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T144

Sigma-Aldrich

(±)-Thalidomide

≥98%, powder

Sinônimo(s):

(±)-2-(2,6-Dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione

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About This Item

Fórmula empírica (Notação de Hill):
C13H10N2O4
Número CAS:
50-35-1
Peso molecular:
258.23
Número CE:
200-031-1
Número MDL:
MFCD00153873
Código UNSPSC:
12352111
eCl@ss:
39180303
ID de substância PubChem:
24278765
NACRES:
NA.77

ligand

thalidomide

Ensaio

≥98%

forma

powder

adequação da reação

reagent type: ligand

cor

white

solubilidade

DMSO: 20 mg/mL, clear

originador

Celgene

cadeia de caracteres SMILES

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)

chave InChI

UEJJHQNACJXSKW-UHFFFAOYSA-N

Informações sobre genes

human ... CRBN(51185) , CUL4A(8451) , DDB1(1642) , LITAF(9516) , RBX1(9978) , TNF(7124)
mouse ... Nos2(18126)
rat ... Nos1(24598)

Procurando produtos similares? Visita Guia de comparação de produtos

Aplicação

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.

Ações bioquímicas/fisiológicas

(±)-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.

Características e benefícios

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

Nota de preparo

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

Aplicação

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Pictogramas

Skull and crossbonesHealth hazard
GHS06,GHS08

Palavra indicadora

Danger

Frases de perigo

H301,H312,H360D

Classificações de perigo

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

Código de classe de armazenamento

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

Classe de risco de água (WGK)

WGK 3

Equipamento de proteção individual

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Certificados de análise (COA)

Busque Certificados de análise (COA) digitando o Número do Lote do produto. Os números de lote e remessa podem ser encontrados no rótulo de um produto após a palavra “Lot” ou “Batch”.

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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
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
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
Karin Lauschke et al.
Archives of toxicology, 95(5), 1659-1670 (2021-03-05)
To test large numbers of chemicals for developmental toxicity, rapid in vitro tests with standardized readouts for automated data acquisition are needed. However, the most widely used assay, the embryonic stem cell test, relies on the counting of beating embryoid
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
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