Drug interactions with Cannabis sativa: Mechanisms and clinical implication

Atena Hasanpoor1, Maryam Akaberi2, Prashant Kesharwani3, Zahra Sobhani1, Amirhossein Sahebkar4,5
1Department of Traditional Pharmacy, School of Pharmacy, Mashhad University of Medical Sciences, Mashhad, Iran
2Department of Pharmacognosy, School of Pharmacy, Mashhad University of Medical Sciences, Mashhad, Iran
3Department of Pharmaceutics, School of Pharmaceutical Education and Research, Jamia Hamdard 110062, New Delhi, India
4Biotechnology Research Center, Pharmaceutical Technology Institute, Mashhad University of Medical Sciences, Mashhad, Iran
5Applied Biomedical Research Center, Mashhad University of Medical Sciences, Mashhad, Iran

Tài liệu tham khảo

Niloy, 2023, Effect of cannabis on memory consolidation, learning and retrieval and its current legal status in India: A review, Biomolecules, 13, 162, 10.3390/biom13010162 Hourfane, 2023, A comprehensive review on cannabis sativa ethnobotany, phytochemistry, molecular docking and biological activities, Plants, 12, 1206, 10.3390/plants12061245 Motaghi, 2023, The effect of tetrahydrocannabinol:cannabidiol oromucosal spray on cognition: A systematic review, Eur J Clin Pharmacol, 79, 371 Bennici, 2021, Safety of medical cannabis in neuropathic chronic pain management, Molecules, 26, 6257, 10.3390/molecules26206257 Bland, 2005, CYP2C-catalyzed delta (9)-tetrahydrocannabinol metabolism: kinetics, pharmacogenetics and interaction with phenytoin, Biochem Pharmacol, 70, 1096, 10.1016/j.bcp.2005.07.007 Machado Rocha, 2008, Therapeutic use of cannabis sativa on chemotherapy-induced nausea and vomiting among cancer patients: systematic review and meta-analysis, Eur J Cancer Care (Engl), 17, 431, 10.1111/j.1365-2354.2008.00917.x Pennant, 2023, The evolution of cannabinoid receptors in cancer, WIREs Mech Dis, 7, e1602, 10.1002/wsbm.1602 Lucas, 2018, The pharmacokinetics and the pharmacodynamics of cannabinoids, Br J Clin Pharmacol, 84, 2477, 10.1111/bcp.13710 Stone, 2020, A systematic review of minor phytocannabinoids with promising neuroprotective potential, Br J Pharmacol, 177, 4330, 10.1111/bph.15185 Radwan, 2021, Cannabinoids, phenolics, terpenes and alkaloids of cannabis, Molecules, 26, 2609, 10.3390/molecules26092774 Lu, 2016, An introduction to the endogenous cannabinoid system, Biol Psychiatry, 79, 516, 10.1016/j.biopsych.2015.07.028 Evans, 1991, Cannabinoids: The separation of central from peripheral effects on a structural basis, Planta Med, 57, S60, 10.1055/s-2006-960231 Zamarripa, 2022, Spindle. “Factors that impact the pharmacokinetic and pharmacodynamic effects of cannabis: A review of human laboratory studies.”, Current Addiction Reports, 608, 10.1007/s40429-022-00429-4 Bell, 2015, Pyrolysis of drugs of abuse: a comprehensive review, Drug Test Anal, 445, 10.1002/dta.1794 Huestis, 1999, 105 Grotenhermen, 2003, Pharmacokinetics and pharmacodynamics of cannabinoids, Clin Pharmacokinet, 42, 327, 10.2165/00003088-200342040-00003 Gilveray Mc, 2005, Pharmacokinetics of cannabinoids, Pain Res Manag, 22 Perez-Reyes, 1990, Marijuana smoking: Factors that influence the bioavailability of abused substances, NIDA Res Monogr, 42 Toennes, 2008, Kauert GF.“Comparison of cannabinoid pharmacokinetic properties in occasional and heavy users smoking amarijuana or placebo joint.”, J Anal Toxicol, 32, 470, 10.1093/jat/32.7.470 Newmeyer, 2016, Free and glucuronide whole blood cannabinoids’ pharmacokinetics after controlled smoked, vaporized, and oral cannabis administration in frequent and occasional cannabis users: identification of recent cannabis intake, Clin Chem, 62, 1579, 10.1373/clinchem.2016.263475 Therapeutic Goods Administration. Australian public assessment report for nabiximols. Available at https://www.tga.gov.au/sites/default/files/auspar-nabiximols-130927.pdf (last accessed 10 July 2017). Agurell, 1981, Interactions of delta 1-tetrahydrocannabinol with cannabinol and cannabidiol following oral administration in man. Assay of cannabinol and cannabidiol by mass fragmentography, Experientia, 1090, 10.1007/BF02085029 Dinis-Oliveira, 2016, Metabolomics of delta9-tetrahydrocannabinol: implications in toxicity, Drug Metab Rev, 48, 80, 10.3109/03602532.2015.1137307 Challapalli, 2002, In vitro experiment optimization for measuring tetrahydrocannabinol skin permeation, Int J Pharm, 241, 329, 10.1016/S0378-5173(02)00262-4 Stinchcomb, 2004, Human skin permeation of Delta8-tetrahydrocannabinol, cannabidiol and cannabinol, J Pharm Pharmacol, 56, 291, 10.1211/0022357022791 Valiveti, 2004, In vitro/in vivo correlation studies for transdermal delta 8-THC development, J Pharm Sci, 93, 1154, 10.1002/jps.20036 Ohlsson, 1986, Single-dose kinetics of deuterium-labelled cannabidiol in man after smoking and intravenous administration, Biomed Environ Mass Spectrom, 13, 77, 10.1002/bms.1200130206 Lichtman, 1992, The antinociceptive effects of intrathecally administered cannabinoids are influenced by lipophilicity, Pain, 51, 19, 10.1016/0304-3959(92)90004-U Huestis, 2007, Human cannabinoid pharmacokinetics, Chem Biodivers, 4, 1770, 10.1002/cbdv.200790152 Devinsky, 2014, Cannabidiol: pharmacology and potential therapeutic role in epilepsy and other neuropsychiatric disorders, Epilepsia, 55, 791, 10.1111/epi.12631 Lucas, 2018, Cannabinoid disposition after human intraperitoneal use: an insight into intraperitoneal pharmacokinetic properties in metastatic cancer, Clin Ther, 1442, 10.1016/j.clinthera.2017.12.008 Cox, 2019, A marijuana-drug interaction primer: Precipitants, pharmacology, and pharmacokinetics, Pharmacol Ther, 201, 25, 10.1016/j.pharmthera.2019.05.001 Hunt, 1980, Tolerance and disposition of tetrahydrocannabinol in man, J Pharmacol Exp Ther, 215, 35 Huestis, 2007, Human cannabinoid pharmacokinetics, Chem Biodivers, 1770, 10.1002/cbdv.200790152 Ohlsson, 1986, Single-dose kinetics of deuterium-labelled cannabidiol in man after smoking and intravenous administration, Biomed Environ Mass Spectrom, 13, 77, 10.1002/bms.1200130206 Sharma, 2012, Chemistry, metabolism, and toxicology of cannabis: clinical implications, Iran J Psychiatry, 7, 149 Bardhi, 2022, Cannabinoids and drug metabolizing enzymes: potential for drug-drug interactions and implications for drug safety and efficacy, Expert Rev Clin Pharmacol, 15, 1443, 10.1080/17512433.2022.2148655 Toennes, 2008, Comparison of cannabinoid pharmacokinetic properties in occasional and heavy users smoking amarijuana or placebo joint, J Anal Toxicol, 470, 10.1093/jat/32.7.470 Howlett, 2017, CB (1) and CB (2) receptor pharmacology, Adv Pharmacol, 80, 169, 10.1016/bs.apha.2017.03.007 Zou, 2018, Cannabinoid receptors and the endocannabinoid system: Signaling and function in the central nervous system, Int J Mol Sci, 19, 833, 10.3390/ijms19030833 Bayewitch, 1996, (-)-Delta9-tetrahydrocannabinol antagonizes the peripheral cannabinoid receptor-mediated inhibition of adenylyl cyclase, J Biol Chem, 271, 9902, 10.1074/jbc.271.17.9902 Felder, 1995, Comparison of the pharmacology and signal transduction of the human cannabinoid CB1 and CB2 receptors, Mol Pharmacol, 48, 443 Iwamura, 2001, In vitro and in vivo pharmacological characterization of JTE-907, a novel selective ligand for cannabinoid CB2 receptor, J Pharmacol Exp Ther, 296, 420 Rhee, 1997, Cannabinol derivatives: binding to cannabinoid receptors and inhibition of adenylylcyclase, J Med Chem, 40, 3228, 10.1021/jm970126f Pertwee, 2010, International union of basic and clinical pharmacology. LXXIX. cannabinoid receptors and their ligands: beyond CB and CB, Pharmacol Rev, 62, 588, 10.1124/pr.110.003004 Showalter, 1996, Evaluation of binding in a transfected cell line expressing a peripheral cannabinoid receptor (CB2): identification of cannabinoid receptor subtype selective ligands, J Pharmacol Exp Ther, 278, 989 Pertwee, 2008, The diverse CB1 and CB2 receptor pharmacology of three plant cannabinoids: delta9-tetrahydrocannabinol, cannabidiol and delta9-tetrahydrocannabivarin, Br J Pharmacol, 153, 199, 10.1038/sj.bjp.0707442 Tsou, 1998, Immunohistochemical distribution of cannabinoid CB1 receptors in the rat central nervous system, Neuroscience, 83, 393, 10.1016/S0306-4522(97)00436-3 Nachnani, 2021, The pharmacological case for cannabigerol, J Pharmacol Exp Ther, 376, 204, 10.1124/jpet.120.000340 Thomas, 2007, Cannabidiol displays unexpectedly high potency as an antagonist of CB1 and CB2 receptor agonists in vitro, Br J Pharmacol, 150, 613, 10.1038/sj.bjp.0707133 Laprairie, 2015, Cannabidiol is a negative allosteric modulator of the cannabinoid CB1 receptor, Br J Pharmacol, 172, 4790, 10.1111/bph.13250 Bakas, 2017, The direct actions of cannabidiol and 2-arachidonoyl glycerol at GABA(A) receptors, Pharmacol Res, 119, 358, 10.1016/j.phrs.2017.02.022 Ryberg, 2007, The orphan receptor GPR55 is a novel cannabinoid receptor, Br J Pharmacol, 152, 1092, 10.1038/sj.bjp.0707460 Scavone, 2013, Cannabinoid and opioid interactions: implications for opiate dependence and withdrawal, Neuroscience, 248, 637, 10.1016/j.neuroscience.2013.04.034 Muller, 2018, Cannabinoid ligands targeting TRP channels, Front Mol Neurosci, 11, 487, 10.3389/fnmol.2018.00487 Vučković, 2018, Cannabinoids and Pain: New insights from old molecules, Front Pharmacol, 9, 1259, 10.3389/fphar.2018.01259 Carrier, 2006, Inhibition of an equilibrative nucleoside transporter by cannabidiol: A mechanism of cannabinoid immunosuppression, Proc Natl Acad Sci U S A, 103, 7895, 10.1073/pnas.0511232103 Rios, 2006, μ opioid and CB1 cannabinoid receptor interactions: Reciprocal inhibition of receptor signaling and neuritogenesis, Br J Pharmacol, 148, 387, 10.1038/sj.bjp.0706757 O'Sullivan, 2007, Cannabinoids go nuclear: Evidence for activation of peroxisome proliferator-activated receptors, Br J Pharmacol, 152, 576, 10.1038/sj.bjp.0707423 Jimenez, 2020, TRPM Channels in Human Diseases, Cells, 9, 2604, 10.3390/cells9122604 Russo, 2005, Agonistic properties of cannabidiol at 5-HT1a receptors, Neurochem Res, 30, 1037, 10.1007/s11064-005-6978-1 Venkatachalam, 2014, Evolutionarily conserved, multitasking TRP channels: lessons from worms and flies, Handb Exp Pharmacol, 223, 937, 10.1007/978-3-319-05161-1_9 Qin, 2008, TRPV2 is activated by cannabidiol and mediates CGRP release in cultured rat dorsal root ganglion neurons, J Neurosci, 28, 6231, 10.1523/JNEUROSCI.0504-08.2008 Zanger, 2013, Cytochrome P450 enzymes in drug metabolism: Regulation of gene expression, enzyme activities, and impact of genetic variation, Pharmacol Ther, 138, 103, 10.1016/j.pharmthera.2012.12.007 Nasrin, 2021, Cannabinoid metabolites as inhibitors of major hepatic CYP450 enzymes, with implications for cannabis-drug interactions, Drug Metab Dispos, 49, 1070, 10.1124/dmd.121.000442 Yamaori, 2011, Potent inhibition of human cytochrome P450 3A isoforms by cannabidiol: Role of phenolic hydroxyl groups in the resorcinol moiety, Life Sci, 88, 730, 10.1016/j.lfs.2011.02.017 Yamaori, 2012, Comparison in the in vitro inhibitory effects of major phytocannabinoids and polycyclic aromatic hydrocarbons contained in marijuana smoke on cytochrome P450 2C9 activity, Drug Metab Pharmacokinet, 27, 294, 10.2133/dmpk.DMPK-11-RG-107 Jiang, 2013, Cannabidiol is a potent inhibitor of the catalytic activity of cytochrome P450 2C19, Drug Metab Pharmacokinet, 28, 332, 10.2133/dmpk.DMPK-12-RG-129 Yamaori, 2010, Characterization of major phytocannabinoids, cannabidiol and cannabinol, as isoform-selective and potent inhibitors of human CYP1 enzymes, Biochem Pharmacol, 79, 1691, 10.1016/j.bcp.2010.01.028 Zanger, 2013, Cytochrome P450 enzymes in drug metabolism: regulation of gene expression, enzyme activities, and impact of genetic variation, Pharmacol Ther, 138, 103, 10.1016/j.pharmthera.2012.12.007 Zhu, 2006, Characterization of P-glycoprotein inhibition by major cannabinoids from marijuana, J Pharmacol Exp Ther, 317, 850, 10.1124/jpet.105.098541 Mayer, 1997, Full blockade of intestinal P-glycoprotein and extensive inhibition of blood-brain barrier P-glycoprotein by oral treatment of mice with PSC833, J Clin Invest, 100, 2430, 10.1172/JCI119784 Brzozowska, 2017, The differential binding of antipsychotic drugs to the ABC transporter P-Glycoprotein predicts cannabinoid–antipsychotic drug interactions, Neuropsychopharmacology, 42, 2222, 10.1038/npp.2017.50 Hao-Jie, 2006, Characterization of P-glycoprotein inhibition by major cannabinoids from marijuana, J Pharmacol Exp Ther, 317, 850, 10.1124/jpet.105.098541 Holland, 2006, The effects of cannabinoids on P-glycoprotein transport and expression in multidrug resistant cells, Biochem Pharmacol, 71, 1146, 10.1016/j.bcp.2005.12.033 Feinshtein, 2013, Cannabidiol enhances xenobiotic permeability through the human placental barrier by direct inhibition of breast cancer resistance protein: an ex vivo study, Am J Obstet Gynecol, 209, 573, 10.1016/j.ajog.2013.08.005 Jarrar, 2021, The functionality of UDP-Glucuronosyltransferase genetic variants and their association with drug responses and human diseases, J Pers Med, 11, 554, 10.3390/jpm11060554 Kocis, 2020, Delta-9-tetrahydrocannabinol and cannabidiol drug-drug interactions, Med Cannabis Cannabinoids, 3, 61, 10.1159/000507998 Al Saabi, 2013, Involvement of UDP-glucuronosyltransferases UGT1A9 and UGT2B7 in ethanol glucuronidation, and interactions with common drugs of abuse, Drug Metab Dispos, 41, 568, 10.1124/dmd.112.047878 Yuli, 2022, Prediction of carboxylesterase 1-mediated in Vivo drug interaction between methylphenidate and cannabinoids using static and physiologically Based pharmacokinetic models, Drug Metab Dispos, 50, 968, 10.1124/dmd.121.000823 Qian, 2022, Prediction of carboxylesterase 1-mediated in vivo drug interaction between methylphenidate and cannabinoids using static and physiologically based pharmacokinetic models, Drug Metab Dispos, 50, 968, 10.1124/dmd.121.000823 Griffin, 2013, Benzodiazepine pharmacology and central nervous system-mediated effects, Ochsner J, 13, 214 Giraud, 2004, In vitro characterization of clobazam metabolism by recombinant cytochrome P450 enzymes: Importance of CYP2C19, Drug Metab Dispos, 32, 1279, 10.1124/dmd.32.11.1279 Alaa Al, 2013, Involvement of UDP-Glucuronosyltransferases UGT1A9 and UGT2B7 in ethanol glucuronidation, and interactions with common drugs of abuse, Drug Metab Dispos, 41, 568, 10.1124/dmd.112.047878 Geffrey, 2015, Drug–drug interaction between clobazam and cannabidiol in children with refractory epilepsy, Epilepsia, 56, 1246, 10.1111/epi.13060 Raffa, 1992, Opioid and nonopioid components independently contribute to the mechanism of action of tramadol, an atypical opioid analgesic, J Pharmacol Exp Ther, 260, 275 Baldo, 2018, Opioid analgesic drugs and serotonin toxicity (syndrome): Mechanisms, animal models, and links to clinical effects, Arch Toxicol, 92, 2457, 10.1007/s00204-018-2244-6 Osborne, 1990, Morphine and metabolite behavior after different routes of morphine administration: Demonstration of the importance of the active metabolite morphine-6-glucuronide, Clin Pharmacol Ther, 47, 12, 10.1038/clpt.1990.2 Birgit, 1998, The glucuronidation of opioids, other xenobiotics, and androgens by human UGT2B7Y(268) and UGT2B7H(268), Drug Metab Dispos, 26, 73 Lalovic, 2006, Pharmacokinetics and pharmacodynamics of oral oxycodone in healthy human subjects: Role of circulating active metabolites, Clin Pharmacol Ther, 79, 461, 10.1016/j.clpt.2006.01.009 Degenhardt, 2015, Experience of adjunctive cannabis use for chronic non-cancer pain: Findings from the pain and opioids in treatment (POINT) study, Drug Alcohol Depend, 147, 144, 10.1016/j.drugalcdep.2014.11.031 Cooper, 2018, Impact of co-administration of oxycodone and smoked cannabis on analgesia and abuse liability, Neuropsychopharmacology, 43, 2046, 10.1038/s41386-018-0011-2 Abrams, 2011, Cannabinoid–opioid interaction in chronic pain, Clin Pharmacol Ther, 90, 844, 10.1038/clpt.2011.188 Yang, 2018, Modulation of opioid transport at the blood-brain barrier by altered ATP-binding cassette (ABC) transporter expression and activity, Pharmaceutics, 10, 192, 10.3390/pharmaceutics10040192 Madden, 2020, Clinically significant drug-drug interaction between methadone and cannabidiol, Pediatrics, 145, 3256, 10.1542/peds.2019-3256 Stott, 2013, A phase i, open-label, randomized, crossover study in three parallel groups to evaluate the effect of rifampicin, ketoconazole, and omeprazole on the pharmacokinetics of THC/CBD oromucosal spray in healthy volunteers, Springerplus, 2, 1, 10.1186/2193-1801-2-236 Yang, 2014, Cannabidiol protects liver from binge alcohol-induced steatosis by mechanisms including inhibition of oxidative stress and increase in autophagy, Free Radic Biol Med, 68, 260, 10.1016/j.freeradbiomed.2013.12.026 Hamelink, 2005, Comparison of cannabidiol, antioxidants, and diuretics in reversing binge ethanol-induced neurotoxicity, J Pharmacol Exp Ther, 314, 780, 10.1124/jpet.105.085779 Hartman, 2015, Controlled cannabis vaporizer administration: blood and plasma cannabinoids with and without alcohol, Clin Chem, 61, 850, 10.1373/clinchem.2015.238287 Walzer, 2012, Pharmacokinetic drug interactions between clobazam and drugs metabolized by cytochrome P450 isoenzymes, Pharmacotherapy, 32, 340, 10.1002/j.1875-9114.2012.01028.x Yamaori, 2011, Cannabidiol, a major phytocannabinoid, as a potent atypical inhibitor for CYP2D6, Drug Metab Dispos, 39, 2049, 10.1124/dmd.111.041384 Walzer, 2012, Pharmacokinetic drug interactions between clobazam and drugs metabolized by cytochrome P450 isoenzymes, Pharmacotherapy, 32, 340, 10.1002/j.1875-9114.2012.01028.x Gaston, 2017, Interactions between cannabidiol and commonly used antiepileptic drugs, Epilepsia, 58, 1586, 10.1111/epi.13852 Ben-Menachem, 2020, A Phase II randomized trial to explore the potential for pharmacokinetic drug-drug interactions with stiripentol or valproate when combined with cannabidiol in patients with epilepsy, CNS Drugs, 34, 661, 10.1007/s40263-020-00726-4 Damkier, 2019, Interaction between warfarin and cannabis, Basic Clin Pharmacol Toxicol, 124, 28, 10.1111/bcpt.13152 Socała, 2019, Acute effect of cannabidiol on the activity of various novel antiepileptic drugs in the maximal electroshock- and 6 Hz-induced seizures in mice: Pharmacodynamic and pharmacokinetic studies, Neuropharmacology, 158, 107733, 10.1016/j.neuropharm.2019.107733 Balachandran, 2021, Cannabidiol interactions with medications, Illicit substances, and alcohol: A comprehensive review, J Gen Intern Med, 36, 2074, 10.1007/s11606-020-06504-8 Leino, 2019, Evidence of a clinically significant drug-drug interaction between cannabidiol and tacrolimus, Am J Transplant, 19, 2944, 10.1111/ajt.15398 Grayson, 2018, An interaction between warfarin and cannabidiol, a case report, Epilepsy Behav Case Rep, 9, 10, 10.1016/j.ebcr.2017.10.001 Hsu, 2020, Probable interaction between warfarin and inhaled and oral administration of cannabis, J Pharm Pract, 33, 915, 10.1177/0897190019854958 Yamreudeewong, 2009, Probable interaction between warfarin and marijuana smoking, Ann Pharmacother, 43, 1347, 10.1345/aph.1M064 Vierke, 2021, Buprenorphine-cannabis interaction in patients undergoing opioid maintenance therapy, Eur Arch Psychiatry Clin Neurosci, 271, 847, 10.1007/s00406-019-01091-0 Zullino, 2002, Tobacco and cannabis smoking cessation can lead to intoxication with clozapine or olanzapine, Int Clin Psychopharmacol, 17, 141, 10.1097/00004850-200205000-00008 Geffrey, 2015, Drug-drug interaction between clobazam and cannabidiol in children with refractory epilepsy, Epilepsia, 1246, 10.1111/epi.13060 Wheless, 2019, Pharmacokinetics and Tolerability of Multiple Doses of Pharmaceutical-Grade Synthetic Cannabidiol in Pediatric Patients with Treatment-Resistant Epilepsy, CNS Drugs, 33, 593, 10.1007/s40263-019-00624-4 Morrison, 2019, A phase 1, open-label, pharmacokinetic trial to investigate possible drug-drug interactions between clobazam, stiripentol, or valproate and cannabidiol in healthy subjects, Clin Pharmacol Drug Dev, 8, 1009, 10.1002/cpdd.665 Brown, 2019, Potential adverse drug events and drug–drug interactions with medical and consumer cannabidiol (CBD) use, J Clin Med, 8, 989, 10.3390/jcm8070989 Gaston, 2019, Drug–drug interactions with cannabidiol (CBD) appear to have no effect on treatment response in an open-label expanded access program, Epilepsy Behav, 98, 201, 10.1016/j.yebeh.2019.07.008