Rotating ibuprofen molecule (click and drag image to manipulate):-
(Click on above diagram for more information)
Ibuprofen, a carboxylic acid, was first introduced in the UK 1969 by the Boot Pure Drug company under the trade name Brufen. It belongs to a class of drugs known as non-steroidal anti-inflammatory drugs or NSAIDs of which there are now more than 50 on the market. Ibuprofen has a powdery white appearance and can come in the form of capsules, tablets, or powder. Today it is sold under several trade names such as Advil, Motrin and Nuprin:-
It is often prescribed for "rheumatic" musculoskeletal complaints and is taken without prescription for minor aches and pains. Ibuprofen is the first choice drug in its class since it has a low incidence of unwanted effects. It is rapidly metabolized, usually leaving the body via urination within 24 hours.
Because ibuprofen has only one stereocentre, it can exist in two enantiomeric forms. The commercially available product is usually the racemate since it is difficult to separate the two enantiomers.The biologically active form is the S enantiomer and the R form is converted to this within the body thus minimizing side effects (c.f. thalidomide problem of the 1950's and 1960's). One may have assumed, therefore, that only 50% of the drug would be active but this is not the case due to biologically catalysed enantiomeric interconversion.
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