permethrin

Synonyms: "transpermethrin", "1RS,cis-permethrin"

Source: permethrin is a broad spectrum insecticide.

Identifiers:

IUPAC Name: (3-phenoxyphenyl)methyl-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
CAS Number: 52645-53-1
PubChem ID: 40326
InChiKey: RLLPVAHGXHCWKJ-UHFFFAOYSA-N
Canonical SMILES: CC1(C(C1C(=O)OCC2=CC(=CC=C2)OC3=CC=CC=C3)C=C(Cl)Cl)C

Structural Properties:

Molecular Formula: C₂₁H₂₀Cl₂O₃
Molecular Weight: 391.288

Pharmacophore Features:

Number of bond donors: 0
Number of bond acceptors: 1
Number of atoms different from hydrogen: 26

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2D structure (.sdf)
3D structure (.sdf)
3D structure (.mol2)
3D structure (.pdb)
3D structure (.pdbqt)

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Evidence Supporting This Chemical as an Endocrine Disruptor
TEDX List of Potential Endocrine Disruptors

Du G, Shen O, Sun H, Fei J, Lu C, Song L, Xia Y, Wang S, Wang X. 2010. Assessing hormone receptor activities of pyrethroid insecticides and their metabolites in reporter gene assays. Toxicol Sci 116(1):58-66.

Eil C, Nisula BC. 1990. The binding properties of pyrethroids to human skin fibroblast androgen receptors and to sex hormone binding globulin. J Steroid Biochem 35(3/4):409-414.

Go V, Garey J, Wolff MS, Pogo BGT. 1999. Estrogenic potential of certain pyrethroid compounds in the MCF-7 human breast carcinoma cell line. Environ Health Perspect 107(3):173-177.

Kojima H, Katsura E, Takeuchi S, Niiyama K, Kobayashi K. 2004. Screening for estrogen and androgen receptor activities in 200 pesticides by in vitro reporter gene assays using Chinese hamster ovary cells. Environ Health Perspect 112(5):524-531.

Lemaire G, Mnif W, Pascussi JM, Pillon A, Rabenoelina F, Fenet H, Gomez E, Casellas C, Nicolas JC, Cavailles V, Duchesne MJ, Balaguer P. 2006. Identification of new human pregnane X receptor ligands among pesticides using a stable reporter cell system. Toxicol Sci 91(2):501-509.