Merck
CN
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安全信息

T151

Sigma-Aldrich

(+)-Thalidomide

≥98% (HPLC), powder

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别名:
R-(+)-2-(2,6-Dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione
经验公式（希尔记法）:
C13H10N2O4
CAS号:
2614-06-4
分子量:
258.23
MDL编号:
MFCD00210220
PubChem化学物质编号:
24899975
NACRES:
NA.77

检测方案

≥98% (HPLC)

形式

powder

反应适用性

reagent type: ligand

颜色

white to beige

溶解性

DMSO: 15 mg/mL, clear

创始人

Celgene

储存温度

room temp

SMILES字符串

O=C1CC[C@@H](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)/t9-/m1/s1

InChI key

UEJJHQNACJXSKW-SECBINFHSA-N

基因信息

human ... LITAF(9516) , TNF(7124)
mouse ... Nos2(18126)
rat ... Nos1(24598)

相关类别

应用

Thalidomide has been used to study its teratogenic effects in chicken embryos and human embryonic cells. This study reported that thalidomide causes limb defects by stabilizing PTEN, inhibiting the expression of Akt and activating caspase-dependent apoptosis. Thalidomide has also been used for studying glutathione mediated teratogenic resistance in mouse embryos.

生化/生理作用

(-)-Thalidomide selectively inhibits biosynthesis of tumor necrosis factor α (TNF-α). (R)-Thalidomide is called "safe enantiomer", but it can be converted in the body to (S)-isomer.

特点和优势

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

制备说明

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

象形图

Exclamation markHealth hazard
GHS07,GHS08

警示用语：

Danger

危险声明

H302 - H360

危险分类

Acute Tox. 4 Oral - Repr. 1B

储存分类代码

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

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

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

法规信息

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Agata Kowalczyk et al.
Biosensors & bioelectronics, 167, 112446-112446 (2020-08-21)
Fast, simple in use and highly effective voltammetric enantiosensor dedicated for determination of thalidomide (TD) enantiomers (especially towards the toxic (S)-enantiomer) in blood plasma is still desirable. Here we have proven that newly synthesized chiral naphthalene diimide (NDI) derivatives are
Jürgen Knobloch et al.
Molecular and cellular biology, 28(2), 529-538 (2008-01-08)
Thalidomide, a drug used for the treatment of multiple myeloma and inflammatory diseases, is also a teratogen that causes birth defects, such as limb truncations and microphthalmia, in humans. Thalidomide-induced limb truncations result from increased cell death during embryonic limb
Jianhui Zhao et al.
Neurochemical research, 41(12), 3171-3180 (2016-08-31)
Opioid analgesics have less efficacy in diabetic neuropathy treatment, and tolerance often occurs after chronic usage. Given that thalidomide can potentiate the morphine efficacy in diabetic neuropathy treatment, we investigated the effects of intrathecal administrations of thalidomide on morphine tolerance
Jürgen Knobloch et al.
Molecular pharmaceutics, 5(6), 1138-1144 (2009-05-13)
Thalidomide as an effective treatment for multiple myeloma and leprosy has also caused birth defects in thousands of children five decades ago particularly in Europe. Thus its use in humans remains limited. The rapid and fatal approval of thalidomide at
S Makonkawkeyoon et al.
Proceedings of the National Academy of Sciences of the United States of America, 90(13), 5974-5978 (1993-07-01)
Thalidomide, a selective inhibitor of tumor necrosis factor alpha (TNF-alpha) synthesis, suppresses the activation of latent human immunodeficiency virus type 1 (HIV-1) in a monocytoid (U1) line. The inhibition is dose dependent and occurs after exposure of the cells to
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