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Volumn 88, Issue 15-16, 2011, Pages 730-736

Potent inhibition of human cytochrome P450 3A isoforms by cannabidiol: Role of phenolic hydroxyl groups in the resorcinol moiety

Author keywords

9 Tetrahydrocannabinol; Cannabidiol; Cannabinol; CYP3A4; CYP3A5; CYP3A7; Inhibition

Indexed keywords

CANNABIDIOL; CANNABIDIOL DIMETHYL ETHER; CANNABIDIOL METHYL ETHER; CANNABINOL; CYTOCHROME P450 3A4; CYTOCHROME P450 3A5; CYTOCHROME P450 3A7; DILTIAZEM N DEMETHYLASE; DRONABINOL; LIMONENE; METHYLTRANSFERASE; OLIVETOL; UNCLASSIFIED DRUG;

EID: 79953287136     PISSN: 00243205     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.lfs.2011.02.017     Document Type: Article
Times cited : (180)

References (50)
  • 2
    • 0024412071 scopus 로고
    • Cytochrome P-450 hPCN3, a novel cytochrome P-450 IIIA gene product that is differentially expressed in adult human liver. cDNA and deduced amino acid sequence and distinct specificities of cDNA-expressed hPCN1 and hPCN3 for the metabolism of steroid hormones and cyclosporine
    • Aoyama T, Yamano S, Waxman DJ, Lapenson DP, Meyer UA, Fischer V, et al. Cytochrome P-450 hPCN3, a novel cytochrome P-450 IIIA gene product that is differentially expressed in adult human liver. cDNA and deduced amino acid sequence and distinct specificities of cDNA-expressed hPCN1 and hPCN3 for the metabolism of steroid hormones and cyclosporine. J Biol Chem 1989;264:10388-95. (Pubitemid 19161599)
    • (1989) Journal of Biological Chemistry , vol.264 , Issue.18 , pp. 10388-10395
    • Aoyama, T.1    Yamano, S.2    Waxman, D.J.3    Lapenson, D.P.4    Meyer, U.A.5    Fischer, V.6    Tyndale, R.7    Inaba, T.8    Kalow, W.9    Gelboin, H.V.10    Gonzalez, F.J.11
  • 3
    • 0014282006 scopus 로고
    • Forensic chemical study on marihuana. I. A detection method of the principal constituents by thin-layer and gas chromatographies
    • Tokyo
    • Aramaki H, Tomiyasu N, Yoshimura H, Tsukamoto H. Forensic chemical study on marihuana. I. A detection method of the principal constituents by thin-layer and gas chromatographies. Chem Pharm Bull (Tokyo) 1968;16:822-6.
    • (1968) Chem Pharm Bull , vol.16 , pp. 822-826
    • Aramaki, H.1    Tomiyasu, N.2    Yoshimura, H.3    Tsukamoto, H.4
  • 5
    • 0018904041 scopus 로고
    • Metabolic and psychophysiologic studies of cannabidiol-hexobarbital interaction
    • Benowitz NL, Nguyen TL, Jones RT, Herning RI, Bachman J. Metabolic and psychophysiologic studies of cannabidiol-hexobarbital interaction. Clin Pharmacol Ther 1980;28:115-20. (Pubitemid 10090694)
    • (1980) Clinical Pharmacology and Therapeutics , vol.28 , Issue.1 , pp. 115-120
    • Benowitz, N.L.1    Nguyen, T.L.2    Jones, R.T.3
  • 6
    • 0026050353 scopus 로고
    • Purification and characterization of the major hepatic cannabinoid hydroxylase in the mouse: A possible member of the cytochrome P- 450IIC subfamily
    • Bornheim LM, Correia MA. Purification and characterization of the major hepatic cannabinoid hydroxylase in the mouse: a possible member of the cytochrome P- 450IIC subfamily. Mol Pharmacol 1991;40:228-34.
    • (1991) Mol Pharmacol , vol.40 , pp. 228-234
    • Bornheim, L.M.1    Correia, M.A.2
  • 8
    • 0018198251 scopus 로고
    • 8-THC) on hepatic microsomal metabolism of testosterone in vitro
    • 8-THC) on hepatic microsomal metabolism of testosterone in vitro. Biochem Pharmacol 1978;27:1725-8.
    • (1978) Biochem Pharmacol , vol.27 , pp. 1725-1728
    • Chan, M.Y.1    Tse, A.2
  • 9
    • 0033835442 scopus 로고    scopus 로고
    • Catalysis of the 4-hydroxylation of retinoic acids by CYP3A7 in human fetal hepatic tissues
    • Chen H, Fantel AG, Juchau MR. Catalysis of the 4-hydroxylation of retinoic acids by CYP3A7 in human fetal hepatic tissues. Drug Metab Dispos 2000;28:1051-7. (Pubitemid 30660359)
    • (2000) Drug Metabolism and Disposition , vol.28 , Issue.9 , pp. 1051-1057
    • Chen, H.1    Fantel, A.G.2    Juchau, M.R.3
  • 10
    • 27844525479 scopus 로고    scopus 로고
    • Chemical constituents of marijuana: The complex mixture of natural cannabinoids
    • DOI 10.1016/j.lfs.2005.09.011, PII S002432050500891X
    • ElSohly MA, Slade D. Chemical constituents of marijuana: the complex mixture of natural cannabinoids. Life Sci 2005;78:539-48. (Pubitemid 41653504)
    • (2005) Life Sciences , vol.78 , Issue.5 , pp. 539-548
    • ElSohly, M.A.1    Slade, D.2
  • 11
    • 0033621602 scopus 로고    scopus 로고
    • Potency trends of delta9- THC and other cannabinoids in confiscated marijuana from 1980-1997
    • ElSohly MA, Ross SA, Mehmedic Z, Arafat R, Yi B, Banahan BF. Potency trends of delta9- THC and other cannabinoids in confiscated marijuana from 1980-1997. J Forensic Sci 2000;45:24-30.
    • (2000) J Forensic Sci , vol.45 , pp. 24-30
    • ElSohly, M.A.1    Ross, S.A.2    Mehmedic, Z.3    Arafat, R.4    Yi, B.5    Banahan, B.F.6
  • 12
    • 0015845360 scopus 로고
    • Interactions of several cannabinoids with the hepatic drug metabolizing system
    • Fernandes M, Warning N, Christ W, Hill R. Interactions of several cannabinoids with the hepatic drug metabolizing system. Biochem Pharmacol 1973;22:2981-7.
    • (1973) Biochem Pharmacol , vol.22 , pp. 2981-2987
    • Fernandes, M.1    Warning, N.2    Christ, W.3    Hill, R.4
  • 13
    • 0024998313 scopus 로고
    • In vivo and in vitro metabolism of cannabidiol monomethyl ether and cannabidiol dimethyl ether in the guinea pig: On the formation mechanism of cannabielsoin-type metabolite from cannabidiol
    • Tokyo
    • Gohda H, Narimatsu S, Yamamoto I, Yoshimura H. In vivo and in vitro metabolism of cannabidiol monomethyl ether and cannabidiol dimethyl ether in the guinea pig: on the formation mechanism of cannabielsoin-type metabolite from cannabidiol. Chem Pharm Bull (Tokyo) 1990;38:1697-701.
    • (1990) Chem Pharm Bull , vol.38 , pp. 1697-1701
    • Gohda, H.1    Narimatsu, S.2    Yamamoto, I.3    Yoshimura, H.4
  • 14
    • 0028234586 scopus 로고
    • Regioselective biotransformation of midazolam by members of the human cytochrome P450 3A (CYP3A) subfamily
    • DOI 10.1016/0006-2952(94)90543-6
    • Gorski JC, Hall SD, Jones DR, VandenBranden M, Wrighton SA. Regioselective biotransformation of midazolam by members of the human cytochrome P450 3A (CYP3A) subfamily. Biochem Pharmacol 1994;47:1643-53. (Pubitemid 24167278)
    • (1994) Biochemical Pharmacology , vol.47 , Issue.9 , pp. 1643-1653
    • Christopher, G.J.1    Hall, S.D.2    Jones, D.R.3    VandenBranden, M.4
  • 15
    • 33645098680 scopus 로고    scopus 로고
    • Differential inhibition of cytochrome P450 3A4, 3A5 and 3A7 by five human immunodeficiency virus (HIV) protease inhibitors in vitro
    • Granfors MT, Wang JS, Kajosaari LI, Laitila J, Neuvonen PJ, Backman JT. Differential inhibition of cytochrome P450 3A4, 3A5 and 3A7 by five human immunodeficiency virus (HIV) protease inhibitors in vitro. Basic Clin Pharmacol Toxicol 2006;98:79-85.
    • (2006) Basic Clin Pharmacol Toxicol , vol.98 , pp. 79-85
    • Granfors, M.T.1    Wang, J.S.2    Kajosaari, L.I.3    Laitila, J.4    Neuvonen, P.J.5    Backman, J.T.6
  • 16
    • 0022998708 scopus 로고
    • Characterization of rat and human liver microsomal cytochrome P-450 forms involved in nifedipine oxidation, a prototype for genetic polymorphism in oxidative drug metabolism
    • Guengerich FP, Martin MV, Beaune PH, Kremers P, Wolff T, Waxman DJ. Characterization of rat and human liver microsomal cytochrome P-450 forms involved in nifedipine oxidation, a prototype for genetic polymorphism in oxidative drug metabolism. J Biol Chem 1986;261:5051-60. (Pubitemid 17204301)
    • (1986) Journal of Biological Chemistry , vol.261 , Issue.11 , pp. 5051-5060
    • Guengerich, F.P.1    Martin, M.V.2    Beaune, P.H.3
  • 17
    • 0021040232 scopus 로고
    • 9-tetrahydrocannabinol and cannabidiol on pentobarbital- induced sleeping time and hepatic microsomal drug metabolizing enzyme systems in mice
    • 9-tetrahydrocannabinol and cannabidiol on pentobarbital- induced sleeping time and hepatic microsomal drug metabolizing enzyme systems in mice. Yakugaku Zasshi 1983;103:1289-97.
    • (1983) Yakugaku Zasshi , vol.103 , pp. 1289-1297
    • Hamajima, K.1    Watanabe, K.2    Narimatsu, S.3    Tateoka, Y.4    Yamamoto, I.5    Yoshimura, H.6
  • 18
    • 0015294082 scopus 로고
    • Prenatal toxicity, maternal distribution and placental transfer of tetrahydrocannabinol
    • Harbison RD, Mantilla-Plata B. Prenatal toxicity, maternal distribution and placental transfer of tetrahydrocannabinol. J Pharmacol Exp Ther 1972;180:446-53.
    • (1972) J Pharmacol Exp Ther , vol.180 , pp. 446-453
    • Harbison, R.D.1    Mantilla-Plata, B.2
  • 19
    • 33645754286 scopus 로고    scopus 로고
    • 9-tetrahydrocannabinol, cannabidiol and cannabinol
    • 9-tetrahydrocannabinol, cannabidiol and cannabinol. Handb Exp Pharmacol 2005;168:657-90.
    • (2005) Handb Exp Pharmacol , vol.168 , pp. 657-690
    • Huestis, M.A.1
  • 20
    • 0026701051 scopus 로고
    • Blood cannabinoids. I. absorption of THC and formation of 11-OH-THC and THCCOOH during and after smoking marijuana
    • Huestis MA, Henningfield JE, Cone EJ. Blood cannabinoids. I. absorption of THC and formation of 11-OH-THC and THCCOOH during and after smoking marijuana. J Anal Toxicol 1992;16:276-82.
    • (1992) J Anal Toxicol , vol.16 , pp. 276-282
    • Huestis, M.A.1    Henningfield, J.E.2    Cone, E.J.3
  • 22
    • 0029917596 scopus 로고    scopus 로고
    • Inhibition of cyclosporine and tetrahydrocannabinol metabolism by cannabidiol in mouse and human microsomes
    • Jaeger W, Benet LZ, Bornheim LM. Inhibition of cyclosporine and tetrahydrocannabinol metabolism by cannabidiol in mouse and human microsomes. Xenobiotica 1996;26:275-84. (Pubitemid 26128232)
    • (1996) Xenobiotica , vol.26 , Issue.3 , pp. 275-284
    • Jaeger, W.1    Benet, L.Z.2    Bornheim, L.M.3
  • 23
    • 0022255668 scopus 로고
    • Purification and properties of cytochrome P-450 from homogenates of human fetal livers
    • DOI 10.1016/0003-9861(85)90383-2
    • Kitada M, Kamataki T, Itahashi K, Rikihisa T, Kato R, Kanakubo Y. Purification and properties of cytochrome P-450 from homogenates of human fetal livers. Arch Biochem Biophys 1985;241:275-80. (Pubitemid 15012034)
    • (1985) Archives of Biochemistry and Biophysics , vol.241 , Issue.1 , pp. 275-280
    • Kitada, M.1    Kamataki, T.2    Itahashi, K.3
  • 24
    • 0023200455 scopus 로고
    • P-450 HFLa, a form of cytochrome P-450 purified from human fetal livers, is the 16α-hydroxylase of dehydroepiandrosterone 3-sulfate
    • Kitada M, Kamataki T, Itahashi K, Rikihisa T, Kanakubo Y. P-450 HFLa, a form of cytochrome P-450 purified from human fetal livers, is the 16α-hydroxylase of dehydroepiandrosterone 3-sulfate. J Biol Chem 1987;262:13534-7. (Pubitemid 17144304)
    • (1987) Journal of Biological Chemistry , vol.262 , Issue.28 , pp. 13534-13537
    • Kitada, M.1    Kamataki, T.2    Itahashi, K.3
  • 25
    • 0036786382 scopus 로고    scopus 로고
    • Interindividual variability and tissue-specificity in the expression of cytochrome P450 3A mRNA
    • Koch I, Weil R, Wolbold R, Brockmöller J, Hustert E, Burk O, et al. Interindividual variability and tissue-specificity in the expression of cytochrome P450 3A mRNA. Drug Metab Dispos 2002;30:1108-14.
    • (2002) Drug Metab Dispos , vol.30 , pp. 1108-1114
    • Koch, I.1    Weil, R.2    Wolbold, R.3    Brockmöller, J.4    Hustert, E.5    Burk, O.6
  • 28
    • 0015893309 scopus 로고
    • Metabolism and distribution of cannabinoids in rats after different methods of administration
    • Leighty EG. Metabolism and distribution of cannabinoids in rats after different methods of administration. Biochem Pharmacol 1973;22:1613-21.
    • (1973) Biochem Pharmacol , vol.22 , pp. 1613-1621
    • Leighty, E.G.1
  • 31
    • 4644331461 scopus 로고    scopus 로고
    • Differences in the inhibition of cytochromes P450 3A4 and 3A5 by metabolite-inhibitor complex-forming drugs
    • McConn II DJ, Lin YS, Allen K, Kunze KL, Thummel KE. Differences in the inhibition of cytochromes P450 3A4 and 3A5 by metabolite-inhibitor complex-forming drugs. Drug Metab Dispos 2004;32:1083-91. (Pubitemid 39287581)
    • (2004) Drug Metabolism and Disposition , vol.32 , Issue.10 , pp. 1083-1091
    • McConn II, D.J.1    Lin, Y.S.2    Allen, K.3    Kunze, K.L.4    Thummel, K.E.5
  • 32
    • 0029007929 scopus 로고
    • The roles of retinoids in vertebrate development
    • Means AL, Gudas LJ. The roles of retinoids in vertebrate development. Annu Rev Biochem 1995;64:201-33.
    • (1995) Annu Rev Biochem , vol.64 , pp. 201-233
    • Means, A.L.1    Gudas, L.J.2
  • 33
    • 0036838389 scopus 로고    scopus 로고
    • Cannabidiol: An overview of some pharmacological aspects
    • Mechoulam R, Parker LA, Gallily R. Cannabidiol: an overview of some pharmacological aspects. J Clin Pharmacol 2002;42:11S-9S.
    • (2002) J Clin Pharmacol , vol.42
    • Mechoulam, R.1    Parker, L.A.2    Gallily, R.3
  • 36
    • 38349158960 scopus 로고    scopus 로고
    • 9-tetrahydrocannabivarin
    • 9- tetrahydrocannabivarin. Br J Pharmacol 2008;153:199-215.
    • (2008) Br J Pharmacol , vol.153 , pp. 199-215
    • Pertwee, R.G.1
  • 37
    • 0036223831 scopus 로고    scopus 로고
    • Summary of information on human CYP enzymes: Human P450 metabolism data
    • DOI 10.1081/DMR-120001392
    • Rendic S. Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev 2002;34:83-448. (Pubitemid 34311090)
    • (2002) Drug Metabolism Reviews , vol.34 , Issue.1-2 , pp. 83-448
    • Rendic, S.1
  • 38
    • 0027180023 scopus 로고
    • Identification of the fetal liver cytochrome CYP3A7 in human endometrium and placenta
    • Schuetz JD, Kauma S, Guzelian PS. Identification of the fetal liver cytochrome CYP3A7 in human endometrium and placenta. J Clin Invest 1993;92:1018-24. (Pubitemid 23262427)
    • (1993) Journal of Clinical Investigation , vol.92 , Issue.2 , pp. 1018-1024
    • Schuetz, J.D.1    Kauma, S.2    Guzelian, P.S.3
  • 39
    • 0028237729 scopus 로고
    • 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 FP. 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. J Pharmacol Exp Ther 1994;270:414-23. (Pubitemid 24229655)
    • (1994) Journal of Pharmacology and Experimental Therapeutics , vol.270 , Issue.1 , pp. 414-423
    • Shimada, T.1    Yamazaki, H.2    Mimura, M.3    Inui, Y.4    Guengerich, F.P.5
  • 40
    • 0242332169 scopus 로고    scopus 로고
    • Impact of cytochrome P450 3A5 genetic polymorphism on tacrolimus doses and concentration-to-dose ratio in renal transplant recipients
    • DOI 10.1097/01.TP.0000090753.99170.89
    • Thervet E, Anglicheau D, King B, Schlageter MH, Cassinat B, Beaune P, et al. Impact of cytochrome P450 3A5 genetic polymorphism on tacrolimus doses and concentration- to-dose ratio in renal transplant recipients. Transplantation 2003;76:1233-5. (Pubitemid 37339651)
    • (2003) Transplantation , vol.76 , Issue.8 , pp. 1233-1235
    • Thervet, E.1    Anglicheau, D.2    King, B.3    Schlageter, M.-H.4    Cassinat, B.5    Beaune, P.6    Legendre, C.7    Daly, A.K.8
  • 41
    • 0019863988 scopus 로고
    • 8- Tetrahydrocannabinol and its metabolites with hepatic microsomal drug metabolizing enzyme systems of mice
    • 8- tetrahydrocannabinol and its metabolites with hepatic microsomal drug metabolizing enzyme systems of mice. J Pharmacobiodyn 1981;4:604-11.
    • (1981) J Pharmacobiodyn , vol.4 , pp. 604-611
    • Watanabe, K.1    Yamamoto, I.2    Oguri, K.3    Yoshimura, H.4
  • 42
    • 0029114516 scopus 로고
    • Involvement of CYP2C in the metabolism of cannabinoids by human hepatic microsomes from an old woman
    • Watanabe K, Matsunaga T, Yamamoto I, Funae Y, Yoshimura H. Involvement of CYP2C in the metabolism of cannabinoids by human hepatic microsomes from an old woman. Biol Pharm Bull 1995;18:1138-41.
    • (1995) Biol Pharm Bull , vol.18 , pp. 1138-1141
    • Watanabe, K.1    Matsunaga, T.2    Yamamoto, I.3    Funae, Y.4    Yoshimura, H.5
  • 43
    • 33847633815 scopus 로고    scopus 로고
    • Cytochrome P450 enzymes involved in the metabolism of tetrahydrocannabinols and cannabinol by human hepatic microsomes
    • DOI 10.1016/j.lfs.2006.12.032, PII S0024320507000495
    • Watanabe K, Yamaori S, Funahashi T, Kimura T, Yamamoto I. Cytochrome P450 enzymes involved in the metabolism of tetrahydrocannabinols and cannabinol by human hepatic microsomes. Life Sci 2007;80:1415-9. (Pubitemid 46367067)
    • (2007) Life Sciences , vol.80 , Issue.15 , pp. 1415-1419
    • Watanabe, K.1    Yamaori, S.2    Funahashi, T.3    Kimura, T.4    Yamamoto, I.5
  • 46
    • 0024400702 scopus 로고
    • Identification of a polymorphically expressed member of the human cytochrome P-450III family
    • Wrighton SA, Ring BJ, Watkins PB, VandenBranden M. Identification of a polymorphically expressed member of the human cytochrome P-450III family. Mol Pharmacol 1989;36:97-105. (Pubitemid 19191265)
    • (1989) Molecular Pharmacology , vol.36 , Issue.1 , pp. 97-105
    • Wrighton, S.A.1    Ring, B.J.2    Watkins, P.B.3    Vandenbranden, M.4
  • 47
    • 0345016882 scopus 로고    scopus 로고
    • 5on drug oxidation activities of human cytochrome P450 (CYP) 3As: Similarity of CYP3A5 with CYP3A4 but not CYP3A7
    • DOI 10.1016/j.bcp.2003.08.004
    • Yamaori S, Yamazaki H, Suzuki A, Yamada A, Tani H, Kamidate T, et al. Effects of cytochrome b5 on drug oxidation activities of human cytochrome P450 (CYP) 3As: similarity of CYP3A5 with CYP3A4 but not CYP3A7. Biochem Pharmacol 2003;66:2333-40. (Pubitemid 37456741)
    • (2003) Biochemical Pharmacology , vol.66 , Issue.12 , pp. 2333-2340
    • Yamaori, S.1    Yamazaki, H.2    Suzuki, A.3    Yamada, A.4    Tani, H.5    Kamidate, T.6    Fujita, K.-I.7    Kamataki, T.8
  • 48
    • 4644263308 scopus 로고    scopus 로고
    • CYP3A5 contributes significantly to CYP3A-mediated drug oxidations in liver microsomes from Japanese subjects
    • Yamaori S, Yamazaki H, Iwano S, Kiyotani K, Matsumura K, Honda G, et al. CYP3A5 contributes significantly to CYP3A-mediated drug oxidations in liver microsomes from Japanese subjects. Drug Metab Pharmacokinet 2004;19:120-9.
    • (2004) Drug Metab Pharmacokinet , vol.19 , pp. 120-129
    • Yamaori, S.1    Yamazaki, H.2    Iwano, S.3    Kiyotani, K.4    Matsumura, K.5    Honda, G.6
  • 49
    • 77950094856 scopus 로고    scopus 로고
    • Characterization of major phytocannabinoids, cannabidiol and cannabinol, as isoform-selective and potent inhibitors of human CYP1 enzymes
    • Yamaori S, Kushihara M, Yamamoto I, Watanabe K. Characterization of major phytocannabinoids, cannabidiol and cannabinol, as isoform-selective and potent inhibitors of human CYP1 enzymes. Biochem Pharmacol 2010;79:1691-8.
    • (2010) Biochem Pharmacol , vol.79 , pp. 1691-1698
    • Yamaori, S.1    Kushihara, M.2    Yamamoto, I.3    Watanabe, K.4


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