Protein Information

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

Compound Information

Name alachlor
CAS

Reference List

PubMed Abstract RScore(About this table)
10475613 Coleman S, Liu S, Linderman R, Hodgson E, Rose RL: In vitro metabolism of alachlor by human liver microsomes and human cytochrome P450 isoforms. Chem Biol Interact. 1999 Aug 30;122(1):27-39.
62(0,2,2,2) Details
11850968 Hanioka N, Watanabe K, Yoda R, Ando M: Effect of alachlor on hepatic cytochrome P450 enzymes in rats. Drug Chem Toxicol. 2002 Feb;25(1):25-37.
25(0,0,4,5) Details
1755024 Moody DE, Narloch BA, Shull LR, Hammock BD: The effect of structurally divergent herbicides on mouse liver xenobiotic-metabolizing enzymes (P-450-dependent mono-oxygenases, epoxide hydrolases and glutathione S-transferases) and carnitine acetyltransferase. Toxicol Lett. 1991 Dec;59(1-3):175-85.

Chlorfiurecol, trifluralin, alachlor, propham, MCPP and 2,4-DP caused increases in phase I (cytochrome P-450, ethoxycoumarin O-deethylase, and/or aminopyrine N-demethylase) and phase II (microsomal epoxide hydrolase and cytosolic glutathione S-transferase) activities.
6(0,0,1,1) Details
11133395 Coleman S, Linderman R, Hodgson E, Rose RL: Comparative metabolism of chloroacetamide herbicides and selected metabolites in human and rat liver microsomes. Environ Health Perspect. 2000 Dec;108(12):1151-7.

We have also shown that the cytochrome P450 isoforms responsible for human metabolism of acetochlor, butachlor, and metolachlor are CYP3A4 and CYP2B6.
Acetochlor [2-chloro-N-(ethoxymethyl)-N-(2-ethyl-6-methyl-phenyl)-acetamide], alachlor [N-(methoxymethyl)-2-chloro-N-(2, 6-diethyl-phenyl) acetamide], butachlor [N-(butoxymethyl)-2-chloro-N-(2,6-diethyl-phenyl) acetamide], and metolachlor [2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-methoxy-1-methylethyl) acetamide] are pre-emergent herbicides used in the production of agricultural crops.
1(0,0,0,1) Details
16315095 Kawahigashi H, Hirose S, Ozawa K, Ido Y, Kojima M, Ohkawa H, Ohkawa Y: Analysis of substrate specificity of pig CYP2B22 and CYP2C49 towards herbicides by transgenic rice plants. Transgenic Res. 2005 Dec;14(6):907-17.

We introduced two novel types of pig (Sus scrofa) cytochrome P450, CYP2B22 and CYP2C49, into rice plants (Oryza sativa L. cv. 'Nipponbare') to produce herbicide-tolerant plants and to confirm the metabolic activities of the cytochrome P450 species.
CYP2C49 rice plants showed tolerance towards 13 herbicides, including chlortoluron (100 microM), norflurazon (0.5 microM), amiprofos-methyl (2.5 microM), alachlor (0.8 microM), and isoxaben (1 microM).
1(0,0,0,1) Details
18217708 Hirose S, Kawahigashi H, Tagiri A, Ohkawa Y: Herbicide-induced anthocyanin accumulation in transgenic rice by expression of rice OSB2 under the control of rice CYP72A21 promoter. J Agric Food Chem. 2008 Feb 27;56(4):1259-63. Epub 2008 Jan 25.

CYP72A21, a rice cytochrome P450 gene, is induced by chloroacetamide herbicides.
Leaves of the transgenic plants turned red upon treatment with the chloroacetamide herbicides acetochlor, alachlor, and metolachlor.
1(0,0,0,1) Details
16277416 Kawahigashi H, Hirose S, Ohkawa H, Ohkawa Y: Phytoremediation of metolachlor by transgenic rice plants expressing human CYP2B6. J Agric Food Chem. 2005 Nov 16;53(23):9155-60.

We introduced the human cytochrome P450 gene CYP2B6 into rice plants (Oryza sativa L. cv.
In particular, CYP2B6 rice plants grown in soil showed tolerance to the chloroacetanilide herbicides alachlor and metolachlor.
1(0,0,0,1) Details
1868789 Babich H, Rosenberg DW, Borenfreund E: In vitro cytotoxicity studies with the fish hepatoma cell line, PLHC-1 (Poeciliopsis lucida). Ecotoxicol Environ Saf. 1991 Jun;21(3):327-36.

The organochlorine pesticides (alachlor and p,p'-methoxychlor) were more cytotoxic than the organophosphorus pesticides (EPN, diazinon, and malathion).
Xenobiotic-metabolizing capacity was temperature dependent, with enzymatic activity increasing as the temperature was increased from 28 to 34 to 37 degrees C, was inducible by Aroclor 1254 (a chemical inducer of cytochrome P450-dependent monooxygenase activity), and was reduced by EPN (an inhibitor of P450 activity).
1(0,0,0,1) Details
18026775 Jin-Clark Y, Anderson TD, Zhu KY: Effect of alachlor and metolachlor on toxicity of chlorpyrifos and major detoxification enzymes in the aquatic midge, Chironomus tentans (Diptera: Chironomidae). Arch Environ Contam Toxicol. 2008 May;54(4):645-52. Epub 2007 Nov 17.

In contrast, metolachlor at 1,000 microg/L reduced protein production by 3.2-fold, which was associated with a 2.8-fold reduction of cytochrome P450 O-deethylation total activity and 1.4- to 1.7-fold reductions of GST total activities in the treated midges.
1(0,0,0,1) Details
11029275 Green T, Lee R, Moore RB, Ashby J, Willis GA, Lund VJ, Clapp MJ: Acetochlor-induced rat nasal tumors: further studies on the mode of action and relevance to humans. Regul Toxicol Pharmacol. 2000 Aug;32(1):127-33.

The herbicide acetochlor, and its analogue alachlor, have similar toxicological properties, the most significant being the induction of nasal adenomas in rats in 2-year feeding studies.
The formation of a quinone-imine from the sulfoxide was facilitated by hydroxylation of the phenyl ring by a cytochrome P450 isoenzyme which was specific to the nasal epithelium in the rat.
1(0,0,0,1) Details
2619326 Leslie C, Reidy GF, Stacey NH: Effect of ofurace, oxadixyl, and alachlor on xenobiotic biotransformation in the rat liver. Arch Environ Contam Toxicol. 1989 Nov;18(6):876-80.

Glutathione S-transferase and aminopyrine N-demethylase activities responded in a non dose-dependent manner, while cytochrome P-450 content and aldrin epoxidase activities were unchanged.
1(0,0,0,1) Details
1566280 Bonfanti M, Taverna P, Chiappetta L, Villa P, D'Incalci M, Bagnati R, Fanelli R: DNA damage induced by alachlor after in vitro activation by rat hepatocytes. Toxicology. 1992;72(2):207-19.

The majority, isolated and identified by GC-MS analysis, were products arising from reactions catalyzed by the P-450 monooxygenase system, arylamidase and flavin mixed-function oxidase/cytochrome P-450 monooxygenase.
1(0,0,0,1) Details
11127290 Genter MB, Burman DM, Dingeldein MW, Clough I, Bolon B: Evolution of alachlor-induced nasal neoplasms in the Long-Evans rat. Toxicol Pathol. 2000 Nov-Dec;28(6):770-81.

0(0,0,0,0) Details