5-Hydroxythalidomide

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 463644

CAS#: 64567-60-8

Description: 5-Hydroxythalidomide is a primary thalidomide metabolite, inducing the SALL4-specific proteasomal degradation.


Chemical Structure

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5-Hydroxythalidomide
CAS# 64567-60-8

Theoretical Analysis

MedKoo Cat#: 463644
Name: 5-Hydroxythalidomide
CAS#: 64567-60-8
Chemical Formula: C13H10N2O5
Exact Mass: 274.06
Molecular Weight: 274.232
Elemental Analysis: C, 56.94; H, 3.68; N, 10.22; O, 29.17

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: 5-Hydroxythalidomide; thalidomide-5-OH;

IUPAC/Chemical Name: 2-(2,6-dioxopiperidin-3-yl)-5-hydroxyisoindoline-1,3-dione

InChi Key: LJBQRRQTZUJWRC-UHFFFAOYSA-N

InChi Code: InChI=1S/C13H10N2O5/c16-6-1-2-7-8(5-6)13(20)15(12(7)19)9-3-4-10(17)14-11(9)18/h1-2,5,9,16H,3-4H2,(H,14,17,18)

SMILES Code: O=C1N(C(CC2)C(NC2=O)=O)C(C3=C1C=CC(O)=C3)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 274.23 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Yamanaka S, Shoya Y, Matsuoka S, Nishida-Fukuda H, Shibata N, Sawasaki T. An IMiD-induced SALL4 degron system for selective degradation of target proteins. Commun Biol. 2020 Sep 18;3(1):515. doi: 10.1038/s42003-020-01240-5. PMID: 32948804; PMCID: PMC7501283.

2: Furihata H, Yamanaka S, Honda T, Miyauchi Y, Asano A, Shibata N, Tanokura M, Sawasaki T, Miyakawa T. Structural bases of IMiD selectivity that emerges by 5-hydroxythalidomide. Nat Commun. 2020 Sep 14;11(1):4578. doi: 10.1038/s41467-020-18488-4. PMID: 32929090; PMCID: PMC7490372.

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4: Yamazaki H, Suemizu H, Kazuki Y, Oofusa K, Kuribayashi S, Shimizu M, Ninomiya S, Horie T, Shibata N, Guengerich FP. 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. Chem Res Toxicol. 2016 Aug 15;29(8):1279-81. doi: 10.1021/acs.chemrestox.6b00210. Epub 2016 Jul 29. PMID: 27464947; PMCID: PMC5282975.

5: Nishiyama S, Suemizu H, Shibata N, Guengerich FP, Yamazaki H. Simulation of Human Plasma Concentrations of Thalidomide and Primary 5-Hydroxylated Metabolites Explored with Pharmacokinetic Data in Humanized TK-NOG Mice. Chem Res Toxicol. 2015 Nov 16;28(11):2088-90. doi: 10.1021/acs.chemrestox.5b00381. Epub 2015 Oct 26. PMID: 26492539; PMCID: PMC6345571.

6: Murayama N, van Beuningen R, Suemizu H, Guillouzo CG, Shibata N, Yajima K, Utoh M, Shimizu M, Chesné C, Nakamura M, Guengerich FP, Houtman R, Yamazaki H. Thalidomide increases human hepatic cytochrome P450 3A enzymes by direct activation of the pregnane X receptor. Chem Res Toxicol. 2014 Feb 17;27(2):304-308. doi: 10.1021/tx4004374. Epub 2014 Feb 5. PMID: 24460184; PMCID: PMC4020009.

7: Chowdhury G, Shibata N, Yamazaki H, Guengerich FP. Human cytochrome P450 oxidation of 5-hydroxythalidomide and pomalidomide, an amino analogue of thalidomide. Chem Res Toxicol. 2014 Jan 21;27(1):147-56. doi: 10.1021/tx4004215. Epub 2013 Dec 24. PMID: 24350712; PMCID: PMC3929586.

8: Yamazaki H, Suemizu H, Shimizu M, Igaya S, Shibata N, Nakamura M, Chowdhury G, Guengerich FP. In vivo formation of dihydroxylated and glutathione conjugate metabolites derived from thalidomide and 5-Hydroxythalidomide in humanized TK- NOG mice. Chem Res Toxicol. 2012 Feb 20;25(2):274-6. doi: 10.1021/tx300009j. Epub 2012 Jan 25. PMID: 22268628; PMCID: PMC3976424.

9: Yamazaki H, Suemizu H, Igaya S, Shimizu M, Shibata N, Nakamura M, Chowdhury G, Guengerich FP. In vivo formation of a glutathione conjugate derived from thalidomide in humanized uPA-NOG mice. Chem Res Toxicol. 2011 Mar 21;24(3):287-9. doi: 10.1021/tx200005g. Epub 2011 Feb 7. PMID: 21299192; PMCID: PMC3838788.

10: Chowdhury G, Murayama N, Okada Y, Uno Y, Shimizu M, Shibata N, Guengerich FP, Yamazaki H. Human liver microsomal cytochrome P450 3A enzymes involved in thalidomide 5-hydroxylation and formation of a glutathione conjugate. Chem Res Toxicol. 2010 Jun 21;23(6):1018-24. doi: 10.1021/tx900367p. PMID: 20443640; PMCID: PMC3843493.

11: Yamamoto T, Shibata N, Sukeguchi D, Takashima M, Nakamura S, Toru T, Matsunaga N, Hara H, Tanaka M, Obata T, Sasaki T. Synthesis, configurational stability and stereochemical biological evaluations of (S)- and (R)-5-hydroxythalidomides. Bioorg Med Chem Lett. 2009 Jul 15;19(14):3973-6. doi: 10.1016/j.bmcl.2009.02.108. Epub 2009 Mar 3. PMID: 19297157.

12: Yamamoto T, Shibata N, Takashima M, Nakamura S, Toru T, Matsunaga N, Hara H. Enzymatic resolution and evaluation of enantiomers of cis-5'-hydroxythalidomide. Org Biomol Chem. 2008 May 7;6(9):1540-3. doi: 10.1039/b802459f. Epub 2008 Mar 28. PMID: 18421383.

13: Kizaki M, Hashimoto Y. New tubulin polymerization inhibitor derived from thalidomide: implications for anti-myeloma therapy. Curr Med Chem. 2008;15(8):754-65. doi: 10.2174/092986708783955473. PMID: 18393844.

14: Iguchi T, Yachide-Noguchi T, Hashimoto Y, Nakazato S, Sagawa M, Ikeda Y, Kizaki M. Novel tubulin-polymerization inhibitor derived from thalidomide directly induces apoptosis in human multiple myeloma cells: possible anti- myeloma mechanism of thalidomide. Int J Mol Med. 2008 Feb;21(2):163-8. PMID: 18204782.

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17: Noguchi T, Shinji C, Kobayashi H, Makishima M, Miyachi H, Hashimoto Y. Enhancement of all-trans retinoic acid-induced HL-60 cell differentiation by thalidomide and its metabolites. Biol Pharm Bull. 2005 Mar;28(3):563-4. doi: 10.1248/bpb.28.563. PMID: 15744093.

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20: Ando Y, Price DK, Dahut WL, Cox MC, Reed E, Figg WD. Pharmacogenetic associations of CYP2C19 genotype with in vivo metabolisms and pharmacological effects of thalidomide. Cancer Biol Ther. 2002 Nov-Dec;1(6):669-73. doi: 10.4161/cbt.318. PMID: 12642692.