Protein Information

Name cis 3
Synonyms ATOD 4; ATOD4; CIS 3; CIS3; Cish3; Cytokine inducible SH2 protein 3; SOCS 3; SOCS3…

Compound Information

Name cypermethrin
CAS cyano(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate

Reference List

PubMed Abstract RScore(About this table)
3376131 Hijzen TH, De Beun R, Slangen JL: Effects of pyrethroids on the acoustic startle reflex in the rat. Toxicology. 1988 May;49(2-3):271-6.

The effects of NAK 1901 (Pentafluorbenzyl (1R, cis)-3-(2,2-dichlorovinyl)-2,2-dimethyl-cyclopropane-carboxylate) and cypermethrin ((S,R)-alpha-cyano-3-phenoxybenzyl-2,2-dimethyl (1R, 1S, cis, trans)-3-(2,2-dichlorovinyl) cyclopropane-carboxylate) (RU 24 501) on amplitude and prepulse inhibition of the acoustic startle reflex were studied in male Wistar rats.
81(1,1,1,1) Details
17701700 Domingues VF, Priolo G, Alves AC, Cabral MF, Delerue-Matos C: Adsorption behavior of alpha -cypermethrin on cork and activated carbon. J Environ Sci Health B. 2007 Aug;42(6):649-54.

Studies were undertaken to determine the adsorption behavior of alpha -cypermethrin [R)-alpha -cyano-3-phenoxybenzyl (1S)-cis-3-(2,2-dichlorovinyl)-2,2-dimethylcycloprop anecarboxylate, and (S)-alpha-cyano-3-phenoxybenzyl (1R)-cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate] in solutions on granules of cork and activated carbon (GAC).
6(0,0,1,1) Details
12191872 Schettgen T, Heudorf U, Drexler H, Angerer J: Pyrethroid exposure of the general population-is this due to diet. Toxicol Lett. 2002 Aug 5;134(1-3):141-5.

The 95th per thousand for the urinary metabolites of pyrethroids, such as permethrin and cypermethrin, cis and trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane-1-carboxylic acid (cis-DCCA and trans-DCCA), was determined to be 0.5 and 1.4 microg/l, respectively. 95th per thousand for cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropane-1-carboxylic acid (DBCA), a specific metabolite of deltamethrin, and 4-fluoro-3-phenoxybenzoic acid (F-PBA), a metabolite of cyfluthrin, were 0.3 and 0.27 microg/l, respectively.
31(0,1,1,1) Details
12827372 Hardt J, Angerer J: Biological monitoring of workers after the application of insecticidal pyrethroids. Int Arch Occup Environ Health. 2003 Sep;76(7):492-8. Epub 2003 Jun 24.

METHODS: Thirty-six workers who applied insecticides and other pesticides in Germany collected samples of their urine (24 h) after having used various pyrethroids (alpha-cypermethrin, cypermethrin, cyfluthrin, deltamethrin, tau-fluvalinate, permethrin, lambda-cyhalothrin) in agriculture, greenhouses or indoor pest control.
Biological monitoring was carried out and metabolites were analysed in 61 urine samples by GC-MS: cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane-1-carboxylic acid and trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane-1-carboxylic acid ( cis-Cl (2) CA and trans-Cl (2) CA), cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropane-1-carboxylic acid ( cis-Br (2) CA), 3-phenoxybenzoic acid (3-PBA) and 4-fluoro-3-phenoxybenzoic acid (FPBA).
1(0,0,0,1) Details
16893784 Raikwar MK, Nag SK: Phototransformation of alphacypermethrin as thin film on glass and soil surface. J Environ Sci Health B. 2006;41(6):973-88.


Photodegradation of alphacypermethrin ((RS)-alpha cyano-3-phenoxy benzyl (1RS) cis-3-(2,2,dichlorovinyl)-2,2-dimethyl cyclopropane carboxylate) was studied as a thin film on glass surface and on black and red soil surfaces.
1(0,0,0,1) Details
9300857 Angerer J, Ritter A: Determination of metabolites of pyrethroids in human urine using solid-phase extraction and gas chromatography-mass spectrometry. J Chromatogr B Biomed Sci Appl. 1997 Aug 1;695(2):217-26.

The described method permits the determination of the five most important metabolites of the pyrethroids permethrin, cypermethrin, deltamethrin, lambda-cyhalothrin, fenvalerate, phenothrin and beta-cyfluthrin in human urine in one run.
The major urinary metabolites of these substances are cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane-1-carboxylic acid (cis-Cl2CA), trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane-1-carboxylic acid (trans-Cl2CA), cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropane-1-carboxylic acid (Br2CA), fluoro-3-phenoxybenzoic acid (F-PBA) and 3-phenoxybenzoic acid (3-PBA).
1(0,0,0,1) Details
12236674 Lee HJ, Shan G, Watanabe T, Stoutamire DW, Gee SJ, Hammock BD: Enzyme-linked immunosorbent assay for the pyrethroid deltamethrin. J Agric Food Chem. 2002 Sep 25;50(20):5526-32.

Two haptens, cyano [3-(4-aminophenoxy) phenyl] methyl 1R-cis-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylate and 3-[(+/-)-cyano [1R-cis-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropan ecarbonyloxy] methyl] phenoxyacetic acid, were synthesized and conjugated with thyroglobulin as immunogens.
This ELISA assay had relatively low cross-reactivities with other major pyrethroids, such as permethrin, phenothrin, bioresmethrin, cyfluthrin, and cypermethrin.
1(0,0,0,1) Details
12708229 Leng G, Ranft U, Sugiri D, Hadnagy W, Berger-Preiss E, Idel H: Pyrethroids used indoors--biological monitoring of exposure to pyrethroids following an indoor pest control operation. Int J Hyg Environ Health. 2003 Mar;206(2):85-92.

Biological monitoring was performed in 57 persons before (T1) as well as 1 day (T2), 3 days (T3), 4-6 months (T4), and 10-12 months (T5) following a pest control operation (PCO) with pyrethroid containing products such as cyfluthrin, cypermethrin, deltamethrin or permethrin.
The respective metabolities cis- and trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylic acid (DCCA), cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropane carboxylic acid (DBCA), 3-phenoxybenzoic acid (3-PBA) and fluorophenoxybenzoic acid (FPBA) were measured in urine using GC/MS.
1(0,0,0,1) Details
11726184 Shan G, Hammock BD: Development of sensitive esterase assays based on alpha-cyano-containing esters. Anal Biochem. 2001 Dec 1;299(1):54-62.


Two substrates, R/S-acetic acid cyano-(6-methoxynaphthalen-2-yl)-methyl ester (compound I) and trans/cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid R/S-cyano-(6-methoxynaphthalen-2-yl)-methyl ester (compound II), were synthesized and evaluated as substrates.
1(0,0,0,1) Details
8719178 Dianovsky J, Sivikova K: In vivo and in vitro cytogenetic effect of supermethrin. Biomed Environ Sci. 1995 Dec;8(4):359-66.


The synthetic pyrethroid insecticide supermethrin (RS)-alpha-cyano-3-phenoxybenzyl-(1RS)-cis-3 (2, 2-dichlorvinyl)-2, 2-dimethyl cyklopropane carboxylate, was tested for its clastogenic ability by in vivo and in vitro assays.
1(0,0,0,1) Details
15639450 Leng G, Gries W: Simultaneous determination of pyrethroid and pyrethrin metabolites in human urine by gas chromatography-high resolution mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Jan 25;814(2):285-94.

A new developed gas chromatographic-high resolution mass spectrometric method for the sensitive simultaneous determination of trans-chrysanthemumdicarboxylic acid, cis- and trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylic acid, cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropane carboxylic acid, 3-phenoxybenzoic acid and 4-fluoro-3-phenoxybenzoic acid in human urine is presented.
These metabolites are biomarkers for an exposure to pyrethrum, allethrin, resmethrin, phenothrin, tetramethrin, cyfluthrin, cypermethrin, deltamethrin or permethrin.
1(0,0,0,1) Details