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ligand
thalidomide
方案
>98%
表单
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)
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.
警示用语：
Danger
危险声明
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
新产品
历史批次信息供参考:
分析证书(COA)
Lot/Batch Number
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)
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
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
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
Chromatograms
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