Drug Metabolism disposition Drug Metabolism and Metabolism A Publication of the American Society for

Drug Metabolism disposition Drug Metabolism and Metabolism A Publication of the American Society for
Drug Metabolism disposition Drug Metabolism and Metabolism A Publication of the American Society for
Drug Metabolism disposition Drug Metabolism and Metabolism A Publication of the American Society for
Drug Metabolism disposition Drug Metabolism and Metabolism A Publication of the American Society for
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Transcript of Drug Metabolism disposition Drug Metabolism and Metabolism A Publication of the American Society for

and dispositionDrug Metabolism

and dispositionDrug Metabolism

A Publication of the American Society for Pharmacology and Experimental Therapeutics

Volume 36 Number 3 March 2008 ISSN 0090-9556

zdd0030800SPC1.qxd 2/14/08 1:48 PM Page 1

March 2008 Vol. 36, No. 3

CONTENTS

SHORT COMMUNICATIONS

Hepatic Synthesis and Urinary Elimination of Acet-aminophen Glucuronide Are Exacerbated in BileDuct-Ligated Rats. Silvina S. M. Villanueva,Mara L. Ruiz, Carolina I. Ghanem, Marcelo G.Luquita, Viviana A. Catania, Aldo D. Mottino . 475

In Vitro-to-in Vivo Prediction of P-glycoprotein-Based Drug Interactions at the Human and Ro-dent Blood-Brain Barrier. Peng Hsiao, Tot Bui,Rodney J. Y. Ho, Jashvant D. Unadkat . . . . . . 481

S Enzymatic C-Demethylation of 1-[2-(5-tert-Butyl-[1,3,4] oxadiazole-2-carbonyl)-4-fluoro-pyrrolidin-1-yl]-2-(2-hydroxy-1,1-dimethyl-ethylamino)-ethanone (LC15-0133) in Rat Liver Microsomes.Hye Hyun Yoo, Hye Jin Chung, Jaeick Lee,Chang-Seok Lee, Min Jung Kang, Dong-HyunKim . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 485

ARTICLES

CYP3A4-Mediated Carbamazepine (CBZ) Metabo-lism: Formation of a Covalent CBZ-CYP3A4Adduct and Alteration of the Enzyme KineticProfile. Ping Kang, Mingxiang Liao, Michael R.Wester, J. Steven Leeder, Robin E. Pearce, andMaria Almira Correia . . . . . . . . . . . . . . . . . 490

A Human Immunodeficiency Virus Protease Inhibitor Isa Novel Functional Inhibitor of Human Pregnane XReceptor. Christine Healan-Greenberg, Jeffrey F.Waring, Dale J. Kempf, Eric A. G. Blomme, Rom-mel G. Tirona, and Richard B. Kim . . . . . . . . . 500

Characterization and Comparative Studies of Ze-brafish and Human Recombinant DihydrofolateReductasesInhibition by Folic Acid and Poly-phenols. Tseng-Ting Kao, Kuan-Chieh Wang,

Wen-Ni Chang, Chia-Ying Lin, Bing-Hung Chen,Hua-Lin Wu, Guey-Yueh Shi, Jen-Ning Tsai, andTzu-Fun Fu . . . . . . . . . . . . . . . . . . . . . . . . . 508

The First Aspartic Acid of the DQxD Motif for HumanUDP-Glucuronosyltransferase 1A10 Interacts withUDP-Glucuronic Acid during Catalysis. Yan Xiong,Anne-Sisko Patana, Michael J. Miley, Agnieszka K.Zielinska, Stacie M. Bratton, Grover P. Miller, Ad-rian Goldman, Moshe Finel, Matt R. Redinbo, andAnna Radominska-Pandya . . . . . . . . . . . . . . . 517

CYP2C19 Inhibition: The Impact of Substrate ProbeSelection on in Vitro Inhibition Profiles. RobertS. Foti and Jan L. Wahlstrom . . . . . . . . . . . . 523

CYP2D6-Mediated Metabolism of a Novel Acyl Co-enzyme A:Cholesterol Acyltransferase Inhibitor,Pactimibe, and Its Unique Plasma Metabolite,R-125528. Masakatsu Kotsuma, Taro Tokui, To-moko Ishizuka-Ozeki, Tomoyo Honda, HaruoIwabuchi, Takahiro Murai, Toshihiko Ikeda, andHideo Saji . . . . . . . . . . . . . . . . . . . . . . . . . 529

Drug Lipophilicity and Microsomal Protein Concen-tration as Determinants in the Prediction of theFraction Unbound in Microsomal Incubations.Michael Gertz, Peter J. Kilford, J. Brian Hous-ton, and Aleksandra Galetin . . . . . . . . . . . . . 535

Regulation of Aryl Hydrocarbon Receptor Expressionand Function by Glucocorticoids in Mouse Hep-atoma Cells. Kirsten A. Bielefeld, Chunja Lee,and David S. Riddick . . . . . . . . . . . . . . . . . . 543

Modulation of Human Multidrug Resistance Protein(MRP) 1 (ABCC1) and MRP2 (ABCC2) Trans-port Activities by Endogenous and ExogenousGlutathione-Conjugated Catechol Metabolites.

DRUG METABOLISMAND DISPOSITION

A Publication of the American Society for Pharmacology and Experimental Therapeutics

Drug Metabolism and Disposition (ISSN 0090-9556) is published monthly (one volume per year) by the American Society for Pharmacology and ExperimentalTherapeutics, 9650 Rockville Pike, Bethesda, MD 20814-3995; e-mail: info@aspet.org; Web site: http://www.aspet.org Periodicals postage paid at Bethesda, MD andat additional mailing offices. POSTMASTER: Send address changes to Drug Metabolism and Disposition, 9650 Rockville Pike, Bethesda, MD 20814-3995.Subscription rates: U.S.: $374.00 for institutions and $195.00 for non-ASPET members. Outside the U.S.: $448.00 for institutions and $269.00 for non-ASPETmembers. Single copy: $36.00. GST Tax Number for Canadian subscribers: BN:13489 2330 RT. Indexed or abstracted by Biochemistry & Biophysics CitationIndex, Biological Abstracts, BIOSIS Previews Database, BioSciences Information Service, Current Awareness in Biological Sciences, Current Contents/LifeSciences, EMBASE/Excerpta Medica, Index Medicus, International Pharmaceutical Abstracts, Medical Documentation Service, Reference Update, ResearchAlert, Science Citation Index, SciSearch, and SIIC Data Bases. Copyright 2008 by the American Society for Pharmacology and Experimental Therapeutics.All rights reserved. Printed in the U.S.A.

Continued on next page

Andrew J. Slot, Dana D. Wise, Roger G. Deeley,Terrence J. Monks, and Susan P. C. Cole . . . . 552

Metabolism of the Trisubstituted Purine Cyclin-De-pendent Kinase Inhibitor Seliciclib (R-Roscovi-tine) in Vitro and in Vivo. Steven J. McClue andIain Stuart . . . . . . . . . . . . . . . . . . . . . . . . . 561

Aryl-Propionamide-Derived Selective Androgen Re-ceptor Modulators: Liquid Chromatography-Tan-dem Mass Spectrometry Characterization of thein Vitro Synthesized Metabolites for DopingControl Purposes. Tiia Kuuranne, Antti Leinonen,Wilhelm Schanzer, Matthias Kamber, Risto Kos-tiainen, and Mario Thevis . . . . . . . . . . . . . . . 571

Physical Incorporation of NADPH-Cytochrome P450Reductase and Cytochrome P450 into Phospho-lipid Vesicles Using Glycocholate and Bio-Beads. James R. Reed, Lauren M. Brignac-Hu-ber, and Wayne L. Backes . . . . . . . . . . . . . . . 582

Hepatobiliary Excretion of Silibinin in Normal andLiver Cirrhotic Rats. Jhy-Wen Wu, Lie-Chwen

Lin, Shih-Chieh Hung, Chi-Hung Lin, Chin-WenChi, and Tung-Hu Tsai . . . . . . . . . . . . . . . . . 589

Down-Regulation of Hepatic Cytochrome P450 En-zymes in Rats with Trinitrobenzene Sulfonic Ac-id-Induced Colitis. Yasuhiro Masubuchi, KanakoEnoki, and Toshiharu Horie . . . . . . . . . . . . . 597

Induction of Metabolism and Transport in HumanIntestine: Validation of Precision-Cut Slices as aTool to Study Induction of Drug Metabolism inHuman Intestine in Vitro. Esther G. van de Kerk-hof, Inge A. M. de Graaf, Anna-Lena B. Ungell,and Geny M. M. Groothuis . . . . . . . . . . . . . . 604

High-Affinity Binding of [H]Cimetidine to a Heme-Containing Protein in Rat Brain. Rebecca Stadel,Jun Yang, Julia W. Nalwalk, James G. Phillips,and Lindsay B. Hough . . . . . . . . . . . . . . . . . 614

ERRATUM

Correction to The Development of Drug MetabolismResearch as Expressed in the Publications of AS-PET: Part 1, 19091958 . . . . . . . . . . . . . . . 622

S Supplemental material is available online at http://dmd.aspetjournals.org.

About the cover: Docking of carbamazepine, testosterone, and erythromycin into the active site of CYP3A4. See article byKang et al. on page 490 of this issue.

Contents (contd.)

DRUG METABOLISM AND DISPOSITIONA Publication of the American Society for Pharmacology and Experimental Therapeutics

Founded by Kenneth C. Leibman1973

Eric F. Johnson, Editor

ASSOCIATE EDITORSStephen D. Hall, Laurence S. Kaminsky, Russell A. Prough, John D. Schuetz, Jeffrey C. Stevens,

Kenneth E. Thummel, Donald J. Tweedie, Steven A. Wrighton, and Garold S. Yost

SCIENTIFIC ADVISORY BOARDM.W. Anders, Minor J. Coon, Ronald W. Estabrook, Frederick P. Guengerich

James R. Halpert, Anthony Y. Lu, Bettie Sue Masters, and Paul R. Ortiz De Montellano

EDITORIAL BOARD MEMBERSTommy B. AnderssonWayne L. BackesThomas BaillieJohn R. BendJeffrey L. BlumerKim L.R. BrouwerArthur CederbaumNathan CherringtonArthur K. ChoDavid D. ChristDeepak DalvieWilliam J. EhlhardtSean Ekins

Cornelis J. ElferinkMichael R. FranklinRonald B. FranklinG. Gordon GibsonJoyce GoldsteinRobert HanzlikRonald N. HinesPaul F. HollenbergJ. Brian HoustonMagnus Ingelman-

SundbergPhilip B. InskeepMargaret O. James

Jeffrey P. JonesRichard KimSang Geon KimThomas KocarekDennis R. KoopLawrence H. LashJ. Steven LeederLois D. Lehman-

McKeemanPeter Ian MackenzieEdward T. MorganSidney D. Nelson

R. Scott ObachK. Sandy PangAnna Radominska-

PandyaJudy L. RaucyAllan RettieDouglas RickertDavid S. RiddickJoseph K. RitterA. David RodriguesMelissa Runge-MorrisMagang Shou

Bill J. SmithGrazyna D. SzklarzYun K. TamTimothy S. TracyMary VorePaul B. WatkinsDavid J. WaxmanRonald E. WhiteLarry C. WienkersPaul WisselYasushi YamazoeCheryl L. Zimmerman

BOARD OF PUBLICATIONS TRUSTEESJames E. Barrett, Chair; P. Jeffrey Conn, Ross Feldman, Lorraine J. Gudas, Eric F. Johnson, John S. Lazo, Edward T. Morgan,

Richard R. Neubig, Rick G. Schnellmann, Darryle D. Schoepp, and Mary Vore

ASPET EXECUTIVE OFFICER: Christine K. CarricoJournals Director: Richard Dodenhoff Managing Editor: Jill Filler Senior Editorial Coordinator: Rhonda Frankenfield

Journal and ASPET Office: 9650 Rockville Pike, Bethesda, MD 20814-3995; telephone: 301-634-7060; fax: 301-634-7061; email: info@aspet.org;web site: www.aspet.org.Correspondence regarding editorial matters should be addressed to Dr.Eric F. Johnson, Editor, Drug Metabolism and Disposition, at the aboveaddress.Official version: The online version of Drug Metabolism and Dispositioncontains all of the information and material contained in the print version plusadditional material that may not appear in print such as videos and large datasets. The online version may be more current than the print version. Wherenoted, the online version has been corrected in departure from the printversi