Thalidomide
featured

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

MedKoo CAT#: 100840

CAS#: 50-35-1

Description: Thalidomide is a synthetic derivative of glutamic acid (alpha-phthalimido-glutarimide) with teratogenic, immunomodulatory, anti-inflammatory and anti-angiogenic properties. Thalidomide acts primarily by inhibiting both the production of tumor necrosis factor alpha (TNF-alpha) in stimulated peripheral monocytes and the activities of interleukins and interferons. This agent also inhibits polymorphonuclear chemotaxis and monocyte phagocytosis. In addition, thalidomide inhibits pro-angiogenic factors such as vascular endothelial growth factor (VEGF) and basic fibroblast growth factor (bFGF), thereby inhibiting angiogenesis.

Chemical Structure

img
Thalidomide
CAS# 50-35-1
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 100840
Name: Thalidomide
CAS#: 50-35-1
Chemical Formula: C13H10N2O4
Exact Mass: 258.06
Molecular Weight: 258.230
Elemental Analysis: C, 60.47; H, 3.90; N, 10.85; O, 24.78

Price and Availability

Size Price Availability Quantity
1g USD 90 Ready to ship
2g USD 150 Ready to ship
5g USD 250 Ready to ship
10g USD 450 Ready to ship
20g USD 750 Ready to ship
50g USD 1450 Ready to ship
100g USD 2650
200g USD 4850
500g USD 7850
Bulk inquiry

Synonym: alphaphthalimidoglutarimide. Nphthaloylglutamimide; Nphthalylglutamic acid imide. US brand names: Synovir; Thalomid. Foreign brand names: Contergan; Distaval; Kevadon; Neurosedyn; Pantosediv; Sedoval K17; Softenon Talimol; Abbreviation: THAL.

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

InChi Key: UEJJHQNACJXSKW-UHFFFAOYSA-N

InChi Code: InChI=1S/C13H10N2O4/c16-10-6-5-9(11(17)14-10)15-12(18)7-3-1-2-4-8(7)13(15)19/h1-4,9H,5-6H2,(H,14,16,17)

SMILES Code: O=C1N(C(CC2)C(NC2=O)=O)C(C3=C1C=CC=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, not in water

Shelf Life: >2 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

Product Data:
Product Data
Instruction:
View handling instruction
Biological target: Thalidomide-5-OH is the Thalidomide-based cereblon ligand used in the recruitment of CRBN protein.
In vitro activity: Thalidomide upregulated five genes (AICDA, BMP, LEFTY1, LEFTY2, and TBX3) and downregulated one gene (ACTC1) (Table 1, Fig. 1B and C). The ratio of regulated genes, genes without change, and downregulated genes (5, 55, 1) was significantly different from the hypothetical ratio without change (0, 61, 0) (Fig. 1D, Fisher's exact test, P = 0.027). However, the ratio (5, 55, 1) was not significantly different from the hypothetical ratio with equal up- and downregulation (3, 55, 3) (Fig. 1D, Fisher's exact test, P = 0.581). These results suggest that although thalidomide affects undifferentiated hiPSCs, it might not facilitate or inhibit the undifferentiated state. Notably, three transforming growth factor β (TGF-β) genes (BMP2, LEFTY1, and LEFTY2), which are related to mesoderm differentiation, including limb formation, were upregulated (Fig. 1B). Reference: Biochem Biophys Rep. 2021 Mar 13;26:100978. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7973312/
In vivo activity: The CRBN protein is involved in thalidomide-induced degradation of EGFL6. Overexpression of EGFL6 induced the development of abnormal subintestinal vein vessels in a zebrafish model, a process that was impaired by knocking down PAX6 or treatment with thalidomide. These findings established that thalidomide regulates EGFL6 expression through proteasome degradation to inhibit the EGFL6/PAX6 axis-driven angiogenesis in SBVM. Reference: Cell Mol Life Sci. 2020; 77(24): 5207–5221. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7671996/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 33.0 127.79
DMSO:PBS (pH 7.2) (1:8) 0.1 0.43
DMF 12.0 46.47

Preparing Stock Solutions

The following data is based on the product molecular weight 258.230000000000000000000000000000 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: 1. Shimizu M, Tachikawa S, Saitoh N, Nakazono K, Yu-Jung L, Suga M, Ohnuma K. Thalidomide affects limb formation and multiple myeloma related genes in human induced pluripotent stem cells and their mesoderm differentiation. Biochem Biophys Rep. 2021 Mar 13;26:100978. doi: 10.1016/j.bbrep.2021.100978. PMID: 33763605; PMCID: PMC7973312. 2. Liao H, Li Y, Zhang X, Zhao X, Zheng D, Shen D, Li R. Protective Effects of Thalidomide on High-Glucose-Induced Podocyte Injury through In Vitro Modulation of Macrophage M1/M2 Differentiation. J Immunol Res. 2020 Aug 27;2020:8263598. doi: 10.1155/2020/8263598. PMID: 32908940; PMCID: PMC7474395. 3. Tang CT, Zhang QW, Wu S, Tang MY, Liang Q, Lin XL, Gao YJ, Ge ZZ. Thalidomide targets EGFL6 to inhibit EGFL6/PAX6 axis-driven angiogenesis in small bowel vascular malformation. Cell Mol Life Sci. 2020 Dec;77(24):5207-5221. doi: 10.1007/s00018-020-03465-3. Epub 2020 Feb 1. PMID: 32008086; PMCID: PMC7671996. 4. Chen LX, Ni XL, Zhang H, Wu M, Liu J, Xu S, Yang LL, Fu SZ, Wu J. Preparation, characterization, in vitro and in vivo anti-tumor effect of thalidomide nanoparticles on lung cancer. Int J Nanomedicine. 2018 Apr 23;13:2463-2476. doi: 10.2147/IJN.S159327. PMID: 29719394; PMCID: PMC5922239.
In vitro protocol: 1. Shimizu M, Tachikawa S, Saitoh N, Nakazono K, Yu-Jung L, Suga M, Ohnuma K. Thalidomide affects limb formation and multiple myeloma related genes in human induced pluripotent stem cells and their mesoderm differentiation. Biochem Biophys Rep. 2021 Mar 13;26:100978. doi: 10.1016/j.bbrep.2021.100978. PMID: 33763605; PMCID: PMC7973312. 2. Liao H, Li Y, Zhang X, Zhao X, Zheng D, Shen D, Li R. Protective Effects of Thalidomide on High-Glucose-Induced Podocyte Injury through In Vitro Modulation of Macrophage M1/M2 Differentiation. J Immunol Res. 2020 Aug 27;2020:8263598. doi: 10.1155/2020/8263598. PMID: 32908940; PMCID: PMC7474395.
In vivo protocol: 1. Tang CT, Zhang QW, Wu S, Tang MY, Liang Q, Lin XL, Gao YJ, Ge ZZ. Thalidomide targets EGFL6 to inhibit EGFL6/PAX6 axis-driven angiogenesis in small bowel vascular malformation. Cell Mol Life Sci. 2020 Dec;77(24):5207-5221. doi: 10.1007/s00018-020-03465-3. Epub 2020 Feb 1. PMID: 32008086; PMCID: PMC7671996. 2. Chen LX, Ni XL, Zhang H, Wu M, Liu J, Xu S, Yang LL, Fu SZ, Wu J. Preparation, characterization, in vitro and in vivo anti-tumor effect of thalidomide nanoparticles on lung cancer. Int J Nanomedicine. 2018 Apr 23;13:2463-2476. doi: 10.2147/IJN.S159327. PMID: 29719394; PMCID: PMC5922239.

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x