Oxygen and Ibuprofen

Topics: Ibuprofen, Dipole, Cyclooxygenase Pages: 3 (800 words) Published: April 18, 2012


Ibuprofen is a well-known drug that possesses analgesic (pain-relieving) and antipyretic (fever-reducing) properties. It is particularly known for its use in pain relief from arthritis. Ibuprofen was discovered by Dr. Stewart Adams and his colleagues in the United Kingdom in the 1950s, patented in 1961, and first made available in 1969. It became available in the United States in 1974. Ibuprofen tablets are sold under the trade names Advil and Motrin. (K. Adrjanowicz) This pharmaceutical drug has important factors such as its properties/structure, how it works, hybridization/bond angles, and effects of dipole moment. Ibuprofen (C13H18O2) has the systematic name 2-(4-isobutylphenyl)propanoic acid, making it an organic compound in the class of propionic acid derivatives. Its melting point is 74 - 77° C. It is a stable white crystalline powder, slightly soluble in water and very soluble in ethanol. Its formula is also written (CH3)2CHCH2C6H4CH(CH3)COOH, which lays out the chemical structure of ibuprofen. Ibuprofen is a chiral molecule, meaning that two mirror-image forms (called enantiomers) are possible.

In the diagram, the wavy line represents a molecular bond that is bent "upward" for so-called (R)-ibuprofen and "downward" for (S)-ibuprofen. In the human body, only (S)-ibuprofen is active, but an enzyme readily converts (R)-ibuprofen to the active (S)-ibuprofen form. (P.R. Cullis) This is a representation as configurational isomers but only one isomer is effective (the S isomer) in treating pain. Ibuprofen works by inhibiting the activity of an enzyme called cyclooxygenase (abbreviated COX). The COX enzyme converts certain fatty acids to prostaglandins, molecules with important functions in the human body. The prostaglandins at the end of the "chain" of reactions that starts with the COX enzyme cause an increased sensitivity to pain, fever, and vasodilation (increased blood flow or inflammation). By...

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Z. Wojnarowska, K. Grzybowska, K. Adrjanowicz, K. Kaminski, M. Paluch, L. Hawelek, R. Wrzalik, and M. Dulski, W. Sawicki, J. Mazgalski and A. Tukalska, T. BiegMolecular Pharmaceutics 2010, 7 (5), 1692-1707
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