| Name | cytochrome P450 (protein family or complex) |
|---|---|
| Synonyms | cytochrome P450; cytochrome P 450; CYP450; CYP 450 |
| Name | methoxychlor |
|---|---|
| CAS | 1,1′-(2,2,2-trichloroethylidene)bis[4-methoxybenzene] |
| PubMed | Abstract | RScore(About this table) | |
|---|---|---|---|
| 7082334 | Lamartiniere CA, Luther MA, Lucier GW, Illsley NP: Altered imprinting of rat liver monoamine oxidase by o, p'-DDT and methoxychlor. Biochem Pharmacol. 1982 Mar 1;31(5):647-51. However, glutathione S-transferase activities and cytochrome P-450 content were higher in prepubertal animals treated neonatally with o,p'-DDT. |
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| 14613717 | Mikamo E, Harada S, Nishikawa J, Nishihara T: Endocrine disruptors induce cytochrome P450 by affecting transcriptional regulation via pregnane X receptor. Toxicol Appl Pharmacol. 2003 Nov 15;193(1):66-72. In our study, 7 of 54 xenobiotics compounds interacted with PXR, including methoxychlor and benzophenone. |
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| 9266808 | Schlenk D, Stresser DM, McCants JC, Nimrod AC, Benson WH: Influence of beta-naphthoflavone and methoxychlor pretreatment on the biotransformation and estrogenic activity of methoxychlor in channel catfish (Ictalurus punctatus). Toxicol Appl Pharmacol. 1997 Aug;145(2):349-56. While microsomal demethylation occurs readily in the liver of fish, little is known about the enzyme (s) responsible or the effect of cytochrome P450 (CYP) inducers, other than those of CYP1A and CYP2K, on biotransformation. |
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| 9047321 | Stresser DM, Kupfer D: Catalytic characteristics of CYP3A4: requirement for a phenolic function in ortho hydroxylation of and mono-O-demethylated methoxychlor. Biochemistry. 1997 Feb 25;36(8):2203-10. CYP3A4 is the major human cytochrome P-450 in a superfamily of heme-thiolate proteins that catalyze the oxidation of numerous lipophilic compounds. |
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| 18279978 | Blum JL, Nyagode BA, James MO, Denslow ND: Effects of the pesticide methoxychlor on gene expression in the liver and testes of the male largemouth bass (Micropterus salmoides). Aquat Toxicol. 2008 Mar 26;86(4):459-69. Epub 2008 Jan 3. The liver and testes were then assayed for changes in expression of the three bass estrogen receptors (ERs alpha, beta a, and beta b) in tissues, as well as Vtg and cytochrome P450 (CYP) 3A isoform 68 in the liver and steroidogenic acute regulatory protein (StAR) in the testes. |
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| 2893703 | Juedes MJ, Bulger WH, Kupfer D: Monooxygenase-mediated activation of chlorotrianisene (TACE) in covalent binding to rat hepatic microsomal proteins. Drug Metab Dispos. 1987 Nov-Dec;15(6):786-93. Chlorotrianisene is a therapeutic and contaminant of the pesticide methoxychlor. Furthermore, these bands were sensitive to protease degradation, indicating that the recipient macromolecules were proteins and possibly cytochrome P-450 (s). |
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| 6857671 | Bulger WH, Temple JE, Kupfer D: Covalent binding of [14C] methoxychlor metabolite (s) to rat liver microsomal components. Toxicol Appl Pharmacol. 1983 May;68(3):367-74. and SKF 525-A, inhibitors of hepatic cytochrome P-450-linked monooxygenase activity, inhibited the binding. |
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| 16760418 | Miller KP, Gupta RK, Flaws JA: Methoxychlor metabolites may cause ovarian toxicity through -regulated pathways. Toxicol Sci. 2006 Sep;93(1):180-8. Epub 2006 Jun 7. Cytochrome P450 enzymes metabolize MXC to mono-OH MXC (1,1,1-trichloro-2-(4-hydroxyphenyl)-2-(4-methoxyphenyl) ethane [mono-OH]) and bis-OH MXC (1,1,1-trichloro-2,2-bis (4-hydroxyphenyl) ethane [HPTE]), two compounds that are proposed to be more toxic than the parent compound, can interact with the estrogen receptor (ER), and are proposed to be responsible for ovarian toxicity. |
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| 16684644 | Stresser DM: David Kupfer: a career retrospective. Drug Metab Rev. 2006;38(1-2):3-12. Although best known for his work centering on cytochrome P450 metabolism of prostaglandins, steroids, and proestrogenic compounds, David's research also contributed key advances in the areas of P450 induction and catalytic mechanism, breast cancer therapy, and analytical methodology. |
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| 11452134 | Yoshihara S, Makishima M, Suzuki N, Ohta S: Metabolic activation of bisphenol A by rat liver S9 fraction. Toxicol Sci. 2001 Aug;62(2):221-7. This metabolic activation was inhibited by SKF 525-A, an inhibitor of cytochrome P450. Bisphenol B and methoxychlor were also activated by incubation with rat liver S9, whereas 4-tert-octylphenol and 4-nonylphenol, as well as 17beta- were metabolically inactivated. |
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| 1868789 | Babich H, Rosenberg DW, Borenfreund E: In vitro cytotoxicity studies with the fish hepatoma cell line, PLHC-1 (Poeciliopsis lucida). Ecotoxicol Environ Saf. 1991 Jun;21(3):327-36. The organochlorine pesticides (alachlor and p,p'-methoxychlor) were more cytotoxic than the organophosphorus pesticides (EPN, diazinon, and malathion). Xenobiotic-metabolizing capacity was temperature dependent, with enzymatic activity increasing as the temperature was increased from 28 to 34 to 37 degrees C, was inducible by Aroclor 1254 (a chemical inducer of cytochrome P450-dependent monooxygenase activity), and was reduced by EPN (an inhibitor of P450 activity). |
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| 18848953 | Armenti AE, Zama AM, Passantino L, Uzumcu M: Developmental methoxychlor exposure affects multiple reproductive parameters and ovarian folliculogenesis and gene expression in adult rats. Toxicol Appl Pharmacol. 2008 Dec 1;233(2):286-96. Epub 2008 Sep 24. High dose MXC significantly reduced LH receptor expression in large antral follicles (P <0.01), and down-regulated cytochrome P450 side-chain cleavage. |
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| 15466163 | Yueh MF, Kawahara M, Raucy J: High volume bioassays to assess CYP3A4-mediated drug interactions: induction and inhibition in a single cell line. Drug Metab Dispos. 2005 Jan;33(1):38-48. Epub 2004 Oct 1. Exposure to certain xenochemicals can alter the catalytic activity of the major drug-metabolizing enzyme, CYP3A4, either by enhancing expression of this cytochrome P450 or inhibiting its activity. Treatment of stable transformants, namely DPX-2, with various concentrations of inducers including rifampicin, mifepristone, troglitazone, methoxychlor, and kava produced dose-dependent increases in luciferase expression (between 2- and 40-fold above -treated cells). |
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| 15690762 | Ohyama K, Maki S, Sato K, Kato Y: In vitro metabolism of [14C] methoxychlor in rat, mouse, Japanese quail and rainbow trout in precision-cut liver slices. Xenobiotica. 2004 Aug;34(8):741-54. The different metabolic profiles of MXC observed in the four animal species are possibly due to substrate specificity of contributing CYP450 monooxgenase enzyme (s) in different animal species. |
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| 10684797 | Akingbemi BT, Ge RS, Klinefelter GR, Gunsalus GL, Hardy MP: A metabolite of methoxychlor, 2,2-bis (p-hydroxyphenyl)-1,1, 1-trichloroethane, reduces biosynthesis in rat leydig cells through suppression of steady-state messenger ribonucleic acid levels of the cholesterol side-chain cleavage enzyme. Biol Reprod. 2000 Mar;62(3):571-8. This finding suggested that HPTE-induced inhibition of T production is related to a decrease in the activity of cytochrome P450 cholesterol side-chain cleavage enzyme (P450 (scc)) and utilization. |
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| 9241656 | Ekins S, VandenBranden M, Ring BJ, Wrighton SA: Examination of purported probes of human CYP2B6. . Pharmacogenetics. 1997 Jun;7(3):165-79. 7-Ethoxy-4-trifluoromethylcoumarin (7-EFC) was examined as a substrate for cytochrome P450 (P450) in microsomes from human livers and expressed in B-lymphoblastoid cells. Methoxychlor and S-mephenytoin inhibited expressed CYP2B6 but not CYP1A2 mediated 7-EFC O-deethylation. |
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| 12948398 | Makinen J, Reinisalo M, Niemi K, Viitala P, Jyrkkarinne J, Chung H, Pelkonen O, Honkakoski P: Dual action of oestrogens on the mouse constitutive androstane receptor. . Biochem J. 2003 Dec 1;376(Pt 2):465-72. mCAR (mouse constitutive androstane receptor; NR1I3) controls the expression of cytochrome P450 as well as other enzymes involved in drug and steroid metabolism. This novel dual action is not limited to oestrogens, but is shared by some xenobiotic CYP2B inducers such as and methoxychlor. |
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| 11509743 | Waters KM, Safe S, Gaido KW: Differential gene expression in response to methoxychlor and through ERalpha, ERbeta, and AR in reproductive tissues of female mice. Toxicol Sci. 2001 Sep;63(1):47-56. |
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| 11353743 | Blizard D, Sueyoshi T, Negishi M, Dehal SS, Kupfer D: Mechanism of induction of cytochrome p450 enzymes by the proestrogenic endocrine disruptor pesticide-methoxychlor: interactions of methoxychlor metabolites with the constitutive androstane receptor system. Drug Metab Dispos. 2001 Jun;29(6):781-5. |
162(2,2,2,2) | Details |
| 9733665 | Stresser DM, Kupfer D: Human cytochrome P450-catalyzed conversion of the proestrogenic pesticide methoxychlor into an Drug Metab Dispos. 1998 Sep;26(9):868-74. |
162(2,2,2,2) | Details |
| 19691325 | Keum YS, Lee YH, Kim JH: Metabolism of methoxychlor by Cunninghamella elegans ATCC36112. J Agric Food Chem. 2009 Sep 9;57(17):7931-7. Major activation of methoxychlor is through cytochrome P450-catalyzed demethylation to bisphenol A-like metabolites. |
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| 8114062 | Li HC, Mani C, Kupfer D: Reversible and time-dependent inhibition of the hepatic cytochrome P450 steroidal hydroxylases by the proestrogenic pesticide methoxychlor in rat and human. J Biochem Toxicol. 1993 Dec;8(4):195-206. Methoxychlor, a currently used pesticide, is demethylated and hydroxylated by several hepatic microsomal cytochrome P450 enzymes. |
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| 7574712 | Zhou LX, Dehal SS, Kupfer D, Morrell S, McKenzie BA, Eccleston ED Jr, Holtzman JL: Cytochrome P450 catalyzed covalent binding of methoxychlor to rat hepatic, microsomal iodothyronine 5'-monodeiodinase, type I: does exposure to methoxychlor disrupt thyroid hormone metabolism?. Arch Biochem Biophys. 1995 Oct 1;322(2):390-4. |
81(1,1,1,1) | Details |
| 15205390 | Hazai E, Gagne PV, Kupfer D: Glucuronidation of the oxidative cytochrome P450-mediated phenolic metabolites of the endocrine disruptor pesticide: methoxychlor by human hepatic UDP-glucuronosyl transferases. Drug Metab Dispos. 2004 Jul;32(7):742-51. |
81(1,1,1,1) | Details |
| 2390114 | Bulger WH, Kupfer D: Studies on the formation of methoxychlor-protein adduct in rat and human liver microsomes. Biochem Pharmacol. 1990 Sep 1;40(5):937-45. Is demethylation of methoxychlor essential for cytochrome P450 catalyzed covalent binding?. |
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| 18585438 | Bikadi Z, Hazai E: In silico description of differential enantioselectivity in methoxychlor O-demethylation by CYP2C enzymes. Biochim Biophys Acta. 2008 Sep;1780(9):1070-9. Epub 2008 Jun 9. Methoxychlor undergoes metabolism by cytochrome P450 (CYP) enzymes forming a chiral mono-phenolic derivative (Mono-OH-M) as main metabolite. |
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| 15486075 | Hazai E, Kupfer D: Interactions between CYP2C9 and CYP2C19 in reconstituted binary systems influence their catalytic activity: possible rationale for the inability of CYP2C19 to catalyze methoxychlor demethylation in human liver microsomes. Drug Metab Dispos. 2005 Jan;33(1):157-64. Epub 2004 Oct 14. Previous studies in our laboratory showed that among cDNA-expressed human cytochrome P450 (P450) supersomes, CYP2C19 was the most active in methoxychlor-O-demethylation. |
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| 12389925 | Katchamart S, Miranda CL, Henderson MC, Pereira CB, Buhler DR: Effect of xenoestrogen exposure on the expression of cytochrome P450 isoforms in rainbow trout liver. Environ Toxicol Chem. 2002 Nov;21(11):2445-51. These findings suggest that methoxychlor, diethylstilbestrol, 4-tert-octylphenol, and were all estrogenic and mimicked 17beta- (E2) in repressing the expression of cytochrome P450 isoforms (CYP2KI, CYP2M1, and CYP3A27) in the rainbow trout liver. |
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| 15649640 | Dehn PF, Allen-Mocherie S, Karek J, Thenappan A: Organochlorine insecticides: impacts on human HepG2 cytochrome P4501A, 2B activities and levels. Toxicol In Vitro. 2005 Mar;19(2):261-73. This study examined the effects of the organochlorine (OC) insecticides chlordane, o,p'-DDT, dieldrin, endosulfan, kepone, methoxychlor, and toxaphene on human HepG2 cytochrome P450 (1A-EROD and 2B-PROD) activities and (GSH) levels. |
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| 9736480 | Li HC, Kupfer D: Mechanism of induction of rat hepatic CYP2B and 3A by the pesticide methoxychlor. J Biochem Mol Toxicol. 1998;12(6):315-23. Our earlier investigation demonstrated that methoxychlor treatment induced hepatic cytochrome P450 2B1/2B2 and 3A proteins in rats and enhanced their respective enzymatic activities. |
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| 16280380 | Symonds DA, Miller KP, Tomic D, Flaws JA: Effect of methoxychlor and on cytochrome p450 enzymes in the mouse ovarian surface epithelium. Toxicol Sci. 2006 Feb;89(2):510-4. Epub 2005 Nov 9. |
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| 12919727 | Oropeza-Hernandez LF, Lopez-Romero R, Albores A: Hepatic CYP1A, 2B, 2C, 2E and 3A regulation by methoxychlor in male and female rats. Toxicol Lett. 2003 Sep 15;144(1):93-103. The effect on liver cytochrome P450 (CYP) by i.p. injections of methoxychlor (MXC) in corn oil at 0, 100, 150, 200 or 250 mg/kg twice daily for 3 days was investigated in adult male and female Wistar rats. |
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| 15620088 | Sheweita SA: Carcinogen-metabolizing enzymes and insecticides. J Environ Sci Health B. 2004;39(5-6):805-18. The present study was under taken to demonstrate the effect of some commonly used insecticides on the activity of cytochrome P450 system including cytochrome b5, aryl hydrocarbon [benzo (a) pyrene] hydroxylase (AHH), N-nirosodimethylamine N-demethylase I [NDMA-dI] and -cytochrome c reductase as phase I of drug oxidation. In addition, the activity of glutathione S-transferase (GST), glutathione reductase (GR), and the level of (GSH) were determined in the liver of male mice after oral administration of sumithion, dursban, chlordane, methoxychlor, heptachlor epoxide, and lindane as single (24h) or as repeated doses for six consecutive days. |
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| 9714305 | Stresser DM, Kupfer D: Prosubstrates of CYP3A4, the major human hepatic cytochrome P450: transformation into substrates by other P450 isoforms. Biochem Pharmacol. 1998 Jun 1;55(11):1861-71. Incubation of methoxychlor with CYP2C19 yields the phenolic monodemethylated derivative (mono-OH-M). |
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| 17975887 | Van Liempd SM, Kool J, Meerman JH, Irth H, Vermeulen NP: Metabolic profiling of endocrine-disrupting compounds by on-line cytochrome p450 bioreaction coupled to on-line receptor affinity screening. Chem Res Toxicol. 2007 Dec;20(12):1825-32. Epub 2007 Nov 1. |
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| 10101147 | Stresser DM, Kupfer D: Monospecific antipeptide antibody to cytochrome P-450 2B6. Drug Metab Dispos. 1999 Apr;27(4):517-25. To study cytochrome P-450 (CYP) 2B6 contribution to methoxychlor metabolism within human liver microsomes and to initiate an investigation of CYP2B6 protein expression, we developed a polyclonal antibody targeted to a 20-residue peptide within that protein. |
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