Thalidomide

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.

Product information

CAS Number: 50-35-1

Molecular Weight: 258.23

Formula: C13H10N2O4

Synonym:

Sedoval K17

Synovir

Thalomid

Contergan

Distaval

Kevadon

Neurosedyn

Pantosediv

Softenon Talimol

THAL

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

Smiles: O=C1CCC(C(=O)N1)N1C(=O)C2=CC=CC=C2C1=O

InChiKey: UEJJHQNACJXSKW-UHFFFAOYSA-N

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)

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: DMSO: 51 mg/mL (197.50 mM) Water: Insoluble

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

Thalidomide must be metabolized by the liver to form an epoxide that may be the active teratogenic metabolite. Thalidomide selectively inhibits the production of human monocyte tumor necrosis factor alpha (TNF-alpha) when human monocytes are triggered with lipopolysaccharide and other agonists in culture. Thalidomide exerts its inhibitory action on tumor necrosis factor alpha by enhancing mRNA degradation. Thalidomide acts directly, by inducing apoptosis or G1 growth arrest, in MM cell lines and in patient MM cells that are resistant to melphalan, doxorubicin, and dexamethasone (Dex). Thalidomide enhances the anti-MM activity of Dex and, conversely, are inhibited by interleukin 6. 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. Thalidomide also increases the primary CD8+ cytotoxic T cell response induced by allogeneic dendritic cells in the absence of CD4+ T cells.

In Vivo:

Thalidomide (200 mg/kg) results in an inhibition of the area of vascularized cornea of rabbits that ranged from 30% to 51% in three experiments with a median inhibition of 36%.

References:

1. D'Amato RJ, et al. Proc Natl Acad Sci U S A, 1994, 91(9), 4082-4085.
2. Sampaio EP, et al. J Exp Med, 1991, 173(3), 699-703.
3. Moreira AL, et al. J Exp Med, 1993, 177(6), 1675-1680.
4. Hideshima T, et al. Blood, 2000, 96(9), 2943-2950.
5. Haslett PA, et al. J Exp Med, 1998, 187(11), 1885-1892.
6. Eric S Fischer, et al. Nature . 2014 Aug 7;512(7512):49-53.

Products are for research use only. Not for human use.