Protein Information

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

Compound Information

Name propiconazole
CAS

Reference List

PubMed Abstract RScore(About this table)
3789734 Sanglard D, Kappeli O, Fiechter A: The distinction of different types of cytochromes P-450 from the yeasts Candida tropicalis and Saccharomyces uvarum. Arch Biochem Biophys. 1986 Nov 15;251(1):276-86.

One cytochrome P-450 form catalyzed the 14 alpha-demethylation of lanosterol and bound propiconazole with an equimolar ratio.
145(1,3,3,5) Details
3097533 Niggli B, Friederich U, Hann D, Wurgler FE: Endogenous promutagen activation in the yeast Saccharomyces cerevisiae: factors influencing aflatoxin B1 mutagenicity. Mutat Res. 1986 Dec;175(4):223-9.

The fact that different cytochrome P-450 inhibitors (ellipticine, penconazole and propiconazole as yeast-specific P-450 inhibitors) abolished the AFB1-induced mutagenicity indicates that activation of the promutagen AFB1 depends on the cytochrome P-450-catalyzed electron-transfer reactions.
82(1,1,1,2) Details
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
15603923 Sun G, Thai SF, Tully DB, Lambert GR, Goetz AK, Wolf DC, Dix DJ, Nesnow S: Propiconazole-induced cytochrome P450 gene expression and enzymatic activities in rat and mouse liver. Toxicol Lett. 2005 Feb 15;155(2):277-87.
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
10336094 Egaas E, Sandvik M, Fjeld E, Kallqvist T, Goksoyr A, Svensen A: Some effects of the fungicide propiconazole on cytochrome P450 and glutathione S-transferase in brown trout (Salmo trutta). Comp Biochem Physiol C Pharmacol Toxicol Endocrinol. 1999 Mar;122(3):337-44.
6(0,0,1,1) Details
7986207 Ronis MJ, Ingelman-Sundberg M, Badger TM: Induction, suppression and inhibition of multiple hepatic cytochrome P450 isozymes in the male rat and bobwhite quail (Colinus virginianus) by ergosterol biosynthesis inhibiting fungicides (EBIFs). Biochem Pharmacol. 1994 Nov 16;48(10):1953-65.

In the current study, we examined the effects of two EBIFs in clinical use, clotrimazole and ketoconazole, and two agricultural EBIFs, propiconazole and vinclozolin, on hepatic monooxygenase activities and P450 apoprotein expression in the male Sprague-Dawley rat and the male bobwhite quail.
3(0,0,0,3) Details
2561184 Vanden Bossche H, Marichal P, Gorrens J, Coene MC, Willemsens G, Bellens D, Roels I, Moereels H, Janssen PA: Biochemical approaches to selective antifungal activity. Mycoses. 1989;32 Suppl 1:35-52.

Azole antifungals (e.g. the imidazoles: miconazole, clotrimazole, bifonazole, imazalil, ketoconazole, and the triazoles: diniconazole, triadimenol, propiconazole, fluconazole and itraconazole) inhibit in fungal cells the 14 alpha-demethylation of lanosterol or 24-methylenedihydrolanosterol.
The consequent inhibition of ergosterol synthesis originates from binding of the unsubstituted nitrogen (N-3 or N-4) of their imidazole or triazole moiety to the heme iron and from binding of their N-1 substituent to the apoprotein of a cytochrome P-450 (P-450 (14) DM) of the endoplasmic reticulum.
1(0,0,0,1) Details
9972464 Ronis MJ, Celander M, Badger TM: Cytochrome P450 enzymes in the kidney of the bobwhite quail (Colinus virginianus): induction and inhibition by ergosterol biosynthesis inhibiting fungicides. Comp Biochem Physiol C Pharmacol Toxicol Endocrinol. 1998 Nov;121(1-3):221-9.

The effects of treatment with the fungicides: propiconazole, vinclozolin, clotrimazole and ketoconazole were examined.
3(0,0,0,3) 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
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
9972451 Walker CH: Avian forms of cytochrome P450. . Comp Biochem Physiol C Pharmacol Toxicol Endocrinol. 1998 Nov;121(1-3):65-72.

Fungicides which act as ergosterol biosynthesis inhibitors (EBI fungicides) such as prochloraz and propiconazole potentiate the toxicity of certain phosphorothionates to birds.
1(0,0,0,1) Details
12408568 Almli B, Egaas E, Christiansen A, Eklo OM, Lode O, Kallqvist T: Effects of three fungicides alone and in combination on glutathione S-transferase activity (GST) and cytochrome P-450 (CYP 1A1) in the liver and gill of brown trout (Salmo trutta). Mar Environ Res. 2002 Sep-Dec;54(3-5):237-40.

In order to evaluate the gill glutathione S-transferase (GST) activity as a biomarker of effect of fungicide exposure in juvenile brown trout (Salmo trutta), the fungicides propiconazole [(R,S)-1-[2-(2,4-diclophenyl)-4-propyl-1,3-dioolan-2-ylmetyl]-1H-1,2,4-tri azole] and fenpropimorph [(+/-)-cis-4-[3-(4-tert-butylphenyl)-2-metyl propyl]-2,6 dimetylmorfolinc] were administrated in the water separately and together in a static system (80 microg/l for each pesticide) for 5 days.
1(0,0,0,1) Details
7871535 Ronis MJ, Badger TM: Toxic interactions between fungicides that inhibit ergosterol biosynthesis and phosphorothioate insecticides in the male rat and bobwhite quail (Colinus virginianus). Toxicol Appl Pharmacol. 1995 Feb;130(2):221-8.

Male Sprague-Dawley rats (300 g) were administered corn oil or the following EBIFs: propiconazole (400 mg/kg/day), vinclozolin (400 mg/kg/day), clotrimazole (100 mg/kg/day), or ketoconazole (100 mg/kg/day) for 3 days by oral gavage.
Induction of cytochrome P450 in rat and quail liver by EBIFs was accompanied by enhanced oxidative desulfuration of malathion, parathion, and diazinon to toxic oxon products.
1(0,0,0,1) Details
3190755 Leslie C, Reidy GF, Stacey NH: The effects of propiconazole on hepatic xenobiotic biotransformation in the rat. Biochem Pharmacol. 1988 Nov 1;37(21):4177-81.

Induction was seen for cytochrome P-450, ethoxyresorufin-O-deethylase, ethoxycoumarin-O-deethylase, aldrin epoxidase, aminopyrine N-demethylase and microsomal expoxide hydrolase activities.
1(0,0,0,1) Details
18024679 Luo CX, Schnabel G: The cytochrome P450 lanosterol 14alpha-demethylase gene is a demethylation inhibitor fungicide resistance determinant in Monilinia fructicola field isolates from Georgia. Appl Environ Microbiol. 2008 Jan;74(2):359-66. Epub 2007 Nov 16.

Gene expression was not induced in mycelium of DMI-R or DMI-S isolates treated with 0.3 mug of propiconazole/ml.
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