Research paperParticular ability of cytochromes P450 3A to form inhibitory P450-iron-metabolite complexes upon metabolic oxidation of aminodrugs
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The mechanisms of interactions of psychotropic drugs with liver and brain cytochrome P450 and their significance for drug effect and drug-drug interactions
2022, Biochemical PharmacologyCitation Excerpt :On the other hand, some psychotropics, such as tricyclic antidepressants, phenothiazine neuroleptics or haloperidol produce reactive metabolites, which irreversibly bind to CYP enzymes, in this way inhibiting enzyme activity (Fig. 3). Tricyclic antidepressants and fluoxetine have been shown to form inhibitory CYP-iron(II)-nitrosoalkane metabolite complexes, affecting CYP3A, CYP2C11 and CYP2A [57,58]. Likewise, epoxide intermediates of imipramine (and probably of other antidepressants) formed during hydroxylation process, radical cations of phenothiazine neuroleptics mediating their sulfoxidation and ring hydroxylation, and haloperidol pyridinium metabolites (HPP+) irreversibly inhibit CYP2D6 activity [51,59,60].
The nitrosoamphetamine metabolite is accommodated in the active site of human hemoglobin: Spectroscopy and crystal structure
2020, Journal of Inorganic BiochemistryCitation Excerpt :A hydrogen bond was evident between the nitroso O-atom of the AmphNO and the distal His63 residue (Fig. 6B), with the nitroso NO bond nearly eclipsing an Fe–N(heme) bond (with a N(por)–Fe–N–O torsion angle of ~2°). As we note in the Introduction, nitrosoalkane binding to the Fe centers of heme proteins are known to inhibit the functions of these proteins [8,13–24]. To verify the Fe oxidation states extant in the crystal obtained from the Hb/AmphNHOH reaction, we retrieved the crystal used in the X-ray diffraction data collection and obtained its UV–vis spectrum (after dissolving the used crystal in buffer).
Time-dependent enzyme inactivation: Numerical analyses of in vitro data and prediction of drug-drug interactions
2020, Pharmacology and TherapeuticsCitation Excerpt :The amine group is hydroxylated and further oxidized to form a nitroso group that coordinates with the heme. The heme is then reduced to a more stable ferrous form (Bensoussan et al., 1995; Mansuy, Gans, Chottard, & Bartoli, 1977) with an absorbance maximum of 448 to 456 nm (Franklin, 1977). The MIC is stable and can be isolated (Ekroos & Sjögren, 2006; Murray & Reidy, 1990).
Effect of antidepressant drugs on cytochrome P450 2C11 (CYP2C11) in rat liver
2013, Pharmacological ReportsCitation Excerpt :Like in rats, the investigated antidepressants are not regarded as potent inhibitors of human CYP2C9 [19, 33, 43]. As has been mentioned elsewhere, tricyclic antidepressants and fluoxetine can form reactive/intermediate metabolites, which irreversibly inactivate a few CYP isoforms (CYP2C11, CYP2D, CYP3A and CYP2A) after prolonged incubation in vitro with high concentrations of antidepressants, or after in vivo administration of high doses of the drugs [5, 27, 28, 30, 31], as well as when used at therapeutic concentrations in vivo after a 24-h exposure to antidepressants [11, 12, 18]. The present results suggest that CYP2C11 inactivation via this mechanism by imipramine, desipramine and fluoxetine (used in therapeutic concentrations) via this mechanism is also possible, since a one-day treatment with pharmacological doses of the above-mentioned antidepressants diminishes (down to 66–70% of the control values) the enzyme activity in rats (Model II).
Evaluation of the inhibitory effects of antihypertensive drugs on human carboxylesterase in vitro
2013, Drug Metabolism and PharmacokineticsHeterocycle-substituted proline dipeptides as potent VLA-4 antagonists
2010, Bioorganic and Medicinal Chemistry Letters