T150

(−)-Thalidomide

>98%, solid

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

Propiedades

• ligand: thalidomide
• Ensayo: >98%
• Formulario: solid
• actividad óptica: [α]23/D −62.6°, c = 2 in DMF(lit.)
• idoneidad de la reacción: reagent type: ligand
• técnicas: cell culture | embryo: suitable
• color: white
• solubilidad: DMSO: soluble; H₂O: insoluble; ethanol: insoluble
• emisor: Celgene
• cadena 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
• Clave InChI: UEJJHQNACJXSKW-VIFPVBQESA-N
• Información sobre el gen: human ... LITAF(9516) , TNF(7124) ; mouse ... Nos2(18126) ; rat ... Nos1(24598)

Descripción

Descripción general

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.

Aplicación

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.

Acciones bioquímicas o 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 y beneficios

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

Nota de preparación

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

Información de seguridad

• Pictogramas: GHS08,GHS07
• Palabra de señalización: Danger
• Frases de peligro: H302,H360
• Consejos de prudencia: P201 - P301 + P312 + P330 - P308 + P313
• Clasificaciones de peligro: Acute Tox. 4 Oral - Repr. 1B
• Código de clase de almacenamiento: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• Clase de riesgo para el agua (WGK): WGK 3
• Equipo de protección personal: Eyeshields, Gloves, type P3 (EN 143) respirator cartridges