Protein Information

Name CYP2B6
Synonyms CPB 6; CPB6; CYP2B; CYP2B protein; CYP2B6; CYPIIB 6; CYPIIB6; Cytochrome P450 2B6…

Compound Information

Name chlorpyrifos
CAS

Reference List

PubMed Abstract RScore(About this table)
19326769 Das PC, Cao Y, Roset RL, Cherrington N, Hodgson E: Enzyme induction and cytotoxicity in human hepatocytes by chlorpyrifos and N,N-diethyl-m-toluamide (DEET). Drug Metabol Drug Interact. 2008;23(3-4):237-60.

Chlorpyrifos and DEET also mediated the expression of CYP isoforms, particularly CYP3A4, CYP2B6 and CYP1A1, as shown by CYP3A4-specific protein expression, testosterone metabolism and CYP1Al-specific activity assays.
87(1,1,2,2) Details
12385721 Tang J, Cao Y, Rose RL, Hodgson E: In vitro metabolism of carbaryl by human cytochrome P450 and its inhibition by chlorpyrifos. Chem Biol Interact. 2002 Oct 20;141(3):229-41.

Chlorpyrifos inhibited the generation of carbaryl methylol, catalyzed predominately by CYP2B6, more than other pathways, correlating with an earlier observation that chlorpyrifos is metabolized to its oxon primarily by CYP2B6.
82(1,1,1,2) Details
18322939 Hodgson E, Rose RL: Metabolic interactions of agrochemicals in humans. Pest Manag Sci. 2008 Jun;64(6):617-21.

The insecticides chlorpyrifos, carbaryl, carbofuran and fipronil, as well as the repellant DEET, are all extensively metabolized by human liver microsomes and, although a number of CYP isoforms may be involved, CYP2B6 and CYP3A4 are usually the most important.
81(1,1,1,1) Details
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 CYP2B6 with chlorpyrifos completely inhibited the metabolism of DEET.
33(0,1,1,3) Details
17079358 Foxenberg RJ, McGarrigle BP, Knaak JB, Kostyniak PJ, Olson JR: Human hepatic cytochrome p450-specific metabolism of parathion and chlorpyrifos. Drug Metab Dispos. 2007 Feb;35(2):189-93. Epub 2006 Nov 1.

With K (m) and V (max) values of 0.61 microM, 4827 pmol/min/nmol P450 and 0.81 microM, 12,544 pmol/min/nmol for formation of paraoxon and chlorpyrifos-oxon, respectively, CYP2B6 favored the desulfation reaction.
32(0,1,1,2) 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.

Generally organophosphorus insecticides were the most potent and extensive inhibitors, especially towards CYP1A1/2 (IC (50) values of chlorpyrifos, fenitrothion and profenofos approximately 3 micro M), CYP2B6 (IC (50) values of chlorpyrifos and fenitrothion 2.5 micro M), CYP2C8 (fenitrothion 4.3 micro M), CYP2C9 (fenitrothion and malathion 4.8 and 2.5 micro M, respectively), CYP2D6 (chlorpyrifos and phenthoate approximately 3 micro M) and CYP3A4 (chlorpyrifos, fenitrothion and phenthoate 3-4 micro M).
31(0,1,1,1) Details
15764407 Sams C, Cocker J, Lennard MS: Biotransformation of chlorpyrifos and diazinon by human liver microsomes and recombinant human cytochrome P450s (CYP). Xenobiotica. 2004 Oct;34(10):861-73.

Recombinant human CYP2B6 possessed the highest desulphuration activity for chlorpyrifos, whereas CYP2C19 had the highest dearylation activity.
7(0,0,1,2) Details
11502728 Tang J, Cao Y, Rose RL, Brimfield AA, Dai D, Goldstein JA, Hodgson E: Metabolism of chlorpyrifos by human cytochrome P450 isoforms and human, mouse, and rat liver microsomes. Drug Metab Dispos. 2001 Sep;29(9):1201-4.

CYP2B6 has the highest desulfuration activity, whereas dearylation activity is highest for 2C19.
3(0,0,0,3) Details
18447001 Cho TM, Rose RL, Hodgson E: The effect of chlorpyrifos-oxon and other xenobiotics on the human cytochrome P450-dependent metabolism of naphthalene and deet. Drug Metabol Drug Interact. 2007;22(4):235-62.

CYP2B6, the most efficient isoform for BALC production, was inhibited by CPO, while CYP3A4, the most efficient isoform for ET production, was activated by CPO.
2(0,0,0,2) Details
17936932 Hodgson E, Rose RL: Human metabolic interactions of environmental chemicals. J Biochem Mol Toxicol. 2007;21(4):182-6.

It has also been shown that the esterase (s) responsible for the initial step in permethrin metabolism in human liver is inhibited by both chlorpyrifos oxon and carbaryl.
Endosulfan-alpha, which has shown promise as a model substrate for phenotyping CYP3A4 and CYP2B6 in human liver microsomes, is also an inducer of CYP2B6, acting through the PXR receptor.
1(0,0,0,1) Details
17427179 Joo H, Choi K, Rose RL, Hodgson E: Inhibition of fipronil and nonane metabolism in human liver microsomes and human cytochrome P450 isoforms by chlorpyrifos. J Biochem Mol Toxicol. 2007;21(2):76-80.

CPS significantly inhibited the metabolism of fipronil by CYP3A4 as well as the metabolism of nonane by CYP2B6.
1(0,0,0,1) Details
12620367 Buratti FM, Volpe MT, Meneguz A, Vittozzi L, Testai E: CYP-specific bioactivation of four organophosphorothioate pesticides by human liver microsomes. Toxicol Appl Pharmacol. 2003 Feb 1;186(3):143-54.

The contribution of CYP2B6 to total hepatic oxon formation was relevant in a wide range of pesticide concentrations, being a very efficient catalyst of both the high- and low-affinity phase.
The bioactivation of azinphos-methyl (AZIN), chlorpyrifos (CPF), diazinon (DIA), and parathion (PAR), four widely used organophosphorothioate (OPT) pesticides has been investigated in human liver microsomes (HLM).
1(0,0,0,1) Details