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Xenobiotica
the fate of foreign compounds in biological systems
Volume 12, 1982 - Issue 11
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Original Article

Cytochrome P-450 metabolic-intermediate complex formation and induction by macrolide antibiotics; a new class of agents

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Pages 687-699 | Received 01 Jun 1982, Published online: 30 Sep 2009

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Ai-Hong Yang, Lei Zhang, De-Xian Zhi, Wen-Li Liu, Xue Gao & Xin He. (2018) Identification and analysis of the reactive metabolites related to the hepatotoxicity of safrole. Xenobiotica 48:11, pages 1164-1172.
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Shufeng Zhou, Eli Chan, Wei Duan, Min Huang & Yu-Zong Chen. (2005) Drug Bioactivation Covalent Binding to Target Proteins and Toxicity Relevance. Drug Metabolism Reviews 37:1, pages 41-213.
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M. Delaforge, R. Rivière, E. Sartori, J. L. Doignon & J. M. Grognet. (1989) Metabolism of dihydroergotamine by a cytochrome P-450 similar to that involved in the metabolism of macrolide antibiotics. Xenobiotica 19:11, pages 1285-1295.
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Articles from other publishers (47)

Luc R.A. Rougée, David W. Bedwell, Kasi Hansen, Trent L. Abraham & Stephen D. Hall. (2023) Impact of Heterotropic Allosteric Modulation on the Time-Dependent Inhibition of Cytochrome P450 3A4. Drug Metabolism and Disposition 51:10, pages 1372-1380.
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Xu Yanjiao, Zhang Chengliang, Li Xiping, Wu Tao, Ren Xiuhua & Liu Dong. (2013) Evaluation of the Inhibitory Effects of Antihypertensive Drugs on Human Carboxylesterase In Vitro. Drug Metabolism and Pharmacokinetics 28:6, pages 468-474.
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R Leurs, D Donnell, H Timmerman & A Bast. (1989) Interaction of Nefopam and Orphenadrine with the Cytochrome P-450 and the Glutathione System in Rat Liver. Journal of Pharmacy and Pharmacology 41:6, pages 388-393.
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Irina F. SevrioukovaThomas L. Poulos. (2010) Structure and mechanism of the complex between cytochrome P4503A4 and ritonavir. Proceedings of the National Academy of Sciences 107:43, pages 18422-18427.
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Dan Rock & Larry C. Wienkers. 2010. Pharmaceutical Sciences Encyclopedia. Pharmaceutical Sciences Encyclopedia 1 56 .
Xin Zhang, Raymond E. Galinsky, Robert E. Kimura, Sara K. Quinney, David R. Jones & Stephen D. Hall. (2010) Inhibition of CYP3A by Erythromycin: In Vitro-In Vivo Correlation in Rats. Drug Metabolism and Disposition 38:1, pages 61-72.
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Dan Rock & Larry C. Wienkers. 2009. Drug Metabolism Handbook. Drug Metabolism Handbook 479 534 .
Michael R. Franklin & Laura B. Hathaway. (2008) 2-Diethylaminoethyl-2,2-diphenylvalerate-HCl (SKF525A) Revisited: Comparative Cytochrome P450 Inhibition in Human Liver Microsomes by SKF525A, Its Metabolites, and SKF-Acid and SKF-Alcohol. Drug Metabolism and Disposition 36:12, pages 2539-2546.
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Shu-Feng Zhou, Charlie Changli Xue, Xue-Qing Yu, Chunguang Li & Guangji Wang. (2007) Clinically Important Drug Interactions Potentially Involving Mechanism-based Inhibition of Cytochrome P450 3A4 and the Role of Therapeutic Drug Monitoring. Therapeutic Drug Monitoring 29:6, pages 687-710.
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David R. Jones, Sean Ekins, Lang Li & Stephen D. Hall. (2007) Computational Approaches That Predict Metabolic Intermediate Complex Formation with CYP3A4 (+ b 5 ) . Drug Metabolism and Disposition 35:9, pages 1466-1475.
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W.F. Trager. 2007. Comprehensive Medicinal Chemistry II. Comprehensive Medicinal Chemistry II 87 132 .
Ying-Hong Wang, David R. Jones & Stephen D. Hall. (2005) DIFFERENTIAL MECHANISM-BASED INHIBITION OF CYP3A4 AND CYP3A5 BY VERAPAMIL. Drug Metabolism and Disposition 33:5, pages 664-671.
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C. Steven ErnestIIII, Stephen D. Hall & David R. Jones. (2005) Mechanism-Based Inactivation of CYP3A by HIV Protease Inhibitors. Journal of Pharmacology and Experimental Therapeutics 312:2, pages 583-591.
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Shufeng Zhou, Sui Yung Chan, Boon Cher Goh, Eli Chan, Wei Duan, Min Huang & Howard L McLeod. (2005) Mechanism-Based Inhibition of Cytochrome P450 3A4 by Therapeutic Drugs. Clinical Pharmacokinetics 44:3, pages 279-304.
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Mei-Fei Yueh, Marleen Kawahara & Judy Raucy. (2005) HIGH VOLUME BIOASSAYS TO ASSESS CYP3A4-MEDIATED DRUG INTERACTIONS: INDUCTION AND INHIBITION IN A SINGLE CELL LINE. Drug Metabolism and Disposition 33:1, pages 38-48.
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Donavon J. McConnIIII, Yvonne S. Lin, Kyle Allen, Kent L. Kunze & Kenneth E. Thummel. (2004) DIFFERENCES IN THE INHIBITION OF CYTOCHROMES P450 3A4 AND 3A5 BY METABOLITE-INHIBITOR COMPLEX-FORMING DRUGS. Drug Metabolism and Disposition 32:10, pages 1083-1091.
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Ying-Hong Wang, David R. Jones & Stephen D. Hall. (2004) PREDICTION OF CYTOCHROME P450 3A INHIBITION BY VERAPAMIL ENANTIOMERS AND THEIR METABOLITES. Drug Metabolism and Disposition 32:2, pages 259-266.
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Yong-Jin Wu, Carl D. Davis, Steven Dworetzky, William C. Fitzpatrick, David Harden, Huan He, Ronald J. Knox, Amy E. Newton, Thomas Philip, Craig Polson, Digavalli V. Sivarao, Li-Qiang Sun, Svetlana Tertyshnikova, David Weaver, Suresh Yeola, Mary Zoeckler & Michael W. Sinz. (2003) Fluorine Substitution Can Block CYP3A4 Metabolism-Dependent Inhibition:  Identification of ( S ) -N -[1-(4-Fluoro-3- morpholin-4-ylphenyl)ethyl]-3- (4-fluorophenyl)acrylamide as an Orally Bioavailable KCNQ2 Opener Devoid of CYP3A4 Metabolism-Dependent Inhibition . Journal of Medicinal Chemistry 46:18, pages 3778-3781.
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Michael Murray, Eva Fiala-Beer & Dylan Sutton. (2003) Upregulation of cytochromes P 450 2B in rat liver by orphenadrine . British Journal of Pharmacology 139:4, pages 787-796.
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David Jones & Stephen Hall. 2001. Drug-Drug Interactions. Drug-Drug Interactions 387 413 .
Gondi N. Kumar & Sekhar Surapaneni. (2001) Role of drug metabolism in drug discovery and development. Medicinal Research Reviews 21:5, pages 397-411.
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Vish S Watkins, Ron E Polk & Jennifer L Stotka. (2017) Drug Interactions of Macrolides: Emphasis on Dirithromycin. Annals of Pharmacotherapy 31:3, pages 349-356.
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Marie-Anne PEYRONNEAU, Marcel DELAFORGE, Rene RIVIERE, Jean-Paul RENAUD & Daniel MANSUY. (1994) High affinity of ergopeptides for cytochromes P450 3A. Importance of their peptide moiety for P450 recognition and hydroxylation of bromocriptine. European Journal of Biochemistry 223:3, pages 947-956.
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Peter H. Roos, Beata Golub-Ciosk, Petra Kallweit, Detlef Kauczinski & Walter G. Hanstein. (1993) Formation of ligand and metabolite complexes as a means for selective quantitation of cytochrome P450 isozymes. Biochemical Pharmacology 45:11, pages 2239-2250.
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T D LindstromB R HanssenS A Wrighton. (1993) Cytochrome P-450 complex formation by dirithromycin and other macrolides in rat and human livers. Antimicrobial Agents and Chemotherapy 37:2, pages 265-269.
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M. Delaforge, P. Ladam, G. Bouillé, J. Gharbi Benarous, M. Jaouen & J.P. Girault. (1992) pH effects on the N-demethylation and formation of the cytochrome P-450 iron II nitrosoalkane complex for erythromycin derivatives. Chemico-Biological Interactions 85:2-3, pages 215-227.
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Karl‐Henrik Jönsson & Björn Lindeke. (2004) Cytochrome p‐455 nm complex formation in the metabolism of phenylalkylamines. XII. Enantioselectivity and temperature dependence in microsomes and reconstituted cytochrome p‐450 systems from rat liver. Chirality 4:8, pages 469-477.
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Ieva Stupans & Lloyd N. Sansom. (1991) The inhibition of drug oxidation by anhydroerythromycin, an acid degradation product of erythromycin. Biochemical Pharmacology 42:11, pages 2085-2090.
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Christian Mougin, Nicholas Polge, Rene Scalla & Ferdinand Cabanne. (1991) Interactions of various agrochemicals with cytochrome P-450-dependent monooxygenases of wheat cells. Pesticide Biochemistry and Physiology 40:1, pages 1-11.
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Michael R. Franklin. 1991. Cytochrome P450. Cytochrome P450 559 573 .
M. Delaforge & E. Sartori. (1990) In vivo effects of erythromycin, oleandomycin and erythralosamine derivatives on hepatic cytochrome P-450. Biochemical Pharmacology 40:2, pages 223-228.
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A. Bast, A. J. Valk & H. Timmerman. (1990) Cytochrome P-450 metabolic-intermediate complex formation with a series of diphenhydramine analogues. Agents and Actions 30:1-2, pages 161-165.
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Craig B. Marcus, Neil M. Wilson, Colin R. Jefcoate, Christopher F. Wilkinson & Curtis J. Omiecinski. (1990) Selective induction of cytochrome P450 isozymes in rat liver by 4-n-alkyl-methylenedioxybenzenes. Archives of Biochemistry and Biophysics 277:1, pages 8-16.
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Karl-Henrik Jönsson & Björn Lindeke. (1990) Cytochrome P-455 nm complex formation in the metabolism of phenylalkylamines. XI. Peroxygenase versus monooxygenase function of cytochrome P-450 in rat liver microsomes. Chemico-Biological Interactions 75:3, pages 267-279.
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E. Sartori & M. Delaforge. (1990) Specific drug binding to rat liver cytochrome P-450 isozymes induced by pregnenolone-16α-carbonitrile and macrolide antibiotics. Implications for drug interactions. Chemico-Biological Interactions 73:2-3, pages 297-307.
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Ben van Ommen, Willem Hendriks, Jos G.M. Bessems, Geert Geesink, Franz Müller & Peter J. van Bladeren. (1989) The relation between the oxidative biotransformation of hexachlorobenzene and its porphyrinogenic activity. Toxicology and Applied Pharmacology 100:3, pages 517-528.
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Gordon F. Reidy & Michael Murray. (1989) In vitro inhibition of hepatic steroid hydroxylation by tamoxifen, a series of tamoxifen analogues and related compounds. Biochemical Pharmacology 38:1, pages 195-199.
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Michael Murray. (1988) Complexation of cytochrome P-450 isozymes in hepatic microsomes from SKF 525-A-induced rats. Archives of Biochemistry and Biophysics 262:1, pages 381-388.
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R. Carubelli, R.B. Palakodety & M.J. Griffin. (1986) Loss of cytochrome p-450 from hepatic nuclear membranes of rats fed 2-acetylaminofluorene. Chemico-Biological Interactions 58, pages 125-136.
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Z. Liu & M.R. Franklin. (1985) Cytochrome P-450 ligands: Metyrapone revisited. Archives of Biochemistry and Biophysics 241:2, pages 397-402.
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Eric Sartori, Marcel Delaforge, Daniel Mansuy & Philippe Beaune. (1985) Some erythromycin derivatives are strong inducers in rats of a cytochrome P-450 very similar to that induced by 16 ?-pregnenol one carbonitrile. Biochemical and Biophysical Research Communications 128:3, pages 1434-1439.
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Steven A. Wrighton, Patrick Maurel, Erin G. Schuetz, Paul B. Watkins, Beverly Young & Philip S. Guzelian. (2002) Identification of the cytochrome P-450 induced by macrolide antibiotics in rat liver as the glucocorticoid responsive cytochrome P-450p. Biochemistry 24:9, pages 2171-2178.
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M. Delaforge, M. Jaouen & D. Mansuy. (1984) The cytochrome P-450 metabolite complex derived from troleandomycin: Properties in vitro and stability in vivo. Chemico-Biological Interactions 51:3, pages 371-376.
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Zhiqiang Liu & Michael R. Franklin. (1984) Cytochrome P-450 metabolic — intermediate complex formation from p-aminobenzoic acid esters and other arylamines. European Journal of Drug Metabolism and Pharmacokinetics 9:2, pages 155-159.
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