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MedKoo Cat#: 463644 | Name: 5-Hydroxythalidomide

Description:

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

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

Chemical Structure

5-Hydroxythalidomide
5-Hydroxythalidomide
CAS#64567-60-8

Theoretical Analysis

MedKoo Cat#: 463644

Name: 5-Hydroxythalidomide

CAS#: 64567-60-8

Chemical Formula: C13H10N2O5

Exact Mass: 274.0590

Molecular Weight: 274.23

Elemental Analysis: C, 56.94; H, 3.68; N, 10.22; O, 29.17

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
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

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
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. 3: Murayama N, Kazuki Y, Satoh D, Arata K, Harada T, Shibata N, Guengerich FP, Yamazaki H. Induction of human cytochrome P450 3A enzymes in cultured placental cells by thalidomide and relevance to bioactivation and toxicity. J Toxicol Sci. 2017;42(3):343-348. doi: 10.2131/jts.42.343. PMID: 28496040; PMCID: PMC5776038. 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. 15: Luzzio FA, Duveau DY, Lepper ER, Figg WD. Synthesis of racemic cis-5-hydroxy-3-phthalimidoglutarimide. A metabolite of thalidomide isolated from human plasma. J Org Chem. 2005 Nov 25;70(24):10117-20. doi: 10.1021/jo0514772. PMID: 16292851. 16: Noguchi T, Fujimoto H, Sano H, Miyajima A, Miyachi H, Hashimoto Y. Angiogenesis inhibitors derived from thalidomide. Bioorg Med Chem Lett. 2005 Dec 15;15(24):5509-13. doi: 10.1016/j.bmcl.2005.08.086. Epub 2005 Sep 23. PMID: 16183272. 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. 18: Inatsuki S, Noguchi T, Miyachi H, Oda S, Iguchi T, Kizaki M, Hashimoto Y, Kobayashi H. Tubulin-polymerization inhibitors derived from thalidomide. Bioorg Med Chem Lett. 2005 Jan 17;15(2):321-5. doi: 10.1016/j.bmcl.2004.10.072. PMID: 15603947. 19: Lu J, Helsby N, Palmer BD, Tingle M, Baguley BC, Kestell P, Ching LM. Metabolism of thalidomide in liver microsomes of mice, rabbits, and humans. J Pharmacol Exp Ther. 2004 Aug;310(2):571-7. doi: 10.1124/jpet.104.067793. Epub 2004 Apr 9. PMID: 15075384. 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.