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N-Desmethyl-o-O-sulfate rosiglitazone N-Desmethyl-p-hydroxyrosiglitazone N-Desmethyl-p-O-sulfate rosiglitazone N-Despyridinyl rosiglitazone 22547081 ChemSpider 17215925 ChemSpider HMDB0061240 HMDB HMDB0061241 HMDB para-hydroxyrosiglitazone ortho-hydroxyrosiglitazone 937 ChemSpider o-O-glucuronide rosiglitazone p-O-glucuronide rosiglitazone N-desmethylrosiglitazone 86278298 PubChem-compound 439153 PubChem-compound SMILES O HMDB0061357 HMDB 1.0 N-Desmethyl-O-hydroxy rosiglitazone NADPH 8040009 ChemSpider HMDB0060837 HMDB HMDB0060836 HMDB 1.0 HMDB0060839 HMDB HMDB0060838 HMDB SMP0000653 SMPDB CHEBI:15846 ChEBI 53-59-8 CAS BTO:0000759 BRENDA TISSUE ONTOLOGY 1038 PubChem-compound C17H17N3O4S N-Desmethyl-O-hydroxy rosiglitazone 359.09396 1.0 Phenoxyacetic acid derivative Cytochrome P450 2C8 CHEBI:16474 ChEBI Hydrogen Ion 952 ChemSpider ortho-hydroxyrosiglitazone CH2O Formaldehyde 30.010565 1.0 1.0 CHEBI:16908 ChEBI p-O-sulfate rosiglitazone P11712 UniProt C17H17N3O7S2 N-Desmethyl-o-O-sulfate rosiglitazone 439.05078 C17H17N3O4S N-Desmethyl-p-hydroxyrosiglitazone 359.09396 C17H17N3O7S2 N-Desmethyl-p-O-sulfate rosiglitazone 439.05078 C13H16N2O3S N-Despyridinyl rosiglitazone 280.08817 N-desmethyl glucuronide rosiglitazone C24H27N3O10S o-O-glucuronide rosiglitazone 549.1417 C24H27N3O10S p-O-glucuronide rosiglitazone 549.1417 C17H17N3O3S N-desmethylrosiglitazone 343.09906 C18H19N3O4S para-hydroxyrosiglitazone 373.10962 9846723 PubChem-compound C18H19N3O4S ortho-hydroxyrosiglitazone 373.10962 Cytochrome P450 2C9 1010 ChemSpider 1.0 1.0 C21H30N7O17P3 NADPH 745.0911 C21H29N7O17P3 NADP 744.08325 HMDB0061105 HMDB NADPH BioCyc FORMALDEHYDE BioCyc para-hydroxyrosiglitazone CPD-6641 BioCyc 1.0 CHEBI:50122 ChEBI 10172795 ChemSpider 58-68-4 CAS C18H19N3O3S Rosiglitazone 357.11472 HMDB0000217 HMDB SMILES C=O HMDB0001426 HMDB 692 ChemSpider 1.0 HMDB0060862 HMDB NADH C00007 KEGG Compound Oxygen C00006 KEGG Compound CHEBI:18009 ChEBI Formaldehyde C00001 KEGG Compound C00005 KEGG Compound C00004 KEGG Compound C00003 KEGG Compound Liver SMILES NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O HMDB0000221 HMDB SMILES NC(=O)C1=CN(C=CC1)[C@H]1O[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2O[C@@H]([C@@H](OP(O)(O)=O)[C@H]2O)N2C=NC3=C(N)N=CN=C23)[C@H](O)[C@@H]1O 1.0 53-57-6 CAS C21H28N7O14P2 NAD 664.11694 HMDB0000902 HMDB 1.0 Extracellular Space Rosiglitazone Rosiglitazone NAD(P) BioCyc C21H29N7O14P2 NADH 665.12476 Rosiglitazone Solute carrier organic anion transporter family member 1B1 1.14.14.1 false 1.14.14.1 NADH + Oxygen + Rosiglitazone → Formaldehyde + N-desmethylrosiglitazone + NAD + Water LEFT_TO_RIGHT Reaction2047 false Rosiglitazone → N-Despyridinyl rosiglitazone LEFT_TO_RIGHT HMDB0060842 HMDB Reaction2048 false N-desmethylrosiglitazone → N-Desmethyl-p-hydroxyrosiglitazone LEFT_TO_RIGHT 1.0 H Hydrogen Ion 1.007825 122320-73-4 CAS 1.0 HMDB0060981 HMDB CHEBI:16842 ChEBI HMDB0060980 HMDB 78069861 PubChem-compound 53-84-9 CAS GO:0005615 GENE ONTOLOGY GO:0005737 GENE ONTOLOGY HMDB0060857 HMDB PW000629 PathWhiz 1.0 1.0 10356320 PubChem-compound Endoplasmic Reticulum Membrane SMILES NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O SMILES OC1=C(NCCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)N=CC=C1 5682 ChemSpider SMILES NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O 1.0 1.14.14.1 false 1.14.14.1 Hydrogen Ion + NADPH + Oxygen + Rosiglitazone → NADP + Water + ortho-hydroxyrosiglitazone LEFT_TO_RIGHT Reaction2063 false ortho-hydroxyrosiglitazone → o-O-glucuronide rosiglitazone LEFT_TO_RIGHT Reaction2061 false N-Desmethyl-O-hydroxy rosiglitazone → N-Desmethyl-o-O-sulfate rosiglitazone LEFT_TO_RIGHT SMILES OC1=CC=C(NCCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)N=C1 SMILES OS(=O)(=O)OC1=C(NCCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)N=CC=C1 SMILES CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=C(OC2OC(C(O)C(O)C2O)C(O)=O)C=CC=N1 SMILES CNCCOC1=CC=C(CC2SC(=O)NC2=O)C=C1 SMILES OS(=O)(=O)OC1=CC=C(NCCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)N=C1 SMILES CN(CCOC1=CC=C(CC2SC(=O)N=C2O)C=C1)C1=C(O)C=CC=N1 SMILES CN(CCOC1=CC=C(CC2SC(=O)N=C2O)C=C1)C1=NC=C(O)C=C1 SMILES OC1=NC(=O)SC1CC1=CC=C(OCCNC2=CC=CC=N2)C=C1 SMILES CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=CC=C(OC2OC(C(O)C(O)C2O)C(O)=O)C=N1 5675 ChemSpider 8022437 ChemSpider Reaction2057 false para-hydroxyrosiglitazone → N-Desmethyl-p-hydroxyrosiglitazone LEFT_TO_RIGHT 9864316 PubChem-compound Q9Y6L6 UniProt Reaction2055 false para-hydroxyrosiglitazone → p-O-sulfate rosiglitazone LEFT_TO_RIGHT Reaction2052 false ortho-hydroxyrosiglitazone → N-Desmethyl-O-hydroxy rosiglitazone LEFT_TO_RIGHT 1.14.14.1 false 1.14.14.1 Hydrogen Ion + NADPH + Oxygen + Rosiglitazone → NADP + Water + para-hydroxyrosiglitazone LEFT_TO_RIGHT N-desmethylrosiglitazone Reaction2051 false N-desmethylrosiglitazone → N-Desmethyl-O-hydroxy rosiglitazone LEFT_TO_RIGHT NAD Cytoplasm HMDB0005031 HMDB Reaction2058 false N-Desmethyl-p-hydroxyrosiglitazone → N-Desmethyl-p-O-sulfate rosiglitazone LEFT_TO_RIGHT Reaction2059 false N-desmethylrosiglitazone → N-desmethyl glucuronide rosiglitazone LEFT_TO_RIGHT SMILES CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=CC=C(OS(O)(=O)=O)C=N1 Cytochrome P450 2C8 SMILES OC1C(OC2=C(NCCOC3=CC=C(CC4SC(=O)N=C4O)C=C3)N=CC=C2)OC(C(O)C1O)C(O)=O TransportCatalysis184 ACTIVATION Rosiglitazone Homo sapiens 1.0 7732-18-5 CAS 388299 ChemSpider 1.0 77999 PubChem-compound Water HMDB0001487 HMDB 1.0 Cytochrome P450 2C9 O2 Oxygen 31.98983 Reaction2088 false Rosiglitazone → Phenoxyacetic acid derivative LEFT_TO_RIGHT Reaction2086 false para-hydroxyrosiglitazone → p-O-glucuronide rosiglitazone LEFT_TO_RIGHT Solute carrier organic anion transporter family member 1B1 GO:0005789 GENE ONTOLOGY 1.0 BiologicalState10 Homo sapiens, Liver C00067 KEGG Compound SMILES OC(=O)COC1=CC=CC=C1 1.0 7782-44-7 CAS HMDB0001377 HMDB 1.0 1.0 9606 TAXONOMY 962 PubChem-compound C23H25N3O10S N-desmethyl glucuronide rosiglitazone 535.12604 C18H19N3O7S2 p-O-sulfate rosiglitazone 453.06644 P10632 UniProt 1.0 1.0 1.0 5893 PubChem-compound 12000328 PubChem-compound C00080 KEGG Compound SMILES O=O ReactionCatalysis1922 ACTIVATION ReactionCatalysis1921 ACTIVATION ReactionCatalysis1924 ACTIVATION 8531772 ChemSpider HMDB0002111 HMDB CHEBI:15377 ChEBI CHEBI:15379 ChEBI CHEBI:15378 ChEBI SMILES [H+] 712 PubChem-compound 70383 ChemSpider C8H8O3 Phenoxyacetic acid derivative 152.04735 ReactionCatalysis1925 ACTIVATION 5886 PubChem-compound ReactionCatalysis1935 ACTIVATION ReactionCatalysis1934 ACTIVATION 1.0 32702400 ChemSpider 22833512 PubChem-compound 1.0 SMILES CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=CC=CC=N1 H2O Water 18.010565 NADH BioCyc Rosiglitazone Metabolism Pathway NADP NAD BioCyc 977 PubChem-compound HMDB0059597 HMDB 50-00-0 CAS Transport224 false Rosiglitazone (→) Transport: Homo sapiens, Extracellular Space to Homo sapiens, Liver, Cell, Cytoplasm LEFT_TO_RIGHT Solute carrier organic anion transporter family member 1B1 Cytochrome P450 2C8 Cytochrome P450 2C9 Cytochrome P450 2C8 Cytochrome P450 2C9 Cytochrome P450 2C8 Cytochrome P450 2C9 Rosiglitazone Rosiglitazone N-Despyridinyl rosiglitazone N-desmethylrosiglitazone N-Desmethyl-p- hydroxyrosiglitazone N-Desmethyl-O-hydroxy rosiglitazone ortho-hydroxyrosiglitazone para-hydroxyrosiglitazone p-O-sulfate rosiglitazone N-Desmethyl-p-O-sulfate rosiglitazone N-desmethyl glucuronide rosiglitazone N-Desmethyl-o-O-sulfate rosiglitazone o-O-glucuronide rosiglitazone o-O-sulfate rosiglitazone p-O-glucuronide rosiglitazone Phenoxyacetic acid derivative O 2 NADPH H + H 2 O NADP O 2 NADH Formaldehyde NAD H 2 O O 2 NADPH H + H 2 O NADP Heme Heme Heme Heme Heme Heme
N-Desmethyl-o-O-sulfate rosiglitazone N-Desmethyl-p-hydroxyrosiglitazone N-Desmethyl-p-O-sulfate rosiglitazone N-Despyridinyl rosiglitazone 22547081 ChemSpider 17215925 ChemSpider HMDB0061240 HMDB HMDB0061241 HMDB para-hydroxyrosiglitazone ortho-hydroxyrosiglitazone 937 ChemSpider o-O-glucuronide rosiglitazone p-O-glucuronide rosiglitazone N-desmethylrosiglitazone 86278298 PubChem-compound 439153 PubChem-compound SMILES O HMDB0061357 HMDB 1.0 N-Desmethyl-O-hydroxy rosiglitazone NADPH 8040009 ChemSpider HMDB0060837 HMDB HMDB0060836 HMDB 1.0 HMDB0060839 HMDB HMDB0060838 HMDB SMP0000653 SMPDB CHEBI:15846 ChEBI 53-59-8 CAS BTO:0000759 BRENDA TISSUE ONTOLOGY 1038 PubChem-compound C17H17N3O4S N-Desmethyl-O-hydroxy rosiglitazone 359.09396 1.0 Phenoxyacetic acid derivative Cytochrome P450 2C8 CHEBI:16474 ChEBI Hydrogen Ion 952 ChemSpider ortho-hydroxyrosiglitazone CH2O Formaldehyde 30.010565 1.0 1.0 CHEBI:16908 ChEBI p-O-sulfate rosiglitazone P11712 UniProt C17H17N3O7S2 N-Desmethyl-o-O-sulfate rosiglitazone 439.05078 C17H17N3O4S N-Desmethyl-p-hydroxyrosiglitazone 359.09396 C17H17N3O7S2 N-Desmethyl-p-O-sulfate rosiglitazone 439.05078 C13H16N2O3S N-Despyridinyl rosiglitazone 280.08817 N-desmethyl glucuronide rosiglitazone C24H27N3O10S o-O-glucuronide rosiglitazone 549.1417 C24H27N3O10S p-O-glucuronide rosiglitazone 549.1417 C17H17N3O3S N-desmethylrosiglitazone 343.09906 C18H19N3O4S para-hydroxyrosiglitazone 373.10962 9846723 PubChem-compound C18H19N3O4S ortho-hydroxyrosiglitazone 373.10962 Cytochrome P450 2C9 1010 ChemSpider 1.0 1.0 C21H30N7O17P3 NADPH 745.0911 C21H29N7O17P3 NADP 744.08325 HMDB0061105 HMDB NADPH BioCyc FORMALDEHYDE BioCyc para-hydroxyrosiglitazone CPD-6641 BioCyc 1.0 CHEBI:50122 ChEBI 10172795 ChemSpider 58-68-4 CAS C18H19N3O3S Rosiglitazone 357.11472 HMDB0000217 HMDB SMILES C=O HMDB0001426 HMDB 692 ChemSpider 1.0 HMDB0060862 HMDB NADH C00007 KEGG Compound Oxygen C00006 KEGG Compound CHEBI:18009 ChEBI Formaldehyde C00001 KEGG Compound C00005 KEGG Compound C00004 KEGG Compound C00003 KEGG Compound Liver SMILES NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O HMDB0000221 HMDB SMILES NC(=O)C1=CN(C=CC1)[C@H]1O[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2O[C@@H]([C@@H](OP(O)(O)=O)[C@H]2O)N2C=NC3=C(N)N=CN=C23)[C@H](O)[C@@H]1O 1.0 53-57-6 CAS C21H28N7O14P2 NAD 664.11694 HMDB0000902 HMDB 1.0 Extracellular Space Rosiglitazone Rosiglitazone NAD(P) BioCyc C21H29N7O14P2 NADH 665.12476 Rosiglitazone Solute carrier organic anion transporter family member 1B1 1.14.14.1 false 1.14.14.1 NADH + Oxygen + Rosiglitazone → Formaldehyde + N-desmethylrosiglitazone + NAD + Water LEFT_TO_RIGHT Reaction2047 false Rosiglitazone → N-Despyridinyl rosiglitazone LEFT_TO_RIGHT HMDB0060842 HMDB Reaction2048 false N-desmethylrosiglitazone → N-Desmethyl-p-hydroxyrosiglitazone LEFT_TO_RIGHT 1.0 H Hydrogen Ion 1.007825 122320-73-4 CAS 1.0 HMDB0060981 HMDB CHEBI:16842 ChEBI HMDB0060980 HMDB 78069861 PubChem-compound 53-84-9 CAS GO:0005615 GENE ONTOLOGY GO:0005737 GENE ONTOLOGY HMDB0060857 HMDB PW000629 PathWhiz 1.0 1.0 10356320 PubChem-compound Endoplasmic Reticulum Membrane SMILES NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O SMILES OC1=C(NCCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)N=CC=C1 5682 ChemSpider SMILES NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O 1.0 1.14.14.1 false 1.14.14.1 Hydrogen Ion + NADPH + Oxygen + Rosiglitazone → NADP + Water + ortho-hydroxyrosiglitazone LEFT_TO_RIGHT Reaction2063 false ortho-hydroxyrosiglitazone → o-O-glucuronide rosiglitazone LEFT_TO_RIGHT Reaction2061 false N-Desmethyl-O-hydroxy rosiglitazone → N-Desmethyl-o-O-sulfate rosiglitazone LEFT_TO_RIGHT SMILES OC1=CC=C(NCCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)N=C1 SMILES OS(=O)(=O)OC1=C(NCCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)N=CC=C1 SMILES CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=C(OC2OC(C(O)C(O)C2O)C(O)=O)C=CC=N1 SMILES CNCCOC1=CC=C(CC2SC(=O)NC2=O)C=C1 SMILES OS(=O)(=O)OC1=CC=C(NCCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)N=C1 SMILES CN(CCOC1=CC=C(CC2SC(=O)N=C2O)C=C1)C1=C(O)C=CC=N1 SMILES CN(CCOC1=CC=C(CC2SC(=O)N=C2O)C=C1)C1=NC=C(O)C=C1 SMILES OC1=NC(=O)SC1CC1=CC=C(OCCNC2=CC=CC=N2)C=C1 SMILES CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=CC=C(OC2OC(C(O)C(O)C2O)C(O)=O)C=N1 5675 ChemSpider 8022437 ChemSpider Reaction2057 false para-hydroxyrosiglitazone → N-Desmethyl-p-hydroxyrosiglitazone LEFT_TO_RIGHT 9864316 PubChem-compound Q9Y6L6 UniProt Reaction2055 false para-hydroxyrosiglitazone → p-O-sulfate rosiglitazone LEFT_TO_RIGHT Reaction2052 false ortho-hydroxyrosiglitazone → N-Desmethyl-O-hydroxy rosiglitazone LEFT_TO_RIGHT 1.14.14.1 false 1.14.14.1 Hydrogen Ion + NADPH + Oxygen + Rosiglitazone → NADP + Water + para-hydroxyrosiglitazone LEFT_TO_RIGHT N-desmethylrosiglitazone Reaction2051 false N-desmethylrosiglitazone → N-Desmethyl-O-hydroxy rosiglitazone LEFT_TO_RIGHT NAD Cytoplasm HMDB0005031 HMDB Reaction2058 false N-Desmethyl-p-hydroxyrosiglitazone → N-Desmethyl-p-O-sulfate rosiglitazone LEFT_TO_RIGHT Reaction2059 false N-desmethylrosiglitazone → N-desmethyl glucuronide rosiglitazone LEFT_TO_RIGHT SMILES CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=CC=C(OS(O)(=O)=O)C=N1 Cytochrome P450 2C8 SMILES OC1C(OC2=C(NCCOC3=CC=C(CC4SC(=O)N=C4O)C=C3)N=CC=C2)OC(C(O)C1O)C(O)=O TransportCatalysis184 ACTIVATION Rosiglitazone Homo sapiens 1.0 7732-18-5 CAS 388299 ChemSpider 1.0 77999 PubChem-compound Water HMDB0001487 HMDB 1.0 Cytochrome P450 2C9 O2 Oxygen 31.98983 Reaction2088 false Rosiglitazone → Phenoxyacetic acid derivative LEFT_TO_RIGHT Reaction2086 false para-hydroxyrosiglitazone → p-O-glucuronide rosiglitazone LEFT_TO_RIGHT Solute carrier organic anion transporter family member 1B1 GO:0005789 GENE ONTOLOGY 1.0 BiologicalState10 Homo sapiens, Liver C00067 KEGG Compound SMILES OC(=O)COC1=CC=CC=C1 1.0 7782-44-7 CAS HMDB0001377 HMDB 1.0 1.0 9606 TAXONOMY 962 PubChem-compound C23H25N3O10S N-desmethyl glucuronide rosiglitazone 535.12604 C18H19N3O7S2 p-O-sulfate rosiglitazone 453.06644 P10632 UniProt 1.0 1.0 1.0 5893 PubChem-compound 12000328 PubChem-compound C00080 KEGG Compound SMILES O=O ReactionCatalysis1922 ACTIVATION ReactionCatalysis1921 ACTIVATION ReactionCatalysis1924 ACTIVATION 8531772 ChemSpider HMDB0002111 HMDB CHEBI:15377 ChEBI CHEBI:15379 ChEBI CHEBI:15378 ChEBI SMILES [H+] 712 PubChem-compound 70383 ChemSpider C8H8O3 Phenoxyacetic acid derivative 152.04735 ReactionCatalysis1925 ACTIVATION 5886 PubChem-compound ReactionCatalysis1935 ACTIVATION ReactionCatalysis1934 ACTIVATION 1.0 32702400 ChemSpider 22833512 PubChem-compound 1.0 SMILES CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=CC=CC=N1 H2O Water 18.010565 NADH BioCyc Rosiglitazone Metabolism Pathway NADP NAD BioCyc 977 PubChem-compound HMDB0059597 HMDB 50-00-0 CAS Transport224 false Rosiglitazone (→) Transport: Homo sapiens, Extracellular Space to Homo sapiens, Liver, Cell, Cytoplasm LEFT_TO_RIGHT Endoplasmic Reticulum SLCO1B1 CYP2C8 CYP2C9 CYP2C8 CYP2C9 CYP2C8 CYP2C9 Rosiglitazone Rosiglitazone N-Despyridinyl rosiglitazone N- desmethylrosiglitazone N-Desmethyl- p- hydroxyrosiglitazone N-Desmethyl- O-hydroxy rosiglitazone ortho- hydroxyrosiglitazone para- hydroxyrosiglitazone p-O-sulfate rosiglitazone N-Desmethyl- p-O-sulfate rosiglitazone N-desmethyl glucuronide rosiglitazone N-Desmethyl- o-O-sulfate rosiglitazone o-O-glucuronide rosiglitazone o-O-sulfate rosiglitazone p-O-glucuronide rosiglitazone Phenoxyacetic acid derivative Oxygen NADPH Hydrogen Ion Water NADP