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T144

(±)-Thalidomide

Name: (±)-Thalidomide
Brand: SIGMA

≥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:

50-35-1

Molecular Weight:

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

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Properties

Product Name

(±)-Thalidomide, ≥98%, powder

ligand

thalidomide

Quality Level

200

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)

Description

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.

hcodes

H301,H312,H360D

pictograms

GHS06,GHS08

signalword

Danger

pcodes

P202 - P264 - P280 - P301 + P310 - P302 + P352 + P312 - P362 + P364

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

wgk

WGK 3

ppe

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

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Articles

Dihydropinene Pinane Greener Solvent for Organic Synthesis

Effective in key synthesis reactions like Knoevenagel condensation, thalidomide synthesis, and Suzuki coupling for sustainable chemical transformations.

Effect of Thalidomide on Clinical Remission in Children and Adolescents with Ulcerative Colitis Refractory to Other Immunosuppressives: Pilot Randomized Clinical Trial.

Marzia Lazzerini et al.

Inflammatory bowel diseases, 21(8), 1739-1749 (2015-07-18)

In a randomized controlled trial, thalidomide has shown to be effective in refractory Crohn's disease in children. This pilot study aimed at evaluating thalidomide in refractory pediatric ulcerative colitis (UC). Double-blind, placebo-controlled randomized clinical trial on thalidomide 1.5 to 2.5

Teratogen screening using transcriptome profiling of differentiating human embryonic stem cells.

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

Angiogenesis inhibitors derived from thalidomide.

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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Global Trade Item Number

SKU	GTIN
T144-100MG	04061837337475
T144-1G	04061826739945