Protein Information

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

Compound Information

Name pyrethrins
CAS pyrethrins

Reference List

PubMed Abstract RScore(About this table)
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.
1(0,0,0,1) Details
15195798 Baker SE, Olsson AO, Barr DB: Isotope dilution high-performance liquid chromatography-tandem mass spectrometry method for quantifying urinary metabolites of synthetic pyrethroid insecticides. Arch Environ Contam Toxicol. 2004 Apr;46(3):281-8.


This paper describes a method for measuring cis- and trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane-1-carboxylic acids (cis-DCCA and trans-DCCA), cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropane-1-carboxylic acid (DBCA), 3-phenoxybenzoic acid (3PBA), and 4-fluoro-3-phenoxybenzoic acid (4F3PBA) in human urine.
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.
1(0,0,0,1) 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).
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.


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
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.
1(0,0,0,1) Details
17576809 Godin SJ, Crow JA, Scollon EJ, Hughes MF, DeVito MJ, Ross MK: Identification of rat and human cytochrome p450 isoforms and a rat serum esterase that metabolize the pyrethroid insecticides deltamethrin and esfenvalerate. Drug Metab Dispos. 2007 Sep;35(9):1664-71. Epub 2007 Jun 18.


The metabolism of (alphaS)-cyano-3-phenoxybenzyl (1R, 3R)-cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropane carboxylate (deltamethrin) and (alphaS)-cyano-3-phenoxybenzyl 2-(4-chlorophenyl)-3-methylbutyrate (esfenvalerate) by rat and human liver microsomes differs with respect to the biotransformation pathway (oxidation versus hydrolysis) responsible for their clearance.
1(0,0,0,1) Details
11333180 Heudorf U, Angerer J: Metabolites of pyrethroid insecticides in urine specimens: current exposure in an urban population in Germany. Environ Health Perspect. 2001 Mar;109(3):213-7.


Urine specimens were analyzed for cis-3-(2,2-dibromo-vinyl)-2,2-dimethylcyclo-propanecarboxylic acid (Br (2) CA), cis- and trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane-carboxylic acid (cis-Cl (2) CA and trans-Cl (2) CA), and 4-fluoro-3-phenoxybenzoic acid (F-PBA) using a gas chromatographic method with mass-selective detection.
1(0,0,0,1) Details
12376120 Schettgen T, Koch HM, Drexler H, Angerer J: New gas chromatographic-mass spectrometric method for the determination of urinary pyrethroid metabolites in environmental medicine. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Oct 5;778(1-2):121-30.


After acidic hydrolysis for the cleavage of conjugates, the analytes cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane-1-carboxylic acid (cis-Cl (2) CA), trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane-1-carboxylic acid (trans-Cl (2) CA), cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropane-1-carboxylic acid (Br (2) CA), 4-fluoro-3-phenoxybenzoic acid (F-PBA) and 3-phenoxybenzoic acid (3-PBA) were extracted from the matrix with a liquid-liquid extraction procedure using n-hexane under acidic conditions.
1(0,0,0,1) 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.


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
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
15929904 Ortiz-Perez MD, Torres-Dosal A, Batres LE, Lopez-Guzman OD, Grimaldo M, Carranza C, Perez-Maldonado IN, Martinez F, Perez-Urizar J, Diaz-Barriga F: Environmental health assessment of deltamethrin in a malarious area of Mexico: environmental persistence, toxicokinetics, and genotoxicity in exposed children. Environ Health Perspect. 2005 Jun;113(6):782-6.


Children's exposure to deltamethrin was assessed using as biomarkers the urinary concentrations of the metabolites 3-phenoxybenzoic acid (3-PBA) and cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropane-1-carboxylic acid (Br2CA).
1(0,0,0,1) Details
15380718 Ding Y, White CA, Muralidhara S, Bruckner JV, Bartlett MG: Determination of deltamethrin and its metabolite 3-phenoxybenzoic acid in male rat plasma by high-performance liquid chromatography. J Chromatogr B Analyt Technol Biomed Life Sci. 2004 Oct 25;810(2):221-7.


The pyrethroid insecticide-deltamethrin [(S)-alpha-cyano-3-phenoxybenzyl-(1R)-cis-3-(2,2-dibromovinyl)-2,2-dimethy lcyclopropane carboxylate] is widely used throughout the world in agricultural applications.
1(0,0,0,1) Details
11675667 Colume A, Cardenas S, Gallego M, Valcarcel M: A solid phase extraction method for the screening and determination of pyrethroid metabolites and organochlorine pesticides in human urine. Rapid Commun Mass Spectrom. 2001;15(21):2007-13.


A screening method has been developed for the determination of 23 organochlorine pesticides (OCPs) and 3-pyrethroid metabolities [cis- and trans-3-(2,2-dichlorovinyl)-2,2-dimethyl-(1-cyclopropane) carboxylic acid, cis-3-(2,2-dibromovinyl)-2,2-dimethyl-(1-cyclopropane) carboxylic acid and 3-phenoxybenzoic acid] from human urine.
1(0,0,0,1) Details
14551781 Heudorf U, Angerer J, Drexler H: Current internal exposure to pesticides in children and adolescents in Germany: urinary levels of metabolites of pyrethroid and organophosphorus insecticides. Int Arch Occup Environ Health. 2004 Jan;77(1):67-72. Epub 2003 Oct 9.


We analysed their spot urine samples for six metabolites of organophosphorus insecticides [dimethyl-phosphate (DMP), diethyl-phosphate (DEP), dimethyl-thiophosphate (DMTP), diethyl-thiophosphate (DETP), dimethyl-dithiophosphate (DMDTP) and diethyl-dithiophosphate (DEDTP)] and for four metabolites of pyrethroids [cis-3-(2,2-dibromo-vinyl)-2,2-dimethyl-cyclopropane carboxylic acid (Br2CA), cis-3-(2,2-dichloro-vinyl)-2,2-dimethyl-cyclopropane carboxylic acid (cis-Cl2-CA ), trans-3-(2,2-dichloro-vinyl)-2,2-dimethyl-cyclopropane carboxylic acid (trans-Cl2-CA) and 4-fluoro-3-phenoxy-benzoic acid (F-PBA)] using gas chromatographic methods with mass-selective detection.
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