Protein Information

Name cytochrome P450 (protein family or complex)
Synonyms cytochrome P450; cytochrome P 450; CYP450; CYP 450

Compound Information

Name cresol
CAS methylphenol

Reference List

PubMed Abstract RScore(About this table)
9010638 Ohe T, Mashino T, Hirobe M: Substituent elimination from p-substituted phenols by cytochrome P450. ipso-Substitution by the oxygen atom of the active species. Drug Metab Dispos. 1997 Jan;25(1):116-22.

6(0,0,0,6) Details
1417939 Sequeira DJ, Eyer CS, Cawley GF, Nick TG, Backes WL: Ethylbenzene-mediated induction of cytochrome P450 isozymes in male and female rats. Biochem Pharmacol. 1992 Sep 25;44(6):1171-82.

3(0,0,0,3) Details
12237102 Madyastha KM, Raj CP: Stereoselective hydroxylation of 4-methyl-2-cyclohexenone in rats: its relevance to R-(+)-pulegone-mediated hepatotoxicity. Biochem Biophys Res Commun. 2002 Sep 20;297(2):202-5.


The present study documents for the first time the involvement of cytochrome P-450 system and the stereochemical preference in this hydroxylation reaction.
2(0,0,0,2) Details
9253143 Kim H, Wang RS, Elovaara E, Raunio H, Pelkonen O, Aoyama T, Vainio H, Nakajima T: Cytochrome P450 isozymes responsible for the metabolism of toluene and styrene in human liver microsomes. Xenobiotica. 1997 Jul;27(7):657-65.

2(0,0,0,2) Details
16174805 Yan Z, Zhong HM, Maher N, Torres R, Leo GC, Caldwell GW, Huebert N: Bioactivation of 4-methylphenol (p-cresol) via cytochrome P450-mediated aromatic oxidation in human liver microsomes. Drug Metab Dispos. 2005 Dec;33(12):1867-76. Epub 2005 Sep 20.

1(0,0,0,1) Details
3508090 Rottero AE, Kissinger P: Detection and identification of three thioether conjugates of 2-hydroxyacetanilide by liquid chromatography/electrochemistry. Biomed Chromatogr. 1987 Feb;2(1):24-9.


Production of the three isomers by microsomal protein occurs only in the presence of NADPH and shows that 2HAA proceeds through a cytochrome P-450 mediated pathway to a reactive intermediate similar to acetaminophen, possibly N-acetyl-o-quinoneimine.
1(0,0,0,1) Details
3615351 Gadeholt G: Spectral interaction between 4-methylphenol and beta-oestradiol on hepatic microsomal cytochrome P-450: difference between ethanol and phenobarbital pretreatment. Pharmacol Toxicol. 1987 May;60(5):399-400.

1(0,0,0,1) Details
17447796 Madsen KG, Olsen J, Skonberg C, Hansen SH, Jurva U: Development and evaluation of an electrochemical method for studying reactive phase-I metabolites: correlation to in vitro drug metabolism. Chem Res Toxicol. 2007 May;20(5):821-31. Epub 2007 Apr 21.


Reactive metabolites can be formed via, for example, cytochrome P450-mediated phase 1 reactions, and in this study, we report the development and evaluation of an electrochemical method for generating reactive metabolites.
1(0,0,0,1) Details
9065730 Nakajima T, Wang RS, Elovaara E, Gonzalez FJ, Gelboin HV, Raunio H, Pelkonen O, Vainio H, Aoyama T: Toluene metabolism by cDNA-expressed human hepatic cytochrome P450. . Biochem Pharmacol. 1997 Feb 7;53(3):271-7.

1(0,0,0,1) Details
19383676 Artigot MP, Loiseau N, Laffitte J, Mas-Reguieg L, Tadrist S, Oswald IP, Puel O: Molecular cloning and functional characterization of two CYP619 cytochrome P450s involved in biosynthesis of patulin in Aspergillus clavatus. Microbiology. 2009 May;155(Pt 5):1738-47. Epub 2009 Apr 21.


In the present study, two cytochrome P450 genes were identified in the genome sequence of Aspergillus clavatus, a patulin-producing species.
1(0,0,0,1) Details
8477696 Eltis LD, Karlson U, Timmis KN: Purification and characterization of cytochrome P450RR1 from Rhodococcus rhodochrous. Eur J Biochem. 1993 Apr 1;213(1):211-6.


A soluble cytochrome P450 whose synthesis is induced by and that binds 2-ethoxyphenol was purified to apparent homogeneity from Rhodococcus rhodochrous strain 116.
1(0,0,0,1) Details
1427333 Arkhipova OG, Kasparov AA, Kuz'mina LP, Krzhechkovskaia VV, Kuznetsova IA: [The function of mono-oxygenase system in exposure to tricresol (experimental research)]. Gig Tr Prof Zabol. 1992;(4):27-9.


Changes of cytochrome P-450 enzyme system are the main principle of tricresol harmful action.
1(0,0,0,1) Details
1994898 Nakajima T, Wang RS, Elovaara E, Park SS, Gelboin HV, Hietanen E, Vainio H: Monoclonal antibody-directed characterization of cytochrome P450 isozymes responsible for toluene metabolism in rat liver. Biochem Pharmacol. 1991 Feb 1;41(3):395-404.

1(0,0,0,1) Details
2719701 Ling KH, Hanzlik RP: Deuterium isotope effects on toluene metabolism. Biochem Biophys Res Commun. 1989 Apr 28;160(2):844-9.

Product release as a rate-limiting step in cytochrome P-450 catalysis..
Throughout the series (i.e. d0, d1, d2, d3) the ratios of cresol isomers remain constant.
1(0,0,0,1) Details
1536817 Wang RS, Nakajima T: Effects of ethanol and phenobarbital treatments on the pharmacokinetics of toluene in rats. Br J Ind Med. 1992 Feb;49(2):104-12.


The Michaelis constant (Km) and the maximum rate of metabolic excretion in urine during six hours exposure (Vmax) of isozymes involved in the excretion of toluene metabolites were calculated, and correlated with the subtypes of cytochrome P-450.
1(0,0,0,1) Details
10771747 Imbriani M, Ghittori S, Cavalleri A: [Significance of urinary concentrations of S-benzyl-N-acetylcysteine (S-BMA) in subjects exposed to toluene]. G Ital Med Lav Ergon. 1999 Oct-Dec;21(4):329-33.


Once absorbed into the body, toluene is metabolized in man to benzoic acid, followed by hepatic cytochrome P450 catalyzed glycine conjugation to form hippuric acid.
1(0,0,0,1) Details
2856075 Strohm BH, Kulkarni AP: Peroxidase, an alternate pathway to cytochrome P-450 for xenobiotic metabolism in skin: partial purification and properties of the enzyme from neonatal rat skin. J Biochem Toxicol. 1986 Dec;1(4):83-97.

1(0,0,0,1) Details
10651645 Pikus JD, Mitchell KH, Studts JM, McClay K, Steffan RJ, Fox BG: Threonine 201 in the diiron enzyme toluene 4-monooxygenase is not required for catalysis. Biochemistry. 2000 Feb 1;39(4):791-9.


In the methane monooxygenase hydroxylase, active site residue T213 has been proposed to participate in O (2) activation by analogy to certain proposals made for cytochrome P450.
1(0,0,0,1) Details
2065626 Braunbeck T, Volkl A: Induction of biotransformation in the liver of Eel (Anguilla anguilla L.) by sublethal exposure to dinitro-o-cresol: an ultrastructural and biochemical study. Ecotoxicol Environ Saf. 1991 Apr;21(2):109-27.


An increase in NADPH-cytochrome c reductase and cytochrome P450 as well as UDP-glucuronyltransferase and arylsulfotransferase activities in the microsomal fraction document an induction of hepatic biotransformation as a functional correlate to SER proliferation.
1(0,0,0,1) Details
7703367 Thompson DC, Perera K, London R: Quinone methide formation from para isomers of methylphenol (cresol), ethylphenol, and isopropylphenol: relationship to toxicity. Chem Res Toxicol. 1995 Jan-Feb;8(1):55-60.

Enhancement of cellular thiol levels with N-acetylcysteine protected cells from the toxic effects of all three compounds as did inhibition of cytochrome P450 activity with metyrapone.
1(0,0,0,1) Details
1739413 Nakajima T, Wang RS, Elovaara E, Park SS, Gelboin HV, Vainio H: A comparative study on the contribution of cytochrome P450 isozymes to metabolism of benzene, toluene and trichloroethylene in rat liver. Biochem Pharmacol. 1992 Jan 22;43(2):251-7.

1(0,0,0,1) Details
11356136 Lloyd Raven E, Celik A, Cullis PM, Sangar R, Sutcliffe MJ: Engineering the active site of ascorbate peroxidase. Biochem Soc Trans. 2001 May;29(Pt 2):105-11.


These issues are discussed in the general context of peroxidase and cytochrome P450 chemistry, and specific issues relating to the catalytic chemistry of ascorbate peroxidase are highlighted.
1(0,0,0,1) Details
107617 Riviere JL, De Lavaur E, Grolleau G: Effect of polychlorinated biphenyls on drug metabolism in Japanese quail and its progeny. Toxicology. 1978 Dec;11(4):329-34.


PCB (DP5, 1 and 5 mg/female/day, orally for 40 days) induce microsomal hepatic enzymes (cytochrome P-450, aniline hydroxylase, aldrin epoxidase, p-nitroanisole demethylase, p-nitrophenol: UDPGA-transferase) in adult female Japanese quail.
1(0,0,0,1) Details
12653586 Kamijo Y, Soma K, Kokuto M, Ohbu M, Fuke C, Ohwada T: Hepatocellular injury with hyperaminotransferasemia after cresol ingestion. Arch Pathol Lab Med. 2003 Mar;127(3):364-6.

A rapid onset of illness with periportal hepatocellular injury is inconsistent with damage due to a hepatotoxic metabolite of p-cresol produced by cytochrome P450, which has been suggested by studies in vitro.
1(0,0,0,1) Details
3396795 Munson AE, White KL Jr, Barnes DW, Musgrove DL, Lysy HH, Holsapple MP: An immunotoxicological evaluation of 4,4'-thiobis-(6-t-butyl-m-cresol) in female B6C3F1 mice. 1. Fundam Appl Toxicol. 1988 May;10(4):691-700.


Liver microsomal protein and cytochrome P-450 levels were increased in a dose-related fashion.
1(0,0,0,1) Details
9056233 Yuan W, Sequeira DJ, Cawley GF, Eyer CS, Backes WL: Time course for the modulation of hepatic cytochrome P450 after administration of ethylbenzene and its correlation with toluene metabolism. Arch Biochem Biophys. 1997 Mar 1;339(1):55-63.

1(0,0,0,1) Details
14672753 Zhou S, Koh HL, Gao Y, Gong ZY, Lee EJ: Herbal bioactivation: the good, the bad and the ugly. Life Sci. 2004 Jan 9;74(8):935-68.


This is exemplified by aristolochic acids present in Aristolochia spp, undergoing reduction of the nitro group by hepatic cytochrome P450 (CYP1A1/2) or peroxidases in extrahepatic tissues to reactive cyclic nitrenium ion.
1(0,0,0,1) Details
16253244 Ullrich R, Hofrichter M: The haloperoxidase of the agaric fungus Agrocybe aegerita hydroxylates toluene and naphthalene. FEBS Lett. 2005 Nov 7;579(27):6247-50. Epub 2005 Oct 19.


The UV-Vis absorption spectrum of purified AaP showed high similarity to a resting state cytochrome P450 with the Soret band at 420 nm and additional maxima at 278, 358, 541 and 571 nm; the AaP CO-complex had a distinct absorption maximum at 445 nm that is characteristic for heme-thiolate proteins.
1(0,0,0,1) Details
1981539 Chapman DE, Moore TJ, Michener SR, Powis G: Metabolism and covalent binding of [14C] toluene by human and rat liver microsomal fractions and liver slices. Drug Metab Dispos. 1990 Nov-Dec;18(6):929-36.

Cresols and cresol conjugates were not detected in human or rat liver slice incubations.
These results suggest that cytochrome P-450, rather than alcohol dehydrogenase, was responsible for the metabolism of benzyl alcohol to benzaldehyde.
1(0,0,0,1) Details