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Triflumizole

Triflumizole is an imidazole pesticide/fungicide with broad antifungal activity. Triflumizole exhibits additional activities in vitro. Triflumizole inhibits the ubiquitin-proteasome system, inducing variation into skp1 protein expression and increasing the risk for Parkinson’s disease. Triflumizole also activates PPARγ, inducing adipogenesis in vitro and in vivo. This compound also displays immunomodulatory activity, acting as an inverse agonist at retinoid acid receptor-related orphan receptor RORγ and inhibiting expression of IL-17 in vitro. Like many azole fungicides, triflumizole likely inhibits 14-α demethylase, inhibiting ergosterol production and fungal cell wall synthesis. Additionally, triflumizole may inhibit aromatase.

References PubMed ID::http://www.ncbi.nlm.nih.gov/pubmed/18978098

Cas No.

68694-11-1

Purity

≥95%

Formula

C15H15ClF3N3O

Formula Wt.

345.75

IUPAC Name

N-[4-chloro-2-(trifluoromethyl)phenyl]-1-imidazol-1-yl-2-propoxyethanimine

Melting Point

63.5°C

Appearance

Yellowish to light yellow powder

Rhodes SL, Fitzmaurice AG, Cockburn M, et al. Pesticides that inhibit the ubiquitin-proteasome system: effect measure modification by genetic variation in SKP1 in Parkinson’s disease. Environ Res. 2013 Oct;126:1-8. PMID: 23988235.

Li X, Pham HT, Janesick AS, et al. Triflumizole is an obesogen in mice that acts through peroxisome proliferator activated receptor gamma (PPARγ). Environ Health Perspect. 2012 Dec;120(12):1720-6. PMID: 23086663.

Kojima H, Muromoto R, Takahashi M, et al. Inhibitory effects of azole-type fungicides on interleukin-17 gene expression via retinoic acid receptor-related orphan receptors α and γ. Toxicol Appl Pharmacol. 2012 Mar 15;259(3):338-45. PMID: 22289359.

Kjærstad MB, Taxvig C, Nellemann C, et al. Endocrine disrupting effects in vitro of conazole antifungals used as pesticides and pharmaceuticals. Reprod Toxicol. 2010 Dec;30(4):573-82. PMID: 20708073.

Shiga N, Matano O, Goto S. Residue analysis of triflumizole and its metabolite in crops by high-performance liquid chromatography. J Chromatogr. 1987 Jun 19;396:327-35. PMID: 3624378.

GS1102