Loperamide oxide

Beubler E, Badhri P (1990) Comparison of the antisecretory effects of loperamide and loperamide oxide in the jejunum and the colon of rats in vivo. J Pharm Pharmacol 42 689-692... 

Synthesis (Kleemann et al. 1999, Janssen (Janssen), 1973 Janssen et al. (Janssen), 1973, Stokbroekx et al., 1973, Niemegeers et al., 1974) ) Treatment of 2-oxo-3,3-diphenyl-tetrahydrofuran, synthesized by treatment of diphenyl-acetic acid ethyl ester with ethylene oxide, with HBr(gas) yields bromo derivative i, which is then converted into butyryl chloride derivative ii by means of thionyl chloride in refluxing chloroform. Reaction of derivative ii with dimethylamine in toluene affords dimethyl (tetrahydro-3,3-diphenyl-2-furylidene)ammonium bromide, which is then condensed with 4-(4-chlorophenyl)-4-piperidinol by means of Na2C03 and Kl in refluxing 4-methyl-2-pentanone to provide loperamide. 

In the N-oxide of loperamide (an antidiarrheal) the hydroxy group and the oxide oxygen have a trans relationship. Draw the structure in a chair form and determine whether the molecule is chiral. Which stereodescriptors must be added to the systematic name to exactly describe the configuration ... 

Attapulgite may decrease the bioavailability of some drugs such as loperamide and riboflavin. Oxidation of hydrocortisone is increased in the presence of attapulgite. ... 

Loperamide N-oxide, an investigational agent, is a site-specific prodrug it is chemically designed for controlled release of loperamide in the intestinal lumen, thereby reducing systemic absorption. 

Kamali F, Huang ML. Increased systemic availability of loperamide after oral administration of loperamide and loperam ide oxide with cotrimoxazole. BrJ CUn Pharmacol (1996) 41,125-8. 

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