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Fluopyram

CAT: 0804-HY-119459-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-119459-01Size:5 mg
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Description
Fluopyram is an orally active succinate dehydrogenase inhibitor, antifungal and nematicide. Fluopyram inhibits succinate dehydrogenase activity, activates CAR/PXR nuclear receptors, and increases caspase-3, TNF-α and NF-κB. Fluopyram inhibits the growth of F. virguliforme, Botrytis cinerea and Alternaria solani with EC50 values of 3.35, 5.389 and 0.244 µg/mL, respectively. Fluopyram induces liver and thyroid tumor formation. Fluopyram is nephrotoxic and embryotoxic[1][2][3][4][5][6][7][8].
CAS Number
658066-35-4
Product Name Alternative
S-18982-d6 (hydrochloride)
UNSPSC
12352005
Hazard Statement
H411
Target
Caspase; Constitutive Androstane Receptor; Fungal; NF-κB; Parasite; Pregnane X Receptor (PXR) ; Succinate Dehydrogenase
Type
Reference compound
Related Pathways
Anti-infection; Apoptosis; Metabolic Enzyme/Protease; NF-κB; Vitamin D Related/Nuclear Receptor
Applications
COVID-19-immunoregulation
Field of Research
Cancer; Infection
Assay Protocol
https://www.medchemexpress.com/fluopyram.html
Purity
99.76
Solubility
DMSO : 125 mg/mL (ultrasonic)
Smiles
FC(F)(F)C1=CC(Cl)=C(CCNC(C2=C(C(F)(F)F)C=CC=C2)=O)N=C1
Molecular Formula
C16H11ClF6N2O
Molecular Weight
396.71
Precautions
H411
References & Citations
[1]Wang J, et al. Baseline Sensitivity of Fusarium virguliforme to Fluopyram Fungicide. Plant Dis. 2017 Apr;101 (4) :576-582.|[2]Schleker ASS, et al. Mode of action of fluopyram in plant-parasitic nematodes. Sci Rep. 2022 Jul 13;12 (1) :11954.|[3]Tinwell H, et al. Liver tumor formation in female rat induced by fluopyram is mediated by CAR/PXR nuclear receptor activation. Regul Toxicol Pharmacol. 2014 Dec;70 (3) :648-58.|[4]Rouquié D, et al. Thyroid tumor formation in the male mouse induced by fluopyram is mediated by activation of hepatic CAR/PXR nuclear receptors. Regul Toxicol Pharmacol. 2014 Dec;70 (3) :673-80.|[5]Zhang T, et al. Combined toxicity of trifloxystrobin and fluopyram to zebrafish embryos and the effect on bone development. Aquat Toxicol. 2024 Mar;268:106834.|[6]Liu Y, et al. Oxidative stress, intestinal damage, and cell apoptosis: Toxicity induced by fluopyram in Caenorhabditis elegans. Chemosphere. 2022 Jan;286 (Pt 3) :131830.|[7]Wang Y, et al. Different Size Formulations of Fluopyram: Preparation, Antifungal Activity, and Accumulation in the Fungal Pathogen Botrytis cinerea. Molecules. 2023 Aug 17;28 (16) :6099.|[8]Özgöçmen M, et al. The Effect of Different Doses of Fluopyram on the Kidney Tissues of Mice. Erzincan University Journal of Science and Technology, 2021, 14 (3) : 970-978.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, sealed storage, away from moisture and light)
Scientific Category
Reference compound1
Clinical Information
No Development Reported
Isoform
Caspase 3

Chemical Information

Fluopyram

Fluopyram is a member of the class of benzamides, obtained by formal condensation of the carboxy group of 2-(trifluoromethyl)benzoic acid with the amino group of 2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethylamine. A fungicide used for foiliar application and as a seed treatment in order to control botrystis, powdery mildew and other diseases. It has a role as an EC 1.3.5.1 [succinate dehydrogenase (quinone)] inhibitor and an antifungal agrochemical. It is a member of benzamides, a member of pyridines, an organochlorine compound, a member of (trifluoromethyl)benzenes and a benzamide fungicide.

CAS Number658066-35-4
PubChem CID11158353
IUPAC NameN-[2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl]-2-(trifluoromethyl)benzamide
Molecular FormulaC16H11ClF6N2O
Molecular Weight396.71
XLogP4.5
Topological Polar Surface Area42
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count8
Rotatable Bond Count4
Heavy Atom Count26
Formal Charge0
Complexity484
SMILES
C1=CC=C(C(=C1)C(=O)NCCC2=C(C=C(C=N2)C(F)(F)F)Cl)C(F)(F)F
InChI
InChI=1S/C16H11ClF6N2O/c17-12-7-9(15(18,19)20)8-25-13(12)5-6-24-14(26)10-3-1-2-4-11(10)16(21,22)23/h1-4,7-8H,5-6H2,(H,24,26)
InChIKey
KVDJTXBXMWJJEF-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Fluopyram
CAS: 658066-35-4
CID: 11158353
Formula: C16H11ClF6N2O
MW: 396.71
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight396.71
XLogP34.5
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count8
Rotatable Bond Count4
Exact Mass396.0464096
Monoisotopic Mass396.0464096
Topological Polar Surface Area42 Ų
Heavy Atom Count26
Formal Charge0
Complexity484
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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