Protein Information

Name cytochrome P450 (protein family or complex)
Synonyms cytochrome P450; cytochrome P 450; CYP450; CYP 450

Compound Information

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

Reference List

PubMed Abstract RScore(About this table)
8980039 Zhang M, Scott JG: Cytochrome b5 Is Essential for Cytochrome P450 6D1-Mediated Cypermethrin Resistance in LPR House Flies. Pestic Biochem Physiol. 1996 Jun;55(2):150-6.
82(1,1,1,2) Details
15315820 Sasabe M, Wen Z, Berenbaum MR, Schuler MA: Molecular analysis of CYP321A1, a novel cytochrome P450 involved in metabolism of plant allelochemicals (furanocoumarins) and insecticides (cypermethrin) in Helicoverpa zea. Gene. 2004 Sep 1;338(2):163-75.
81(1,1,1,1) Details
16413821 Cui Y, Guo J, Xu B, Chen Z: Potential of chlorpyrifos and cypermethrin forming DNA adducts. Mutat Res. 2006 Apr 30;604(1-2):36-41. Epub 2006 Jan 18.

However, cypermethrin didn't form DNA interstrand crosslinks on calf thymus DNA and in hepatocytes treated with SKF-525A, a cytochrome P450 inhibitor, which suggests that active metabolites of cypermethrin instead of cypermethrin itself caused DNA interstrand crosslinks and that cytochrome P450 may be involved in the activation of cypermethrin.
81(1,1,1,1) Details
11428908 El-Tawil OS, Abdel-Rahman MS: The role of enzyme induction and inhibition on cypermethrin hepatotoxicity. Pharmacol Res. 2001 Jul;44(1):33-40.

Coincubation of the hepatocytes with SKF525A, a well-known cytochrome P450 inhibitor, substantially potentiated the effect of cypermethrin on cell viability and enzyme leakage.
43(0,1,3,3) Details
9612934 Scharf ME, Neal JJ, Marcus CB, Bennett GW: Cytochrome P450 purification and immunological detection in an insecticide resistant strain of German cockroach (Blattella germanica, L.). Insect Biochem Mol Biol. 1998 Jan;28(1):1-9.

A German cockroach strain, Munsyana (MA) had 80-fold resistance to the pyrethroid insecticide cypermethrin, 4.5-fold greater total cytochrome P450 content and 2.5-fold greater cytochrome P450-mediated N-demethylation of 4-chloro-N-methylaniline compared to the susceptible Johnson Wax (JWax) strain.
35(0,1,1,5) Details
15365239 Manna S, Bhattacharyya D, Mandal TK, Das S: Repeated dose toxicity of alfa-cypermethrin in rats. J Vet Sci. 2004 Sep;5(3):241-5.

Activities of various enzymes, cytochrome P450 and b5 contents in liver, hepatic antioxidant status, tissue residue concentration, haemogram and pathological changes were studied.
3(0,0,0,3) 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.
7(0,0,1,2) Details
11852648 Park S, Brown TM: Linkage of genes for sodium channel and cytochrome P450 (CYP6B10) in Heliothis virescens. Pest Manag Sci. 2002 Feb;58(2):209-12.

2(0,0,0,2) Details
12144700 Li X, Berenbaum MR, Schuler MA: Plant allelochemicals differentially regulate Helicoverpa zea cytochrome P450 genes. Insect Mol Biol. 2002 Aug;11(4):343-51.

Comparison of the expression levels induced by eight plant allelochemicals, one drug (phenobarbital), and an insecticide (alpha-cypermethrin) indicates that, for the most part, the four P450s respond individually to these inducers, with all four induced strongly by chlorogenic acid, a shikimate pathway intermediate and a lignin biosynthesis intermediate present in a wide variety of plants, and indole-3-carbinol, a glucobrassicin breakdown product present in the Brassicaceae.
2(0,0,0,2) Details
2764708 Catinot R, Hoellinger H, Sonnier M, Do-Cao-Thang, Pichon J, Nguyen-Hoang-Nam: In vitro covalent binding of the pyrethroids cismethrin, cypermethrin and deltamethrin to rat liver homogenate and microsomes. Arch Toxicol. 1989;63(3):214-20.

With microsomes, inhibition of cytochrome P-450 and mixed function oxidases by carbon monoxide and piperonyl butoxide reduced the covalent binding so far as to be nearly absent.
2(0,0,0,2) 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 NADPH.
2(0,0,0,2) Details
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.
2(0,0,0,2) Details
14981232 Li X, Baudry J, Berenbaum MR, Schuler MA: Structural and functional divergence of insect CYP6B proteins: From specialist to generalist cytochrome P450. Proc Natl Acad Sci U S A. 2004 Mar 2;101(9):2939-44. Epub 2004 Feb 23.

Baculovirus-mediated expression of the CYP6B8 and CYP6B1 proteins demonstrates that CYP6B8 metabolizes six biosynthetically diverse plant allelochemicals (xanthotoxin, quercetin, flavone, chlorogenic acid, indole-3-carbinol, and rutin) and three insecticides (diazinon, cypermethrin, and aldrin), whereas CYP6B1 metabolizes only two allelochemicals (xanthotoxin and flavone) and one insecticide (diazinon) of those tested.
2(0,0,0,2) Details
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.
Resistance to the alpha-cyano pyrethroids deltamethrin and cypermethrin was similar to or higher than that observed with permethrin (RR = 70.0, 62.4, 145.3 and 12.1, 32.3, and 27.0 for permethrin, deltamethrin, and cypermethrin in R and NS strains, respectively).
1(0,0,0,1) Details
20183062 Abass K, Turpeinen M, Pelkonen O: An evaluation of the cytochrome P450 inhibition potential of selected pesticides in human hepatic microsomes. J Environ Sci Health B. 2009 Aug;44(6):553-63.

With the exceptions of alpha-cypermethrin, cypermethrin, isoproturon, carbaryl and abamectin, most pesticides inhibited relatively potently at least one CYP-selective activity, which may have relevance for potential interactions in occupational exposures and for further studies on the CYP-associated metabolism of respective pesticides.
1(0,0,0,1) Details
11976062 Valles SM, Woodson WD: Insecticide susceptibility and detoxication enzyme activities among Coptotermes formosanus Shiraki workers sampled from different locations in New Orleans. Comp Biochem Physiol C Toxicol Pharmacol. 2002 Apr;131(4):469-76.

The termites were subsequently assayed to determine their susceptibility to cypermethrin, chlordane and chlorpyrifos, and detoxication enzyme activity.
As with the bioassay data, although significant differences were noted, a great deal of overlap was observed among the colonies for total cytochrome P450 content (difference of 2.2-fold between high and low value) aldrin epoxidation (3.6-fold) and cytosolic esterase (3.9-fold) activity.
1(0,0,0,1) Details
15154513 Ahmad M, Hollingworth RM: Synergism of insecticides provides evidence of metabolic mechanisms of resistance in the obliquebanded leafroller Choristoneura rosaceana (Lepidoptera: Tortricidae). Pest Manag Sci. 2004 May;60(5):465-73.

These studies indicate that enhanced detoxification, often mediated by cytochrome P-450 monooxygenases, but with probable esterase and glutathione S-transferase contributions in some cases, is the major mechanism imparting resistance to different insecticides in C. rosaceana.
The interactions between six insecticides (indoxacarb, cypermethrin, chlorpyrifos, azinphosmethyl, tebufenozide and chlorfenapyr) and three potential synergists, (piperonyl butoxide (PBO), S,S,S-tributyl phosphorotrithioate (DEF) and diethyl maleate (DEM)) were studied by dietary exposure in a multi-resistant and a susceptible strain of the obliquebanded leafroller, Choristoneura rosaceana (Harris).
1(0,0,0,1) Details
18381673 Margaritopoulos JT, Skavdis G, Kalogiannis N, Nikou D, Morou E, Skouras PJ, Tsitsipis JA, Vontas J: Efficacy of the pyrethroid alpha-cypermethrin against Bactrocera oleae populations from Greece, and improved diagnostic for an iAChE mutation. Pest Manag Sci. 2008 Sep;64(9):900-8.

Cytochrome P450 monoxygenase activities showed an association with resistance.
1(0,0,0,1) Details
8294621 Hemingway J, Dunbar SJ, Monro AG, Small GJ: Pyrethroid resistance in German cockroaches (Dictyoptera: Blattelidae): resistance levels and underlying mechanisms. J Econ Entomol. 1993 Dec;86(6):1631-8.

Greater than 2-fold resistance to the pyrethroids cyfluthrin, fenvalerate, cypermethrin, and lambda cyhalothrin appeared in 15 of these strains.
Possible resistance mechanisms detected in these populations included elevated levels of cytochrome P450, general esterase and glutathione S-transferase, and nerve insensitivity (kdr-type resistance).
1(0,0,0,1) Details
10646973 Li X, Berenbaum MR, Schuler MA: Molecular cloning and expression of CYP6B8: a xanthotoxin-inducible cytochrome P450 cDNA from Helicoverpa zea. Insect Biochem Mol Biol. 2000 Jan;30(1):75-84.

Xanthotoxin, a plant allelochemical, induces alpha-cypermethrin insecticide tolerance in Helicoverpa zea (corn earworm); inhibition of tolerance by piperonyl butoxide implicates cytochrome P450 monooxygenases (P450s) in the detoxification of this insecticide.
1(0,0,0,1) Details
11233122 Kranthi KR, Jadhav D, Wanjari R, Kranthi S, Russell D: Pyrethroid resistance and mechanisms of resistance in field strains of Helicoverpa armigera (Lepidoptera: Noctuidae). J Econ Entomol. 2001 Feb;94(1):253-63.

Studies carried out through estimation of detoxification enzyme activity and synergists indicated that enhanced cytochrome p450 and esterase activities were probably important mechanisms for pyrethroid resistance in field strains.
Resistance to cypermethrin, fenvalerate and cyhalothrin also was high with resistance ratios of > 1,000 in four strains collected from central and southern India.
1(0,0,0,1) Details
19562662 Wang Z, Yao M, Wu Y: Cross-resistance, inheritance and biochemical mechanisms of imidacloprid resistance in B-biotype Bemisia tabaci. Pest Manag Sci. 2009 Nov;65(11):1189-94.

The NJ-Imi strain exhibited 490-fold resistance to imidacloprid, high levels of cross-resistance to three other neonicotinoids, low levels of cross-resistance to monosultap, cartap and spinosad, but no cross-resistance to abamectin and cypermethrin.
It is shown that enhanced detoxification mediated by cytochrome-P450-dependent monooxygenases contributes to imidacloprid resistance to some extent in the NJ-Imi strain.
1(0,0,0,1) Details
9397514 Korytko PJ, Scott JG: CYP6D1 protects thoracic ganglia of houseflies from the neurotoxic insecticide cypermethrin. Arch Insect Biochem Physiol. 1998;37(1):57-63.

CYP6D1 is a housefly cytochrome P450 known to metabolize neurotoxic pyrethroid insecticides.
1(0,0,0,1) Details