Details of Xenobiotics-DME Interaction (XEOTIC)

General Information of Drug-Metabolizing Enzyme (DME ID: DME0227)
DME Name Retinoic acid 4-hydroxylase 26A1 (CYP26A1), Homo sapiens DME Info
UniProt ID
CP26A_HUMAN
EC Number    EC: 1.14.13.-     (Click to Show/Hide the Complete EC Tree)
Oxidoreductase
Oxygen paired donor oxidoreductase
NADH/NADPH donor oxidoreductase
EC: 1.14.13.-
Lineage    Species: Homo sapiens     (Click to Show/Hide the Complete Species Lineage)
Kingdom: Metazoa
Phylum: Chordata
Class: Mammalia
Order: Primates
Family: Hominidae
Genus: Homo
Species: Homo sapiens
Interactome
Interactions between Xenobiotics and DME (XEOTIC)
      Fungicide(s), Herbicide(s) or Insecticide(s)
                  Pesticide/Insecticide Click to Show/Hide the Full List of Xenobiotics:        2 Xenobiotics
                              Dieldrin Click to Show/Hide the Detail Induction
                                 XEOTIC ID XEO01051   XEOTIC Info Gene Form mRNA
                                 Classification Pesticide/Insecticide
                                 DME Modulation Dieldrin up-regulates the expression of DME CYP26A1 [1]
                              Endosulfan Click to Show/Hide the Detail Induction
                                 XEOTIC ID XEO01074   XEOTIC Info Gene Form mRNA
                                 Classification Pesticide/Insecticide
                                 DME Modulation Endosulfan up-regulates the expression of DME CYP26A1 [2], [1]
      Health or Environmental Toxicant(s)
                  Acute Toxic Substance Click to Show/Hide the Full List of Xenobiotics:        1 Xenobiotics
                              Fipronil Click to Show/Hide the Detail Induction
                                 XEOTIC ID XEO01302   XEOTIC Info Gene Form mRNA
                                 Classification Acute Toxic Substance
                                 DME Modulation Fipronil up-regulates the expression of DME CYP26A1 [3]
                  Carcinogen Click to Show/Hide the Full List of Xenobiotics:        1 Xenobiotics
                              Aflatoxin B1 Click to Show/Hide the Detail Induction
                                 XEOTIC ID XEO00806   XEOTIC Info Gene Form mRNA
                                 Classification Carcinogen-mycotoxin
                                 DME Modulation Aflatoxin B1 up-regulates the expression of DME CYP26A1 [4]
                  Health Hazard/Toxicant Click to Show/Hide the Full List of Xenobiotics:        7 Xenobiotics
                              Chlordan Click to Show/Hide the Detail Induction
                                 XEOTIC ID XEO01245   XEOTIC Info Gene Form mRNA
                                 Classification Health and Environmental Toxicant
                                 DME Modulation Chlordan up-regulates the expression of DME CYP26A1 [1]
                              4-(2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-1-propenyl)benzoic acid Click to Show/Hide the Detail Induction
                                 XEOTIC ID XEO01145   XEOTIC Info Gene Form mRNA
                                 Classification Health Hazard
                                 DME Modulation 4-(2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-1-propenyl)benzoic acid up-regulates the expression of DME CYP26A1 [1]
                              Butyraldehyde Click to Show/Hide the Detail Induction
                                 XEOTIC ID XEO00999   XEOTIC Info Gene Form mRNA
                                 Classification Health Hazard
                                 DME Modulation Butyraldehyde up-regulates the expression of DME CYP26A1 [5]
                              CD-437 Click to Show/Hide the Detail Induction
                                 XEOTIC ID XEO01241   XEOTIC Info Gene Form mRNA
                                 Classification Health Hazard
                                 DME Modulation CD-437 up-regulates the expression of DME CYP26A1 [6]
                              Diethylhexyl phthalate Click to Show/Hide the Detail Inhibition
                                 XEOTIC ID XEO01004   XEOTIC Info Gene Form mRNA
                                 Classification Health Hazard
                                 DME Modulation Diethylhexyl phthalate inhibits the expression of DME CYP26A1 [7]
                              Retinaldehyde Click to Show/Hide the Detail Induction
                                 XEOTIC ID XEO01454   XEOTIC Info Gene Form Protein
                                 Classification Health Hazard
                                 DME Modulation Retinaldehyde induces the drug-metabolizing activity of DME CYP26A1 [8]
                              Tris(1,3-dichloro-2-propyl)phosphate Click to Show/Hide the Detail Inhibition
                                 XEOTIC ID XEO01031   XEOTIC Info Gene Form mRNA
                                 Classification Health Hazard
                                 DME Modulation Tris(1,3-dichloro-2-propyl)phosphate inhibits the expression of DME CYP26A1 [9], [10]
      Natural Product(s), Extract(s) or Medicine(s)
                  Natural Product Click to Show/Hide the Full List of Xenobiotics:        2 Xenobiotics
                              4-oxoretinoic acid Click to Show/Hide the Detail Induction
                                 XEOTIC ID XEO01154   XEOTIC Info Gene Form mRNA
                                 Classification Natural Product
                                 DME Modulation 4-oxoretinoic acid up-regulates the expression of DME CYP26A1 [11]
                              Walrycin A Click to Show/Hide the Detail Induction
                                 XEOTIC ID XEO01498   XEOTIC Info Gene Form mRNA
                                 Classification Natural Product
                                 DME Modulation Walrycin A up-regulates the expression of DME CYP26A1 [12]
                  Plant Extract Click to Show/Hide the Full List of Xenobiotics:        1 Xenobiotics
                              Plant extracts Click to Show/Hide the Detail Inhibition
                                 XEOTIC ID XEO01574   XEOTIC Info Gene Form Protein
                                 Classification Plant Extract
                                 DME Modulation Plant extracts inhibits the drug-metabolizing activity of DME CYP26A1 [13]
      Pharmaceutical Agent(s)
                  Approved/Marketed Drug Click to Show/Hide the Full List of Xenobiotics:      13 Xenobiotics
                              Acetaminophen Click to Show/Hide the Detail Inhibition
                                 XEOTIC ID XEO00217   XEOTIC Info Gene Form mRNA
                                 Classification Drug Approved by US FDA
                                 DME Modulation Acetaminophen inhibits the expression of DME CYP26A1 [14]
                              Alitretinoin Click to Show/Hide the Detail Induction
                                 XEOTIC ID XEO00167   XEOTIC Info Gene Form mRNA
                                 Classification Drug Approved by US FDA
                                 DME Modulation Alitretinoin up-regulates the expression of DME CYP26A1 [15]
                              Amiodarone hydrochloride Click to Show/Hide the Detail Induction
                                 XEOTIC ID XEO00277   XEOTIC Info Gene Form mRNA
                                 Classification Drug Approved by US FDA
                                 DME Modulation Amiodarone hydrochloride up-regulates the expression of DME CYP26A1 [16]
                              Belinostat Click to Show/Hide the Detail Induction
                                 XEOTIC ID XEO00193   XEOTIC Info Gene Form mRNA
                                 Classification Drug Approved by US FDA
                                 DME Modulation Belinostat up-regulates the expression of DME CYP26A1 [17]
                              Beta carotene Click to Show/Hide the Detail Induction
                                 XEOTIC ID XEO00401   XEOTIC Info Gene Form mRNA
                                 Classification Drug Approved by US FDA
                                 DME Modulation Beta carotene up-regulates the expression of DME CYP26A1 [18], [19]
                              Bexarotene Click to Show/Hide the Detail Induction
                                 XEOTIC ID XEO00144   XEOTIC Info Gene Form mRNA
                                 Classification Drug Approved by US FDA
                                 DME Modulation Bexarotene up-regulates the expression of DME CYP26A1 [20]
                              Calcitriol Click to Show/Hide the Detail Induction
                                 XEOTIC ID XEO00184   XEOTIC Info Gene Form mRNA
                                 Classification Drug Approved by US FDA
                                 DME Modulation Calcitriol up-regulates the expression of DME CYP26A1 [21]
                              Isotretinoin Click to Show/Hide the Detail Induction
                                 XEOTIC ID XEO00186   XEOTIC Info Gene Form mRNA
                                 Classification Drug Approved by US FDA
                                 DME Modulation Isotretinoin up-regulates the expression of DME CYP26A1 [22]
                              Ketoconazole Click to Show/Hide the Detail Inhibition
                                 XEOTIC ID XEO00251   XEOTIC Info Gene Form Protein
                                 Classification Drug Approved by US FDA
                                 DME Modulation Ketoconazole inhibits the drug-metabolizing activity of DME CYP26A1 [11]
                              Nicotine polacrilex Click to Show/Hide the Detail Inhibition
                                 XEOTIC ID XEO00312   XEOTIC Info Gene Form mRNA
                                 Classification Drug Approved by US FDA
                                 DME Modulation Nicotine polacrilex inhibits the expression of DME CYP26A1 [23]
                              Tretinoin Click to Show/Hide the Detail Induction
                                 XEOTIC ID XEO00253   XEOTIC Info Gene Form mRNA
                                 Classification Drug Approved by US FDA
                                 DME Modulation Tretinoin up-regulates the expression of DME CYP26A1 [24]
                              Valproic acid Click to Show/Hide the Detail Inhibition
                                 XEOTIC ID XEO00029   XEOTIC Info Gene Form mRNA
                                 Classification Drug Approved by US FDA
                                 DME Modulation Valproic acid inhibits the expression of DME CYP26A1 [25]
                              Vorinostat Click to Show/Hide the Detail Inhibition
                                 XEOTIC ID XEO00079   XEOTIC Info Gene Form mRNA
                                 Classification Drug Approved by US FDA
                                 DME Modulation Vorinostat inhibits the expression of DME CYP26A1 [17]
                  Drug in Phase 3 Clinical Trial Click to Show/Hide the Full List of Xenobiotics:        1 Xenobiotics
                              Fenretinide Click to Show/Hide the Detail Induction
                                 XEOTIC ID XEO00565   XEOTIC Info Gene Form mRNA
                                 Classification Highest Clinical Status: Phase 3
                                 DME Modulation Fenretinide up-regulates the expression of DME CYP26A1 [26]
                  Drug in Phase 2 Clinical Trial Click to Show/Hide the Full List of Xenobiotics:        3 Xenobiotics
                              Liarozole Click to Show/Hide the Detail Inhibition
                                 XEOTIC ID XEO00607   XEOTIC Info Gene Form Protein
                                 Classification Highest Clinical Status: Phase 2/3
                                 DME Modulation Liarozole inhibits the drug-metabolizing activity of DME CYP26A1 (IC50 = 0.54 microM) [27]
                              MS-275 Click to Show/Hide the Detail Induction
                                 XEOTIC ID XEO00581   XEOTIC Info Gene Form mRNA
                                 Classification Highest Clinical Status: Phase 2
                                 DME Modulation MS-275 up-regulates the expression of DME CYP26A1 [17]
                              R-115866 Click to Show/Hide the Detail Inhibition
                                 XEOTIC ID XEO00666   XEOTIC Info Gene Form Protein
                                 Classification Highest Clinical Status: Phase 2
                                 DME Modulation R-115866 inhibits the drug-metabolizing activity of DME CYP26A1 in Spodoptera frugiperda (Sf9) cell (IC50 = 0.0051 microM) [28]
                  Drug in Phase 1 Clinical Trial Click to Show/Hide the Full List of Xenobiotics:        1 Xenobiotics
                              Trichostatin A Click to Show/Hide the Detail Induction
                                 XEOTIC ID XEO01492   XEOTIC Info Gene Form Protein
                                 Classification Highest Clinical Status: Phase 1
                                 DME Modulation Trichostatin A induces the drug-metabolizing activity of DME CYP26A1 [29], [30]
                  Preclinical/Patented Drug Click to Show/Hide the Full List of Xenobiotics:        1 Xenobiotics
                              AM-580 Click to Show/Hide the Detail Induction
                                 XEOTIC ID XEO00728   XEOTIC Info Gene Form mRNA
                                 Classification Patented Pharmaceutical Agent
                                 DME Modulation AM-580 up-regulates the expression of DME CYP26A1 [6]
      Other Chemical Compound(s) or Element(s)
                  Chemical Compound Click to Show/Hide the Full List of Xenobiotics:        1 Xenobiotics
                              Pentanal Click to Show/Hide the Detail Induction
                                 XEOTIC ID XEO01034   XEOTIC Info Gene Form mRNA
                                 Classification Chemical Compound
                                 DME Modulation Pentanal up-regulates the expression of DME CYP26A1 [17]
References
1 Activation of retinoic acid receptor-dependent transcription by organochlorine pesticides. Toxicol Appl Pharmacol. 2005 Jan 1;202(1):38-49.
2 An integrated genomic and proteomic approach to identify signatures of endosulfan exposure in hepatocellular carcinoma cells. Pestic Biochem Physiol. 2015 Nov;125:8-16.
3 Impact of environmental chemicals on the transcriptome of primary human hepatocytes: potential for health effects. J Biochem Mol Toxicol. 2016 Aug;30(8):375-95.
4 Aflatoxins upregulate CYP3A4 mRNA expression in a process that involves the PXR transcription factor. Toxicol Lett. 2011 Aug 28;205(2):146-53.
5 Integrated analysis of microRNA and mRNA expression profiles highlights aldehyde-induced inflammatory responses in cells relevant for lung toxicity. Toxicology. 2015 Aug 6;334:111-21.
6 Induction of the cytochrome P450 gene CYP26 during mucous cell differentiation of normal human tracheobronchial epithelial cells. Mol Pharmacol. 2000 Sep;58(3):483-90.
7 Di-(2-ethylhexyl)-phthalate induces apoptosis via the PPARgama/PTEN/AKT pathway in differentiated human embryonic stem cells. Food Chem Toxicol. 2019 Sep;131:110552.
8 Differential regulation of CYP1A1 and CYP1B1 expression in resveratrol-treated human medulloblastoma cells. Neurosci Lett. 2004 Jun 17;363(3):257-61.
9 Interleukin-19 as a translational indicator of renal injury. Arch Toxicol. 2015 Jan;89(1):101-6.
10 Transcriptomics hit the target: monitoring of ligand-activated and stress response pathways for chemical testing. Toxicol In Vitro. 2015 Dec 25;30(1 Pt A):7-18.
11 Induction of CYP26A1 by metabolites of retinoic acid: evidence that CYP26A1 is an important enzyme in the elimination of active retinoids. Mol Pharmacol. 2015;87(3):430-41.
12 Discrimination of vanadium from zinc using gene profiling in human bronchial epithelial cells. Environ Health Perspect. 2005 Dec;113(12):1747-54.
13 Effects of Andrographis paniculata extract and Andrographolide on hepatic cytochrome P450 mRNA expression and monooxygenase activities after in vivo administration to rats and in vitro in rat and human hepatocyte cultures. Chem Biol Interact. 2009 May 15;179(2-3):247-55.
14 Gene expression analysis of precision-cut human liver slices indicates stable expression of ADME-Tox related genes. Toxicol Appl Pharmacol. 2011 May 15;253(1):57-69.
15 Regulation of a highly specific retinoic acid-4-hydroxylase (CYP26A1) enzyme and all-trans-retinoic acid metabolism in human intestinal, liver, endothelial, and acute promyelocytic leukemia cells. Leuk Lymphoma. 2005 Oct;46(10):1497-506.
16 Identification by automated screening of a small molecule that selectively eliminates neural stem cells derived from hESCs but not dopamine neurons. PLoS One. 2009 Sep 23;4(9):e7155.
17 A transcriptome-based classifier to identify developmental toxicants by stem cell testing: design, validation and optimization for histone deacetylase inhibitors. Arch Toxicol. 2015 Sep;89(9):1599-618.
18 Co-cultures of enterocytes and hepatocytes for retinoid transport and metabolism. Toxicol In Vitro. 2012 Dec;26(8):1256-64.
19 Beta-Carotene conversion into vitamin A in human retinal pigment epithelial cells. Invest Ophthalmol Vis Sci. 2005 Oct;46(10):3562-9.
20 Identification of biomarkers modulated by the rexinoid LGD1069 (bexarotene) in human breast cells using oligonucleotide arrays. Cancer Res. 2006 Dec 15;66(24):12009-18.
21 Vitamin D3 transactivates the zinc and manganese transporter SLC30A10 via the Vitamin D receptor. J Steroid Biochem Mol Biol. 2016 Oct;163:77-87.
22 Gene microarray analysis of human renal cell carcinoma: the effects of HDAC inhibition and retinoid treatment. Cancer Biol Ther. 2008 Oct;7(10):1607-18.
23 Gene expression changes in human lung cells exposed to arsenic, chromium, nickel or vanadium indicate the first steps in cancer. Metallomics. 2012 Aug;4(8):784-93.
24 A blend of polyphenolic compounds explains the stimulatory effect of red wine on human endothelial NO synthase. Nitric Oxide. 2005 Mar;12(2):97-104.
25 Ethyl carbamate induces cell death through its effects on multiple metabolic pathways. Chem Biol Interact. 2017 Nov 1;277:21-32.
26 Nuclear retinoid receptors are involved in N-(4-hydroxyphenyl) retinamide (Fenretinide)-induced gene expression and growth inhibition in HL-60 acute myeloid leukemia cells. Leuk Lymphoma. 2004 May;45(5):979-85.
27 Synthesis and biological evaluation of 3-(1H-imidazol- and triazol-1-yl)-2,2-dimethyl-3-[4-(naphthalen-2-ylamino)phenyl]propyl derivatives as small molecule inhibitors of retinoic acid 4-hydroxylase (CYP26). J Med Chem. 2011 Oct 13;54(19):6803-11.
28 Development and characterization of novel and selective inhibitors of cytochrome P450 CYP26A1, the human liver retinoic acid hydroxylase. J Med Chem. 2016 Mar 24;59(6):2579-95.
29 Retinoid receptors in human breast carcinoma: possible modulators of in situ estrogen metabolism. Breast Cancer Res Treat. 2001 Jan;65(1):31-40.
30 Organotin compounds enhance 17beta-hydroxysteroid dehydrogenase type I activity in human choriocarcinoma JAr cells: potential promotion of 17beta-estradiol biosynthesis in human placenta. Biochem Pharmacol. 2006 Apr 28;71(9):1349-57.

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