Ketoprofen Degradation Pathway

Ketoprofen Pathway Map

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This pathway was started by Xiaochun Wang, University of Minnesota, BioC/MicE 5309, and completed by Sujana Mittapalli, University of Minnesota.

Ketoprofen (2-(3-Benzoylphenyl)propanoic acid) is a non-steroidal anti-inflammatory drug found in waste water treatment plants. It is used as a non-prescription drug and a topical application of ketoprofen has the side effect of photoallergic contact dermatitis (Devleeschouwer et al., 2008).

Ketoprofen degradation by a microbial consortium shown below proceeds along the pathway known for biphenyl and other compounds. The metabolites between ketoprofen and 2-{3-[Carboxylato(hydroxy)methyl]phenyl}propanoate are proposed. The latter compound and 2-[3-(Carboxylatocarbonyl)phenyl]propanoate were observed in high concentrations (Quintana et al., 2005).

White-rot fungus Trametes versicolor degrades ketoprofen. The initial degradation is reduction of the ketone group, to form 2-[(3-Hydroxy(phenyl)methyl)phenyl]-propanoic acid, the first metabolite below. The metabolites 2-(3-Benzoyl-4-hydroxyphenyl)-propanoic acid and 2-[3-(4-Hydroxybenzoyl)phenyl]-propanoic acid, hydroxylated derivatives, were observed in minor quantities (Marco-Urrea et al., 2010).

The following is a text-format Ketoprofen pathway map. Follow the links for more information on compounds or reactions. This map is also available in graphic (14k) format.


                                                                 Ketoprofen
                                                            microbial consortium
                                                                     |
                                                                     | ketoprofen
                                                                     | oxidoreductase
                                                                     |
                                                                     v
                                                       2-[(3-Hydroxy(phenyl)methyl)
                                                            phenyl]-propanoate
                                                                     |
                                                                     | 2-[(3-hydroxy(phenyl)methyl)
                                                                     | phenyl]-propanoate
                                                                     | dioxygenase
                                                                     |
                                                                     v
	                                                2-{3-[(2,3-Dihydroxyphenyl)
	                                             (hydroxy)methyl]phenyl}propanoate
                                                                     |
                                                                     | 2-{3-[(2,3-dihydroxyphenyl)
                                                                     | (hydroxy)methyl]phenyl}propanoate
                                                                     | dioxygenase
                                                                     |
                                                                     v
                                                      (2E,4Z)-7-[3-(1-Carboxylatoethyl)
                                                      phenyl]-2,7-dihydroxy-6-oxohepta-
                                                              2,4-dienoate
                                                                     |
                                                                     | (2E,4Z)-7-[3-(1-carboxylatoethyl)
                                                                     | phenyl]-2,7-dihydroxy-6-oxohepta-
                                                                     | 2,4-dienoate hydrolase
                                                                     |
                                                                     v
                                                        2-{3-[Carboxylato(hydroxy)
                                                         methyl]phenyl}propanoate
                                                                     |
                                                                     | 2-{3-[carboxylato(hydroxy)
                                                                     | methyl]phenyl}propanoate
                                                                     | dehydrogenase
                                                                     |
                                                                     v
                                                        2-[3-(Carboxylatocarbonyl)
                                                            phenyl]propanoate
                                                                     |
                                                                     |
                                                                     |
                                                                     v A
                                                                     |
                                                                     |
                                                                     |
                                                                     v
								    CO2


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Page Author(s): Xiaochun Wang, Sujana Mittapalli

August 10, 2012 Contact Us

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