T144

(±)-Thalidomide

≥98%, beta-secretase inhibitor, powder

• Synonym(s): (±)-2-(2,6-Dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione
• Empirical Formula (Hill Notation): C₁₃H₁₀N₂O₄
• CAS Number: 50-35-1
• Molecular Weight: 258.23
• UNSPSC Code: 12352111
• eCl@ss: 39180303
• PubChem Substance ID: 24278765
• NACRES: NA.77
• EC Number: 200-031-1
• MDL number: MFCD00153873
• Assay: ≥98%
• Form: powder

Properties

• Product Name: (±)-Thalidomide, ≥98%, powder
• ligand: thalidomide
• Quality Segment: 200
• assay: ≥98%
• form: powder
• reaction suitability: reagent type: ligand
• color: white
• solubility: DMSO: 20 mg/mL, clear
• originator: Celgene
• SMILES string: O=C1CCC(N2C(=O)c3ccccc3C2=O)C(=O)N1
• 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)
• InChI key: UEJJHQNACJXSKW-UHFFFAOYSA-N
• Gene Information: human ... CRBN(51185), CUL4A(8451), DDB1(1642), LITAF(9516), RBX1(9978), TNF(7124) ; mouse ... Nos2(18126) ; rat ... Nos1(24598)

Description

Application

Thalidomide has been used to study its neuropathological effects in mouse models of Alzheimer′s disease (AD). This study reported that long term administration of thalidomide causes beta-secretase inhibition and subsequently alleviates amyloid-like pathology[1]. Furthermore, thalidomide has also been used to evaluate its teratogenic functions. Thalidomide was found to affect endodermal differentiation and neural development in differentiating human embryonic and induced pluripotent stem cells[2].

Biochem/physiol Actions

(±)-Thalidomide selectively inhibits biosynthesis of tumor necrosis factor α (TNF-α). It also functions as an inhibitor of angiogenesis, an immunosuppressive agent, a sedative and a teratogen. Furthermore, thalidomide is known to exhibit antitumor functions in refractory multiple myeloma[3].

Features and Benefits

This compound was developed by Celgene. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Preparation Note

Thalidomide is soluble in DMSO at a concentration that is more than 20 mg/ml. It is insoluble in water and ethanol.

Safety Information

• pictograms: GHS06,GHS08
• signalword: Danger
• hcodes: H301,H312,H360D
• pcodes: P202 - P264 - P280 - P301 + P310 - P302 + P352 + P312 - P362 + P364
• Hazard Classifications: Acute Tox. 3 Oral - Acute Tox. 4 Dermal - Repr. 1A
• Storage Class: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• wgk: WGK 3
• ppe: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges