Thalidomide (Immunoprin, Contergan and Thalomid)

Description: Thalidomide (trade names Immunoprin, Contergan and Thalomid among others) is a potent immunomodulatory agent and a drug approved in the 1950s. It is commonly used as the ligand of E3 ligase in PROTACs (proteolysis targeting chimeras), a protein degradation technology. Thalidomide is the prototypic drug of the thalidomide class of drugs that are used primarily for the treatment of certain cancers (e.g. MM-multiple myeloma) and of a complication of leprosy. It was introduced as a sedative drug, immunomodulatory agent in 1950s by the German pharmaceutical company Grunenthal and also is investigated for treating symptoms of many cancers. Nowadays, Thalidomide is often times used as a PROTAC (Proteolysis Targeting Chimera) building block which acts as a ligand for the E3 ubiquitin ligase cereblon. PROTAC is a technology utilizes hetero-bifunctional small molecules whereby one end of the molecule recruits an E3 ubiquitin ligase while the other end engages the target protein. Thalidomide inhibits an E3 ubiquitin ligase, which is a CRBN-DDB1-Cul4A complex. Thalidomide is a potent costimulator of primary human T cells in vitro, synergizing with stimulation via the T cell receptor complex to increase interleukin 2-mediated T cell proliferation and interferon gamma production.

References: 1 Hideshima T, et al. Blood, 2000, 96(9), 2943-2950.; 2 Haslett PA, et al. J Exp Med, 1998, 187(11), 1885-1892.

Related CAS: 841-67-8 (S)-Thalidomide; 2098488-36-7 (Azido-Thalidomide)

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