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
Page Author(s): Xiaochun Wang, Sujana Mittapalli
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