T150
(−)-Thalidomide
>98%, solid
别名:
S(−)-2-(2,6-Dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione
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关于此项目
经验公式（希尔记法）:
C13H10N2O4
化学文摘社编号:
分子量:
258.23
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352207
MDL number:
产品名称
(−)-Thalidomide, >98%, solid
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
SMILES string
O=C1CC[C@H](N2C(=O)c3ccccc3C2=O)C(=O)N1
InChI key
UEJJHQNACJXSKW-VIFPVBQESA-N
ligand
thalidomide
assay
>98%
form
solid
optical activity
[α]23/D −62.6°, c = 2 in DMF(lit.)
reaction suitability
reagent type: ligand
technique(s)
cell culture | embryo: suitable
color
white
solubility
DMSO: soluble
H2O: insoluble
ethanol: insoluble
originator
Celgene
Gene Information
human ... LITAF(9516), TNF(7124)
mouse ... Nos2(18126)
rat ... Nos1(24598)
Application
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.
Biochem/physiol Actions
(-)-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.
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.
General description
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.
Preparation Note
(-)-Thalidomide is soluble in DMSO, but is insoluble in water and ethanol.
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Repr. 1B
存储类别
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
wgk
WGK 3
ppe
Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
法规信息
新产品
此项目有
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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