distribution... 

Hydrolysis azathioprine benorylate diazepam diphenhydramine frusemide furazolidone nitrofurantoin menaquinone-4 mercaptopurine methotrexate nalidixic acid nicotinamide nicotine nicotinic acid nifedipine... 

Benorylate (315) [4 -(acetamido)phenyl-2-acetoxybenzoate] is another example. It is the ester between two well-known antiinflamatory drugs, aspirin and paracetamol, and is employed in rheumatoid arthritis therapy. In view of the chemical structure with three photolabile groups (two esters and one amide), its possible phototoxicity has been investigated. From the preparative irradiations, it has been concluded that the PFR takes place with breaking of the central C—O bond to yield 5-acetamido-2 -acetoxy-2-hydroxybenzophenone (316). This product undergoes transacetylation to 5 -acetamido-2 -acetoxy-2-hydroxy-benzophenone (318) (Scheme 80) [300]. 

Partition coefficient ofun-ionised compound at acidic pH Octanol/water ca 631. Other drugs containing phenolic ester group metipranolol, vitamin E, benorylate, dipivefrin. 

Castell JV, Gomez Lechon MJ, Mirabet V, Miranda MA, Morea IM. Photo-lytic degradation of benorylate effects of the photoproducts on cultured hepatocytes. J Pharm Sci 1987 76 374-378. 

Acepromazine (- red), adiphenine (-> blue), benorylate, bephenium hydroxynaphthoate, bibenzonium, buclosamide (blue rim), bunamidine, chlorpromazine (-> violet), clefamide (— brown), codeine, colchicine, cyclazocine, cyclomethycaine (— brown), debrisoquine, diaveridine, dibenzepin, diethazine (— violet with excess reagent), diethylthiambutene (-> green-blue), dimethindene, dimethoxanate (— brown), dimoxyline, dipipanone (— blue), dothiepin, doxorubicin, doxycycline (-> yellow), ethopropazine violet), fenpiprane,... 

Apomorphine (— black), azatadine, benorylate, bisacodyl, buprenorphine, butriptyline, captodiame, chloro-pyrilene, chlorpromazine, clofazimine, codeine, diamorphine, diethylthiambutene, dihydrocodeine, dimeth-indene blue), dimethoxanate, doxorubicin, doxylamine, ethopropazine, ethoxazene, guaiphenesin, guanoxan, hexocyclium methylsulphate, mepyramine, 6-monoacetylmorphine, morphine, nalorphine, nor-morphine, oxprenolol, oxyphenisatin, pecazine, penthienate, perazine, perphenazine, phenoxybenzamine, phenyltoloxamine, pholcodine, pimozide, pipoxolan (-> grey), prochlorperazine, procyclidine, promazine, promethazine, proquamezine, solanidine, thenium, thiopropazate, tricyclamol, trimeprazine, viloxazine... 

High Pressure Liquid Chromatography. System HD—benorylate k 0.7, aspirin k 0.5, paracetamol k 0.1 system HW—benorylate k 22.4, aspirin k 2.7, paracetamol k 0.32. 

High Pressure Liquid Chromatography. In plasma benorylate and paracetamol, sensitivity 200 ng/ml for benorylate and 400 ng/ml for paracetamol, UV detection—A. Cailleux et al, ibid. 

Following oral administration of 4 g as a suspension to 20 subjects, mean peak plasma concentrations of 2.2 gg/ml of benorylate and about 120 gg/ ml of salicylate were attained in 0.5 and 3 hours respectively (M. Aylward etal., Scand. J. Rheumatol., 1976, Suppl. 13, 9-12). 

Cyclobenzaprine Hydrochloride Pyrrobutamine Trimeperidine Hydrochloride Propamidine Dydrogesterone Ethisterone Ethopropazine Apomorphine Hydrochloride Molindone Hydrochloride Etidocaine Hydrochloride Benorylate Flunitrazepam Ethylmorphine Acecainide Hydrochloride Amoxapine... 

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