Effect of Psychotropic Drugs on the 21-Hydroxylation of Neurosteroids, Progesterone and Allopregnanolone, Catalyzed by Rat CYP2D4 and Human CYP2D6 in the Brain
We determined the effects of psychotropic drugs on the cytochrome P450 2D (CYP2D)-mediated 21-hydroxylation of progesterone (PROG) and allopregnanolone (ALLO) with the goal of clarifying whether neurosteroid levels are affected by psychotropic drugs in the brain. PROG or ALLO was incubated with rat...
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| Veröffentlicht in: | Biological & Pharmaceutical Bulletin 2008/03/01, Vol.31(3), pp.348-351 |
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| creator | Niwa, Toshiro Okada, Kazushi Hiroi, Toyoko Imaoka, Susumu Narimatsu, Shizuo Funae, Yoshihiko |
| description | We determined the effects of psychotropic drugs on the cytochrome P450 2D (CYP2D)-mediated 21-hydroxylation of progesterone (PROG) and allopregnanolone (ALLO) with the goal of clarifying whether neurosteroid levels are affected by psychotropic drugs in the brain. PROG or ALLO was incubated with rat CYP2D4 or human CYP2D6 in the presence of typical psychotropic drugs, fluoxetine, imipramine, desipramine, mazindol, and GBR12909, and the 21-hydroxylated metabolites of PROG and ALLO were determined by high performance liquid chromatography and liquid chromatography-tandem mass spectrometry, respectively. Fluoxetine competitively inhibited CYP2D4-mediated PROG 21-hydroxylation and increased both Km and Vmax values of CYP2D6-mediated PROG 21-hydroxylation. In addition, fluoxetine competitively inhibited ALLO 21-hydroxylation mediated by CYP2D4 and CYP2D6. Imipramine, desipramine, mazindol, and GBR12909 competitively inhibited PROG 21-hydroxylation mediated by CYP2D4 and/or CYP2D6, and all psychotropic drugs inhibited ALLO 21-hydroxylation mediated by CYP2D4 and/or CYP2D6. The inhibition constants (Ki values) of imipramine, desipramine, and mazindol against the 21-hydroxylation of PROG and ALLO by CYP2D6 were lower than those by CYP2D4. These results indicate that psychotropic drugs including fluoxetine affected the metabolism of neurosteroids, such as PROG and ALLO in the brain, suggesting that the regulation of the neurosteroid levels is modified by central nervous system-active drugs that inhibit brain CYP2D isoforms. |
| doi_str_mv | 10.1248/bpb.31.348 |
| format | Article |
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PROG or ALLO was incubated with rat CYP2D4 or human CYP2D6 in the presence of typical psychotropic drugs, fluoxetine, imipramine, desipramine, mazindol, and GBR12909, and the 21-hydroxylated metabolites of PROG and ALLO were determined by high performance liquid chromatography and liquid chromatography-tandem mass spectrometry, respectively. Fluoxetine competitively inhibited CYP2D4-mediated PROG 21-hydroxylation and increased both Km and Vmax values of CYP2D6-mediated PROG 21-hydroxylation. In addition, fluoxetine competitively inhibited ALLO 21-hydroxylation mediated by CYP2D4 and CYP2D6. Imipramine, desipramine, mazindol, and GBR12909 competitively inhibited PROG 21-hydroxylation mediated by CYP2D4 and/or CYP2D6, and all psychotropic drugs inhibited ALLO 21-hydroxylation mediated by CYP2D4 and/or CYP2D6. The inhibition constants (Ki values) of imipramine, desipramine, and mazindol against the 21-hydroxylation of PROG and ALLO by CYP2D6 were lower than those by CYP2D4. These results indicate that psychotropic drugs including fluoxetine affected the metabolism of neurosteroids, such as PROG and ALLO in the brain, suggesting that the regulation of the neurosteroid levels is modified by central nervous system-active drugs that inhibit brain CYP2D isoforms.</description><identifier>ISSN: 0918-6158</identifier><identifier>EISSN: 1347-5215</identifier><identifier>DOI: 10.1248/bpb.31.348</identifier><identifier>PMID: 18310890</identifier><language>eng</language><publisher>Japan: The Pharmaceutical Society of Japan</publisher><subject>allopregnanolone 21-hydroxylation ; Animals ; Aryl Hydrocarbon Hydroxylases - antagonists & inhibitors ; Aryl Hydrocarbon Hydroxylases - genetics ; Aryl Hydrocarbon Hydroxylases - metabolism ; Brain - drug effects ; Brain - enzymology ; Brain - metabolism ; Catalysis ; Cloning, Molecular ; Cytochrome P-450 CYP2D6 - genetics ; Cytochrome P-450 CYP2D6 - metabolism ; Cytochrome P-450 CYP2D6 Inhibitors ; cytochrome P450 2D4 ; cytochrome P450 2D6 ; Enzyme Inhibitors - pharmacology ; fluoxetine ; Humans ; Hydroxylation ; Microsomes - drug effects ; Microsomes - enzymology ; Microsomes - metabolism ; Pregnanolone - metabolism ; Progesterone - metabolism ; progesterone 21-hydroxylation ; psychotropic drug ; Psychotropic Drugs - pharmacology ; Rats ; Recombinant Proteins - metabolism ; Saccharomyces cerevisiae - genetics ; Substrate Specificity</subject><ispartof>Biological and Pharmaceutical Bulletin, 2008/03/01, Vol.31(3), pp.348-351</ispartof><rights>2008 The Pharmaceutical Society of Japan</rights><rights>Copyright Japan Science and Technology Agency 2008</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c692t-98cfe6d5fef6450d68eb0dcc463679d9de1b9f27072b12c1c01d9ea85a6139ce3</citedby><cites>FETCH-LOGICAL-c692t-98cfe6d5fef6450d68eb0dcc463679d9de1b9f27072b12c1c01d9ea85a6139ce3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,777,781,1877,27905,27906</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/18310890$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Niwa, Toshiro</creatorcontrib><creatorcontrib>Okada, Kazushi</creatorcontrib><creatorcontrib>Hiroi, Toyoko</creatorcontrib><creatorcontrib>Imaoka, Susumu</creatorcontrib><creatorcontrib>Narimatsu, Shizuo</creatorcontrib><creatorcontrib>Funae, Yoshihiko</creatorcontrib><creatorcontrib>bNanobiotechnology Research Center and Department of Bioscience School of Science and Technology Kwansei Gakuin University</creatorcontrib><creatorcontrib>aDepartment of Chemical Biology Osaka City University Graduate School of Medicine</creatorcontrib><creatorcontrib>cLaboratories of Health Chemistry Graduate School of Medicine Dentistry and Pharmaceutical Sciences Okayama University</creatorcontrib><title>Effect of Psychotropic Drugs on the 21-Hydroxylation of Neurosteroids, Progesterone and Allopregnanolone, Catalyzed by Rat CYP2D4 and Human CYP2D6 in the Brain</title><title>Biological & Pharmaceutical Bulletin</title><addtitle>Biol Pharm Bull</addtitle><description>We determined the effects of psychotropic drugs on the cytochrome P450 2D (CYP2D)-mediated 21-hydroxylation of progesterone (PROG) and allopregnanolone (ALLO) with the goal of clarifying whether neurosteroid levels are affected by psychotropic drugs in the brain. PROG or ALLO was incubated with rat CYP2D4 or human CYP2D6 in the presence of typical psychotropic drugs, fluoxetine, imipramine, desipramine, mazindol, and GBR12909, and the 21-hydroxylated metabolites of PROG and ALLO were determined by high performance liquid chromatography and liquid chromatography-tandem mass spectrometry, respectively. Fluoxetine competitively inhibited CYP2D4-mediated PROG 21-hydroxylation and increased both Km and Vmax values of CYP2D6-mediated PROG 21-hydroxylation. In addition, fluoxetine competitively inhibited ALLO 21-hydroxylation mediated by CYP2D4 and CYP2D6. Imipramine, desipramine, mazindol, and GBR12909 competitively inhibited PROG 21-hydroxylation mediated by CYP2D4 and/or CYP2D6, and all psychotropic drugs inhibited ALLO 21-hydroxylation mediated by CYP2D4 and/or CYP2D6. The inhibition constants (Ki values) of imipramine, desipramine, and mazindol against the 21-hydroxylation of PROG and ALLO by CYP2D6 were lower than those by CYP2D4. These results indicate that psychotropic drugs including fluoxetine affected the metabolism of neurosteroids, such as PROG and ALLO in the brain, suggesting that the regulation of the neurosteroid levels is modified by central nervous system-active drugs that inhibit brain CYP2D isoforms.</description><subject>allopregnanolone 21-hydroxylation</subject><subject>Animals</subject><subject>Aryl Hydrocarbon Hydroxylases - antagonists & inhibitors</subject><subject>Aryl Hydrocarbon Hydroxylases - genetics</subject><subject>Aryl Hydrocarbon Hydroxylases - metabolism</subject><subject>Brain - drug effects</subject><subject>Brain - enzymology</subject><subject>Brain - metabolism</subject><subject>Catalysis</subject><subject>Cloning, Molecular</subject><subject>Cytochrome P-450 CYP2D6 - genetics</subject><subject>Cytochrome P-450 CYP2D6 - metabolism</subject><subject>Cytochrome P-450 CYP2D6 Inhibitors</subject><subject>cytochrome P450 2D4</subject><subject>cytochrome P450 2D6</subject><subject>Enzyme Inhibitors - pharmacology</subject><subject>fluoxetine</subject><subject>Humans</subject><subject>Hydroxylation</subject><subject>Microsomes - drug effects</subject><subject>Microsomes - enzymology</subject><subject>Microsomes - metabolism</subject><subject>Pregnanolone - metabolism</subject><subject>Progesterone - metabolism</subject><subject>progesterone 21-hydroxylation</subject><subject>psychotropic drug</subject><subject>Psychotropic Drugs - pharmacology</subject><subject>Rats</subject><subject>Recombinant Proteins - metabolism</subject><subject>Saccharomyces cerevisiae - genetics</subject><subject>Substrate Specificity</subject><issn>0918-6158</issn><issn>1347-5215</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkc1u1DAQxyMEokvhwgMgS0gcULPYseM4p6psSxepghWCAyfLcSa7XmXjYCcS4WV4VabN0kpcuHjkmd_85ytJXjK6ZJlQ76q-WnK25EI9ShaMiyLNM5Y_Tha0ZCqVLFcnybMY95TSgmb8aXLCFGdUlXSR_L5qGrAD8Q3ZxMnu_BB87yy5DOM2Et-RYQckY-l6qoP_ObVmcOhE-hOMwccBgnd1PCOb4Ldw9-2AmK4mF23r-wDbznS-RecZWZnBtNMvqEk1kS9mIKvvm-xS3NHr8WC62SGJm6u-D8Z1z5MnjWkjvDja0-Tbh6uvq3V68_n64-riJrWyzIa0VLYBWecNNFLktJYKKlpbKySXRVmXNbCqbLKCFlnFMsssZXUJRuVGMl5a4KfJm1m3D_7HiJPog4sW2tZ04MeoC4rrZVz-F8yoxD0rheDrf8C9H0OHQ2gmRMlRMRdIvZ0pi9uMARrdB3cwYdKM6tvraryu5kxjeYRfHSXH6gD1A3o8JwLXM4BRZw3uvXUdPBS2sagcngO7pEpTimkcjdC30-GTM0ZpSQVHpfNZaR8Hs4X7UiYMzrZw39Xxwey_EbszQUPH_wCHRMzN</recordid><startdate>20080301</startdate><enddate>20080301</enddate><creator>Niwa, Toshiro</creator><creator>Okada, Kazushi</creator><creator>Hiroi, Toyoko</creator><creator>Imaoka, Susumu</creator><creator>Narimatsu, Shizuo</creator><creator>Funae, Yoshihiko</creator><general>The Pharmaceutical Society of Japan</general><general>Pharmaceutical Society of Japan</general><general>Japan Science and Technology Agency</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QP</scope><scope>7QR</scope><scope>7TK</scope><scope>7U9</scope><scope>8FD</scope><scope>FR3</scope><scope>H94</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>20080301</creationdate><title>Effect of Psychotropic Drugs on the 21-Hydroxylation of Neurosteroids, Progesterone and Allopregnanolone, Catalyzed by Rat CYP2D4 and Human CYP2D6 in the Brain</title><author>Niwa, Toshiro ; Okada, Kazushi ; Hiroi, Toyoko ; Imaoka, Susumu ; Narimatsu, Shizuo ; Funae, Yoshihiko</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c692t-98cfe6d5fef6450d68eb0dcc463679d9de1b9f27072b12c1c01d9ea85a6139ce3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>allopregnanolone 21-hydroxylation</topic><topic>Animals</topic><topic>Aryl Hydrocarbon Hydroxylases - antagonists & inhibitors</topic><topic>Aryl Hydrocarbon Hydroxylases - genetics</topic><topic>Aryl Hydrocarbon Hydroxylases - metabolism</topic><topic>Brain - drug effects</topic><topic>Brain - enzymology</topic><topic>Brain - metabolism</topic><topic>Catalysis</topic><topic>Cloning, Molecular</topic><topic>Cytochrome P-450 CYP2D6 - genetics</topic><topic>Cytochrome P-450 CYP2D6 - metabolism</topic><topic>Cytochrome P-450 CYP2D6 Inhibitors</topic><topic>cytochrome P450 2D4</topic><topic>cytochrome P450 2D6</topic><topic>Enzyme Inhibitors - pharmacology</topic><topic>fluoxetine</topic><topic>Humans</topic><topic>Hydroxylation</topic><topic>Microsomes - drug effects</topic><topic>Microsomes - enzymology</topic><topic>Microsomes - metabolism</topic><topic>Pregnanolone - metabolism</topic><topic>Progesterone - metabolism</topic><topic>progesterone 21-hydroxylation</topic><topic>psychotropic drug</topic><topic>Psychotropic Drugs - pharmacology</topic><topic>Rats</topic><topic>Recombinant Proteins - metabolism</topic><topic>Saccharomyces cerevisiae - genetics</topic><topic>Substrate Specificity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Niwa, Toshiro</creatorcontrib><creatorcontrib>Okada, Kazushi</creatorcontrib><creatorcontrib>Hiroi, Toyoko</creatorcontrib><creatorcontrib>Imaoka, Susumu</creatorcontrib><creatorcontrib>Narimatsu, Shizuo</creatorcontrib><creatorcontrib>Funae, Yoshihiko</creatorcontrib><creatorcontrib>bNanobiotechnology Research Center and Department of Bioscience School of Science and Technology Kwansei Gakuin University</creatorcontrib><creatorcontrib>aDepartment of Chemical Biology Osaka City University Graduate School of Medicine</creatorcontrib><creatorcontrib>cLaboratories of Health Chemistry Graduate School of Medicine Dentistry and Pharmaceutical Sciences Okayama University</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Calcium & Calcified Tissue Abstracts</collection><collection>Chemoreception Abstracts</collection><collection>Neurosciences Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Biological & Pharmaceutical Bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Niwa, Toshiro</au><au>Okada, Kazushi</au><au>Hiroi, Toyoko</au><au>Imaoka, Susumu</au><au>Narimatsu, Shizuo</au><au>Funae, Yoshihiko</au><aucorp>bNanobiotechnology Research Center and Department of Bioscience School of Science and Technology Kwansei Gakuin University</aucorp><aucorp>aDepartment of Chemical Biology Osaka City University Graduate School of Medicine</aucorp><aucorp>cLaboratories of Health Chemistry Graduate School of Medicine Dentistry and Pharmaceutical Sciences Okayama University</aucorp><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Effect of Psychotropic Drugs on the 21-Hydroxylation of Neurosteroids, Progesterone and Allopregnanolone, Catalyzed by Rat CYP2D4 and Human CYP2D6 in the Brain</atitle><jtitle>Biological & Pharmaceutical Bulletin</jtitle><addtitle>Biol Pharm Bull</addtitle><date>2008-03-01</date><risdate>2008</risdate><volume>31</volume><issue>3</issue><spage>348</spage><epage>351</epage><pages>348-351</pages><issn>0918-6158</issn><eissn>1347-5215</eissn><abstract>We determined the effects of psychotropic drugs on the cytochrome P450 2D (CYP2D)-mediated 21-hydroxylation of progesterone (PROG) and allopregnanolone (ALLO) with the goal of clarifying whether neurosteroid levels are affected by psychotropic drugs in the brain. PROG or ALLO was incubated with rat CYP2D4 or human CYP2D6 in the presence of typical psychotropic drugs, fluoxetine, imipramine, desipramine, mazindol, and GBR12909, and the 21-hydroxylated metabolites of PROG and ALLO were determined by high performance liquid chromatography and liquid chromatography-tandem mass spectrometry, respectively. Fluoxetine competitively inhibited CYP2D4-mediated PROG 21-hydroxylation and increased both Km and Vmax values of CYP2D6-mediated PROG 21-hydroxylation. In addition, fluoxetine competitively inhibited ALLO 21-hydroxylation mediated by CYP2D4 and CYP2D6. Imipramine, desipramine, mazindol, and GBR12909 competitively inhibited PROG 21-hydroxylation mediated by CYP2D4 and/or CYP2D6, and all psychotropic drugs inhibited ALLO 21-hydroxylation mediated by CYP2D4 and/or CYP2D6. The inhibition constants (Ki values) of imipramine, desipramine, and mazindol against the 21-hydroxylation of PROG and ALLO by CYP2D6 were lower than those by CYP2D4. These results indicate that psychotropic drugs including fluoxetine affected the metabolism of neurosteroids, such as PROG and ALLO in the brain, suggesting that the regulation of the neurosteroid levels is modified by central nervous system-active drugs that inhibit brain CYP2D isoforms.</abstract><cop>Japan</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>18310890</pmid><doi>10.1248/bpb.31.348</doi><tpages>4</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | allopregnanolone 21-hydroxylation Animals Aryl Hydrocarbon Hydroxylases - antagonists & inhibitors Aryl Hydrocarbon Hydroxylases - genetics Aryl Hydrocarbon Hydroxylases - metabolism Brain - drug effects Brain - enzymology Brain - metabolism Catalysis Cloning, Molecular Cytochrome P-450 CYP2D6 - genetics Cytochrome P-450 CYP2D6 - metabolism Cytochrome P-450 CYP2D6 Inhibitors cytochrome P450 2D4 cytochrome P450 2D6 Enzyme Inhibitors - pharmacology fluoxetine Humans Hydroxylation Microsomes - drug effects Microsomes - enzymology Microsomes - metabolism Pregnanolone - metabolism Progesterone - metabolism progesterone 21-hydroxylation psychotropic drug Psychotropic Drugs - pharmacology Rats Recombinant Proteins - metabolism Saccharomyces cerevisiae - genetics Substrate Specificity |
| title | Effect of Psychotropic Drugs on the 21-Hydroxylation of Neurosteroids, Progesterone and Allopregnanolone, Catalyzed by Rat CYP2D4 and Human CYP2D6 in the Brain |
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