Metabolism of Bioactive Endogenous and Exogenous Compounds Oxidation Dehydrogenases Oxidases Cytochrome P450 enzymes Reduction Dehydrogenases Reductases Conjugation Sulfotransferases 3´-Phosphoadenosine 5´-phosphosulfate (PAPS) 3´,5´-adenosine bisphosphate sulfotransferase R OH R O S O O O O S O O O OH O CH 2 O N N N N NH 2 P O O O P O O O 3´-Phosphoadenosine 5´-phosphosulfate (PAPS)
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Metabolism of Bioactive Endogenous and …brandt/Chem430/Xenobiotic and...Metabolism of Bioactive Endogenous and Exogenous Compounds Oxidation Dehydrogenases Oxidases Cytochrome P450
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Metabolism of Bioactive Endogenous and Exogenous Compounds Oxidation Dehydrogenases Oxidases Cytochrome P450 enzymes Reduction Dehydrogenases Reductases Conjugation Sulfotransferases
CYP5 CYP5A1 Platelet thromboxane A synthase 1 CYP7 CYP7A1
CYP7B1 7A1 is liver enzyme: 7α-hydroxylase; catalyzes the main regulated step in bile acid synthesis 7B1 is non-liver, and may be involved in steroid metabolism
CYP8 CYP8A1 CYP8B1
8A1 is prostaglandin I2 (prostacyclin) synthase 8B1 intronless; 12α-hydroxylase in bile acid synthesis pathway
CYP11 CYP11A1 CYP11B1 CYP11B2
Mitochondrial steroid hormone biosynthesis enzymes 11A1 is cholesterol side-chain cleavage enzyme, the main regulated step in steroid hormone biosynthesis. 11B1 is 11β-hydroxylase 11B2 is 18-hydroxylase
CYP17 CYP17A1 17α-hydroxylase/17-20 lyase in steroid hormone biosynthesis pathway
CYP19 CYP19A1 Aromatase CYP20 CYP20A1 Present in many species, but deviates from P450 consensus
sequence; function unknown CYP21 CYP21A2 21-hydroxylase (pseudogene nearby causes high rate of
inborn errors) CYP24 CYP24A1 24-hydroxylase for 1α-25-dihydroxyvitamin D in breakdown
pathway CYP26 CYP26A1
CYP26B1 CYP26C1
Retinoid 4-hydroxylase and 18 hydroxylase
CYP27 CYP27A1 CYP27B1 CYP27C1
27A1 hydroxylase in bile acid synthesis pathway 27B1 1α-hydroxylase of 25-hydroxyvitamin D; catalyzes regulated activation step for vitamin D 27C1 function unknown
CYP39 CYP39A1 7α-hydroxylase in bile acid synthesis pathway CYP46 CYP46A1 Cholesterol 24S-hydroxylase in brain CYP51 CYP51A1 Lanosterol 14-demethylase in cholesterol synthesis pathway Inducers and inhibitors
HN
NH
O
O OPhenobarbital
O OO
O
Bergamottin
O OO
O
Dihydroxybergamottin
OH
HO
Tamoxifen Metabolism
Additional demethylation Isomerization Sulfotransferases N- and O-glucuronide formation