Currently, there are no salt forms of this compound available.
T144
(±)-Thalidomide
≥98%, beta-secretase inhibitor, powder
Synonym(s):
(±)-2-(2,6-Dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione
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About This Item
Empirical Formula (Hill Notation):
C13H10N2O4
CAS Number:
Molecular Weight:
258.23
EC Number:
MDL number:
UNSPSC Code:
12352111
eCl@ss:
39180303
PubChem Substance ID:
NACRES:
NA.77
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Product Name
(±)-Thalidomide, ≥98%, powder
ligand
thalidomide
Quality Level
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)
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This Item | T151 | SML2686 | T150 |
|---|---|---|---|
| assay ≥98% | assay ≥98% (HPLC) | assay ≥98% (HPLC) | assay >98% |
| form powder | form powder | form powder | form solid |
| solubility DMSO: 20 mg/mL, clear | solubility DMSO: 15 mg/mL, clear | solubility DMSO: 2 mg/mL, clear | solubility DMSO: soluble, H2O: insoluble, ethanol: insoluble |
| originator Celgene | originator Celgene | originator - | originator Celgene |
| color white | color white to beige | color white to beige | color white |
| ligand thalidomide | ligand thalidomide | ligand pomalidomide | ligand thalidomide |
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.
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Description
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Danger
hcodes
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
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WGK 3
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Yoav Mayshar et al.
Journal of cellular and molecular medicine, 15(6), 1393-1401 (2010-06-22)
Teratogens are substances that may cause defects in normal embryonic development while not necessarily being toxic in adults. Identification of possible teratogenic compounds has been historically beset by the species-specific nature of the teratogen response. To examine teratogenic effects on
Tomomi Noguchi et al.
Bioorganic & medicinal chemistry letters, 15(24), 5509-5513 (2005-09-27)
5-Hydroxy-2-(2,6-diisopropylphenyl)-1H-isoindole-1,3-dione (5HPP-33: 10), which was obtained during our previous structural development studies on thalidomide, was revealed to possess potent anti-angiogenic activity in a human umbilical vein endothelial cell (HUVEC) assay. Thalidomide (1) and its metabolite, 5-hydroxythalidomide (5-HT: 2), which possesses
Yang Yang et al.
Pharmaceutics, 15(4) (2023-04-28)
Thalidomide (THD), a synthetic derivative of glutamic acid, was initially used as a sedative and antiemetic until the 1960s, when it was found to cause devastating teratogenic effects. However, subsequent studies have clearly demonstrated the anti-inflammatory, anti-angiogenic, and immunomodulatory properties
Marzia Lazzerini et al.
JAMA, 310(20), 2164-2173 (2013-11-28)
Pediatric-onset Crohn disease is more aggressive than adult-onset disease, has high rates of resistance to existing drugs, and can lead to permanent impairments. Few trials have evaluated new drugs for refractory Crohn disease in children. To determine whether thalidomide is
S Singhal et al.
The New England journal of medicine, 341(21), 1565-1571 (1999-11-24)
Patients with myeloma who relapse after high-dose chemotherapy have few therapeutic options. Since increased bone marrow vascularity imparts a poor prognosis in myeloma, we evaluated the efficacy of thalidomide, which has antiangiogenic properties, in patients with refractory disease. Eighty-four previously
Articles
Effective in key synthesis reactions like Knoevenagel condensation, thalidomide synthesis, and Suzuki coupling for sustainable chemical transformations.
Chromatograms
application for HPLC
application for HPLC
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