(S) -Thalidomide

(S) -Thalidomide ((S) - (-) -Thalidomide) is the S-enantiomer of Thalidomide. (S) -Thalidomide has immunomodulatory, anti-inflammatory, antiangiogenic and pro-apoptotic effects[1][2][3]. (S) -Thalidomide induces teratogenic effects by binding to cereblon (CRBN) [4].

Product Specifications

CAS Number

[841-67-8]

Product Name Alternative

(S) - (-) -Thalidomide

UNSPSC

12352005

Hazard Statement

H302, H360

Target

Apoptosis; Autophagy; Ligands for E3 Ligase; Molecular Glues

Type

Reference compound

Related Pathways

Apoptosis; Autophagy; PROTAC

Applications

Metabolism-protein/nucleotide metabolism

Field of Research

Metabolic Disease; Inflammation/Immunology

Assay Protocol

https://www.medchemexpress.com/s-thalidomide.html

Purity

99.52

Solubility

DMSO : 83.33 mg/mL (ultrasonic)

Smiles

O=C1N([C@@H](CC2)C(NC2=O)=O)C(C3=C1C=CC=C3)=O

Molecular Formula

C13H10N2O4

Molecular Weight

258.23

Precautions

H302, H360

References & Citations

[1]Stephens TD. The effect of thalidomide in chicken embryos. Birth Defects Res A Clin Mol Teratol. 2009 Aug;85 (8) :725-31.|[2]Murphy S, et al. Enantioselectivity of thalidomide serum and tissue concentrations in a rat glioma model and effects of combination treatment with cisplatin and BCNU. J Pharm Pharmacol. 2007 Jan;59 (1) :105-14.|[3]Liu WM, et al. s-thalidomide has a greater effect on apoptosis than angiogenesis in a multiple myeloma cell line. Hematol J. 2004;5 (3) :247-54.|[4]Tokunaga E, et al. Understanding the Thalidomide Chirality in Biological Processes by the Self-disproportionation of Enantiomers. Sci Rep. 2018 Nov 20;8 (1) :17131.