| Name | cytochrome P450 (protein family or complex) |
|---|---|
| Synonyms | cytochrome P450; cytochrome P 450; CYP450; CYP 450 |
| Name | permethrin |
|---|---|
| CAS | (3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate |
| PubMed | Abstract | RScore(About this table) | |
|---|---|---|---|
| 12547628 | Fisher T, Crane M, Callaghan A: Induction of cytochrome P-450 activity in individual Chironomus riparius Meigen larvae exposed to xenobiotics. Ecotoxicol Environ Saf. 2003 Jan;54(1):1-6. The sensitivity of this biomarker was tested by exposing larvae to phenobarbital (0.5 and 1.0 mM) and permethrin (1 and 10 microg/g). |
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| 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. |
1(0,0,0,1) | Details |
| 14722249 | Bauer D, Wolfram N, Kahl GF, Hirsch-Ernst KI: Transcriptional regulation of CYP2B1 induction in primary rat hepatocyte cultures: repression by epidermal growth factor is mediated via a distal enhancer region. Mol Pharmacol. 2004 Jan;65(1):172-80. Phenobarbital-dependent induction of cytochrome P-450 2B1 (CYP2B1) is subject to regulation by cytokines [e.g., by epidermal growth factor (EGF)], hormones [e.g., by growth hormone (GH)], or the cellular redox status. The 2679-bp native 5'-flanking region of the CYP2B1 gene conferred reporter gene activation by PB and the potent PB-like inducer permethrin (PM). |
1(0,0,0,1) | Details |
| 15271210 | Ranson H, Paton MG, Jensen B, McCarroll L, Vaughan A, Hogan JR, Hemingway J, Collins FH: Genetic mapping of genes conferring permethrin resistance in the malaria vector, Anopheles gambiae. Insect Mol Biol. 2004 Aug;13(4):379-86. The second two loci are located on the third chromosome and one of these, rtp2, flanks a large cluster of cytochrome P450 genes. |
1(0,0,0,1) | Details |
| 18817570 | Zhu F, Li T, Zhang L, Liu N: Co-up-regulation of three P450 genes in response to permethrin exposure in permethrin resistant house flies, Musca domestica. BMC Physiol. 2008 Sep 25;8:18. For example, increased cytochrome P450 detoxification is known to play an important role in many insect species. |
1(0,0,0,1) | 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. All P450 activities were inhibited approximately 50% by carbaryl, and none were inhibited by permethrin. |
1(0,0,0,1) | Details |
| 10696592 | Kasai S, Weerashinghe IS, Shono T, Yamakawa M: Molecular cloning, nucleotide sequence and gene expression of a cytochrome P450 (CYP6F1) from the pyrethroid-resistant mosquito, Culex quinquefasciatus Say. Insect Biochem Mol Biol. 2000 Feb;30(2):163-71. Primers were used in the reverse transcription-polymerase chain reaction (RT-PCR) of gut mRNA from 4th-instar larvae of the permethrin-susceptible or resistant C. quinquefasciatus. |
1(0,0,0,1) | Details |
| 19043575 | Muller P, Warr E, Stevenson BJ, Pignatelli PM, Morgan JC, Steven A, Yawson AE, Mitchell SN, Ranson H, Hemingway J, Paine MJ, Donnelly MJ: Field-caught permethrin-resistant Anopheles gambiae overexpress CYP6P3, a P450 that metabolises pyrethroids. PLoS Genet. 2008 Nov;4(11):e1000286. Epub 2008 Nov 28. A cytochrome P450, CYP6P3, was significantly overexpressed in the survivors, and we show that the translated enzyme metabolises both alpha-cyano and non-alpha-cyano pyrethroids. |
1(0,0,0,1) | Details |
| 19014539 | Djouaka RF, Bakare AA, Coulibaly ON, Akogbeto MC, Ranson H, Hemingway J, Strode C: Expression of the cytochrome P450s, CYP6P3 and CYP6M2 are significantly elevated in multiple pyrethroid resistant populations of Anopheles gambiae s.s. from Southern Benin and Nigeria. BMC Genomics. 2008 Nov 13;9:538. The cytochrome P450 genes, CYP6P3 and CYP6M2 are upregulated in all three resistant populations analysed. There were high levels of permethrin resistance in an agricultural area (Akron) and an urban area (Gbedjromede), low levels of resistance in mosquito samples from an oil contaminated site (Ojoo) and complete susceptibility in the rural Orogun location. |
1(0,0,0,1) | Details |
| 16164607 | Vontas J, Blass C, Koutsos AC, David JP, Kafatos FC, Louis C, Hemingway J, Christophides GK, Ranson H: Gene expression in insecticide resistant and susceptible Anopheles gambiae strains constitutively or after insecticide exposure. Insect Mol Biol. 2005 Oct;14(5):509-21. Short-term (6 and 10 h) effects of exposure of the pyrethroid resistant RSP strain to permethrin were also detected. |
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| 18237281 | Amenya DA, Naguran R, Lo TC, Ranson H, Spillings BL, Wood OR, Brooke BD, Coetzee M, Koekemoer LL: Over expression of a cytochrome P450 (CYP6P9) in a major African malaria vector, Anopheles Funestus, resistant to pyrethroids. Insect Mol Biol. 2008 Feb;17(1):19-25. |
1(0,0,0,1) | Details |
| 18237282 | Zhu F, Feng JN, Zhang L, Liu N: Characterization of two novel cytochrome P450 genes in insecticide-resistant house-flies. Insect Mol Biol. 2008 Feb;17(1):27-37. |
1(0,0,0,1) | Details |
| 2067468 | Pereguda TA, Agashkova TM: [The characteristics of the development in houseflies of resistance to synergized and nonsynergized permethrin]. Med Parazitol. 1991 Jan-Feb;(1):26-8. It has been established that the basic mechanism regulating resistance to permetrine is an increase in cytochrome P-450 monooxygenases. |
1(0,0,0,1) | Details |
| 6768169 | Carlson GP, Schoenig GP: Induction of liver microsomal cytochrome C reductase and cytochrome P-450 by some new synthetic pyrethroids. Toxicol Appl Pharmacol. 1980 Mar 15;52(3):507-12. |
1(0,0,0,1) | Details |
| 10985040 | Valles SM, Oi FM, Wagner T, Brenner RJ: Toxicity and in vitro metabolism of t-permethrin in eastern subterranean termite (Isoptera: Rhinotermitidae). J Econ Entomol. 2000 Aug;93(4):1259-64. |
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| 11854147 | Usmani KA, Rose RL, Goldstein JA, Taylor WG, Brimfield AA, Hodgson E: In vitro human metabolism and interactions of repellent N,N-diethyl-m-toluamide. Drug Metab Dispos. 2002 Mar;30(3):289-94. Preincubation of human or rodent microsomes with chlorpyrifos, permethrin, and pyridostigmine bromide alone or in combination can lead to either stimulation or inhibition of DEET metabolism. CYP2B6 is the principal cytochrome P450 involved in the metabolism of DEET to its major BALC metabolite, whereas CYP2C19 had the greatest activity for the formation of the ET metabolite. |
1(0,0,0,1) | Details |
| 19326768 | Das PC, Streit TM, Cao Y, Rose RL, Cherrington N, Ross MK, Wallace AD, Hodgson E: Pyrethroids: cytotoxicity and induction of CYP isoforms in human hepatocytes. Drug Metabol Drug Interact. 2008;23(3-4):211-36. Deltamethrin [(S)-alpha-cyano-3-phenoxybenzyl-cis-(1 R,3R)-3 (2,2-dibromovinyl)(2,2-dimethyl-cyclopropane-carboxylate] and permethrin [3-phenoxybenzyl (1RS)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethyl-cyclopr opanecarboxylate] are pyrethroid insecticides used in agriculture, public health and military deployments. Pyrethroids are known to be capable of inducing cytochrome P450 (CYP) 2B1/2B2, CYP1A1 and overall CYP content in rat liver. |
1(0,0,0,1) | Details |
| 18957322 | Bautista MA, Miyata T, Miura K, Tanaka T: RNA interference-mediated knockdown of a cytochrome P450, CYP6BG1, from the diamondback moth, Plutella xylostella, reduces larval resistance to permethrin. Insect Biochem Mol Biol. 2009 Jan;39(1):38-46. Epub 2008 Oct 11. |
87(1,1,2,2) | Details |
| 17451859 | Nakamura Y, Sugihara K, Sone T, Isobe M, Ohta S, Kitamura S: The in vitro metabolism of a pyrethroid insecticide, permethrin, and its hydrolysis products in rats. Toxicology. 2007 Jun 25;235(3):176-84. Epub 2007 Mar 19. Thus, permethrin was hydrolyzed by CES, and PBAlc formed was oxidized to PBAld and PBAcid by the cytochrome P450 system in rats. |
82(1,1,1,2) | Details |
| 17261170 | Wondji CS, Morgan J, Coetzee M, Hunt RH, Steen K, Black WC 4th, Hemingway J, Ranson H: Mapping a quantitative trait locus (QTL) conferring pyrethroid resistance in the African malaria vector Anopheles funestus. BMC Genomics. 2007 Jan 29;8:34. The rp1 QTL appears to present a major effect since it accounts for more than 60% of the variance in susceptibility to permethrin. |
0(0,0,0,0) | Details |
| 2132992 | Hemingway J, Callaghan A, Amin AM: Mechanisms of organophosphate and resistance in Culex quinquefasciatus from Saudi Arabia. Med Vet Entomol. 1990 Jul;4(3):275-82. There was a significant increase in the amount of Cytochrome P450 in Cx quinquefasciatus lines selected with the pyrethroid permethrin or with the organophosphate pirimiphos-methyl, but no change in lines selected with five other organophosphates or propoxur, compared to the parental strain, which suggests that oxidases are involved in the P450 mediated resistance to both permethrin and pirimiphos-methyl. |
0(0,0,0,0) | 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. CONCLUSION: The cytochrome P450-mediated permethrin detoxification resistance in Cx. p. quinquefasciatus can have an associated fitness cost in the absence of permethrin, relative to a susceptible allele. |
81(1,1,1,1) | Details |
| 3083808 | Scott JG, Georghiou GP: The biochemical genetics of permethrin resistance in the Learn-PyR strain of house fly. Biochem Genet. 1986 Feb;24(1-2):25-37. Permethrin resistance factors on chromosome 1 consisted of a piperonyl butoxide (PB)-suppressible mechanism correlated with increased levels of cytochromes P-450 and b5; on chromosome 2, a PB-suppressible mechanism associated with elevated amounts of cytochrome P-450; on chromosome 3, decreased cuticular penetration, kdr, and increased amounts of P-450 reductase activity; and on chromosome 5, a largely PB-suppressible mechanism correlated with elevated levels of cytochrome P-450 and P-450 reductase activity. |
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| 15747499 | Hodgson E, Rose RL: Human metabolism and metabolic interactions of deployment-related chemicals. Drug Metab Rev. 2005;37(1):1-39. These initial studies have examined the human metabolism by cytochrome P450, other phase I enzymes, and their isoforms and, in some cases, their polymorphic variants of compounds such as chlorpyrifos, carbaryl, DEET, permethrin, and pyridostigmine bromide, and, to a lesser extent, other chemicals from the same chemical and use classes, including solvents, jet fuel components, and mustard metabolites. |
31(0,1,1,1) | Details |
| 17463061 | Zhang SY, Ito Y, Yamanoshita O, Yanagiba Y, Kobayashi M, Taya K, Li C, Okamura A, Miyata M, Ueyama J, Lee CH, Kamijima M, Nakajima T: Permethrin may disrupt biosynthesis via mitochondrial membrane damage of Leydig cells in adult male mouse. Endocrinology. 2007 Aug;148(8):3941-9. Epub 2007 Apr 26. Moreover, cis-permethrin exposure significantly diminished the testicular mitochondrial mRNA expression levels of peripheral benzodiazepine receptor (PBR), steroidogenic acute regulatory protein (StAR), and cytochrome P450 side-chain cleavage (P450scc) and enzyme and protein expression levels of StAR and P450scc. |
31(0,1,1,1) | Details |
| 12542634 | Zhu YC, Snodgrass GL: Cytochrome P450 CYP6X1 cDNAs and mRNA expression levels in three strains of the tarnished plant bug Lygus lineolaris (Heteroptera: Miridae) having different susceptibilities to pyrethroid insecticide. Insect Mol Biol. 2003 Feb;12(1):39-49. Topical treatment with 10 ng permethrin elevated cytochrome P450 mRNA levels by approximately 2-fold. |
10(0,0,1,5) | Details |
| 10620039 | Ranasinghe C, Hobbs AA: Induction of cytochrome P450 CYP6B7 and cytochrome b5 mRNAs from Helicoverpa armigera (Hubner) by pyrethroid insecticides in organ culture. Insect Mol Biol. 1999 Nov;8(4):443-7. Substantial induction of cytochrome P450, CYP6B7 and cytochrome b5 mRNAs by alpha-pinene, and the pyrethroids, fenvalerate, cypermethrin and permethrin were observed in fat body culture. |
9(0,0,1,4) | Details |
| 11377398 | Heder AF, Hirsch-Ernst KI, Bauer D, Kahl GF, Desel H: Induction of cytochrome P450 2B1 by pyrethroids in primary rat hepatocyte cultures. Biochem Pharmacol. 2001 Jul 1;62(1):71-9. In this project, we examined the influence of pyrethroids (permethrin, cypermethrin, and fenvalerate) on the expression and activity of the phenobarbital (PB)-inducible cytochrome P450 2B1 isoform (CYP2B1) in primary rat hepatocyte cultures. |
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| 9535163 | Kasai S, Shono T, Yamakawa M: Molecular cloning and nucleotide sequence of a cytochrome P450 cDNA from a pyrethroid-resistant mosquito, Culex quinquefasciatus say. Insect Mol Biol. 1998 May;7(2):185-90. A novel cDNA clone encoding a cytochrome P450 was screened from a gut cDNA library of permethrin-resistant Culex quinquefasciatus larvae. |
7(0,0,1,2) | Details |
| 20009351 | Abdou R, Khalil W, Shah S, Murasawa Y, Sasaki K, Shimoda M: Effects of Several Pyrethroids on Hepatic Cytochrome P450 Activities in Rats. J Vet Med Sci. 2009 Dec 10. Four commonly used pyrethroids (permethrin, bifenthrin, ethofenprox, and fenpropathrin) were orally administered to Sprague-Dawley rats for 5 days to study their effects on the liver cytochrome P450 (CYP) activities. |
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| 9432699 | Kostka G, Palut D, Wiadrowska B: [The effect of permethrin and DDT on the activity of cytochrome P-450 1A and 2B molecular forms in rat liver]. Rocz Panstw Zakl Hig. 1997;48(3):229-37. |
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| 18508027 | Daaboub J, Ben Cheikh R, Lamari A, Ben Jha I, Feriani M, Boubaker C, Ben Cheikh H: Resistance to pyrethroid insecticides in Culex pipiens pipiens (Diptera: Culicidae) from Tunisia. Acta Trop. 2008 Jul;107(1):30-6. Epub 2008 Apr 22. The use of synergists showed that the cytochrome P450-dependent monooxygenases had a major contribution to the permethrin and deltamethrin resistance and that the esterases (and/or glutathione-S-transferases) had only a minor contribution. |
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| 8980024 | Thomas JD, Ottea JA, Boethel DJ, Ibrahim S: Factors Influencing Pyrethroid Resistance in a Permethrin-Selected Strain of the Soybean Looper, Pseudoplusia includens (Walker). Pestic Biochem Physiol. 1996 May;55(1):1-9. Cytochrome P450 monooxgenase activity toward p-nitroanisole was measured in larvae of three strains of soybean looper, Pseudoplusia includens (Walker), including a laboratory susceptible (S) strain, a resistant (R) strain selected for several generations with permethrin, and a nonselected (NS) strain from the same field collections as the R strain. |
6(0,0,1,1) | Details |
| 8541882 | Wang XP, Hobbs AA: Isolation and sequence analysis of a cDNA clone for a pyrethroid inducible cytochrome P450 from Helicoverpa armigera. Insect Biochem Mol Biol. 1995 Oct;25(9):1001-9. Induction studies indicate that the smaller mRNA is inducible by phenobarbital while the larger mRNA is inducible by the pyrethroid insecticide permethrin. |
4(0,0,0,4) | Details |
| 18948380 | Scollon EJ, Starr JM, Godin SJ, DeVito MJ, Hughes MF: In vitro metabolism of pyrethroid pesticides by rat and human hepatic microsomes and cytochrome p450 isoforms. Drug Metab Dispos. 2009 Jan;37(1):221-8. Epub 2008 Oct 23. The pyrethroids bifenthrin, S-bioallethrin, bioresmethrin, beta-cyfluthrin, cypermethrin, cis-permethrin, and trans-permethrin were incubated in rat and human hepatic microsomes in the presence or absence of |
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| 10534945 | Miller RJ, Davey RB, George JE: Characterization of pyrethroid resistance and susceptibility to coumaphos in Mexican Boophilus microplus (Acari: Ixodidae). J Med Entomol. 1999 Sep;36(5):533-8. One was characteristic of a kdr mutation and the other involved esterase and cytochrome P450 enzyme systems. Very high resistance to permethrin, cypermethrin, and flumethrin, not synergized by TPP and PBO and high resistance to DDT, characterized the kdr-like pattern found in the Corrales and San Felipe strains. |
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