T150

(−)-Thalidomide

>98%, solid

• Sinônimo(s): S(−)-2-(2,6-Dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione
• Fórmula empírica (Notação de Hill): C₁₃H₁₀N₂O₄
• Número CAS: 841-67-8
• Peso molecular: 258.23
• Número MDL: MFCD00210219
• Código UNSPSC: 12352207
• ID de substância PubChem: 24899969
• NACRES: NA.77

Propriedades

• ligand: thalidomide
• Ensaio: >98%
• Formulário: solid
• atividade óptica: [α]23/D −62.6°, c = 2 in DMF(lit.)
• adequação da reação: reagent type: ligand
• técnica(s): cell culture | embryo: suitable
• cor: white
• solubilidade: DMSO: soluble; H₂O: insoluble; ethanol: insoluble
• originador: Celgene
• cadeia de caracteres SMILES: 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
• chave InChI: UEJJHQNACJXSKW-VIFPVBQESA-N
• Informações sobre genes: human ... LITAF(9516) , TNF(7124) ; mouse ... Nos2(18126) ; rat ... Nos1(24598)

Descrição

Descrição geral

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.

Aplicação

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.

Ações bioquímicas/fisiológicas

(-)-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.

Características e benefícios

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

Nota de preparo

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

Informações de segurança

• Pictogramas: GHS08,GHS07
• Palavra indicadora: Danger
• Frases de perigo: H302,H360
• Declarações de precaução: P201 - P301 + P312 + P330 - P308 + P313
• Classificações de perigo: Acute Tox. 4 Oral - Repr. 1B
• Código de classe de armazenamento: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• Classe de risco de água (WGK): WGK 3
• Equipamento de proteção individual: Eyeshields, Gloves, type P3 (EN 143) respirator cartridges