Characterization of major phytocannabinoids, cannabidiol and cannabinol, as isoform-selective and potent inhibitors of human CYP1 enzymes

Yamaori, Satoshi; Kushihara, Mika; Yamamoto, Ikuo; Watanabe, Kazuhito

doi:10.1016/j.bcp.2010.01.028

Cited by 165Cannabis and Cannabinoid ResearchPharmacogenetics and Drug MetabolismForensic Toxicology and Drug Analysis

Characterization of major phytocannabinoids, cannabidiol and cannabinol, as isoform-selective and potent inhibitors of human CYP1 enzymes

Yamaori, Satoshi, Kushihara, Mika, Yamamoto, Ikuo, Watanabe, Kazuhito·2010·Biochemical Pharmacology

DOI 10.1016/j.bcp.2010.01.028

Open this paper in CoChat — free account

Abstract

Inhibitory effects of Delta(9)-tetrahydrocannabinol (Delta(9)-THC), cannabidiol (CBD), and cannabinol (CBN), the three major constituents in marijuana, on catalytic activities of human cytochrome P450 (CYP) 1 enzymes were investigated. These cannabinoids inhibited 7-ethoxyresorufin O-deethylase activity of recombinant CYP1A1, CYP1A2, and CYP1B1 in a competitive manner. CBD most potently inhibited the CYP1A1 activity; the apparent K(i) value (0.155microM) was at least one-seventeenth of the values for other CYP1 isoforms. On the other hand, CBN more effectively decreased the activity of CYP1A2 and CYP1B1 (K(i)=0.0790 and 0.148microM, respectively) compared with CYP1A1 (K(i)=0.541microM). Delta(9)-THC less potently inhibited the CYP1 activity than CBD and CBN, and showed low selectivity against the CYP1 inhibition (K(i)=2.47-7.54microM). The preincubation of CBD resulted in a time- and concentration-dependent decrease in catalytic activity of all the recombinant CYP1 enzymes and human liver microsomes. Similarly, the preincubation of Delta(9)-THC or CBN caused a time- and concentration-dependent inhibition of recombinant CYP1A1. The inactivation of CYP1A1 by CBD indicated the highest k(inact)/K(I) value (540l/mmol/min) among the CYP1 enzyme sources tested. The inactivation of recombinant CYP1A1 and human liver microsomes by CBD required NADPH, was not influenced by dialysis and by glutathione, N-acetylcysteine, and superoxide dismutase as trapping agents. These results indicated that CBD and CBN showed CYP1 isoform-selective direct inhibition and that CBD was characterized as a potent mechanism-based inhibitor of human CYP1 enzymes, especially CYP1A1.

Integrity signals

Registry

Crossref · 10.1016/j.bcp.2010.01.028

Cites

54 of 54 references verified0 citation errors · 0 not checkable

Statistics

Recomputing p-values needs the paper’s full text.

Claims the paper makes

This paper’s full text isn’t openly available, so its claims and self-check weren’t run. The registry and citation checks still apply.

Claims other papers make about this one

Each is checked against this paper’s own text: does it say what the citing paper says it does?

In vitro studies suggest that THC inhibits CYP3A4, CYP3A5, CYP2C9, and CYP2C19, whereas CBD inhibits CYP2C19, CYP3A4, and CYP3A5.
“in vitro studies suggest that THC inhibits CYP3A4, CYP3A5, CYP2C9, and CYP2C19, whereas CBD inhibits CYP2C19, CYP3A4, and CYP3A5.”
From Clinical Practice Guidelines for Cannabis and Cannabinoid-Based Medicines in the Management of Chronic Pain and Co-Occurring Conditions (2024) · cites this paper as [106]
Due to the weak inhibitory effect of these cannabinoids, higher concentrations than those seen clinically are likely to be required for clinical inhibitory effect.
“Due to the weak inhibitory effect of these cannabinoids, higher concentrations than those seen clinically are likely to be required for clinical inhibitory effect.106”
From Clinical Practice Guidelines for Cannabis and Cannabinoid-Based Medicines in the Management of Chronic Pain and Co-Occurring Conditions (2024) · cites this paper as [106]

Interindividual variations in human liver cytochrome P-450 enzymes involved in the oxidation of drugs, carcinogens and toxic chemicals: studies with liver microsomes of 30 Japanese and 30 Caucasians
Shimada, T., Yamazaki, H., Mimura, M., Inui, Y., & Guengerich, F. P. (1994) · The Journal of Pharmacology and Experimental Therapeutics · doi:10.1016/s0022-3565(25)22379-5 · Cited by 2,785 · see citing works
The diverse CB 1 and CB 2 receptor pharmacology of three plant cannabinoids: Δ 9 ‐tetrahydrocannabinol, cannabidiol and Δ 9 ‐tetrahydrocannabivarin
Pertwee, R. G. (2007) · British Journal of Pharmacology · doi:10.1038/sj.bjp.0707442 · Cited by 1,953 · see citing works
Chemical constituents of marijuana: The complex mixture of natural cannabinoids
ElSohly, M. A., & Slade, D. (2005) · Life Sciences · doi:10.1016/j.lfs.2005.09.011 · Cited by 1,094 · see citing works
Metabolic activation of polycyclic aromatic hydrocarbons to carcinogens by cytochromes P450 1A1 and1B1
Shimada, T., & Fujii‐Kuriyama, Y. (2004) · Cancer Science · doi:10.1111/j.1349-7006.2004.tb03162.x · Cited by 805 · see citing works
Activation of chemically diverse procarcinogens by human cytochrome P-450 1B1.
Shimada, T., Hayes, C. L., Yamazaki, H., et al. (1996) · PubMed · Cited by 793 · see citing works
Blood cannabinoids. I. Absorption of THC and formation of 11-OH-THC and THCCOOH during and after smoking marijuana.
Huestis, M., Henningfield, J., & Cone, E. (1992) · Journal of Analytical Toxicology · doi:10.1093/jat/16.5.276 · Cited by 514 · see citing works
Complete cDNA sequence of a human dioxin-inducible mRNA identifies a new gene subfamily of cytochrome P450 that maps to chromosome 2.
Sutter, T. R., Tang, Y. M., Hayes, C. L., Wo, Y. Y., Jabs, E. W., Li, X., Yin, H., Cody, C. W., & Greenlee, W. F. (1994) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(17)36803-5 · Cited by 508 · see citing works
Purification and characterization of the human liver cytochromes P-450 involved in debrisoquine 4-hydroxylation and phenacetin O-deethylation, two prototypes for genetic polymorphism in oxidative drug metabolism.
Distlerath, L. M., Reilly, P. E. B., Martin, M. V., Davis, G., Wilkinson, G. R., & Guengerich, F. P. (1985) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(17)39456-5 · Cited by 319 · see citing works
Specificity of substrate and inhibitor probes for human cytochromes P450 1A1 and 1A2.
Tassaneeyakul, W., Birkett, D., Veronese, M., et al. (1993) · Journal of Pharmacology and Experimental Therapeutics · doi:10.1016/s0022-3565(25)38136-x · Cited by 318 · see citing works
Pharmacokinetics and Metabolism of the Plant Cannabinoids, Δ 9-Tetrahydrocannibinol, Cannabidiol and Cannabinol
Huestis, M. A. (2005) · Handbook of experimental pharmacology · doi:10.1007/3-540-26573-2_23 · Cited by 278 · see citing works
Specificity of substrate and inhibitor probes for cytochrome P450s: evaluation ofin vitrometabolism using cDNA-expressed human P450s and human liver microsomes
Ono, S., Hatanaka, T., Hotta, H., Satoh, T., Gonzalez, F. J., & Tsutsui, M. (1996) · Xenobiotica · doi:10.3109/00498259609046742 · Cited by 273 · see citing works
Cytochrome P450 enzymes involved in the metabolism of tetrahydrocannabinols and cannabinol by human hepatic microsomes
Watanabe, K., Yamaori, S., Funahashi, T., Kimura, T., & Yamamoto, I. (2007) · Life Sciences · doi:10.1016/j.lfs.2006.12.032 · Cited by 237 · see citing works
Self-citation
Characterization of human lung microsomal cytochrome P-450 1A1 and its role in the oxidation of chemical carcinogens.
Shimada, T., Yun, C., Yamazaki, H., Gautier, J., Beaune, P. H., & Guengerich, F. P. (1992) · Molecular Pharmacology · doi:10.1016/s0026-895x(25)09132-1 · Cited by 235 · see citing works
Human CYP1B1 and Anticancer Agent Metabolism: Mechanism for Tumor-Specific Drug Inactivation?
Rochat, B., Morsman, J. M., Murray, G. I., et al. (2001) · Journal of Pharmacology and Experimental Therapeutics · doi:10.1016/s0022-3565(24)38762-2 · Cited by 200 · see citing works
The Cannabinoids: Chemical, Pharmacologic, and Therapeutic Aspects
(1984) · Elsevier eBooks · doi:10.1016/b978-0-12-044620-9.x5001-5 · Cited by 189 · see citing works
Oxidation of xenobiotics by recombinant human cytochrome P450 1B1.
Shimada, T., Gillam, E. M. J., Sutter, T. R., et al. (1997) · PubMed · Cited by 169 · see citing works
Expression of cytochromes P450 1A1 and 1B1 in human lung from smokers, non-smokers, and ex-smokers
Kim, J. H. (2004) · Toxicology and Applied Pharmacology · doi:10.1016/j.taap.2003.11.015 · Cited by 166 · see citing works
Cannabidiol--antiepileptic drug comparisons and interactions in experimentally induced seizures in rats.
Consroe, P. F., & Wolkin, A. L. (1977) · Journal of Pharmacology and Experimental Therapeutics · doi:10.1016/s0022-3565(25)30824-4 · Cited by 152 · see citing works
Differential Inhibition and Inactivation of Human CYP1 Enzymes bytrans-Resveratrol: Evidence for Mechanism-Based Inactivation of CYP1A2
Chang, T. K. H., Chen, J., & Lee, W. B. K. (2001) · Journal of Pharmacology and Experimental Therapeutics · doi:10.1016/s0022-3565(24)29205-3 · Cited by 145 · see citing works
A new selective and potent inhibitor of human cytochrome P450 1B1 and its application to antimutagenesis.
Chun, Y., Kim, S., Kim, D., et al. (2001) · PubMed · Cited by 137 · see citing works
Characterization of human liver cytochromes P-450 involved in theophylline metabolism.
Sarkar, M. A., Hunt, C. M., Guzelian, P. S., & Karnes, H. T. (1992) · Drug Metabolism and Disposition · doi:10.1016/s0090-9556(25)08515-0 · Cited by 135 · see citing works
Effect of cannabis and certain of its constituents on pentobarbitone sleeping time and phenazone metabolism
Paton, W. D. M., & Pertwee, R. G. (1972) · British Journal of Pharmacology · doi:10.1111/j.1476-5381.1972.tb07261.x · Cited by 134 · see citing works
Metabolic activation of dacarbazine by human cytochromes P450: the role of CYP1A1, CYP1A2, and CYP2E1.
Reid, J. M., Kuffel, M. J., Miller, J. K., Ríos, R., & Ames, M. M. (1999) · PubMed · Cited by 133 · see citing works
Quantitative RT-PCR Measurement of Cytochromes p450 1A1, 1B1, and 2B7, Microsomal Epoxide Hydrolase, and NADPH Oxidoreductase Expression in Lung Cells of Smokers and Nonsmokers
Willey, J. C., Coy, E. L., Frampton, M. W., et al. (1997) · American Journal of Respiratory Cell and Molecular Biology · doi:10.1165/ajrcmb.17.1.2783 · Cited by 132 · see citing works
Inhibition of Human Cytochrome P450 Enzymes by 1,2-Dithiole-3-thione, Oltipraz and Its Derivatives, and Sulforaphane
Langouët, S., Furge, L. L., Kerriguy, N., et al. (2000) · Chemical Research in Toxicology · doi:10.1021/tx990189w · Cited by 114 · see citing works
Identification of a human liver cytochrome P-450 homologous to the major isosafrole-inducible cytochrome P-450 in the rat.
Wrighton, S. A., Campanile, C., Thomas, P. E., et al. (1986) · Molecular Pharmacology · doi:10.1016/s0026-895x(25)10261-7 · Cited by 113 · see citing works
Metabolism of the antiandrogenic drug (Flutamide) by human CYP1A2.
Shet, M. S., McPhaul, M. J., Fisher, C., et al. (1997) · PubMed · Cited by 111 · see citing works
Theophylline metabolism in human liver microsomes: inhibition studies.
Tjia, J., Colbert, J. E., & Back, D. J. (1996) · Journal of Pharmacology and Experimental Therapeutics · doi:10.1016/s0022-3565(25)12414-2 · Cited by 97 · see citing works
Human hepatic microsomal metabolism of delta 1-tetrahydrocannabinol.
Bornheim, L. M., Lasker, J. M., & Raucy, J. L. (1992) · Drug Metabolism and Disposition · doi:10.1016/s0090-9556(25)08572-1 · Cited by 97 · see citing works
Induction and Regulation of the Carcinogen-Metabolizing Enzyme CYP1A1 by Marijuana Smoke and Δ9-Tetrahydrocannabinol
Roth, M. D., Marques-Magallanes, J. A., Yuan, M., Sun, W., Tashkin, D. P., & Hankinson, O. (2001) · American Journal of Respiratory Cell and Molecular Biology · doi:10.1165/ajrcmb.24.3.4252 · Cited by 95 · see citing works
Forensic Chemical Study on Marihuana. I. A Detection Method of the Principal Constituents by Thin-layer and Gas Chromatographies
ARAMAKI, H., TOMIYASU, N., Yoshimura, H., et al. (1968) · Chemical and Pharmaceutical Bulletin · doi:10.1248/cpb.16.822 · Cited by 95 · see citing works
Mechanism-based inhibition of human cytochrome P450 1A1 by rhapontigenin.
Chun, Y., Ryu, S. Y., Jeong, T. C., & Kim, M. Y. (2001) · PubMed · Cited by 85 · see citing works
Characterization of Cytochrome P450 3A Inactivation by Cannabidiol: Possible Involvement of Cannabidiol-Hydroxyquinone as a P450 Inactivator
Bornheim, L. M., & Grillo, M. P. (1998) · Chemical Research in Toxicology · doi:10.1021/tx9800598 · Cited by 83 · see citing works
Effect of Ginkgo biloba extract on procarcinogen-bioactivating human CYP1 enzymes: Identification of isorhamnetin, kaempferol, and quercetin as potent inhibitors of CYP1B1
Chang, T. K. H., Chen, J., & Yeung, E. Y. H. (2005) · Toxicology and Applied Pharmacology · doi:10.1016/j.taap.2005.09.007 · Cited by 80 · see citing works
Distinction of CYP1A1 and CYP1A2 activity by selective inhibition using fluvoxamine and isosafrole
Pastrakuljic, A., Tang, B. K., Roberts, E. A., et al. (1997) · Biochemical Pharmacology · doi:10.1016/s0006-2952(96)00769-1 · Cited by 78 · see citing works
Metabolic and psychophysiologic studies of cannabidiol-hexobarbital interaction
Benowitz, N. L., Nguyen, T., Jones, R. T., Herning, R. I., & Bachman, J. (1980) · Clinical Pharmacology & Therapeutics · doi:10.1038/clpt.1980.139 · Cited by 67 · see citing works
Interactions of several cannabinoids with the hepatic drug metabolizing system
Fernandes, M. S., Warning, N., Christ, W., & Hill, R. (1973) · Biochemical Pharmacology · doi:10.1016/0006-2952(73)90184-6 · Cited by 65 · see citing works
Involvement of CYP2C in the Metabolism of Cannabinoids by Human Hepatic Microsomes from an Old Woman.
Watanabe, K., Matsunaga, T., YAMAMOTO, I., et al. (1995) · Biological and Pharmaceutical Bulletin · doi:10.1248/bpb.18.1138 · Cited by 65 · see citing works
Self-citation
Characterization of cannabidiol-mediated cytochrome P450 inactivation
Bornheim, L. M., Everhart, E. T., Li, J., et al. (1993) · Biochemical Pharmacology · doi:10.1016/0006-2952(93)90286-6 · Cited by 64 · see citing works
Inhibition of cyclosporine and tetrahydrocannabinol metabolism by cannabidiol in mouse and human microsomes
Jaeger, W., Benet, L. Z., & Bornheim, L. M. (1996) · Xenobiotica · doi:10.3109/00498259609046707 · Cited by 63 · see citing works
Recent advances in the metabolism of cannabinoids
Yamamoto, I., Watanabe, K., Narimatsu, S., & Yoshimura, H. (1995) · The International Journal of Biochemistry & Cell Biology · doi:10.1016/1357-2725(95)00043-o · Cited by 59 · see citing works
Self-citation
Different Mechanisms for Inhibition of Human Cytochromes P450 1A1, 1A2, and 1B1 by Polycyclic Aromatic Inhibitors
Shimada, T., Murayama, N., Okada, K., et al. (2007) · Chemical Research in Toxicology · doi:10.1021/tx600299p · Cited by 59 · see citing works
Metabolism and distribution of cannabinoids in rats after different methods of administration
Leighty, E. G. (1973) · Biochemical Pharmacology · doi:10.1016/0006-2952(73)90028-2 · Cited by 56 · see citing works
CYP1A1 Is a Major Enzyme Responsible for the Metabolism of Granisetron in Human Liver Microsomes
Nakamura, H., Ariyoshi, N., Okada, K., et al. (2005) · Current Drug Metabolism · doi:10.2174/138920005774330666 · Cited by 43 · see citing works
Direct characterization of the selectivity of furafylline as an inhibitor of human cytochromes P450 1A1 and 1A2
Tassaneeyakul, W., Birkett, D., Veronese, M. E., et al. (1994) · Pharmacogenetics · doi:10.1097/00008571-199410000-00007 · Cited by 38 · see citing works
Single-dose kinetics of deuterium-labelled cannabinol in man after intravenous administration and smoking
Johansson, E., Ohlsson, A., Lindgren, J., Agurell, S., Gillespie, H. K., & Hollister, L. E. (1987) · Journal of Mass Spectrometry · doi:10.1002/bms.1200140904 · Cited by 35 · see citing works
Purification and characterization of the major hepatic cannabinoid hydroxylase in the mouse: a possible member of the cytochrome P-450IIC subfamily.
Bornheim, L. M., & Correia, M. A. (1991) · Molecular Pharmacology · doi:10.1016/s0026-895x(25)12946-5 · Cited by 32 · see citing works
SINGLE DOSE KINETICS OF CANNABIDIOL IN MAN
Ohlsson, A., Lindgren, J. ‐., Andersson, S. K., Agurell, S., Gillespie, H. K., & Hollister, L. E. (1984) · Elsevier eBooks · doi:10.1016/b978-0-12-044620-9.50020-8 · Cited by 28 · see citing works
CYP3A4 is a major isoform responsible for oxidation of 7-hydroxy-Delta(8)-tetrahydrocannabinol to 7-oxo-delta(8)-tetrahydrocannabinol in human liver microsomes.
Matsunaga, T., Kishi, N., Higuchi, S., et al. (2000) · PubMed · Cited by 21 · see citing works
Catalytic activity of cytochrome P450 isozymes purified from rat liver in converting 11-oxo-Δ8-tetrahydrocannabinol to Δ8-tetrahydrocannabinol-11-oic acid
Watanabe, K., Matsunaga, T., Narimatsu, S., et al. (1991) · Biochemical Pharmacology · doi:10.1016/0006-2952(91)90262-4 · Cited by 16 · see citing works
Self-citation
CYP3A4 Is a Major Isoform Responsible for Oxidation of 7-Hydroxy-Δ8-tetrahydrocannabinol to 7-Oxo-Δ8-tetrahydrocannabinol in Human Liver Microsomes
Matsunaga, T., Kishi, N., Higuchi, S., et al. (2000) · Drug Metabolism and Disposition · doi:10.1016/s0090-9556(24)15075-1 · Cited by 14 · see citing works
8-Hydroxycannabinol: a new metabolite of cannabinol formed by human hepatic microsomes
Watanabe, K., Yamaori, S., Funahashi, T., et al. (2006) · Forensic Toxicology · doi:10.1007/s11419-006-0016-0 · Cited by 13 · see citing works
Self-citation
Effects of unsaturated side-chain analogs of tetrahydrocannabinol on cytochromes P450
Bornheim, L. M. (2000) · Biochemical Pharmacology · doi:10.1016/s0006-2952(00)00431-7 · Cited by 6 · see citing works
In Vitro Inhibitory Effects of Cannabinoids on Progesterone 17.ALPHA.-Hydroxylase Activity in Rat Testis Microsomes
Funahashi, T., Ikeuchi, H., Yamaori, S., et al. (2005) · Eisei kagaku · doi:10.1248/jhs.51.369 · Cited by 6 · see citing works
Self-citation

Flagged first, then by citations

Sorted by citations

Clinical Practice Guidelines for Cannabis and Cannabinoid-Based Medicines in the Management of Chronic Pain and Co-Occurring Conditions
Bell, A. D., MacCallum, C., Margolese, S., Walsh, Z., Wright, P., Daeninck, P. J., Mandarino, E., Lacasse, G., Kaur Deol, J., de Freitas, L., et al. (2024) · Cannabis & Cannabinoid Research · doi:10.1089/can.2021.0156 · Cited by 78 · see citing works
“106 This, however, may be of concern when cannabinoids are co-administered with drugs having a narrow therapeutic window and also metabolized by these enzymes, such as direct acting oral anticoagulants metabolized through CYP3A4 107,108 and clopidogrel requiring conversion to its active metabolite…”
Background

Interactions ofΔ 11-tetrahydrocannabinol with cannabinol and cannabidiol following oral administration in man. Assay of cannabinol and cannabidiol by mass fragmentographywith cannabinol and cannabidiol following oral administration in man. Assay of cannabinol and cannabidiol by mass fragmentography
Agurell, S., Carlsson, S., Lindgren, J. E., Ohlsson, A., Gillespie, H., & Hollister, L. (1981) · Experientia · doi:10.1007/bf02085029 · Cited by 129 · see citing works
Cannabinoids and metabolites in expectorated oral fluid following controlled smoked cannabis
Milman, G., Schwope, D. M., Gorelick, D. A., & Huestis, M. A. (2012) · Clinica Chimica Acta · doi:10.1016/j.cca.2012.01.011 · Cited by 61 · see citing works
Étude des cinétiques sanguines et cérébrales du Δ9-tétrahydrocannabinol, de ses métabolites, du cannabidiol et du cannabinol chez la souris. Application à l'homme Kinetic study of Δ9-tetrahydrocannabinol, its metabolites, cannabidiol and cannabinol in the blood and brain of mice. Application to humans
Duverneuil-Mayer, C., Charlier, P., Abé, E., et al. (2011) · Cited by 1 · see citing works
Interactions in man of delta‐9‐tetrahydrocannabinol; II. Cannabinol and cannabidiol
Hollister, L. E., & Gillespie, H. K. (1975) · Clinical Pharmacology & Therapeutics · doi:10.1002/cpt197518180 · Cited by 84 · see citing works
Cannabidiol attenuates Δ9-tetrahydrocannabinol-like discriminative stimulus effects of cannabinol
Hiltunen, A. J., & Järbe, T. U. C. (1986) · European Journal of Pharmacology · doi:10.1016/0014-2999(86)90042-7 · Cited by 13 · see citing works

Authors: Yamaori, S., Kushihara, M., Yamamoto, I., & Watanabe, K.
Affiliations: Hokuriku University (JP)
Kyushu University of Medical Science (JP)
Corresponding author: Watanabe, Kazuhito
ORCID: Yamamoto, Ikuo
Watanabe, Kazuhito
Venue: Biochemical Pharmacology
Publisher: Elsevier BV
Published: 2010-06
Volume: 79
Issue: 11
Pages: 1691-1698
ISSN: 0006-2952 (ISSN-L)
DOI: 10.1016/j.bcp.2010.01.028
OpenAlex: W2090940110
Cited by: 165
References: 54
Citations by year: 2026: 7 · 2025: 11 · 2024: 11 · 2023: 12 · 2022: 11 · 2021: 17 · 2020: 16 · 2019: 10 · 2018: 15 · 2017: 13 · 2016: 9 · 2015: 6 · 2014: 5 · 2013: 10 · 2012: 6
FWCI: 5.16
Type: journal article
Language: en
Open access: closed
Licence: www.elsevier.com/tdm/userlicense/1.0/ (tdm)
www.elsevier.com/legal/tdmrep-license (tdm)
Locations: Biochemical Pharmacology (publishedVersion)
PubMed (publishedVersion)
Funders: Ministry of Education, Culture, Sports, Science and Technology
Topics: Health Sciences › Medicine › Pharmacology › Cannabis and Cannabinoid Research
Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Pharmacology › Pharmacogenetics and Drug Metabolism
Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Toxicology › Forensic Toxicology and Drug Analysis
Keywords: cannabidiol, cannabinol, delta-9-tetrahydrocannabinol, phytocannabinoids, CYP1A1, CYP1A2, CYP1B1, enzyme inhibition, mechanism-based inhibition, ethoxyresorufin-O-deethylase, drug interactions
MeSH terms: Aryl Hydrocarbon Hydroxylases, Cannabidiol, Cannabinoids, Cannabinol, Catalysis, Humans, Microsomes, Liver, Cytochrome P-450 CYP1A1, Cytochrome P-450 CYP1A2, Protein Isoforms, Cytochrome P-450 CYP1A2 Inhibitors, Cytochrome P-450 CYP1B1

About these checks

Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.

Statistics and arithmetic are recomputed, not judged.

Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.

What counts as a claim ›How we measure confidence ›How we check this ›

Are you an author, or do you see a problem with this page? Request a review

Characterization of major phytocannabinoids, cannabidiol and cannabinol, as isoform-selective and potent inhibitors of human CYP1 enzymes

Abstract

Integrity signals

Claims the paper makes

Claims other papers make about this one

Cites

Cited by

Related

Record

About these checks