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Merck

T144

(±)-Thalidomide

≥98%, beta-secretase inhibitor, powder

Synonyme(s) :

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

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A propos de cet article

Formule empirique (notation de Hill) :
C13H10N2O4
Numéro CAS:
50-35-1
Poids moléculaire :
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
Quality level:
200

Principaux documents

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Nom du produit

(±)-Thalidomide, ≥98%, powder

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

ligand

thalidomide

assay

≥98%

form

powder

reaction suitability

reagent type: ligand

color

white

solubility

DMSO: 20 mg/mL, clear

originator

Celgene

Quality Level

200

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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Catégories apparentées

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.

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

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

Classe de stockage

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

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Certificats d'analyse (COA)

Lot/Batch Number
0000238502
0000234466
0000218013
0000234466
0000238502

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Consulter la Bibliothèque de documents

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
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
Fortunato Morabito et al.
American journal of hematology, 89(4), 355-362 (2013-11-26)
Novel agents in combination with melphalan and prednisone (MP) significantly improved progression-free survival (PFS) and overall survival (OS) in multiple myeloma (MM). Randomized trials comparing MP plus bortezomib (VMP) versus MP plus thalidomide (MPT) are lacking. Nine hundred and fifty-six
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
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