Protein Information

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

Compound Information

Name triadimefon
CAS

Reference List

PubMed Abstract RScore(About this table)
19938956 Goetz AK, Rockett JC, Ren H, Thillainadarajah I, Dix DJ: Inhibition of rat and human steroidogenesis by triazole antifungals. Syst Biol Reprod Med. 2009 Dec;55(5-6):214-26.

Three agricultural antifungal triazoles that are known to modulate expression of cytochrome P450 (CYP) genes and enzymatic activities were tested for effects on steroidogenesis using rat in vivo (triadimefon), rat in vitro (myclobutanil and triadimefon), and human in vitro (myclobutanil, propiconazole, and triadimefon) model systems.
31(0,1,1,1) Details
19010342 Chen PJ, Padgett WT, Moore T, Winnik W, Lambert GR, Thai SF, Hester SD, Nesnow S: Three conazoles increase hepatic microsomal retinoic acid metabolism and decrease mouse hepatic retinoic acid levels in vivo. Toxicol Appl Pharmacol. 2009 Jan 15;234(2):143-55. Epub 2008 Oct 29.

The goals of this study were to examine effects of propiconazole, triadimefon, and myclobutanil, three triazole-containing conazoles, on the microsomal metabolism of atRA, the associated hepatic cytochrome P450 (P450) enzyme (s) involved in atRA metabolism, and their effects on hepatic atRA levels in vivo.
31(0,1,1,1) Details
3545213 Yoshida Y, Aoyama Y: Interaction of azole antifungal agents with cytochrome P-45014DM purified from Saccharomyces cerevisiae microsomes. Biochem Pharmacol. 1987 Jan 15;36(2):229-35.

Mechanism of action of azole antifungal agents was studied by analyzing interaction of ketoconazole, itraconazole, triadimefon and triadimenol with a purified yeast cytochrome P-450 which catalyzes lanosterol 14 alpha-demethylation (P-45014DM).
31(0,1,1,1) Details
16971344 Barton HA, Tang J, Sey YM, Stanko JP, Murrell RN, Rockett JC, Dix DJ: Metabolism of myclobutanil and triadimefon by human and rat cytochrome P450 enzymes and liver microsomes. Xenobiotica. 2006 Sep;36(9):793-806.
31(0,1,1,1) Details
17484520 Sun G, Grindstaff RD, Thai SF, Lambert GR, Tully DB, Dix DJ, Nesnow S: Induction of cytochrome P450 enzymes in rat liver by two conazoles, myclobutanil and triadimefon. Xenobiotica. 2007 Feb;37(2):180-93.
12(0,0,2,2) Details
17178687 Allen JW, Wolf DC, George MH, Hester SD, Sun G, Thai SF, Delker DA, Moore T, Jones C, Nelson G, Roop BC, Leavitt S, Winkfield E, Ward WO, Nesnow S: Toxicity profiles in mice treated with hepatotumorigenic and non-hepatotumorigenic triazole conazole fungicides: Propiconazole, triadimefon, and myclobutanil. Toxicol Pathol. 2006;34(7):853-62.

As a component of a large-scale study aimed at determining the mode (s) of action for tumorigenic conazoles, we report the results from comparative evaluations of liver and body weights, liver histopathology, cell proliferation, cytochrome P450 (CYP) activity, and serum cholesterol, high-density lipoprotein and triglyceride levels after exposure to propiconazole, triadimefon, and myclobutanil.
6(0,0,1,1) Details
11396979 Lamb DC, Cannieux M, Warrilow AG, Bak S, Kahn RA, Manning NJ, Kelly DE, Kelly SL: Plant sterol 14 alpha-demethylase affinity for azole fungicides. Biochem Biophys Res Commun. 2001 Jun 15;284(3):845-9.


Azole fungicides were thought to have much greater affinity for the fungal cytochrome P450 enzyme, sterol 14 alpha-demthylase (CYP51) than the plant orthologue.
1(0,0,0,1) Details
19541826 Mazur CS, Kenneke JF, Goldsmith MR, Brown C: Contrasting influence of NADPH and a NADPH-regenerating system on the metabolism of carbonyl-containing compounds in hepatic microsomes. Drug Metab Dispos. 2009 Sep;37(9):1801-5. Epub 2009 Jun 18.

Carbonyl containing xenobiotics may be susceptible to NADPH-dependent cytochrome P450 (P450) and carbonyl-reduction reactions.
In this study, we compared the effects of direct addition of NADPH and use of an NRS on the P450-mediated transformation of propiconazole and 11 beta-hydroxysteroid dehydrogenase type 1 (HSD1) carbonyl reduction of cortisone and the xenobiotic triadimefon in hepatic microsomes.
1(0,0,0,1) Details
16643972 Tully DB, Bao W, Goetz AK, Blystone CR, Ren H, Schmid JE, Strader LF, Wood CR, Best DS, Narotsky MG, Wolf DC, Rockett JC, Dix DJ: Gene expression profiling in liver and testis of rats to characterize the toxicity of triazole fungicides. Toxicol Appl Pharmacol. 2006 Sep 15;215(3):260-73. Epub 2006 Apr 27.

Adult male Sprague-Dawley rats were dosed for 14 days by gavage with fluconazole, myclobutanil, propiconazole, or triadimefon.
Triazole fungicides are designed to inhibit fungal cytochrome P450 (CYP) 51 enzyme but can also modulate the expression and function of mammalian CYP genes and enzymes.
1(0,0,0,1) Details
19572650 Cao X, Hu M, Zhang J, Li F, Yang Y, Liu D, Liu SH: Determination of stereoselective interaction between enantiomers of chiral gamma-aryl-1H-1,2,4-triazole derivatives and Penicillium digitatum. J Agric Food Chem. 2009 Aug 12;57(15):6914-9.

In vitro experiments were indicative of a strong inhibitory effect of all of the compounds on P. digitatum, and seven of the compounds 5 exhibited better inhibition than the commercial fungicides triadimefon and triadimenol.
These observations suggest that P. digitatum discriminates the enantiomers and that the R enantiomer better fits the active site of cytochrome P450.
1(0,0,0,1) Details
16910123 Papis E, Bernardini G, Gornati R, Prati M: Triadimefon causes branchial arch malformations in Xenopus laevis embryos. . Environ Sci Pollut Res Int. 2006 Jul;13(4):251-5.

They act by inhibiting the cytochrome P-450 conversion of lanosterol to ergosterol, thus resulting in faulty fungal cell wall synthesis.
1(0,0,0,1) Details
16730040 Goetz AK, Bao W, Ren H, Schmid JE, Tully DB, Wood C, Rockett JC, Narotsky MG, Sun G, Lambert GR, Thai SF, Wolf DC, Nesnow S, Dix DJ: Gene expression profiling in the liver of CD-1 mice to characterize the hepatotoxicity of triazole fungicides. Toxicol Appl Pharmacol. 2006 Sep 15;215(3):274-84. Epub 2006 May 26.

Besides organ weight, histopathology, and cytochrome P450 (CYP) enzyme induction, DNA microarrays were used to generate gene expression profiles and hypotheses on potential mechanisms of action for this class of chemicals.
Adult male CD-1 mice were exposed daily for 14 days to fluconazole, myclobutanil, propiconazole, or triadimefon at three dose levels by oral gavage.
1(0,0,0,1) Details
20026392 Crowell SR, Henderson WM, Fisher JW, Kenneke JF: Gender and species differences in triadimefon metabolism by rodent hepatic microsomes. Toxicol Lett. 2010 Mar 1;193(1):101-7. Epub 2009 Dec 22.

Understanding the potential differences in metabolic capacity and kinetics between various common laboratory species as well as between genders is an important facet of chemical risk assessment that is often overlooked, particularly for chemicals which undergo non-cytochrome P450 mediated metabolism.
1(0,0,0,1) Details