Protein Information

Name CYP3A4
Synonyms CP33; CYP3; HLP; CYP3A; CP34; CYP 3A4; CYP 3; CYP3A3…

Compound Information

Name imidacloprid
CAS

Reference List

PubMed Abstract RScore(About this table)
12230409 Schulz-Jander DA, Leimkuehler WM, Casida JE: Neonicotinoid insecticides: reduction and cleavage of imidacloprid nitroimine substituent by liver microsomal and cytosolic enzymes. Chem Res Toxicol. 2002 Sep;15(9):1158-65.

The major insecticide imidacloprid (IMI) is known to be metabolized by human cytochrome P450 3A4 with NADPH by imidazolidine hydroxylation and dehydrogenation to give 5-hydroxy-imidacloprid and the olefin, respectively, and by nitroimine reduction and cleavage to yield the nitrosoimine, guanidine, and urea derivatives.
81(1,1,1,1) Details
16153789 Honda H, Tomizawa M, Casida JE: Neo-nicotinoid metabolic activation and inactivation established with coupled nicotinic receptor-CYP3A4 and -aldehyde oxidase systems. Toxicol Lett. 2006 Feb 20;161(2):108-14. Epub 2005 Sep 8.

With the vertebrate alpha4 beta2 nAChR, AOX enhances imidacloprid potency but CYP3 A4 does not.
9(0,0,1,4) Details
12084621 Schulz-Jander DA, Casida JE: Imidacloprid insecticide metabolism: human cytochrome P450 isozymes differ in selectivity for imidazolidine oxidation versus nitroimine reduction. Toxicol Lett. 2002 Jun 7;132(1):65-70.

Isozymes selective for imidazolidine oxidation in order of decreasing overall activity are CYP3A4> CYP2C19 or CYP2A6> CYP2C9, while those selective for nitroimine reduction are CYP1A2, CYP2B6, CYP2D6 and CYP2E1.
2(0,0,0,2) Details
19391582 Shi X, Dick RA, Ford KA, Casida JE: Enzymes and inhibitors in neonicotinoid insecticide metabolism. . J Agric Food Chem. 2009 Jun 10;57(11):4861-6.

Human CYP450 recombinant enzymes carry out the following conversions: CYP3A4, 2C19, and 2B6 for thiamethoxam (TMX) to clothianidin (CLO); 3A4, 2C19, and 2A6 for CLO to desmethyl-CLO; 2C19 for TMX to desmethyl-TMX.
Imidacloprid (IMI), CLO, and several of their metabolites do not give detectable N-glucuronides but 5-hydroxy-IMI, 4,5-diol-IMI, and 4-hydroxythiacloprid are converted to O-glucuronides in vitro with mouse liver microsomes and UDP-glucuronic acid or in vivo in mice.
1(0,0,0,1) Details