[{"id":104,"uid":"NPDI-vniY7Q","name":"Comparison in the in vitro inhibitory effects of major phytocannabinoids and polycyclic aromatic hydrocarbons contained in marijuana smoke on cytochrome P450 2C9 activity.","napdiIdentifier":"PMID: 22166891","overallSummary":"Inhibitory effects of Δ⁹-tetrahydrocannabinol (Δ⁹-THC), cannabidiol (CBD), and cannabinol (CBN), the three major constituents in marijuana, and polycyclic aromatic hydrocarbons (PAHs) contained in marijuana smoke on catalytic activity of human cytochrome P450 (CYP) 2C9 were investigated. These phytocannabinoids concentration-dependently inhibited S-warfarin 7-hydroxylase and diclofenac 4'-hydroxylase activities of human liver microsomes (HLMs) and recombinant CYP2C9 (rCYP2C9). In contrast, none of the twelve PAHs including benz[a]anthracene and benzo[a]pyrene exerted substantial inhibition (IC₅₀ > 10 µM). The inhibitory potentials of Δ⁹-THC (Ki = 0.937-1.50 µM) and CBN (Ki = 0.882-1.29 µM) were almost equivalent regardless of the enzyme sources used, whereas the inhibitory potency of CBD (Ki > = 0.954-9.88 µM) varied depending on the enzyme sources and substrates used. Δ⁹-THC inhibited both S-warfarin 7-hydroxylase and diclofenac 4'-hydroxylase activities of HLMs and rCYP2C9 in a mixed manner. CBD and CBN competitively inhibited the activities of HLMs and rCYP2C9, with the only notable difference being that CBD and CBN exhibited mixed-type inhibitions against diclofenac 4'-hydroxylation and S-warfarin 7-hydroxylation, respectively, by rCYP2C9. None of Δ⁹-THC, CBD, and CBN exerted metabolism-dependent inhibition. These results indicated that the three major phytocannabinoids but not PAHs contained in marijuana smoke potently inhibited CYP2C9 activity and that these cannabinoidscan be characterized as direct inhibitors for CYP2C9.","pubmedId":22166891,"embaseId":null,"croIdentifier":"22166891","croInformation":"Hokuriku University","dateStart":null,"dateEnd":null,"internalComment":null,"status":"published","compoundId":null,"naturalProductUid":"NP-0162af79-839e-40e2-af47-361c659061e9","naturalProductSampleId":null,"studySourceTypeId":1,"naturalProduct":{"uid":"NP-0162af79-839e-40e2-af47-361c659061e9","binomial":"Cannabis sativa","name":"Cannabis","itis":null,"srs":"4495dd37-943e-434d-bf30-ea9172d543c8","source_id":"","conceptId":null},"compound":null,"studySourceType":{"id":1,"name":"Published report"},"experiments":[{"id":385,"uid":"NPDI-jZO6oQ","name":"pHLM: THC-warfarin","overallEffect":1,"isControlData":false,"isIc50Shift":false,"croCutoff":"Not specified","croIdentifier":null,"comment":null,"experimentalConditionsComment":null,"resultsComment":"Tables 2, 3, and 4.
IC50 pre-incubation recorded at 20 min","internalComment":null,"objectCompoundId":168,"objectMetaboliteCompoundId":167,"precipitantCompoundId":118,"cytochromeB5Id":null,"studyId":104,"experimentTypeId":1,"testSystemId":6,"ic50ShiftExperimentId":null,"controlDataExperimentId":null,"controlDataForExperimentId":null,"naturalProductSampleId":null,"experimentType":{"id":1,"name":"In Vitro Enzyme Inhibition","isInVitro":true,"isTransporter":false,"isEnzyme":true,"purl":"http://purl.obolibrary.org/obo/DIDEO_00000058"},"objectCompound":{"id":168,"name":"(s)-warfarin","unii":null,"inChIKey":"PJVWKTKQMONHTI-HNNXBMFYSA-N","publicDescription":null,"internalComment":null,"conceptId":null,"enantiomerOfId":null},"precipitantCompound":{"id":118,"name":"delta-9-tetrahydrocannabinol","unii":null,"inChIKey":"CYQFCXCEBYINGO-UHFFFAOYSA-N","publicDescription":null,"internalComment":null,"conceptId":null,"enantiomerOfId":null},"objectMetaboliteCompound":{"id":167,"name":"7-hydroxywarfarin","unii":null,"inChIKey":"SKFYEJMLNMTTJA-UHFFFAOYSA-N","publicDescription":null,"internalComment":null,"conceptId":null,"enantiomerOfId":null},"enzymes":[{"id":8,"name":"CYP2C9","conceptId":4309227,"experiment_enzyme_xref":{"enzymeId":8,"experimentId":385}}],"transporters":[],"quantifiedMetabolites":[]},{"id":386,"uid":"NPDI-XouN0Q","name":"pHLM: CBD-warfarin","overallEffect":1,"isControlData":false,"isIc50Shift":false,"croCutoff":"Not specified","croIdentifier":null,"comment":null,"experimentalConditionsComment":null,"resultsComment":"Tables 2, 3, and 4.
IC50 pre-incubation recorded at 20 min","internalComment":null,"objectCompoundId":168,"objectMetaboliteCompoundId":167,"precipitantCompoundId":115,"cytochromeB5Id":null,"studyId":104,"experimentTypeId":1,"testSystemId":6,"ic50ShiftExperimentId":null,"controlDataExperimentId":null,"controlDataForExperimentId":null,"naturalProductSampleId":null,"experimentType":{"id":1,"name":"In Vitro Enzyme Inhibition","isInVitro":true,"isTransporter":false,"isEnzyme":true,"purl":"http://purl.obolibrary.org/obo/DIDEO_00000058"},"objectCompound":{"id":168,"name":"(s)-warfarin","unii":null,"inChIKey":"PJVWKTKQMONHTI-HNNXBMFYSA-N","publicDescription":null,"internalComment":null,"conceptId":null,"enantiomerOfId":null},"precipitantCompound":{"id":115,"name":"cannabidiol","unii":null,"inChIKey":"QHMBSVQNZZTUGM-ZWKOTPCHSA-N","publicDescription":null,"internalComment":null,"conceptId":null,"enantiomerOfId":null},"objectMetaboliteCompound":{"id":167,"name":"7-hydroxywarfarin","unii":null,"inChIKey":"SKFYEJMLNMTTJA-UHFFFAOYSA-N","publicDescription":null,"internalComment":null,"conceptId":null,"enantiomerOfId":null},"enzymes":[{"id":8,"name":"CYP2C9","conceptId":4309227,"experiment_enzyme_xref":{"enzymeId":8,"experimentId":386}}],"transporters":[],"quantifiedMetabolites":[]},{"id":387,"uid":"NPDI-mGu2ew","name":"pHLM: CBN-warfarin","overallEffect":1,"isControlData":false,"isIc50Shift":false,"croCutoff":"Not specified","croIdentifier":null,"comment":null,"experimentalConditionsComment":null,"resultsComment":"Tables 2, 3, and 4.
IC50 pre-incubation recorded at 20 min","internalComment":null,"objectCompoundId":168,"objectMetaboliteCompoundId":167,"precipitantCompoundId":153,"cytochromeB5Id":null,"studyId":104,"experimentTypeId":1,"testSystemId":6,"ic50ShiftExperimentId":null,"controlDataExperimentId":null,"controlDataForExperimentId":null,"naturalProductSampleId":null,"experimentType":{"id":1,"name":"In Vitro Enzyme Inhibition","isInVitro":true,"isTransporter":false,"isEnzyme":true,"purl":"http://purl.obolibrary.org/obo/DIDEO_00000058"},"objectCompound":{"id":168,"name":"(s)-warfarin","unii":null,"inChIKey":"PJVWKTKQMONHTI-HNNXBMFYSA-N","publicDescription":null,"internalComment":null,"conceptId":null,"enantiomerOfId":null},"precipitantCompound":{"id":153,"name":"cannabinol","unii":null,"inChIKey":"VBGLYOIFKLUMQG-UHFFFAOYSA-N","publicDescription":null,"internalComment":null,"conceptId":null,"enantiomerOfId":null},"objectMetaboliteCompound":{"id":167,"name":"7-hydroxywarfarin","unii":null,"inChIKey":"SKFYEJMLNMTTJA-UHFFFAOYSA-N","publicDescription":null,"internalComment":null,"conceptId":null,"enantiomerOfId":null},"enzymes":[{"id":8,"name":"CYP2C9","conceptId":4309227,"experiment_enzyme_xref":{"enzymeId":8,"experimentId":387}}],"transporters":[],"quantifiedMetabolites":[]},{"id":388,"uid":"NPDI-vUechg","name":"iHLM: THC-warfarin","overallEffect":1,"isControlData":false,"isIc50Shift":false,"croCutoff":"Not specified","croIdentifier":null,"comment":null,"experimentalConditionsComment":null,"resultsComment":"Tables 2 and 3","internalComment":null,"objectCompoundId":168,"objectMetaboliteCompoundId":167,"precipitantCompoundId":118,"cytochromeB5Id":null,"studyId":104,"experimentTypeId":1,"testSystemId":7,"ic50ShiftExperimentId":null,"controlDataExperimentId":null,"controlDataForExperimentId":null,"naturalProductSampleId":null,"experimentType":{"id":1,"name":"In Vitro Enzyme Inhibition","isInVitro":true,"isTransporter":false,"isEnzyme":true,"purl":"http://purl.obolibrary.org/obo/DIDEO_00000058"},"objectCompound":{"id":168,"name":"(s)-warfarin","unii":null,"inChIKey":"PJVWKTKQMONHTI-HNNXBMFYSA-N","publicDescription":null,"internalComment":null,"conceptId":null,"enantiomerOfId":null},"precipitantCompound":{"id":118,"name":"delta-9-tetrahydrocannabinol","unii":null,"inChIKey":"CYQFCXCEBYINGO-UHFFFAOYSA-N","publicDescription":null,"internalComment":null,"conceptId":null,"enantiomerOfId":null},"objectMetaboliteCompound":{"id":167,"name":"7-hydroxywarfarin","unii":null,"inChIKey":"SKFYEJMLNMTTJA-UHFFFAOYSA-N","publicDescription":null,"internalComment":null,"conceptId":null,"enantiomerOfId":null},"enzymes":[{"id":8,"name":"CYP2C9","conceptId":4309227,"experiment_enzyme_xref":{"enzymeId":8,"experimentId":388}}],"transporters":[],"quantifiedMetabolites":[]},{"id":389,"uid":"NPDI-dvyC1w","name":"iHLMs: CBD-warfarin","overallEffect":1,"isControlData":false,"isIc50Shift":false,"croCutoff":"Not specified","croIdentifier":null,"comment":null,"experimentalConditionsComment":null,"resultsComment":"Tables 2 and 3","internalComment":null,"objectCompoundId":168,"objectMetaboliteCompoundId":167,"precipitantCompoundId":115,"cytochromeB5Id":null,"studyId":104,"experimentTypeId":1,"testSystemId":7,"ic50ShiftExperimentId":null,"controlDataExperimentId":null,"controlDataForExperimentId":null,"naturalProductSampleId":null,"experimentType":{"id":1,"name":"In Vitro Enzyme Inhibition","isInVitro":true,"isTransporter":false,"isEnzyme":true,"purl":"http://purl.obolibrary.org/obo/DIDEO_00000058"},"objectCompound":{"id":168,"name":"(s)-warfarin","unii":null,"inChIKey":"PJVWKTKQMONHTI-HNNXBMFYSA-N","publicDescription":null,"internalComment":null,"conceptId":null,"enantiomerOfId":null},"precipitantCompound":{"id":115,"name":"cannabidiol","unii":null,"inChIKey":"QHMBSVQNZZTUGM-ZWKOTPCHSA-N","publicDescription":null,"internalComment":null,"conceptId":null,"enantiomerOfId":null},"objectMetaboliteCompound":{"id":167,"name":"7-hydroxywarfarin","unii":null,"inChIKey":"SKFYEJMLNMTTJA-UHFFFAOYSA-N","publicDescription":null,"internalComment":null,"conceptId":null,"enantiomerOfId":null},"enzymes":[{"id":8,"name":"CYP2C9","conceptId":4309227,"experiment_enzyme_xref":{"enzymeId":8,"experimentId":389}}],"transporters":[],"quantifiedMetabolites":[]},{"id":390,"uid":"NPDI-ZNPhvw","name":"iHLM: CBN-warfarin","overallEffect":1,"isControlData":false,"isIc50Shift":false,"croCutoff":"Not specified","croIdentifier":null,"comment":null,"experimentalConditionsComment":null,"resultsComment":"Tables 2 and 3","internalComment":null,"objectCompoundId":168,"objectMetaboliteCompoundId":167,"precipitantCompoundId":153,"cytochromeB5Id":null,"studyId":104,"experimentTypeId":1,"testSystemId":7,"ic50ShiftExperimentId":null,"controlDataExperimentId":null,"controlDataForExperimentId":null,"naturalProductSampleId":null,"experimentType":{"id":1,"name":"In Vitro Enzyme Inhibition","isInVitro":true,"isTransporter":false,"isEnzyme":true,"purl":"http://purl.obolibrary.org/obo/DIDEO_00000058"},"objectCompound":{"id":168,"name":"(s)-warfarin","unii":null,"inChIKey":"PJVWKTKQMONHTI-HNNXBMFYSA-N","publicDescription":null,"internalComment":null,"conceptId":null,"enantiomerOfId":null},"precipitantCompound":{"id":153,"name":"cannabinol","unii":null,"inChIKey":"VBGLYOIFKLUMQG-UHFFFAOYSA-N","publicDescription":null,"internalComment":null,"conceptId":null,"enantiomerOfId":null},"objectMetaboliteCompound":{"id":167,"name":"7-hydroxywarfarin","unii":null,"inChIKey":"SKFYEJMLNMTTJA-UHFFFAOYSA-N","publicDescription":null,"internalComment":null,"conceptId":null,"enantiomerOfId":null},"enzymes":[{"id":8,"name":"CYP2C9","conceptId":4309227,"experiment_enzyme_xref":{"enzymeId":8,"experimentId":390}}],"transporters":[],"quantifiedMetabolites":[]},{"id":391,"uid":"NPDI-59dZ4A","name":"rCYP2C9: THC-warfarin","overallEffect":1,"isControlData":false,"isIc50Shift":false,"croCutoff":"Not specified","croIdentifier":null,"comment":null,"experimentalConditionsComment":null,"resultsComment":"
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
Tables 2, 3, and 4
IC50 preincubation time recorded at 20 min
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
","internalComment":null,"objectCompoundId":168,"objectMetaboliteCompoundId":167,"precipitantCompoundId":118,"cytochromeB5Id":3,"studyId":104,"experimentTypeId":1,"testSystemId":14,"ic50ShiftExperimentId":null,"controlDataExperimentId":null,"controlDataForExperimentId":null,"naturalProductSampleId":null,"experimentType":{"id":1,"name":"In Vitro Enzyme Inhibition","isInVitro":true,"isTransporter":false,"isEnzyme":true,"purl":"http://purl.obolibrary.org/obo/DIDEO_00000058"},"objectCompound":{"id":168,"name":"(s)-warfarin","unii":null,"inChIKey":"PJVWKTKQMONHTI-HNNXBMFYSA-N","publicDescription":null,"internalComment":null,"conceptId":null,"enantiomerOfId":null},"precipitantCompound":{"id":118,"name":"delta-9-tetrahydrocannabinol","unii":null,"inChIKey":"CYQFCXCEBYINGO-UHFFFAOYSA-N","publicDescription":null,"internalComment":null,"conceptId":null,"enantiomerOfId":null},"objectMetaboliteCompound":{"id":167,"name":"7-hydroxywarfarin","unii":null,"inChIKey":"SKFYEJMLNMTTJA-UHFFFAOYSA-N","publicDescription":null,"internalComment":null,"conceptId":null,"enantiomerOfId":null},"enzymes":[{"id":8,"name":"CYP2C9","conceptId":4309227,"experiment_enzyme_xref":{"enzymeId":8,"experimentId":391}}],"transporters":[],"quantifiedMetabolites":[]},{"id":392,"uid":"NPDI-P2rdYg","name":"rCYP2C9: CBD-warfarin","overallEffect":1,"isControlData":false,"isIc50Shift":false,"croCutoff":"Not specified","croIdentifier":null,"comment":null,"experimentalConditionsComment":null,"resultsComment":"
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
Tables 2, 3, and 4
IC50 preincubation time recorded at 20 min
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
","internalComment":null,"objectCompoundId":168,"objectMetaboliteCompoundId":167,"precipitantCompoundId":115,"cytochromeB5Id":3,"studyId":104,"experimentTypeId":1,"testSystemId":14,"ic50ShiftExperimentId":null,"controlDataExperimentId":null,"controlDataForExperimentId":null,"naturalProductSampleId":null,"experimentType":{"id":1,"name":"In Vitro Enzyme Inhibition","isInVitro":true,"isTransporter":false,"isEnzyme":true,"purl":"http://purl.obolibrary.org/obo/DIDEO_00000058"},"objectCompound":{"id":168,"name":"(s)-warfarin","unii":null,"inChIKey":"PJVWKTKQMONHTI-HNNXBMFYSA-N","publicDescription":null,"internalComment":null,"conceptId":null,"enantiomerOfId":null},"precipitantCompound":{"id":115,"name":"cannabidiol","unii":null,"inChIKey":"QHMBSVQNZZTUGM-ZWKOTPCHSA-N","publicDescription":null,"internalComment":null,"conceptId":null,"enantiomerOfId":null},"objectMetaboliteCompound":{"id":167,"name":"7-hydroxywarfarin","unii":null,"inChIKey":"SKFYEJMLNMTTJA-UHFFFAOYSA-N","publicDescription":null,"internalComment":null,"conceptId":null,"enantiomerOfId":null},"enzymes":[{"id":8,"name":"CYP2C9","conceptId":4309227,"experiment_enzyme_xref":{"enzymeId":8,"experimentId":392}}],"transporters":[],"quantifiedMetabolites":[]},{"id":393,"uid":"NPDI-wt2yDg","name":"rCYP2C9: CBN-warfarin","overallEffect":1,"isControlData":false,"isIc50Shift":false,"croCutoff":"Not specified","croIdentifier":null,"comment":null,"experimentalConditionsComment":null,"resultsComment":"
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
Tables 2, 3, and 4
IC50 preincubation time recorded at 20 min
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
\r\n
","internalComment":null,"objectCompoundId":168,"objectMetaboliteCompoundId":167,"precipitantCompoundId":153,"cytochromeB5Id":3,"studyId":104,"experimentTypeId":1,"testSystemId":14,"ic50ShiftExperimentId":null,"controlDataExperimentId":null,"controlDataForExperimentId":null,"naturalProductSampleId":null,"experimentType":{"id":1,"name":"In Vitro Enzyme Inhibition","isInVitro":true,"isTransporter":false,"isEnzyme":true,"purl":"http://purl.obolibrary.org/obo/DIDEO_00000058"},"objectCompound":{"id":168,"name":"(s)-warfarin","unii":null,"inChIKey":"PJVWKTKQMONHTI-HNNXBMFYSA-N","publicDescription":null,"internalComment":null,"conceptId":null,"enantiomerOfId":null},"precipitantCompound":{"id":153,"name":"cannabinol","unii":null,"inChIKey":"VBGLYOIFKLUMQG-UHFFFAOYSA-N","publicDescription":null,"internalComment":null,"conceptId":null,"enantiomerOfId":null},"objectMetaboliteCompound":{"id":167,"name":"7-hydroxywarfarin","unii":null,"inChIKey":"SKFYEJMLNMTTJA-UHFFFAOYSA-N","publicDescription":null,"internalComment":null,"conceptId":null,"enantiomerOfId":null},"enzymes":[{"id":8,"name":"CYP2C9","conceptId":4309227,"experiment_enzyme_xref":{"enzymeId":8,"experimentId":393}}],"transporters":[],"quantifiedMetabolites":[]},{"id":394,"uid":"NPDI-Jb4JFA","name":"iHLM: THC-diclofenac","overallEffect":1,"isControlData":false,"isIc50Shift":false,"croCutoff":"Not specified","croIdentifier":null,"comment":null,"experimentalConditionsComment":null,"resultsComment":"Tables 2 and 3","internalComment":null,"objectCompoundId":14,"objectMetaboliteCompoundId":2,"precipitantCompoundId":118,"cytochromeB5Id":null,"studyId":104,"experimentTypeId":1,"testSystemId":7,"ic50ShiftExperimentId":null,"controlDataExperimentId":null,"controlDataForExperimentId":null,"naturalProductSampleId":null,"experimentType":{"id":1,"name":"In Vitro Enzyme Inhibition","isInVitro":true,"isTransporter":false,"isEnzyme":true,"purl":"http://purl.obolibrary.org/obo/DIDEO_00000058"},"objectCompound":{"id":14,"name":"diclofenac","unii":"144O8QL0L1","inChIKey":"DCOPUUMXTXDBNB-UHFFFAOYSA-N","publicDescription":null,"internalComment":null,"conceptId":1124300,"enantiomerOfId":null},"precipitantCompound":{"id":118,"name":"delta-9-tetrahydrocannabinol","unii":null,"inChIKey":"CYQFCXCEBYINGO-UHFFFAOYSA-N","publicDescription":null,"internalComment":null,"conceptId":null,"enantiomerOfId":null},"objectMetaboliteCompound":{"id":2,"name":"4'-hydroxydiclofenac","unii":null,"inChIKey":"KGVXVPRLBMWZLG-UHFFFAOYSA-N","publicDescription":null,"internalComment":null,"conceptId":null,"enantiomerOfId":null},"enzymes":[{"id":8,"name":"CYP2C9","conceptId":4309227,"experiment_enzyme_xref":{"enzymeId":8,"experimentId":394}}],"transporters":[],"quantifiedMetabolites":[]},{"id":395,"uid":"NPDI-Fqa3JA","name":"iHLM: CBD-diclofenac","overallEffect":1,"isControlData":false,"isIc50Shift":false,"croCutoff":"Not specified","croIdentifier":null,"comment":null,"experimentalConditionsComment":null,"resultsComment":"Tables 2 and 3","internalComment":null,"objectCompoundId":14,"objectMetaboliteCompoundId":2,"precipitantCompoundId":115,"cytochromeB5Id":null,"studyId":104,"experimentTypeId":1,"testSystemId":7,"ic50ShiftExperimentId":null,"controlDataExperimentId":null,"controlDataForExperimentId":null,"naturalProductSampleId":null,"experimentType":{"id":1,"name":"In Vitro Enzyme Inhibition","isInVitro":true,"isTransporter":false,"isEnzyme":true,"purl":"http://purl.obolibrary.org/obo/DIDEO_00000058"},"objectCompound":{"id":14,"name":"diclofenac","unii":"144O8QL0L1","inChIKey":"DCOPUUMXTXDBNB-UHFFFAOYSA-N","publicDescription":null,"internalComment":null,"conceptId":1124300,"enantiomerOfId":null},"precipitantCompound":{"id":115,"name":"cannabidiol","unii":null,"inChIKey":"QHMBSVQNZZTUGM-ZWKOTPCHSA-N","publicDescription":null,"internalComment":null,"conceptId":null,"enantiomerOfId":null},"objectMetaboliteCompound":{"id":2,"name":"4'-hydroxydiclofenac","unii":null,"inChIKey":"KGVXVPRLBMWZLG-UHFFFAOYSA-N","publicDescription":null,"internalComment":null,"conceptId":null,"enantiomerOfId":null},"enzymes":[{"id":8,"name":"CYP2C9","conceptId":4309227,"experiment_enzyme_xref":{"enzymeId":8,"experimentId":395}}],"transporters":[],"quantifiedMetabolites":[]},{"id":396,"uid":"NPDI-V1SemA","name":"iHLM: CBN-diclofenac","overallEffect":1,"isControlData":false,"isIc50Shift":false,"croCutoff":"Not specified","croIdentifier":null,"comment":null,"experimentalConditionsComment":null,"resultsComment":"Tables 2 and 3","internalComment":null,"objectCompoundId":14,"objectMetaboliteCompoundId":2,"precipitantCompoundId":153,"cytochromeB5Id":null,"studyId":104,"experimentTypeId":1,"testSystemId":7,"ic50ShiftExperimentId":null,"controlDataExperimentId":null,"controlDataForExperimentId":null,"naturalProductSampleId":null,"experimentType":{"id":1,"name":"In Vitro Enzyme Inhibition","isInVitro":true,"isTransporter":false,"isEnzyme":true,"purl":"http://purl.obolibrary.org/obo/DIDEO_00000058"},"objectCompound":{"id":14,"name":"diclofenac","unii":"144O8QL0L1","inChIKey":"DCOPUUMXTXDBNB-UHFFFAOYSA-N","publicDescription":null,"internalComment":null,"conceptId":1124300,"enantiomerOfId":null},"precipitantCompound":{"id":153,"name":"cannabinol","unii":null,"inChIKey":"VBGLYOIFKLUMQG-UHFFFAOYSA-N","publicDescription":null,"internalComment":null,"conceptId":null,"enantiomerOfId":null},"objectMetaboliteCompound":{"id":2,"name":"4'-hydroxydiclofenac","unii":null,"inChIKey":"KGVXVPRLBMWZLG-UHFFFAOYSA-N","publicDescription":null,"internalComment":null,"conceptId":null,"enantiomerOfId":null},"enzymes":[{"id":8,"name":"CYP2C9","conceptId":4309227,"experiment_enzyme_xref":{"enzymeId":8,"experimentId":396}}],"transporters":[],"quantifiedMetabolites":[]},{"id":397,"uid":"NPDI-bM6NOQ","name":"rCYP2C9: THC-diclofenac","overallEffect":1,"isControlData":false,"isIc50Shift":false,"croCutoff":"Not specified","croIdentifier":null,"comment":null,"experimentalConditionsComment":null,"resultsComment":"Tables 2 and 3","internalComment":null,"objectCompoundId":14,"objectMetaboliteCompoundId":2,"precipitantCompoundId":118,"cytochromeB5Id":3,"studyId":104,"experimentTypeId":1,"testSystemId":14,"ic50ShiftExperimentId":null,"controlDataExperimentId":null,"controlDataForExperimentId":null,"naturalProductSampleId":null,"experimentType":{"id":1,"name":"In Vitro Enzyme Inhibition","isInVitro":true,"isTransporter":false,"isEnzyme":true,"purl":"http://purl.obolibrary.org/obo/DIDEO_00000058"},"objectCompound":{"id":14,"name":"diclofenac","unii":"144O8QL0L1","inChIKey":"DCOPUUMXTXDBNB-UHFFFAOYSA-N","publicDescription":null,"internalComment":null,"conceptId":1124300,"enantiomerOfId":null},"precipitantCompound":{"id":118,"name":"delta-9-tetrahydrocannabinol","unii":null,"inChIKey":"CYQFCXCEBYINGO-UHFFFAOYSA-N","publicDescription":null,"internalComment":null,"conceptId":null,"enantiomerOfId":null},"objectMetaboliteCompound":{"id":2,"name":"4'-hydroxydiclofenac","unii":null,"inChIKey":"KGVXVPRLBMWZLG-UHFFFAOYSA-N","publicDescription":null,"internalComment":null,"conceptId":null,"enantiomerOfId":null},"enzymes":[{"id":8,"name":"CYP2C9","conceptId":4309227,"experiment_enzyme_xref":{"enzymeId":8,"experimentId":397}}],"transporters":[],"quantifiedMetabolites":[]},{"id":398,"uid":"NPDI-LKS7Ow","name":"rCYP2C9: CBD-diclofenac","overallEffect":1,"isControlData":false,"isIc50Shift":false,"croCutoff":"Not specified","croIdentifier":null,"comment":null,"experimentalConditionsComment":null,"resultsComment":"Tables 2 and 3","internalComment":null,"objectCompoundId":14,"objectMetaboliteCompoundId":2,"precipitantCompoundId":115,"cytochromeB5Id":3,"studyId":104,"experimentTypeId":1,"testSystemId":14,"ic50ShiftExperimentId":null,"controlDataExperimentId":null,"controlDataForExperimentId":null,"naturalProductSampleId":null,"experimentType":{"id":1,"name":"In Vitro Enzyme Inhibition","isInVitro":true,"isTransporter":false,"isEnzyme":true,"purl":"http://purl.obolibrary.org/obo/DIDEO_00000058"},"objectCompound":{"id":14,"name":"diclofenac","unii":"144O8QL0L1","inChIKey":"DCOPUUMXTXDBNB-UHFFFAOYSA-N","publicDescription":null,"internalComment":null,"conceptId":1124300,"enantiomerOfId":null},"precipitantCompound":{"id":115,"name":"cannabidiol","unii":null,"inChIKey":"QHMBSVQNZZTUGM-ZWKOTPCHSA-N","publicDescription":null,"internalComment":null,"conceptId":null,"enantiomerOfId":null},"objectMetaboliteCompound":{"id":2,"name":"4'-hydroxydiclofenac","unii":null,"inChIKey":"KGVXVPRLBMWZLG-UHFFFAOYSA-N","publicDescription":null,"internalComment":null,"conceptId":null,"enantiomerOfId":null},"enzymes":[{"id":8,"name":"CYP2C9","conceptId":4309227,"experiment_enzyme_xref":{"enzymeId":8,"experimentId":398}}],"transporters":[],"quantifiedMetabolites":[]},{"id":399,"uid":"NPDI-KqafWg","name":"rCYP2C9: CBN-diclofenac","overallEffect":1,"isControlData":false,"isIc50Shift":false,"croCutoff":"Not specified","croIdentifier":null,"comment":null,"experimentalConditionsComment":null,"resultsComment":"Tables 2 and 3","internalComment":null,"objectCompoundId":14,"objectMetaboliteCompoundId":2,"precipitantCompoundId":153,"cytochromeB5Id":3,"studyId":104,"experimentTypeId":1,"testSystemId":14,"ic50ShiftExperimentId":null,"controlDataExperimentId":null,"controlDataForExperimentId":null,"naturalProductSampleId":null,"experimentType":{"id":1,"name":"In Vitro Enzyme Inhibition","isInVitro":true,"isTransporter":false,"isEnzyme":true,"purl":"http://purl.obolibrary.org/obo/DIDEO_00000058"},"objectCompound":{"id":14,"name":"diclofenac","unii":"144O8QL0L1","inChIKey":"DCOPUUMXTXDBNB-UHFFFAOYSA-N","publicDescription":null,"internalComment":null,"conceptId":1124300,"enantiomerOfId":null},"precipitantCompound":{"id":153,"name":"cannabinol","unii":null,"inChIKey":"VBGLYOIFKLUMQG-UHFFFAOYSA-N","publicDescription":null,"internalComment":null,"conceptId":null,"enantiomerOfId":null},"objectMetaboliteCompound":{"id":2,"name":"4'-hydroxydiclofenac","unii":null,"inChIKey":"KGVXVPRLBMWZLG-UHFFFAOYSA-N","publicDescription":null,"internalComment":null,"conceptId":null,"enantiomerOfId":null},"enzymes":[{"id":8,"name":"CYP2C9","conceptId":4309227,"experiment_enzyme_xref":{"enzymeId":8,"experimentId":399}}],"transporters":[],"quantifiedMetabolites":[]}]}]