(S)-Thalidomide

• CAT Number: R002607
• CAS Number: 841-67-8
• Molecular Formula: C13H10N2O4
• Molecular Weight: 258.23
• Purity: ≥95%
• Synonyms: 2-[(3S)-2,6-dioxopiperidin-3-yl]isoindole-1,3-dione
• InChI: 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)/t9-/m0/s1
• InChIKey: UEJJHQNACJXSKW-VIFPVBQESA-N
• SMILES: C1CC(=O)NC(=O)C1N2C(=O)C3=CC=CC=C3C2=O

(S)-Thalidomide(CAT: R002607) is the stereoisomer of thalidomide, a glutamic acid derivative with diverse pharmacological activities. Unlike its (R)-enantiomer, which exhibits sedative effects, (S)-thalidomide is primarily responsible for the compound’s notorious teratogenicity, causing severe birth defects when administered during pregnancy. Despite this history, controlled use of racemic thalidomide and its analogs has revealed significant therapeutic potential. (S)-Thalidomide contributes to immunomodulatory and anti-angiogenic effects, making it relevant in the treatment of multiple myeloma, erythema nodosum leprosum, and inflammatory conditions. Its study provides crucial insights into enantiomer-specific pharmacology, drug safety, and the design of safer immunomodulatory imide drugs (IMiDs).