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Merck

T150

Sigma-Aldrich

(−)-Thalidomide

>98%, solid

别名:

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

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About This Item

经验公式(希尔记法):
C13H10N2O4
CAS号:
分子量:
258.23
MDL號碼:
分類程式碼代碼:
12352207
PubChem物質ID:
NACRES:
NA.77

ligand

thalidomide

化驗

>98%

形狀

solid

光學活性

[α]23/D −62.6°, c = 2 in DMF(lit.)

反應適用性

reagent type: ligand

技術

cell culture | embryo: suitable

顏色

white

溶解度

DMSO: soluble
H2O: insoluble
ethanol: insoluble

起源

Celgene

SMILES 字串

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 密鑰

UEJJHQNACJXSKW-VIFPVBQESA-N

基因資訊

一般說明

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.

應用

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.

特點和優勢

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

準備報告

(-)-Thalidomide is soluble in DMSO, but is insoluble in water and ethanol.

象形圖

Health hazardExclamation mark

訊號詞

Danger

危險聲明

危險分類

Acute Tox. 4 Oral - Repr. 1B

儲存類別代碼

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

水污染物質分類(WGK)

WGK 3

個人防護裝備

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


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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)
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
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

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