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
スポンサーリンク
概要
- 論文の詳細を見る
Oxidative metabolism of cannabidiol monomethyl ether (CBDM), one of the components of marihuana, was studied in the guinea pig. Cannabielsoin monomethyl ether (CBEM) was found to be formed with hepatic microsomes by gas chromatography-mass spectrometry (GC-MS). Experiments using various modifiers of enzymatic reaction suggested that, as in the case of cannabielsoin (CBE) formation from canabidiol (CBD), CBEM was formed from CBDM by the monooxygenase system including cytochrome P450. When cannabidiol dimethyl ether (CBDD), in which phenolic hydroxyl groups of CBD are masked with methyl groups, was incubated with liver microsomes and an reduced nicotinamide adenine dinucleotide phosphate-generating system, 1S, 2R-epoxy-CBDD was identified by GC-MS. The epoxy metabolite was also found in the liver of a guinea pig pretreated with CBDD (100mg/kg, intraperitoneally) 1h before sacrifice. Rate of 1S, 2R-epoxide metabolism was slower than that of 1R, 2S-epoxy-CBDD under the conditions, as in the microsomal oxidation of CBDD described above. These results indicate that 1S, 2R-epoxides are formed from CBD, CBDM and CBDD and that the epoxides are quickly converted to elsoin-type metabolites in the cases of CBD and CBDM.
- 公益社団法人日本薬学会の論文
- 1990-06-25
著者
-
吉村 英敏
中村学園大学
-
成松 鎮雄
千葉大・薬
-
山本 郁男
Department of Hygienic Chemistry, Faculty of Pharmaceutical Sciences, Hokuriku University
-
吉村 英敏
Department of Food and Nutrition, Nakamura Gakuen University
-
成松 鎮雄
岡山大・薬・衛生化学
-
成松 鎭雄
Laboratory Of Biopharmaceutics Faculty Of Pharmaceutical Sciences Chiba University
-
成松 鎮雄
Department of Hygienic Chemistry, Faculty of Pharmaceutical Sciences, Hokuriku University
-
郷田 浩志
Department of Hygienic Chemistry, Faculty of Pharmaceutical Sciences, Hokuriku University
-
郷田 浩志
Department Of Hygienic Chemistry Faculty Of Pharmaceutical Sciences Hokuriku University
-
Yoshida H
Lab. Of Food & Nutritional Sciences Dep. Of Nutritional Sci. Kobe-gakuin Univ.
-
Narimatsu S
Laboratory Of Biopharmaceutics Faculty Of Pharmaceutical Sciences Chiba University
-
成松 鎮雄
Department Of Hygienic Chemistry Faculty Of Pharmaceutical Sciences Hokuriku University
-
吉村 英敏
Department Of Food And Nutrition Nakamura Gakuen University
関連論文
- 交感神経β-受容体遮断薬PropranololとCytochrome P450との相互作用 - 代謝的活性化, 酵素阻害と酵素誘導 -
- カンナビノイドの代謝的活性化とシトクロムP450分子種
- Involvement of CYP2C in the Metabolism of Cannabinoids by Human Hepatic Microsomes from an Old Woman
- Synthesis and Hypnotic and Anti-Human Immunodeficiency Virus-1 Activities of N^3-Substituted 2'-Deoxy-2'-fluorouridines
- マウス肝Microsomal Alcohol Oxygenase (MALCO)の解明とその反応機構解析
- ヒト肝のMicrosomal Alcohol Oxygenase(MALCO)活性に関与するP450分子種
- サル腎ミクロソームによるTetrahydrocannabinolの代謝
- Formation of p-Hydroxycocaine from Cocaine by Hepatic Microsomes of Animals and Its Pharmacological Effects in Mice
- CYP2D6のN末端アミノ酸配列修飾の薬物酸化活性に及ぼす影響 - 大腸菌発現CYP2D6とSF9細胞発現CYP2D6の比較 -
- 薬剤誘発自己免疫性肝炎の基礎的検討 - ジヒドララジン標的タンパクの探索 -
- Identification of in Vitro Metabolites of 2,4,6,2', 4', 6'-Hexachlorobiphenyl from Phenobarbital-Treated Dog Liver Microsomes
- 市販の大麻種子中のカンナビノイドの定量とその薬毒理作用
- カンナビジオール及びカンナビジオールヒドロキシキノンの活性酸素生成に関する分光学的及びESRによる検討
- アニスアルデヒド(o-, m-及びp-異性体)のマウス肝による酸化的及び還元的代謝
- マウス肝ミクロソームアナンダミドアミドヒドロラーゼ活性の誘導剤処理による影響
- サル肝ミクロソーム酵素によるレチナールからレチノイン酸への代謝
- アナンダミド加水分解酵素の阻害による薬理効果の増強
- Analysis of Nitrogen Containing Compounds, p-Coumaroyltyramine and Feruloyltyramine, for Discrimination of Cannabis Seeds by HPLC
- 大麻主成分の活性代謝物 11-Hydroxy-Δ^8-tetrahydrocannabinol の脂肪酸抱合体の生成及び分解酵素系 - THCの蓄積と慢性毒性に関連して -
- ヒト肝 MALDO活性の主たる P450 分子種
- CYP2C29に高い相同性を有するサル肝ミクロソーム中のP450精製とその性質
- 3,4,5-Trimethoxyphenylacetaldehyde, an Intermediate Metabolite of Mescaline, Is a Substrate for Microsomal Aldehyde Oxygenase in the Mouse Liver
- Formation of Carbon Monoxide during Mouse Hepatic Microsomal Oxidative Metabolism of Cannabidiol ; Identification and Determination
- Synthesis and Pharmacological Effects in Mice of Halogenated Cannabinol Derivatives
- In Vitro Metabolic Formation of a New Metabolite, 6β-Hydroxymethyl-Δ^9-tetrahydrocannabinol from Cannabidiol through an Epoxide Intermediate and Its Pharmacological Effects on Mice
- Metabolic and Toxicologic Evaluation of 2,3,4,3', 4'-Pentachlorobiphenyl in Rats and Mice
- Cytochrome P450 Isozymes Involved in Aromatic Hydroxylation and Side-Chain N-Desisopropylation of Alprenolol in Rat Liver Microsomes
- Involvement of a Cytochrome P4502D Subfamily in Human Liver Microsomal Bunitrolol 4-Hydroxylation
- Synthesis and Pharmacological Evaluation in Mice of Halogenated Cannabidiol Derivatives.
- Synthesis and Pharmacological Evaluation in Mice of Halogenated Cannabidiol Derivatives
- Pharmacologica Efects in Mice of Anandamide and Its Related Fatty Acid Ethanolamides, and Enhancement of Cataleptogenic Effect of Anandamide by Phenylmethylsulfonyl Fluoride
- Synthesis and Pharmacological Activities in Mice of Halogenated Δ^9-Tetrahydrocannabinol Derivatives
- BrucineによるCYP2B subfamily P450の誘導:種差による検討
- フェノバルビタール型PCBのウサギ肝における代謝
- Effect of Cytochrome P450 Inducers on Liver Microsomal Metabolism of Tetrachlorobiphenyls in Rats, Guinea Pigs and Hamsters
- Metabolic Formation of Dimethylamine and Methylamine from Basic Drugs Containing N-Methyl Group : A Newly Established Chromatographic Assay and Its Application to the Determination of Deaminase Activity
- Purification and Characterization of a Morphine UDP-Glucuronyltransferase Isoform from Untreated Rat Liver
- A New Metabolite of 2,4,3', 4'-Tetrachlorobiphenyl in Rat Feces
- P-100 In-tube SPME/LC/MS法による変異原性ヘテロサイクリックアミンの分析
- Cytochrome P450 Isozymes Catalyzing the Hepatic Microsomal Oxidation of 9-Anthraldehyde to 9-Anthracene Carboxylic Acid in Adult Male Rats
- 大麻幻覚成分Δ^9-Tetrahydrocannabinolのヒト尿中主代謝物Δ^9-Tetrahydrocannabinol-11-oic AcidのGC-MSによる定性・定量
- リコンビナント・ヒトP450 2D6の大腸菌における発現系の構築
- A Cytochrome P450 Enzyme Responsible for the Carbon Monoxide Formation by Cannabidiol in Mouse Hepatic Microsomes.
- Inhibition of Mouse Hepatic Glutathione S-Transferase by Δ^8-Tetrahydrocannabinol p-Quinone and Cannabidiol Hydroxy-quinone.
- Microsomal Aldehyde Oxygenase (MALDO) for Tolualdehydes, Active Metabolites of Xylenes, in the Mouse Liver and Lung
- "B-4 Hydrolysis of Xenobiotics by ES46.5K, a Novel Esterase from Mouse Liver Microsomes
- Microsomal Aldehyde Oxygenase (MALDO): Purification and Characterization of a Cytochrome P450 Isozyme Responsible for Oxidation of 9-Anthraldehyed to 9-Anthracenecarboxylic Acid in Monkey Liver
- Mechanism of Inhibitory Effects of Cannabidiol and Cannabidiol Hydroxy-quinone on the Hepatic Microsomal Drug-Metabolizing Enzymes in Mice (Proceedings of the 23rd Symposium on Toxicology and Environmental Health)
- Involvement of a Novel Mouse Hepatic Microsomal Esterase, ES46.5K, in the Hydrolysis of Phthalate Esters
- The Structure and Function of Carboxypeptidase C_N
- ヒトシトクロムP450-2D6によるブニトロロール代謝の立体選択性
- P-101 ドナウ川河川水中の変異原性ヘテロサイクリックアミンの分離同定
- Galactosyldiacylglycerol, a Mammalian DNA Polymerase α-Specific Inhibitor from a Sea Alga, Petalonia bingbamiae
- Comparison of Pharmacological Effects of Tetrahydrocannabinols and Their 11-Hydroxy-Metabolites in Mice
- 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
- Inhibition of Hepatic Microsomal Cytochrome P450 by Cannabidiol in Adult Male Rats
- THE PHARMACOLOGICAL ACTIVITY OF CANNABINOL AND ITS MAJOR METABOLITE, 11-HYDROXYCANNABINOL(Communication to the Editor)
- 第12回環境汚染物質とそのトキシコロジーシンポジウム
- Pharmacological Activities in the Mouse of Δ^9-Tetrahydrocannabinol Metabolites Oxidized at the 8-Position
- 大麻主成分Δ^9-Tetrahydrocannabinol(Δ^9-THC)およびCannabidiol(CBD)のPentobarbital睡眠および肝薬物代謝酵素系に及ぼす影響-マウスにおける性差
- HUMAN LIVER MICROSOMAL OXIDATION OF Δ^8-TETRAHYDROCANNABINOL
- Synthesis of 8α, 9α- and 8β, 9β-Epoxyhexahydrocannabinols
- Suppression of Liver Microsomal Drug-Metabolizing Enzyme Activities in Adult Female Rats Pretreated with Cannabidiol
- 空洞表示プログラムによる酵素活性中心の視覚化 : シトクロムP450と基質の相互作用の研究
- Compertitive Inhibition of Δ^8-Tetrahydrocannabinol and Its Active Metabolites for Cannabinoid Receptor Binding
- Anandamide, an Endogenous Cannabinoid Receptor Ligand, Also Interacts with 5-Hydroxytryptamine (5-HT) Receptor
- Inhibitory effect of coenzyme Q_1 on eukaryotic DNA polymerase γ and DNA topoisomerase II activities on the growth of a human cancer cell line
- Molecular Action Mode of Hippospongic Acid A, an Inhibitor of Gastrulation of Starfish Embryos
- Selective Inhibition of Mammalian DNA Polymerase α by Vitamin D_2 and D_3
- Potentiating Effects of N^1,N^3-Diallyluracil, N^1,N^3-Diallylthymine and N^1,N^3-Diallyl-6-methyluracil on Pentobarbital-Induced Sleep and Diazepam-Induced Motor Incoordination(Pharmacological,Chemical)
- Potentiation of Barbiturate-Induced Narcosis by N,N'-(or N,S-) Diallyl-Substituted Derivatives of Phenobarbital, Amobarbital and Thiopental in Mice(Pharmacological)
- A novel DNA topoisomerase inhibitor : dehydroebriconic acid, one of the lanostane-type triterpene acids from Poria cocos
- DNA polymerase γ inhibition by vitamin K3 induces mitochondria-mediated cytotoxicity in human cancer cells
- Spectral Interaction of 11-Hydroxy-Δ^8-tetrahydrocannabinol with Rabbit and Rat Liver Microsomal Cytochrome P-450
- Synthesis of Δ^8-Tetrahydrocannabinol Glucuronide and Sulfate, and Their Metabolic Disposition in Rats
- Cyanogenic glycoside from Taraxacum officinale
- Three-Dimensional Structural Model Analysis of the Binding Site of Lithocholic Acid, an Inhibitor of DNA Polymerase β and DNA Topoisomerase II^1
- 生を衛る化学 薬物代謝学
- 大麻成分の代謝と薬理作用
- Relationship between the Metabolic Chiral Inversion and Chemical Structure of 4-Phenyl-4-oxobutanoic Acids, Derivatives of Anti-rheumatic Agent KE-298
- Identification of Metabolites of KE-298,a New Antirheumatic Drug, and Its Physiological Properties in Rats
- Synthetic Studies on Kohamaic Acids : Synthesis of Structurally Simplified Analogs of Kohamaic Acid A
- Identification and Determination of Cannabinoids in Commercially Available Cannabis Seeds
- Novel Terpenoids, Trichoderonic Acids A and B Isolated from Trichoderma virens, Are Selective Inhibitors of Family X DNA Polymerases
- Stereoselectivity and Species Difference in Plasma Protein Binding of KE-298 and Its Metabolites
- Mechanism of Pulmonary Cytochrome P450 Inactivation by Tolualdehydes, Active Metabolites of Xylenes (Proceedings of the 22nd Symposium on Toxicology and Environmental Health)
- Metabolic Reaction of Tolualdehydes by Microsomal Aldehyde Oxygenase (MALDO) in Lung (Proceedings of the 19th Symposium on Toxicology and Environmental Health)
- INTERACTIONS OF ACTIVE CANNABINOID METABOLITES WITH GABA_A RECEPTOR
- INHIBITION OF ANANDAMIDE AMIDASE ACTIVITY IN MOUSE BRAIN MICROSOMES BY CANNABINOIDS
- Involvement of a Novel Mouse Hepatic Esterase (ES46.5K) in the Hydrolysis of Phthalate Esters (Proceedings of the 21st Symposium on Toxicology and Environmental Health)
- Involvement of Microsomal Aldehyde Oxygenase (MALDO) in the Metabolism of Aliphatic Aldehydes in the Mouse Liver (Proceedings of the 20th Symposium on Toxicology and Environmental Health)
- Studies on Metabolism and Toxicity of Organic Solvents, Toluene and Related Compounds : Metabolism of Benzaldehydes by Microsomal Aldehyde Oxygenase (MALDO) (Proceedings of the 18th Symposium on Toxicology, and Environmental Health)
- マウス肝ミクロゾーム中のカンナビノール11位水酸化に関与する酵素系の諸性質について
- 大麻成分, テトラヒドロカンナビノール, カンナビジオール及び活性代謝物とシンナー及びその含有成分との相互作用
- Cyanogenic glycoside from Taraxacum officinale