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Pharmacokinetics of primary metabolites 5-hydroxythalidomide and 5'-hydroxythalidomide formed after oral administration of thalidomide in the rabbit, a thalidomide-sensitive species.
Kuwagata M, Hasegawa T, Takashima H, Shimizu M, Kitajima S, Yamazaki H. Kuwagata M, et al. J Toxicol Sci. 2021;46(12):553-560. doi: 10.2131/jts.46.553. J Toxicol Sci. 2021. PMID: 34853241 Free article.
The primary oxidation of thalidomide in previously investigated rodents predominantly resulted in the formation of deactivated 5'-hydroxythalidomide. In the current study, similar in vivo biotransformations to 5-hydroxythalidomide and 5'-hydr …
The primary oxidation of thalidomide in previously investigated rodents predominantly resulted in the formation of deactivated 5'- …
Thalidomide and its metabolite 5-hydroxythalidomide induce teratogenicity via the cereblon neosubstrate PLZF.
Yamanaka S, Murai H, Saito D, Abe G, Tokunaga E, Iwasaki T, Takahashi H, Takeda H, Suzuki T, Shibata N, Tamura K, Sawasaki T. Yamanaka S, et al. EMBO J. 2021 Feb 15;40(4):e105375. doi: 10.15252/embj.2020105375. Epub 2021 Jan 20. EMBO J. 2021. PMID: 33470442 Free PMC article.
PLZF is degraded by the ubiquitin ligase CRL4(CRBN) in complex with thalidomide, its derivatives or 5-hydroxythalidomide in a manner dependent on the conserved first and third zinc finger domains of PLZF. Surprisingly, thalidomide and 5-hydroxythalidomide …
PLZF is degraded by the ubiquitin ligase CRL4(CRBN) in complex with thalidomide, its derivatives or 5-hydroxythalidomide in a …
Structural bases of IMiD selectivity that emerges by 5-hydroxythalidomide.
Furihata H, Yamanaka S, Honda T, Miyauchi Y, Asano A, Shibata N, Tanokura M, Sawasaki T, Miyakawa T. Furihata H, et al. Nat Commun. 2020 Sep 14;11(1):4578. doi: 10.1038/s41467-020-18488-4. Nat Commun. 2020. PMID: 32929090 Free PMC article.
Here, we report the structural bases for the SALL4-specific proteasomal degradation induced by 5-hydroxythalidomide, a primary thalidomide metabolite generated by the enzymatic activity of cytochrome P450 isozymes, through the interaction with cereblon (CRBN). The c …
Here, we report the structural bases for the SALL4-specific proteasomal degradation induced by 5-hydroxythalidomide, a primary …
Human cytochrome P450 oxidation of 5-hydroxythalidomide and pomalidomide, an amino analogue of thalidomide.
Chowdhury G, Shibata N, Yamazaki H, Guengerich FP. Chowdhury G, et al. Chem Res Toxicol. 2014 Jan 21;27(1):147-56. doi: 10.1021/tx4004215. Epub 2013 Dec 24. Chem Res Toxicol. 2014. PMID: 24350712 Free PMC article.
We now show that the dihydroxythalidomide metabolite can be further oxidized to a quinone intermediate. Human P450s 2J2, 2C18, and 4A11 were also found to oxidize 5-hydroxythalidomide to dihydroxy products. Unlike P450s 2C19 and 3A4, neither P450 2J2, 2C18, nor 4A11 …
We now show that the dihydroxythalidomide metabolite can be further oxidized to a quinone intermediate. Human P450s 2J2, 2C18, and 4A11 were …
Assessment of Protein Binding of 5-Hydroxythalidomide Bioactivated in Humanized Mice with Human P450 3A-Chromosome or Hepatocytes by Two-Dimensional Electrophoresis/Accelerator Mass Spectrometry.
Yamazaki H, Suemizu H, Kazuki Y, Oofusa K, Kuribayashi S, Shimizu M, Ninomiya S, Horie T, Shibata N, Guengerich FP. Yamazaki H, et al. Chem Res Toxicol. 2016 Aug 15;29(8):1279-81. doi: 10.1021/acs.chemrestox.6b00210. Epub 2016 Jul 29. Chem Res Toxicol. 2016. PMID: 27464947 Free PMC article.
Liver cytosolic retinal dehydrogenase 1 and glutathione transferase A1 were targets in humanized mice with P450 3A and hepatocytes, respectively. 5-Hydroxythalidomide is bioactivated by human P450 3A enzymes and trapped with proteins nonspecifically in humanized mic …
Liver cytosolic retinal dehydrogenase 1 and glutathione transferase A1 were targets in humanized mice with P450 3A and hepatocytes, respecti …
In vivo formation of dihydroxylated and glutathione conjugate metabolites derived from thalidomide and 5-Hydroxythalidomide in humanized TK-NOG mice.
Yamazaki H, Suemizu H, Shimizu M, Igaya S, Shibata N, Nakamura M, Chowdhury G, Guengerich FP. Yamazaki H, et al. Chem Res Toxicol. 2012 Feb 20;25(2):274-6. doi: 10.1021/tx300009j. Epub 2012 Jan 25. Chem Res Toxicol. 2012. PMID: 22268628 Free PMC article.
The formation of dihydroxythalidomide and glutathione (GSH) conjugate(s) of 5-hydroxythalidomide was investigated in chimeric mice modified with "humanized" liver: novel humanized TK-NOG mice were prepared by the introduction of thymidine kinase, followed by inducti …
The formation of dihydroxythalidomide and glutathione (GSH) conjugate(s) of 5-hydroxythalidomide was investigated in chimeric …
Pharmacokinetics of primary oxidative metabolites of thalidomide in rats and in chimeric mice humanized with different human hepatocytes.
Miura T, Uehara S, Shimizu M, Suemizu H, Yamazaki H. Miura T, et al. J Toxicol Sci. 2021;46(7):311-317. doi: 10.2131/jts.46.311. J Toxicol Sci. 2021. PMID: 34193768 Free article.
Probable metabolites 5'-hydroxythalidomide sulfate and glucuronide were extensively formed, with approximately tenfold and onefold peak areas, respectively, to the primary 5'-hydroxythalidomide measured using authentic standards. As a minor metabolite, …
Probable metabolites 5'-hydroxythalidomide sulfate and glucuronide were extensively formed, with approximately tenfold and one …
5'-OH-thalidomide, a metabolite of thalidomide, inhibits angiogenesis.
Price DK, Ando Y, Kruger EA, Weiss M, Figg WD. Price DK, et al. Ther Drug Monit. 2002 Feb;24(1):104-10. doi: 10.1097/00007691-200202000-00017. Ther Drug Monit. 2002. PMID: 11805730
Thalidomide undergoes very little metabolism by the cytochrome P 450 system in vitro, but at least two hydroxylated metabolites have been found in humans. The two metabolites are 5-hydroxythalidomide, formed by hydroxylation of the phthalimide ring, possibly via are …
Thalidomide undergoes very little metabolism by the cytochrome P 450 system in vitro, but at least two hydroxylated metabolites have been fo …
Species Specificity and Selection of Models for Drug Oxidations Mediated by Polymorphic Human Enzymes.
Yamazaki H, Shimizu M. Yamazaki H, et al. Drug Metab Dispos. 2023 Jan;51(1):123-129. doi: 10.1124/dmd.121.000742. Epub 2022 Jun 30. Drug Metab Dispos. 2023. PMID: 35772770
The primary oxidation product of the teratogen thalidomide in rats is deactivated 5'-hydroxythalidomide plus sulfate and glucuronide conjugates; however, similar 5'-hydroxythalidomide and 5-hydroxythalidomide are formed in rabbits in vivo …
The primary oxidation product of the teratogen thalidomide in rats is deactivated 5'-hydroxythalidomide plus sulfate and glucu …
Human liver microsomal cytochrome P450 3A enzymes involved in thalidomide 5-hydroxylation and formation of a glutathione conjugate.
Chowdhury G, Murayama N, Okada Y, Uno Y, Shimizu M, Shibata N, Guengerich FP, Yamazaki H. Chowdhury G, et al. Chem Res Toxicol. 2010 Jun 21;23(6):1018-24. doi: 10.1021/tx900367p. Chem Res Toxicol. 2010. PMID: 20443640 Free PMC article.
(R)-Thalidomide was oxidized to 5-hydroxythalidomide and 5'-hydroxythalidomide by NADPH-fortified liver microsomes from humans and monkeys. ...P450 2C19 showed a rather nonsaturable substrate-velocity curve; however, P450s 3A4 and 3A5 showed sigmoidal …
(R)-Thalidomide was oxidized to 5-hydroxythalidomide and 5'-hydroxythalidomide by NADPH-fortified liver microsom …
32 results