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Two-dimensional chromatography for enantiomeric analysis of mitotane and its metabolite o,p'-DDA in patients with adrenocortical carcinoma indicates enantioselective metabolism.
Stadler G, de Almeida Veiga A, Rita Corso C, Bach de Assis C, de Toledo Nogueira B, Regina Rocha Martins L, Cruz Bonk B, Lada Degaut Pontes F, Cavalcante de Figueiredo B, Mera de Souza L. Stadler G, et al. Bioorg Chem. 2023 Dec;141:106835. doi: 10.1016/j.bioorg.2023.106835. Epub 2023 Sep 3. Bioorg Chem. 2023. PMID: 37713949
Mitotane is a chiral drug used to treat adrenocortical carcinoma, being metabolized to the o,p'-dichlorodiphenyl acetic acid (o,p'-DDA), also a chiral compound. Despite of its therapeutic significance, the overall ratios and enantiomers have not been known. I …
Mitotane is a chiral drug used to treat adrenocortical carcinoma, being metabolized to the o,p'-dichlorodiphenyl acetic acid (o,p …
The lack of antitumor effects of o,p'DDA excludes its role as an active metabolite of mitotane for adrenocortical carcinoma treatment.
Hescot S, Paci A, Seck A, Slama A, Viengchareun S, Trabado S, Brailly-Tabard S, Al Ghuzlan A, Young J, Baudin E, Lombès M. Hescot S, et al. Horm Cancer. 2014 Oct;5(5):312-23. doi: 10.1007/s12672-014-0189-7. Epub 2014 Jul 16. Horm Cancer. 2014. PMID: 25026941 Free PMC article.
While o,p'DDD concentration was significantly reduced by 40 % in H295R cell supernatants after 48 h incubation, o,p'DDA levels remained unchanged suggesting that o,p'DDA was not efficiently transported into the cells. o,p' …
While o,p'DDD concentration was significantly reduced by 40 % in H295R cell supernatants after 48 h incubation, o,p'DDA …
Plasma concentrations of o,p'DDD, o,p'DDA, and o,p'DDE as predictors of tumor response to mitotane in adrenocortical carcinoma: results of a retrospective ENS@T multicenter study.
Hermsen IG, Fassnacht M, Terzolo M, Houterman S, den Hartigh J, Leboulleux S, Daffara F, Berruti A, Chadarevian R, Schlumberger M, Allolio B, Haak HR, Baudin E. Hermsen IG, et al. J Clin Endocrinol Metab. 2011 Jun;96(6):1844-51. doi: 10.1210/jc.2010-2676. Epub 2011 Apr 6. J Clin Endocrinol Metab. 2011. PMID: 21470991
An o,p'DDD level 20 mg/liter or greater or 14 mg/liter or greater combined with o,p'DDA level 92 mg/liter or greater was associated with a specificity of 90 and 92%, respectively. ...Furthermore, our results suggest additional benefit of higher levels of o,p' …
An o,p'DDD level 20 mg/liter or greater or 14 mg/liter or greater combined with o,p'DDA level 92 mg/liter or greater wa …
Effects of o,p'-DDE, a Mitotane Metabolite, in an Adrenocortical Carcinoma Cell Line.
Bach C, Corso CR, Veiga AA, Paraizo MM, de Souza LM. Bach C, et al. Pharmaceuticals (Basel). 2022 Nov 29;15(12):1486. doi: 10.3390/ph15121486. Pharmaceuticals (Basel). 2022. PMID: 36558937 Free PMC article.
The mitotane metabolism occurs via two main reactions: the beta-hydroxylation, which yields the final product o,p'-DDA, and the alpha-hydroxylation, which will give the final product o,p'-DDE. It is speculated that o,p'-DDE may be an active metabolite since i …
The mitotane metabolism occurs via two main reactions: the beta-hydroxylation, which yields the final product o,p'-DDA, …
Determination of mitotane (o,p-DDD) and its metabolites o,p-DDA and o,p-DDE in plasma by high-performance liquid chromatography.
Andersen A, Kasperlik-Zaluska AA, Warren DJ. Andersen A, et al. Ther Drug Monit. 1999 Jun;21(3):355-9. doi: 10.1097/00007691-199906000-00020. Ther Drug Monit. 1999. PMID: 10365653 Clinical Trial.
The adrenolytic agent mitotane (o,p'-DDD or 1,1-(o,p'-dichlorodiphenyl)-2,2-dichoroethane) is believed to be metabolically activated, resulting in the generation of reactive intermediates or the formation of o,p'-DDA. A new high-performance liquid chromatogra …
The adrenolytic agent mitotane (o,p'-DDD or 1,1-(o,p'-dichlorodiphenyl)-2,2-dichoroethane) is believed to be metabolically activated, result …
Use of GC/MS/SIM for rapid determination of plasma levels of o,p'-DDD, o,p'-DDE and o,p'-DDA.
Inouye M, Mio T, Sumino K. Inouye M, et al. Clin Chim Acta. 1987 Dec;170(2-3):305-14. doi: 10.1016/0009-8981(87)90141-0. Clin Chim Acta. 1987. PMID: 3436064
In addition, this procedure also carried out the simultaneous methylation of o,p'-DDA, one of the metabolites. Mass numbers of 199, 210, 235 and 246 were selected from the mass spectra of o,p'-DDD and its related substances, and they were monitored. ...Quanti …
In addition, this procedure also carried out the simultaneous methylation of o,p'-DDA, one of the metabolites. Mass num …
Metabolism of 1-(0-chlorophenyl)-1-(p-chlorophenyl)-2,2-dichloroethane (o,p'-DDD) in rats.
Reif VD, Sinsheimer JE. Reif VD, et al. Drug Metab Dispos. 1975 Jan-Feb;3(1):15-25. Drug Metab Dispos. 1975. PMID: 234830
The urine was found to contain o,p'-dichlorodiphenylacetic acid (o,p'-DDA) as well as 4-hydroxy-, 3-hydroxy-, and 3,4-dihydroxy-substituted o,p'-DDA. The serine and glycine conjugates of o,p'-DDA were also identified. …
The urine was found to contain o,p'-dichlorodiphenylacetic acid (o,p'-DDA) as well as 4-hydroxy-, 3-hydroxy-, and 3,4-d …
Effects of adrenolytic mitotane on drug elimination pathways assessed in vitro.
Theile D, Haefeli WE, Weiss J. Theile D, et al. Endocrine. 2015 Aug;49(3):842-53. doi: 10.1007/s12020-014-0517-2. Epub 2014 Dec 27. Endocrine. 2015. PMID: 25542188
P-gp induction was confirmed at the protein level. o,p'-DDE revealed a similar induction profile, however, with less potency and o,p'-DDA had only minor effects. Reporter gene assays clearly confirmed o,p'-DDD to be a PXR activator and for the first time demo …
P-gp induction was confirmed at the protein level. o,p'-DDE revealed a similar induction profile, however, with less potency and o, …
RRM1 modulates mitotane activity in adrenal cancer cells interfering with its metabolization.
Germano A, Rapa I, Volante M, De Francia S, Migliore C, Berruti A, Papotti M, Terzolo M. Germano A, et al. Mol Cell Endocrinol. 2015 Feb 5;401:105-10. doi: 10.1016/j.mce.2014.11.027. Epub 2014 Dec 9. Mol Cell Endocrinol. 2015. PMID: 25497672 Free article.
The anti-proliferative activity of mitotane (o,p'DDD) in adrenocortical cancer is mediated by its metabolites o,p'DDE and o,p'DDA. We previously demonstrated a functional link between ribonucleotide reductase M1(RRM1) expression and o,p'DDD activity, but the …
The anti-proliferative activity of mitotane (o,p'DDD) in adrenocortical cancer is mediated by its metabolites o,p'DDE and o,p' …
Toxicity, ultrastructural effects, and metabolic studies with 1-(o-chlorophenyl)-1-(p-chlorophenyl)-2,2-dichloroethane(o,p'-DDD) and its methyl analog in the guinea pig and rat.
Jensen BL, Caldwell MW, French LG, Briggs DG. Jensen BL, et al. Toxicol Appl Pharmacol. 1987 Jan;87(1):1-9. doi: 10.1016/0041-008x(87)90078-0. Toxicol Appl Pharmacol. 1987. PMID: 3798445
In fact, the dominant metabolite from Lysodren biotransformation was the corresponding carboxylic acid o,p'-DDA (III). On the other hand, Mitometh resisted side-chain oxidative metabolism and was less toxic than Lysodren. ...
In fact, the dominant metabolite from Lysodren biotransformation was the corresponding carboxylic acid o,p'-DDA (III). …
19 results