Protein Information

Name cytochrome P450 monooxygenases
Synonyms CYP M; CYP20A1; CYP20A1 protein; Cytochrome P450 family 20 subfamily A polypeptide 1; Cytochrome P450 monooxygenase; CYP20A1 proteins; Cytochrome P450 family 20 subfamily A polypeptide 1s; Cytochrome P450 monooxygenases

Compound Information

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

Reference List

PubMed Abstract RScore(About this table)
19196389 Hardstone MC, Leichter CA, Scott JG: Multiplicative interaction between the two major mechanisms of permethrin resistance, kdr and cytochrome P450-monooxygenase detoxification, in mosquitoes. J Evol Biol. 2009 Feb;22(2):416-23.

The two major mechanisms that confer resistance to permethrin in Culex mosquitoes are target site insensitivity (i.e. kdr) and enhanced detoxification by cytochrome P450 monooxygenases.
112(1,2,2,2) Details
19228410 Hardstone MC, Lazzaro BP, Scott JG: The effect of three environmental conditions on the fitness of cytochrome P450 monooxygenase-mediated permethrin resistance in Culex pipiens quinquefasciatus. BMC Evol Biol. 2009 Feb 19;9:42.
81(1,1,1,1) Details
16032654 Xu Q, Liu H, Zhang L, Liu N: Resistance in the mosquito, Culex quinquefasciatus, and possible mechanisms for resistance. Pest Manag Sci. 2005 Nov;61(11):1096-102.

Resistance to permethrin in MAmCq (G1) and HAmCq (G3) was partially suppressed by piperonyl butoxide (PBO), S,S,S-tributylphosphorotrithioate (DEF) and diethyl maleate (DEM), inhibitors of cytochrome P450 monooxygenases, hydrolases and glutathione S-transferases (GST), respectively, suggesting these three enzyme families are important in conferring permethrin resistance in both strains.
81(1,1,1,1) Details
9461845 Liu N, Scott JG: Inheritance of CYP6D1-mediated pyrethroid resistance in house fly (Diptera: Muscidae). J Econ Entomol. 1997 Dec;90(6):1478-81.

The inheritance of cytochrome P450 monooxygenase-mediated (i.e., CYP6D1) resistance in the LPR strain of house fly, Musca domestica L., was investigated by comparing levels of monooxygenase-mediated permethrin resistance and CYP6D1 messenger RNA in 7 populations of house flies.
31(0,1,1,1) Details
15962785 Gonzalez Audino P, Barrios S, Vassena C, Mougabure Cueto G, Zerba E, Picollo MI: Increased monooxygenase activity associated with resistance to permethrin in Pediculus humanus capitis (Anoplura: Pediculidae) from Argentina. J Med Entomol. 2005 May;42(3):342-5.

To elucidate the possible involvement of the cytochrome P450 monooxygenase system in conferring permethrin resistance, ethoxycoumarin-O-deethylase (ECOD) activity was measured in abdomens of individual third instars and adults by using a fluorometric assay.
6(0,0,1,1) Details
18405832 Poupardin R, Reynaud S, Strode C, Ranson H, Vontas J, David JP: Cross-induction of detoxification genes by environmental xenobiotics and insecticides in the mosquito Aedes aegypti: impact on larval tolerance to chemical insecticides. Insect Biochem Mol Biol. 2008 May;38(5):540-51. Epub 2008 Feb 5.

Cytochrome P450 monooxygenases activities were induced in larvae exposed to permethrin, fluoranthene and copper while glutathione S-transferase activities were induced after exposure to fluoranthene and repressed after exposure to copper.
6(0,0,1,1) Details
19125173 Pasay C, Arlian L, Morgan M, Gunning R, Rossiter L, Holt D, Walton S, Beckham S, McCarthy J: The effect of insecticide synergists on the response of scabies mites to pyrethroid acaricides. PLoS Negl Trop Dis. 2009;3(1):e354. Epub 2009 Jan 6.

BACKGROUND: Permethrin is the active component of topical creams widely used to treat human scabies.
Then, to investigate the relative role of specific metabolic pathways inhibited by these synergists, enzyme assays were developed to measure esterase, glutathione S-transferase (GST) and cytochrome P450 monooxygenase (cytochrome P450) activity in mite extracts.
2(0,0,0,2) Details
8980025 Baerg RJ, Barrett M, Polge ND: Insecticide and Insecticide Metabolite Interactions with Cytochrome P450 Mediated Activities in Maize. Pestic Biochem Physiol. 1996 May;55(1):10-20.

In vitro assays were used to determine if organophosphate, carbamate, and synthetic pyrethroid insecticides affected the cytochrome P450 monooxygenase (P450) catalyzed hydroxylation of nicosulfuron, bentazon, cinnamic acid, or lauric acid in maize microsomes.
All P450 activities were inhibited approximately 50% by carbaryl, and none were inhibited by permethrin.
1(0,0,0,1) Details
16190164 Rose RL, Tang J, Choi J, Cao Y, Usmani A, Cherrington N, Hodgson E: Pesticide metabolism in humans, including polymorphisms. Scand J Work Environ Health. 2005;31 Suppl 1:156-63; discussion 119-22.

Pesticides examined using human liver microsomes and cytosolic fractions included chlorpyrifos, carbaryl and permethrin.
The metabolic pathways involved include cytochrome P450 monooxygenases (CYP), esterases, and alcohol and aldehyde dehydrogenases.
1(0,0,0,1) Details
15476966 Foil LD, Coleman P, Eisler M, Fragoso-Sanchez H, Garcia-Vazquez Z, Guerrero FD, Jonsson NN, Langstaff IG, Li AY, Machila N, Miller RJ, Morton J, Pruett JH, Torr S: Factors that influence the prevalence of acaricide resistance and tick-borne diseases. Vet Parasitol. 2004 Oct 28;125(1-2):163-81.

A second mechanism of OP resistance is linked to cytochrome P450 monooxygenase activity.
A PCR-based assay to detect a specific sodium channel gene mutation that is associated with resistance to permethrin has been developed.
1(0,0,0,1) Details
19419775 Riaz MA, Poupardin R, Reynaud S, Strode C, Ranson H, David JP: Impact of glyphosate and benzo [a] pyrene on the tolerance of mosquito larvae to chemical insecticides. Aquat Toxicol. 2009 Jun 4;93(1):61-9. Epub 2009 Mar 31.

The effect of exposure of Aedes aegypti larvae for 72h to sub-lethal concentrations of the herbicide glyphosate and the polycyclic aromatic hydrocarbon benzo [a] pyrene on their subsequent tolerance to the chemical insecticides imidacloprid, permethrin and propoxur, detoxification enzyme activities and transcription of detoxification genes was investigated.
Cytochrome P450 monooxygenases activities were strongly induced in larvae exposed to benzo [a] pyrene and moderately induced in larvae exposed to imidacloprid and glyphosate.
1(0,0,0,1) Details