Introduction. Excessive use of pesticides leads to environmental pollution and poses a danger to human and animal health. Pyethroid insecticides (pyrethroids) are the most commonly used pesticides because they are less toxic to non-target species. It is well-known that prolonged exposure to pyrethroids can result in the endocrine function of the gonads being disrupted. Cypermethrin is a very common pyrethroid, the toxicity of which is widely studied, but little is known about the endocrine-disrupting effect of its stereoisomer, α-cypermethrin. In our opinion, quercetin, a flavonoid that has estrogen-like and antioxidant properties, can be an effective means of protection against the complications of pyrethroid intoxication. Aim. In silico studies of the binding mechanisms of quercetin, α-cypermethrin and its derivatives with the estrogen receptor α, features of pharmacokinetics and toxicity profile of these compounds. Methods. The molecular docking procedure of quercetin, α-cypermethrin, 3-PВA and DCCA was carried out using the crystal structures of the ligand-binding domain of ERα: 3ERT (reference ligand – 4-hydroxytamoxifen), 1ERR (reference ligand – raloxifene), 1GWR and 1ERE (reference ligand – estradiol) from the PDB database of biological macromolecules. Three different docking software packages were used: Glide, AutoDock, and AutoDock Vina. The location of the reference ligand was used to determine the automatic detection of the binding site. The pkCSM platform, admetSAR online server and SwissADME were used for in silico investigation of pharmacokinetic properties and toxicity of quercetin and α-cypermethrin. The results. AutoDock predicts that α-cypermethrin has the lowest binding energy with 1ERE (–10.4 kcal/mol), 1GWR (–10.0 kcal/mol), and 1ERR. This may indicate an agonistic effect of this insecticide on ERα. The predicted Gscore values for α-cypermethrin reflect a stronger interaction with 3ERT: –9.29 kcal/mol. The binding characteristics of α-cypermethrin, its metabolites (3-PBA and DCCA) and 4-hydroxytamoxifen with 3ERT are similar, which may indicate an antagonistic effect of the pyrethroid for ERα. The opposite nature of the interaction of α-cypermethrin with ERα can be explained by the difference in evaluation functions and methods of optimization of protein structures and ligands depending on the software used. The results predicted by both AutoDock, Vina and Schrödinger Maestro Glide show for quercetin the lowest binding energy values with 1ERR, 1GWR and 1ERE, which is a sign of agonistic action. Quercetin binds to the ligand-binding domains of ERα more strongly than 3-PBA and DCCA. Quercetin has toxicity and pharmacokinetic parameters corresponding to the norm and meets all the requirements for drug-like properties. Based on the data obtained in silico, it is possible to assert the expediency of using quercetin as a component of the prevention of complications of the endocrinotoxic action of α-cypermethrin. Conclusions. The toxic effect of α-cypermethrin, which is aimed at disrupting the endocrine function of the gonads, may be associated with the high affinity of this compound and its metabolites for ERα, accompanied by both agonistic and antagonistic effects according to various evaluation criteria. Quercetin, a flavonoid with pronounced ER agonistic properties, can be used to prevent complications of α-cypermethrin intoxication based on its pharmacokinetic and drug-like parameters.