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安全信息

T150

Sigma-Aldrich

(−)-Thalidomide

>98%, solid

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别名:
S(−)-2-(2,6-Dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione
经验公式（希尔记法）:
C13H10N2O4
CAS号:
841-67-8
分子量:
258.23
MDL编号:
MFCD00210219
PubChem化学物质编号:
24899969
NACRES:
NA.77

检测方案

>98%

形式

solid

旋光性

[α]23/D −62.6°, c = 2 in DMF(lit.)

反应适用性

reagent type: ligand

技术

cell culture | embryo: suitable

颜色

white

溶解性

DMSO: soluble
H2O: insoluble
ethanol: insoluble

创始人

Celgene

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-/m0/s1

InChI key

UEJJHQNACJXSKW-VIFPVBQESA-N

基因信息

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

相关类别

一般描述

Thalidomide is a stereoisomer, which exists in two enantiomeric states. The S enantiomer is teratogenic. Thalidomide consists of two linked rings, a phthalimide and glutarimide ring.

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 the biosynthesis of tumor necrosis factor α (TNF-α), which is essential for inflammatory response. It is an anti-emetic drug and is used to treat morning sickness in pregnant women. Thalidomide is also used to treat leprosy, multiple myeloma, Crohn′s disease and human immunodeficiency virus (HIV) infection. Thalidomide also inhibits angiogenesis. It is associated with several diseases such as, peripheral neuropathy, facial palsies, Duane syndrome and autism.

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, but is insoluble in water and ethanol.

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

个人防护装备

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

法规信息

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Guo-Liang Duan et al.
International journal of biological macromolecules, 137, 1112-1120 (2019-07-05)
Six polysaccharides (SF-FB11, SF-HW21, SF-CA31, SF-HA41, SF-FF51, and SF-FR61) of similar molecular weights (MW) (30-50 kDa) were extracted from the fermentation liquor, mycelia, and basidiomata of Sparassis latifolia by different methods. Structural analyses of these purified polysaccharides indicated that they were
John H Sampson et al.
Molecular cancer therapeutics, 8(10), 2773-2779 (2009-10-15)
Conventional therapies for glioblastoma multiforme (GBM) fail to target tumor cells exclusively, such that their efficacy is ultimately limited by nonspecific toxicity. Immunologic targeting of tumor-specific gene mutations, however, may allow more precise eradication of neoplastic cells. The epidermal growth
Thalidomide-induced teratogenesis: History and mechanisms
Vargesson N
Birth Defects Research Part C: Embryo Today - Reviews, 105(2) (2015)
Thalidomide: the tragedy of birth defects and the effective treatment of disease
Kim JH and Scialli AR
Toxicological Sciences, 122(1) (2011)
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
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