General Information of Drug Off-Target (DOT) (ID: OTHQ17JG)

DOT Name Cytochrome P450 2E1 (CYP2E1)
Synonyms EC 1.14.14.1; 4-nitrophenol 2-hydroxylase; EC 1.14.13.n7; CYPIIE1; Cytochrome P450-J
Gene Name CYP2E1
UniProt ID
CP2E1_HUMAN
3D Structure
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2D Sequence (FASTA)
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3D Structure (PDB)
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PDB ID
3E4E; 3E6I; 3GPH; 3KOH; 3LC4; 3T3Z
EC Number
1.14.13.n7; 1.14.14.1
Pfam ID
PF00067
Sequence
MSALGVTVALLVWAAFLLLVSMWRQVHSSWNLPPGPFPLPIIGNLFQLELKNIPKSFTRL
AQRFGPVFTLYVGSQRMVVMHGYKAVKEALLDYKDEFSGRGDLPAFHAHRDRGIIFNNGP
TWKDIRRFSLTTLRNYGMGKQGNESRIQREAHFLLEALRKTQGQPFDPTFLIGCAPCNVI
ADILFRKHFDYNDEKFLRLMYLFNENFHLLSTPWLQLYNNFPSFLHYLPGSHRKVIKNVA
EVKEYVSERVKEHHQSLDPNCPRDLTDCLLVEMEKEKHSAERLYTMDGITVTVADLFFAG
TETTSTTLRYGLLILMKYPEIEEKLHEEIDRVIGPSRIPAIKDRQEMPYMDAVVHEIQRF
ITLVPSNLPHEATRDTIFRGYLIPKGTVVVPTLDSVLYDNQEFPDPEKFKPEHFLNENGK
FKYSDYFKPFSTGKRVCAGEGLARMELFLLLCAILQHFNLKPLVDPKDIDLSPIHIGFGC
IPPRYKLCVIPRS
Function
A cytochrome P450 monooxygenase involved in the metabolism of fatty acids. Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds. Hydroxylates fatty acids specifically at the omega-1 position displaying the highest catalytic activity for saturated fatty acids. May be involved in the oxidative metabolism of xenobiotics (Probable).
KEGG Pathway
Steroid hormone biosynthesis (hsa00140 )
Arachidonic acid metabolism (hsa00590 )
Linoleic acid metabolism (hsa00591 )
Metabolism of xenobiotics by cytochrome P450 (hsa00980 )
Drug metabolism - cytochrome P450 (hsa00982 )
Drug metabolism - other enzymes (hsa00983 )
Metabolic pathways (hsa01100 )
Non-alcoholic fatty liver disease (hsa04932 )
Alcoholic liver disease (hsa04936 )
Chemical carcinogenesis - D. adducts (hsa05204 )
Chemical carcinogenesis - reactive oxygen species (hsa05208 )
Reactome Pathway
CYP2E1 reactions (R-HSA-211999 )
Biosynthesis of maresin-like SPMs (R-HSA-9027307 )
Aspirin ADME (R-HSA-9749641 )
Paracetamol ADME (R-HSA-9753281 )
Xenobiotics (R-HSA-211981 )
BioCyc Pathway
MetaCyc:HS05414-MONOMER

Molecular Interaction Atlas (MIA) of This DOT

Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This DOT
This DOT Affected the Regulation of Drug Effects of 17 Drug(s)
Drug Name Drug ID Highest Status Interaction REF
Hydrogen peroxide DM1NG5W Approved Cytochrome P450 2E1 (CYP2E1) increases the abundance of Hydrogen peroxide. [55]
Methamphetamine DMPM4SK Approved Cytochrome P450 2E1 (CYP2E1) affects the metabolism of Methamphetamine. [56]
Amodiaquine DME4RA8 Approved Cytochrome P450 2E1 (CYP2E1) increases the metabolism of Amodiaquine. [58]
Dronedarone DMA8FS5 Approved Cytochrome P450 2E1 (CYP2E1) increases the metabolism of Dronedarone. [60]
Primaquine DMWQ16I Approved Cytochrome P450 2E1 (CYP2E1) increases the metabolism of Primaquine. [61]
Midazolam DMXOELT Approved Cytochrome P450 2E1 (CYP2E1) increases the metabolism of Midazolam. [63]
PMID28870136-Compound-52 DMFDERP Patented Cytochrome P450 2E1 (CYP2E1) affects the metabolism of PMID28870136-Compound-52. [65]
Vanoxerine DMBQPA5 Discontinued in Phase 1 Cytochrome P450 2E1 (CYP2E1) decreases the degradation of Vanoxerine. [66]
HSDB-41 DMR8VJA Preclinical Cytochrome P450 2E1 (CYP2E1) increases the metabolism of HSDB-41. [67]
Coumarin DM0N8ZM Investigative Cytochrome P450 2E1 (CYP2E1) increases the metabolism of Coumarin. [69]
Acetaldehyde DMJFKG4 Investigative Cytochrome P450 2E1 (CYP2E1) increases the metabolism of Acetaldehyde. [70]
BRN-3548355 DM4KXT0 Investigative Cytochrome P450 2E1 (CYP2E1) increases the metabolism of BRN-3548355. [72]
NAPQI DM8F5LR Investigative Cytochrome P450 2E1 (CYP2E1) increases the abundance of NAPQI. [73]
1,4-Naphthoquinone DMTCMH7 Investigative Cytochrome P450 2E1 (CYP2E1) increases the abundance of 1,4-Naphthoquinone. [74]
Ellipticine DMHPYSM Investigative Cytochrome P450 2E1 (CYP2E1) increases the metabolism of Ellipticine. [75]
Dimethylformamide DML6O4N Investigative Cytochrome P450 2E1 (CYP2E1) increases the abundance of Dimethylformamide. [78]
Lauric Acid DM9C8KQ Investigative Cytochrome P450 2E1 (CYP2E1) increases the metabolism of Lauric Acid. [28]
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⏷ Show the Full List of 17 Drug(s)
This DOT Affected the Drug Response of 9 Drug(s)
Drug Name Drug ID Highest Status Interaction REF
Eicosapentaenoic acid/docosa-hexaenoic acid DMMUCG4 Approved Cytochrome P450 2E1 (CYP2E1) increases the response to substance of Eicosapentaenoic acid/docosa-hexaenoic acid. [57]
Didanosine DMI2QPE Approved Cytochrome P450 2E1 (CYP2E1) increases the Pancreatitis ADR of Didanosine. [62]
Theophylline DMRJFN9 Approved Cytochrome P450 2E1 (CYP2E1) increases the Adverse drug reaction ADR of Theophylline. [62]
Minocycline DMVN5OH Approved Cytochrome P450 2E1 (CYP2E1) increases the Adverse drug reaction ADR of Minocycline. [62]
Amiodarone DMUTEX3 Phase 2/3 Trial Cytochrome P450 2E1 (CYP2E1) decreases the response to substance of Amiodarone. [64]
Amineptine DMGVNJ7 Withdrawn from market Cytochrome P450 2E1 (CYP2E1) increases the Hepatitis ADR of Amineptine. [62]
3R14S-OCHRATOXIN A DM2KEW6 Investigative Cytochrome P450 2E1 (CYP2E1) increases the response to substance of 3R14S-OCHRATOXIN A. [71]
Buthionine sulfoximine DMJ46CB Investigative Cytochrome P450 2E1 (CYP2E1) increases the response to substance of Buthionine sulfoximine. [76]
Deoxythymidine DMR90HY Investigative Cytochrome P450 2E1 (CYP2E1) increases the response to substance of Deoxythymidine. [79]
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⏷ Show the Full List of 9 Drug(s)
This DOT Affected the Biotransformations of 7 Drug(s)
Drug Name Drug ID Highest Status Interaction REF
Lamotrigine DM8SXYG Approved Cytochrome P450 2E1 (CYP2E1) increases the glutathionylation of Lamotrigine. [59]
Urethane DM7NSI0 Phase 4 Cytochrome P450 2E1 (CYP2E1) increases the oxidation of Urethane. [34]
PMID28870136-Compound-48 DMPIM9L Patented Cytochrome P450 2E1 (CYP2E1) increases the chemical synthesis of PMID28870136-Compound-48. [65]
PMID28870136-Compound-50 DM42OYU Patented Cytochrome P450 2E1 (CYP2E1) increases the chemical synthesis of PMID28870136-Compound-50. [65]
Bisphenol A DM2ZLD7 Investigative Cytochrome P450 2E1 (CYP2E1) increases the glutathionylation of Bisphenol A. [68]
Mononitrophenol DM4QO9G Investigative Cytochrome P450 2E1 (CYP2E1) increases the hydroxylation of Mononitrophenol. [77]
ACMC-1AKLT DMRQ70X Investigative Cytochrome P450 2E1 (CYP2E1) increases the chemical synthesis of ACMC-1AKLT. [26]
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⏷ Show the Full List of 7 Drug(s)
65 Drug(s) Affected the Gene/Protein Processing of This DOT
Drug Name Drug ID Highest Status Interaction REF
Valproate DMCFE9I Approved Valproate decreases the expression of Cytochrome P450 2E1 (CYP2E1). [1]
Ciclosporin DMAZJFX Approved Ciclosporin decreases the expression of Cytochrome P450 2E1 (CYP2E1). [2]
Acetaminophen DMUIE76 Approved Acetaminophen decreases the expression of Cytochrome P450 2E1 (CYP2E1). [3]
Estradiol DMUNTE3 Approved Estradiol decreases the expression of Cytochrome P450 2E1 (CYP2E1). [2]
Arsenic DMTL2Y1 Approved Arsenic affects the expression of Cytochrome P450 2E1 (CYP2E1). [4]
Quercetin DM3NC4M Approved Quercetin decreases the activity of Cytochrome P450 2E1 (CYP2E1). [5]
Arsenic trioxide DM61TA4 Approved Arsenic trioxide affects the expression of Cytochrome P450 2E1 (CYP2E1). [6]
Phenobarbital DMXZOCG Approved Phenobarbital affects the expression of Cytochrome P450 2E1 (CYP2E1). [7]
Hydroquinone DM6AVR4 Approved Hydroquinone increases the expression of Cytochrome P450 2E1 (CYP2E1). [8]
Ethanol DMDRQZU Approved Ethanol increases the expression of Cytochrome P450 2E1 (CYP2E1). [9]
Diclofenac DMPIHLS Approved Diclofenac decreases the activity of Cytochrome P450 2E1 (CYP2E1). [10]
Malathion DMXZ84M Approved Malathion decreases the activity of Cytochrome P450 2E1 (CYP2E1). [11]
Obeticholic acid DM3Q1SM Approved Obeticholic acid decreases the expression of Cytochrome P450 2E1 (CYP2E1). [12]
Rifampicin DM5DSFZ Approved Rifampicin decreases the expression of Cytochrome P450 2E1 (CYP2E1). [13]
Lindane DMB8CNL Approved Lindane decreases the expression of Cytochrome P450 2E1 (CYP2E1). [14]
Phenytoin DMNOKBV Approved Phenytoin increases the expression of Cytochrome P450 2E1 (CYP2E1). [15]
Vitamin C DMXJ7O8 Approved Vitamin C decreases the activity of Cytochrome P450 2E1 (CYP2E1). [16]
Chenodiol DMQ8JIK Approved Chenodiol decreases the expression of Cytochrome P450 2E1 (CYP2E1). [17]
Dihydroxyacetone DMM1LG2 Approved Dihydroxyacetone decreases the expression of Cytochrome P450 2E1 (CYP2E1). [18]
Penicillamine DM40EF6 Approved Penicillamine increases the expression of Cytochrome P450 2E1 (CYP2E1). [19]
Cimetidine DMH61ZB Approved Cimetidine decreases the expression of Cytochrome P450 2E1 (CYP2E1). [20]
Thioridazine DM35M8J Approved Thioridazine decreases the activity of Cytochrome P450 2E1 (CYP2E1). [21]
Ethambutol DMR87LC Approved Ethambutol decreases the activity of Cytochrome P450 2E1 (CYP2E1). [22]
Desipramine DMT2FDC Approved Desipramine decreases the activity of Cytochrome P450 2E1 (CYP2E1). [21]
Ademetionine DMYQDBO Approved Ademetionine decreases the activity of Cytochrome P450 2E1 (CYP2E1). [23]
Tranylcypromine DMGB5RE Approved Tranylcypromine decreases the activity of Cytochrome P450 2E1 (CYP2E1). [24]
Yn-968D1 DMMP3Y2 Approved Yn-968D1 affects the activity of Cytochrome P450 2E1 (CYP2E1). [25]
Orphenadrine DMW542E Approved Orphenadrine decreases the activity of Cytochrome P450 2E1 (CYP2E1). [26]
Fomepizole DM6VOWQ Approved Fomepizole decreases the activity of Cytochrome P450 2E1 (CYP2E1). [27]
Pyridine DMF8CJ9 Phase 4 Pyridine decreases the activity of Cytochrome P450 2E1 (CYP2E1). [28]
Chlorpromazine DMBGZI3 Phase 3 Trial Chlorpromazine decreases the activity of Cytochrome P450 2E1 (CYP2E1). [21]
I3C DMIGFOR Phase 3 I3C decreases the activity of Cytochrome P450 2E1 (CYP2E1). [29]
Clomethiazole DMSPN58 Phase 3 Clomethiazole decreases the activity of Cytochrome P450 2E1 (CYP2E1). [30]
Tocopherol DMBIJZ6 Phase 2 Tocopherol increases the expression of Cytochrome P450 2E1 (CYP2E1). [31]
phorbol 12-myristate 13-acetate DMJWD62 Phase 2 phorbol 12-myristate 13-acetate increases the expression of Cytochrome P450 2E1 (CYP2E1). [32]
PEITC DMOMN31 Phase 2 PEITC decreases the activity of Cytochrome P450 2E1 (CYP2E1). [33]
Disulfiram DMCL2OK Phase 2 Trial Disulfiram decreases the activity of Cytochrome P450 2E1 (CYP2E1). [34]
BAICALEIN DM4C7E6 Phase 2 BAICALEIN decreases the activity of Cytochrome P450 2E1 (CYP2E1). [35]
CHIR-99021 DMB8MNU Patented CHIR-99021 increases the expression of Cytochrome P450 2E1 (CYP2E1). [37]
PMID26560530-Compound-34 DMLGZPO Patented PMID26560530-Compound-34 affects the activity of Cytochrome P450 2E1 (CYP2E1). [38]
Taxifolin DMQJSF9 Preclinical Taxifolin decreases the expression of Cytochrome P450 2E1 (CYP2E1). [39]
2-AMINO-1-METHYL-6-PHENYLIMIDAZO[4,5-B]PYRIDINE DMNQL17 Investigative 2-AMINO-1-METHYL-6-PHENYLIMIDAZO[4,5-B]PYRIDINE increases the expression of Cytochrome P450 2E1 (CYP2E1). [40]
Chlorpyrifos DMKPUI6 Investigative Chlorpyrifos decreases the activity of Cytochrome P450 2E1 (CYP2E1). [11]
Arachidonic acid DMUOQZD Investigative Arachidonic acid decreases the activity of Cytochrome P450 2E1 (CYP2E1). [41]
Oleic acid DM54O1Z Investigative Oleic acid increases the expression of Cytochrome P450 2E1 (CYP2E1). [43]
Apigenin DMI3491 Investigative Apigenin decreases the activity of Cytochrome P450 2E1 (CYP2E1). [35]
Farnesol DMV2X1B Investigative Farnesol decreases the expression of Cytochrome P450 2E1 (CYP2E1). [43]
Myricetin DMTV4L0 Investigative Myricetin decreases the activity of Cytochrome P450 2E1 (CYP2E1). [35]
Linoleic acid DMDGPY9 Investigative Linoleic acid decreases the activity of Cytochrome P450 2E1 (CYP2E1). [41]
LICOAGROCHACONE A DMWY0TN Investigative LICOAGROCHACONE A affects the activity of Cytochrome P450 2E1 (CYP2E1). [44]
USNIC ACID DMGOURX Investigative USNIC ACID decreases the expression of Cytochrome P450 2E1 (CYP2E1). [45]
Isoarnebin 4 DM0B7NO Investigative Isoarnebin 4 decreases the activity of Cytochrome P450 2E1 (CYP2E1). [46]
Icosapentum DMF1CM7 Investigative Icosapentum decreases the activity of Cytochrome P450 2E1 (CYP2E1). [41]
Alpha-linolenic acid DMY64HE Investigative Alpha-linolenic acid decreases the activity of Cytochrome P450 2E1 (CYP2E1). [41]
(11-BETA)-11,21-DIHYDROXY-PREGN-4-ENE-3,20-DIONE DMTPQ84 Investigative (11-BETA)-11,21-DIHYDROXY-PREGN-4-ENE-3,20-DIONE increases the expression of Cytochrome P450 2E1 (CYP2E1). [47]
Cinnamic acid DM340FH Investigative Cinnamic acid decreases the activity of Cytochrome P450 2E1 (CYP2E1). [48]
Aniline DMLCAR9 Investigative Aniline decreases the activity of Cytochrome P450 2E1 (CYP2E1). [49]
Purpurin DMYWRL6 Investigative Purpurin decreases the activity of Cytochrome P450 2E1 (CYP2E1). [50]
Fluphenazine DMIT8LX Investigative Fluphenazine decreases the activity of Cytochrome P450 2E1 (CYP2E1). [21]
DIOSMETIN DM4KXIM Investigative DIOSMETIN decreases the activity of Cytochrome P450 2E1 (CYP2E1). [51]
2-(5-fluoro-1H-indol-3-yl)ethanamine DMHW5FT Investigative 2-(5-fluoro-1H-indol-3-yl)ethanamine decreases the activity of Cytochrome P450 2E1 (CYP2E1). [30]
1H-Indole-2,3-dione DMOZ91H Investigative 1H-Indole-2,3-dione increases the expression of Cytochrome P450 2E1 (CYP2E1). [52]
Thiocarbamate DMP7LJH Investigative Thiocarbamate decreases the activity of Cytochrome P450 2E1 (CYP2E1). [53]
1H-1,2,3-benzotriazol-1-amine DM9KAI5 Investigative 1H-1,2,3-benzotriazol-1-amine decreases the activity of Cytochrome P450 2E1 (CYP2E1). [54]
5-MEO-DMT DMG0EL7 Investigative 5-MEO-DMT decreases the activity of Cytochrome P450 2E1 (CYP2E1). [30]
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⏷ Show the Full List of 65 Drug(s)
1 Drug(s) Affected the Post-Translational Modifications of This DOT
Drug Name Drug ID Highest Status Interaction REF
Benzo(a)pyrene DMN7J43 Phase 1 Benzo(a)pyrene increases the methylation of Cytochrome P450 2E1 (CYP2E1). [36]
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1 Drug(s) Affected the Protein Interaction/Cellular Processes of This DOT
Drug Name Drug ID Highest Status Interaction REF
Cycloheximide DMGDA3C Investigative Cycloheximide increases the degradation of Cytochrome P450 2E1 (CYP2E1). [42]
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References

1 Integrative omics data analyses of repeated dose toxicity of valproic acid in vitro reveal new mechanisms of steatosis induction. Toxicology. 2018 Jan 15;393:160-170.
2 Comparison of HepG2 and HepaRG by whole-genome gene expression analysis for the purpose of chemical hazard identification. Toxicol Sci. 2010 May;115(1):66-79.
3 Multiple microRNAs function as self-protective modules in acetaminophen-induced hepatotoxicity in humans. Arch Toxicol. 2018 Feb;92(2):845-858.
4 Drinking-water arsenic exposure modulates gene expression in human lymphocytes from a U.S. population. Environ Health Perspect. 2008 Apr;116(4):524-31. doi: 10.1289/ehp.10861.
5 In vitro inhibition of human CYP2E1 and CYP3A by quercetin and myricetin in hepatic microsomes is not gender dependent. Toxicology. 2017 Apr 15;381:10-18. doi: 10.1016/j.tox.2017.02.012. Epub 2017 Feb 21.
6 Arsenic trioxide induces different gene expression profiles of genes related to growth and apoptosis in glioma cells dependent on the p53 status. Mol Biol Rep. 2008 Sep;35(3):421-9.
7 Proteomic analysis of hepatic effects of phenobarbital in mice with humanized liver. Arch Toxicol. 2022 Oct;96(10):2739-2754. doi: 10.1007/s00204-022-03338-7. Epub 2022 Jul 26.
8 Benzene-induced mouse hematotoxicity is regulated by a protein phosphatase 2A complex that stimulates transcription of cytochrome P4502E1. J Biol Chem. 2019 Feb 15;294(7):2486-2499.
9 An in vitro model of human acute ethanol exposure that incorporates CXCR3- and CXCR4-dependent recruitment of immune cells. Toxicol Sci. 2013 Mar;132(1):131-41.
10 A chemoproteomic platform to assess bioactivation potential of drugs. Chem Res Toxicol. 2017 Oct 16;30(10):1797-1803.
11 The inhibition of major human hepatic cytochrome P450 enzymes by 18 pesticides: comparison of the N-in-one and single substrate approaches. Toxicol In Vitro. 2013 Aug;27(5):1584-8.
12 Pharmacotoxicology of clinically-relevant concentrations of obeticholic acid in an organotypic human hepatocyte system. Toxicol In Vitro. 2017 Mar;39:93-103.
13 Characterization of primary human hepatocytes, HepG2 cells, and HepaRG cells at the mRNA level and CYP activity in response to inducers and their predictivity for the detection of human hepatotoxins. Cell Biol Toxicol. 2012 Apr;28(2):69-87.
14 Xenobiotic-metabolizing cytochromes p450 in human white adipose tissue: expression and induction. Drug Metab Dispos. 2010 Apr;38(4):679-86.
15 Roles of nitric oxide in inflammatory downregulation of human cytochromes P450. Free Radic Biol Med. 2008 Mar 15;44(6):1161-8.
16 Protective effect of vitamin C towards N-nitrosamine-induced DNA damage in the single-cell gel electrophoresis (SCGE)/HepG2 assay. Toxicol In Vitro. 2007 Oct;21(7):1311-7.
17 Chenodeoxycholic acid significantly impacts the expression of miRNAs and genes involved in lipid, bile acid and drug metabolism in human hepatocytes. Life Sci. 2016 Jul 1;156:47-56.
18 The sunless tanning agent dihydroxyacetone induces stress response gene expression and signaling in cultured human keratinocytes and reconstructed epidermis. Redox Biol. 2020 Sep;36:101594. doi: 10.1016/j.redox.2020.101594. Epub 2020 May 29.
19 D-Penicillamine targets metastatic melanoma cells with induction of the unfolded protein response (UPR) and Noxa (PMAIP1)-dependent mitochondrial apoptosis. Apoptosis. 2012 Oct;17(10):1079-94.
20 Expression and inducibility of cytochrome P450s (CYP1A1, 2B6, 2E1, 3A4) in human cord blood CD34(+) stem cell-derived differentiating neuronal cells. Toxicol Sci. 2012 Oct;129(2):392-410.
21 Inhibition of cytochrome P450 enzymes participating in p-nitrophenol hydroxylation by drugs known as CYP2E1 inhibitors. Chem Biol Interact. 2004 Apr 15;147(3):331-40.
22 Inhibition of cytochrome P450 by ethambutol in human liver microsomes. Toxicol Lett. 2014 Aug 17;229(1):33-40.
23 Inhibition of CYP2E1 catalytic activity in vitro by S-adenosyl-L-methionine. Biochem Pharmacol. 2005 Apr 1;69(7):1081-93.
24 Validated assays for human cytochrome P450 activities. Drug Metab Dispos. 2004 Jun;32(6):647-60.
25 Evaluation of the inhibition effects of apatinib on human and rat cytochrome P450. Toxicol Lett. 2018 Nov;297:1-7.
26 Examination of purported probes of human CYP2B6. Pharmacogenetics. 1997 Jun;7(3):165-79.
27 Chemical inhibitors of cytochrome P450 isoforms in human liver microsomes: a re-evaluation of P450 isoform selectivity. Eur J Drug Metab Pharmacokinet. 2011 Mar;36(1):1-16.
28 Essential requirements for substrate binding affinity and selectivity toward human CYP2 family enzymes. Arch Biochem Biophys. 2003 Jan 1;409(1):32-44.
29 Protective effects of isothiocyanates alone or in combination with vitamin C towards N-nitrosodibutylamine or N-nitrosopiperidine-induced oxidative DNA damage in the single-cell gel electrophoresis (SCGE)/HepG2 assay. J Appl Toxicol. 2008 Mar;28(2):196-204.
30 Cytochrome P450 inhibition potential of new psychoactive substances of the tryptamine class. Toxicol Lett. 2016 Jan 22;241:82-94.
31 CYP4F2 repression and a modified alpha-tocopherol (vitamin E) metabolism are two independent consequences of ethanol toxicity in human hepatocytes. Toxicol In Vitro. 2017 Apr;40:124-133.
32 Ethanol cytotoxicity to a transfected HepG2 cell line expressing human cytochrome P4502E1. J Biol Chem. 1996 Sep 27;271(39):23914-9.
33 Metabolism of N-nitrosobenzylmethylamine by human cytochrome P-450 enzymes. J Toxicol Environ Health A. 1999 Dec 10;58(7):397-411.
34 Role of human cytochrome P-450 IIE1 in the oxidation of many low molecular weight cancer suspects. Chem Res Toxicol. 1991 Mar-Apr;4(2):168-79.
35 Drug interaction study of flavonoids toward CYP3A4 and their quantitative structure activity relationship (QSAR) analysis for predicting potential effects. Toxicol Lett. 2018 Sep 15;294:27-36.
36 Air pollution and DNA methylation alterations in lung cancer: A systematic and comparative study. Oncotarget. 2017 Jan 3;8(1):1369-1391. doi: 10.18632/oncotarget.13622.
37 Analysis of glycogen synthase kinase inhibitors that regulate cytochrome P450 expression in primary human hepatocytes by activation of beta-catenin, aryl hydrocarbon receptor and pregnane X receptor signaling. Toxicol Sci. 2015 Nov;148(1):261-75.
38 Inhibition of human cytochrome P450 enzymes by 1,2-dithiole-3-thione, oltipraz and its derivatives, and sulforaphane. Chem Res Toxicol. 2000 Apr;13(4):245-52.
39 The chemopreventive effect of taxifolin is exerted through ARE-dependent gene regulation. Biol Pharm Bull. 2007 Jun;30(6):1074-9.
40 Ethanol potentiates the genotoxicity of the food-derived mammary carcinogen PhIP in human estrogen receptor-positive mammary cells: mechanistic support for lifestyle factors (cooked red meat and ethanol) associated with mammary cancer. Arch Toxicol. 2018 Apr;92(4):1639-1655.
41 The inhibitory effect of polyunsaturated fatty acids on human CYP enzymes. Life Sci. 2006 Nov 25;79(26):2432-40.
42 Characterization of cytochrome P4502E1 turnover in transfected HepG2 cells expressing human CYP2E1. Arch Biochem Biophys. 1997 May 1;341(1):25-33. doi: 10.1006/abbi.1997.9907.
43 Farnesol induces fatty acid oxidation and decreases triglyceride accumulation in steatotic HepaRG cells. Toxicol Appl Pharmacol. 2019 Feb 15;365:61-70.
44 Inhibition of human cytochrome P450 enzymes by licochalcone A, a naturally occurring constituent of licorice. Toxicol In Vitro. 2015 Oct;29(7):1569-76.
45 Effects of usnic acid exposure on human hepatoblastoma HepG2 cells in culture. J Appl Toxicol. 2012 Sep;32(9):722-30.
46 Assessment of the inhibition risk of shikonin on cytochrome P450 via cocktail inhibition assay. Toxicol Lett. 2017 Nov 5;281:74-83.
47 Prenatal ethanol exposure induces dynamic changes of expression and activity of hepatic cytochrome P450 isoforms in male rat offspring. Reprod Toxicol. 2022 Apr;109:101-108. doi: 10.1016/j.reprotox.2022.03.002. Epub 2022 Mar 14.
48 Cinnamic acid based thiazolidinediones inhibit human P450c17 and 3beta-hydroxysteroid dehydrogenase and improve insulin sensitivity independent of PPARgamma agonist activity. J Mol Endocrinol. 2004 Apr;32(2):425-36.
49 Selectivities of human cytochrome P450 inhibitors toward rat P450 isoforms: study with cDNA-expressed systems of the rat. Drug Metab Dispos. 2003 Jul;31(7):833-6.
50 Inhibition of human cytochrome P450 1B1, 1A1 and 1A2 by antigenotoxic compounds, purpurin and alizarin. Mutat Res. 2002 Oct 31;508(1-2):147-56.
51 Effects of diosmetin on nine cytochrome P450 isoforms, UGTs and three drug transporters in vitro. Toxicol Appl Pharmacol. 2017 Nov 1;334:1-7.
52 Comparison of gene expression patterns between 2,3,7,8-tetrachlorodibenzo-p-dioxin and a natural arylhydrocarbon receptor ligand, indirubin. Toxicol Sci. 2004 Jul;80(1):161-9.
53 Study on the potential way of hepatic cytotoxicity of N,N-dimethylformamide. J Biochem Mol Toxicol. 2018 Sep;32(9):e22190.
54 In vitro inhibitory effect of 1-aminobenzotriazole on drug oxidations catalyzed by human cytochrome P450 enzymes: a comparison with SKF-525A and ketoconazole. Drug Metab Pharmacokinet. 2003;18(5):287-95.
55 Human recombinant cytochrome P450 enzymes display distinct hydrogen peroxide generating activities during substrate independent NADPH oxidase reactions. Toxicol Sci. 2014 Oct;141(2):344-52. doi: 10.1093/toxsci/kfu133. Epub 2014 Jul 24.
56 Epoxidation of the methamphetamine pyrolysis product, trans-phenylpropene, to trans-phenylpropylene oxide by CYP enzymes and stereoselective glutathione adduct formation. Toxicol Appl Pharmacol. 2006 Mar 1;211(2):148-56. doi: 10.1016/j.taap.2005.06.017. Epub 2005 Jul 20.
57 Docosahexaenoic acid induces apoptosis in CYP2E1-containing HepG2 cells by activating the c-Jun N-terminal protein kinase related mitochondrial damage. J Nutr Biochem. 2007 May;18(5):348-54.
58 Apoptosis contributes to the cytotoxicity induced by amodiaquine and its major metabolite N-desethylamodiaquine in hepatic cells. Toxicol In Vitro. 2020 Feb;62:104669. doi: 10.1016/j.tiv.2019.104669. Epub 2019 Oct 16.
59 Bioactivation of lamotrigine in vivo in rat and in vitro in human liver microsomes, hepatocytes, and epidermal keratinocytes: characterization of thioether conjugates by liquid chromatography/mass spectrometry and high field nuclear magnetic resonance spectroscopy. Chem Res Toxicol. 2010 Jan;23(1):159-70. doi: 10.1021/tx9003243.
60 The role of hepatic cytochrome P450s in the cytotoxicity of dronedarone. Arch Toxicol. 2018 Jun;92(6):1969-1981. doi: 10.1007/s00204-018-2196-x. Epub 2018 Apr 3.
61 Cytochrome P(450)-dependent toxic effects of primaquine on human erythrocytes. Toxicol Appl Pharmacol. 2009 Nov 15;241(1):14-22. doi: 10.1016/j.taap.2009.07.012. Epub 2009 Jul 17.
62 ADReCS-Target: target profiles for aiding drug safety research and application. Nucleic Acids Res. 2018 Jan 4;46(D1):D911-D917. doi: 10.1093/nar/gkx899.
63 Molecular and functional characterization of drug-metabolizing enzymes and transporter expression in the novel spontaneously immortalized human hepatocyte line HC-04. Toxicol In Vitro. 2007 Dec;21(8):1390-401. doi: 10.1016/j.tiv.2007.05.003. Epub 2007 May 17.
64 Development of HepG2-derived cells expressing cytochrome P450s for assessing metabolism-associated drug-induced liver toxicity. Chem Biol Interact. 2016 Aug 5;255:63-73. doi: 10.1016/j.cbi.2015.10.009. Epub 2015 Oct 22.
65 Biotransformation of caffeine, paraxanthine, theobromine and theophylline by cDNA-expressed human CYP1A2 and CYP2E1. Pharmacogenetics. 1992 Apr;2(2):73-7.
66 Metabolism of vanoxerine, 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine, by human cytochrome P450 enzymes. Drug Metab Dispos. 2001 Sep;29(9):1216-20.
67 The cyp2e1-humanized transgenic mouse: role of cyp2e1 in acetaminophen hepatotoxicity. Drug Metab Dispos. 2005 Mar;33(3):449-57. doi: 10.1124/dmd.104.002402. Epub 2004 Dec 2.
68 Bioactivation of bisphenol A and its analogs (BPF, BPAF, BPZ and DMBPA) in human liver microsomes. Toxicol In Vitro. 2013 Jun;27(4):1267-76. doi: 10.1016/j.tiv.2013.02.016. Epub 2013 Mar 5.
69 Metabolic activation and deactivation of dietary-derived coumarin mediated by cytochrome P450 enzymes in rat and human liver preparations. J Toxicol Sci. 2021;46(8):371-378. doi: 10.2131/jts.46.371.
70 The effects of the ALDH2*1/2, CYP2E1 C1/C2 and C/D genotypes on blood ethanol elimination. Drug Chem Toxicol. 2000 May;23(2):371-9. doi: 10.1081/dct-100100122.
71 Increased cytotoxicity of food-borne mycotoxins toward human cell lines in vitro via enhanced cytochrome p450 expression using the MTT bioassay. Mycopathologia. 1999 Nov;148(2):97-102. doi: 10.1023/a:1007130923558.
72 Effects of cytochrome P450 (CYP) 2A6 gene deletion and CYP2E1 genotypes on gastric adenocarcinoma. Int J Cancer. 2002 Aug 1;100(4):425-8. doi: 10.1002/ijc.10492.
73 Acetaminophen reactive intermediates target hepatic thioredoxin reductase. Chem Res Toxicol. 2014 May 19;27(5):882-94. doi: 10.1021/tx5000443. Epub 2014 Apr 4.
74 In vitro metabolism of naphthalene by human liver microsomal cytochrome P450 enzymes. Drug Metab Dispos. 2006 Jan;34(1):176-83. doi: 10.1124/dmd.105.005785. Epub 2005 Oct 21.
75 Ellipticine oxidation and DNA adduct formation in human hepatocytes is catalyzed by human cytochromes P450 and enhanced by cytochrome b5. Toxicology. 2012 Dec 16;302(2-3):233-41. doi: 10.1016/j.tox.2012.08.004. Epub 2012 Aug 16.
76 Antioxidant and pro-oxidant effects of a manganese porphyrin complex against CYP2E1-dependent toxicity. Free Radic Biol Med. 2002 Jul 1;33(1):111-27. doi: 10.1016/s0891-5849(02)00865-1.
77 Heterologous expression of human cytochrome P450 2E1 in HepG2 cell line. World J Gastroenterol. 2003 Dec;9(12):2732-6. doi: 10.3748/wjg.v9.i12.2732.
78 The essential role of CYP2E1 in metabolism and hepatotoxicity of N,N-dimethylformamide using a novel Cyp2e1 knockout mouse model and a population study. Arch Toxicol. 2019 Nov;93(11):3169-3181. doi: 10.1007/s00204-019-02567-7. Epub 2019 Sep 9.
79 Drinking water contaminants, gene polymorphisms, and fetal growth. Environ Health Perspect. 2004 Aug;112(11):1213-6. doi: 10.1289/ehp.7003.