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Canalicular multispecific organic anion transporter 2 Solute carrier family 22 member 7 Cytochrome P450 2C9 Cytochrome P450 2C19 Cytochrome P450 2C19 UDP- glucuronosyltransferase 2B11 Cytochrome P450 2C19 Cytochrome P450 2C19 Cytochrome P450 1A2 UDP- glucuronosyltransferase 2B11 Sulfotransferase 1A1 Sulfotransferase 1A1 Cytochrome P450 2C9 Cytochrome P450 2C9 Cytochrome P450 2C9 Cytochrome P450 2C9 Cytochrome P450 2C9 Cytochrome P450 2C9 Cytochrome P450 2C9 Omeprazole Omeprazole Omeprazole Omeprazole Warfarin Warfarin O2 FMNH2 S-6- Hydroxywarfarin Flavin Mononucleotide H2O H+ FMNH2 O2 S-4'- Hydroxywarfarin Flavin Mononucleotide H2O H+ FMNH2 O2 R-4'- Hydroxywarfarin Flavin Mononucleotide H2O H+ Uridine diphosphate glucuronic acid R-4'- Hydroxywarfarin glucuronide Uridine 5'-diphosphate H+ O2 FMNH2 R-6- Hydroxywarfarin H2O Flavin Mononucleotide H+ O2 FMNH2 R-8- Hydroxywarfarin H2O Flavin Mononucleotide H+ FMNH2 O2 R-7- Hydroxywarfarin H2O Flavin Mononucleotide H+ Uridine diphosphate glucuronic acid R-7- Hydroxywarfarin glucuronide Uridine 5'-diphosphate H+ Phosphoadenosine phosphosulfate R-7- Hydroxywarfarin sulfate Adenosine 3',5'-diphosphate H+ Phosphoadenosine phosphosulfate R-6- Hydroxywarfarin sulfate Adenosine 3',5'-diphosphate H+ O2 FMNH2 S-7- Hydroxywarfarin Flavin Mononucleotide H2O H+ O2 FMNH2 (R)9- hydroxywarfarin H2O Flavin Mononucleotide H+ FMNH2 O2 (S)9- hydroxywarfarin H2O Flavin Mononucleotide H+ FMNH2 O2 R-Warfarin-R- Alcohol H2O Flavin Mononucleotide H+ FMNH2 O2 S-Warfarin-R- Alcohol Flavin Mononucleotide H2O H+ NADH H2O NAD R-Warfarin-S- Alcohol NADH H2O S-Warfarin-S- Alcohol NAD Heme Heme Heme Heme Heme Heme Heme Heme Heme Heme Heme Heme Heme Cytosol Hepatocyte Intestinal Epithelial Cell Endoplasmic Reticulum Oral administration
ABCC3 SLC22A7 CYP2C9 CYP2C19 CYP2C19 UGT2B11 CYP2C19 CYP2C19 CYP1A2 UGT2B11 SULT1A1 SULT1A1 CYP2C9 CYP2C9 CYP2C9 CYP2C9 CYP2C9 CYP2C9 CYP2C9 Omeprazole Omeprazole Omeprazole Omeprazole Warfarin Warfarin Oxygen FMNH2 S-6- Hydroxywarfarin Flavin Mononucleotide Water Hydrogen Ion FMNH2 Oxygen S-4'- Hydroxywarfarin Flavin Mononucleotide Water Hydrogen Ion FMNH2 Oxygen R-4'- Hydroxywarfarin Flavin Mononucleotide Water Hydrogen Ion Uridine diphosphate glucuronic acid R-4'- Hydroxywarfarin glucuronide Uridine 5'-diphosphate Hydrogen Ion Oxygen FMNH2 R-6- Hydroxywarfarin Water Flavin Mononucleotide Hydrogen Ion Oxygen FMNH2 R-8- Hydroxywarfarin Water Flavin Mononucleotide Hydrogen Ion FMNH2 Oxygen R-7- Hydroxywarfarin Water Flavin Mononucleotide Hydrogen Ion Uridine diphosphate glucuronic acid R-7- Hydroxywarfarin glucuronide Uridine 5'-diphosphate Hydrogen Ion Phosphoadenosine phosphosulfate R-7- Hydroxywarfarin sulfate Adenosine 3',5'-diphosphate Hydrogen Ion Phosphoadenosine phosphosulfate R-6- Hydroxywarfarin sulfate Adenosine 3',5'-diphosphate Hydrogen Ion Oxygen FMNH2 S-7- Hydroxywarfarin Flavin Mononucleotide Water Hydrogen Ion Oxygen FMNH2 (R)9- hydroxywarfarin Water Flavin Mononucleotide Hydrogen Ion FMNH2 Oxygen (S)9- hydroxywarfarin Water Flavin Mononucleotide Hydrogen Ion FMNH2 Oxygen R-Warfarin-R- Alcohol Water Flavin Mononucleotide Hydrogen Ion FMNH2 Oxygen S-Warfarin-R- Alcohol Flavin Mononucleotide Water Hydrogen Ion NADH Water NAD R-Warfarin-S- Alcohol NADH Water S-Warfarin-S- Alcohol NAD
ABCC3 SLC22A7 CYP2C9 CYP2C19 CYP2C19 UGT2B11 CYP2C19 CYP2C19 CYP1A2 UGT2B11 SULT1A1 SULT1A1 CYP2C9 CYP2C9 CYP2C9 CYP2C9 CYP2C9 CYP2C9 CYP2C9 Ompz Ompz Ompz Ompz Warfari Warfari O2 FMNH2 S6H FlvnMnt H2O H+ FMNH2 O2 S4H FlvnMnt H2O H+ FMNH2 O2 R4H FlvnMnt H2O H+ UDPGlcA R-4-H g UDP H+ O2 FMNH2 R6H H2O FlvnMnt H+ O2 FMNH2 R8H H2O FlvnMnt H+ FMNH2 O2 R7H H2O FlvnMnt H+ UDPGlcA R-7-H g UDP H+ Paps R-7-H s A3'5'PP H+ Paps R-6-H s A3'5'PP H+ O2 FMNH2 S-7-Hyd FlvnMnt H2O H+ O2 FMNH2 (R)-hyd H2O FlvnMnt H+ FMNH2 O2 (S)-hyd H2O FlvnMnt H+ FMNH2 O2 R-W-R-A H2O FlvnMnt H+ FMNH2 O2 S-W-R-A FlvnMnt H2O H+ NADH H2O NAD R-W-S-A NADH H2O S-W-S-A NAD Heme Heme Heme Heme Heme Heme Heme Heme Heme Heme Heme Heme Heme Cytosol Hepatocyte Intestinal Epithelial Cell Endoplasmic Reticulum Oral administration
ABCC3 SLC22A7 CYP2C9 CYP2C19 CYP2C19 UGT2B11 CYP2C19 CYP2C19 CYP1A2 UGT2B11 SULT1A1 SULT1A1 CYP2C9 CYP2C9 CYP2C9 CYP2C9 CYP2C9 CYP2C9 CYP2C9 Ompz Ompz Ompz Ompz Warfari Warfari O2 FMNH2 S6H FlvnMnt H2O H+ FMNH2 O2 S4H FlvnMnt H2O H+ FMNH2 O2 R4H FlvnMnt H2O H+ UDPGlcA R-4-H g UDP H+ O2 FMNH2 R6H H2O FlvnMnt H+ O2 FMNH2 R8H H2O FlvnMnt H+ FMNH2 O2 R7H H2O FlvnMnt H+ UDPGlcA R-7-H g UDP H+ Paps R-7-H s A3'5'PP H+ Paps R-6-H s A3'5'PP H+ O2 FMNH2 S-7-Hyd FlvnMnt H2O H+ O2 FMNH2 (R)-hyd H2O FlvnMnt H+ FMNH2 O2 (S)-hyd H2O FlvnMnt H+ FMNH2 O2 R-W-R-A H2O FlvnMnt H+ FMNH2 O2 S-W-R-A FlvnMnt H2O H+ NADH H2O NAD R-W-S-A NADH H2O S-W-S-A NAD