T150

(−)-Thalidomide

>98%, solid

• Synonyme(s) : S(−)-2-(2,6-Dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione
• Formule empirique (notation de Hill): C₁₃H₁₀N₂O₄
• Numéro CAS: 841-67-8
• Poids moléculaire : 258.23
• Numéro MDL: MFCD00210219
• Code UNSPSC : 12352207
• ID de substance PubChem : 24899969
• Nomenclature NACRES : NA.77

Propriétés

• ligand: thalidomide
• Pureté: >98%
• Forme: solid
• Activité optique: [α]23/D −62.6°, c = 2 in DMF(lit.)
• Pertinence de la réaction: reagent type: ligand
• Technique(s): cell culture | embryo: suitable
• Couleur: white
• Solubilité: DMSO: soluble; H₂O: insoluble; ethanol: insoluble
• Auteur: Celgene
• Chaîne 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
• Clé InChI: UEJJHQNACJXSKW-VIFPVBQESA-N
• Informations sur le gène: human ... LITAF(9516) , TNF(7124) ; mouse ... Nos2(18126) ; rat ... Nos1(24598)

Description

Description générale

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.

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.

Actions biochimiques/physiologiques

(-)-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.

Caractéristiques et avantages

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

Notes préparatoires

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

Informations sur la sécurité

• Pictogrammes: GHS08,GHS07
• Mention d'avertissement: Danger
• Mentions de danger: H302,H360
• Conseils de prudence: P201 - P301 + P312 + P330 - P308 + P313
• Classification des risques: Acute Tox. 4 Oral - Repr. 1B
• Code de la classe de stockage: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• Classe de danger pour l'eau (WGK): WGK 3
• Équipement de protection individuelle: Eyeshields, Gloves, type P3 (EN 143) respirator cartridges