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T144

Sigma-Aldrich

(±)-Thalidomide

≥98%, 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:
50-35-1
Molecular Weight:
258.23
EC Number:
200-031-1
MDL number:
MFCD00153873
UNSPSC Code:
12352111
eCl@ss:
39180303
PubChem Substance ID:
24278765
NACRES:
NA.77

ligand

thalidomide

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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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. 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.

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.

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.

Application

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Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H301,H312,H360D

Hazard Classifications

Acute Tox. 3 Oral - Acute Tox. 4 Dermal - Repr. 1A

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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
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
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
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