T150

(−)-Thalidomide

>98%, solid

• Sinonimo/i: S(−)-2-(2,6-Dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione
• Formula empirica (notazione di Hill): C₁₃H₁₀N₂O₄
• Numero CAS: 841-67-8
• Peso molecolare: 258.23
• Numero MDL: MFCD00210219
• Codice UNSPSC: 12352207
• ID PubChem: 24899969
• NACRES: NA.77

Proprietà

• ligand: thalidomide
• Saggio: >98%
• Forma fisica: solid
• Attività ottica: [α]23/D −62.6°, c = 2 in DMF(lit.)
• Impiego in reazioni chimiche: reagent type: ligand
• tecniche: cell culture | embryo: suitable
• Colore: white
• Solubilità: DMSO: soluble; H₂O: insoluble; ethanol: insoluble
• Ideatore: Celgene
• Stringa SMILE: 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; UEJJHQNACJXSKW-VIFPVBQESA-N
• Informazioni sul gene: human ... LITAF(9516) , TNF(7124) ; mouse ... Nos2(18126) ; rat ... Nos1(24598)

Descrizione

Descrizione generale

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.

Applicazioni

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.

Azioni biochim/fisiol

(-)-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.

Caratteristiche e vantaggi

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

Nota sulla preparazione

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

Informazioni sulla sicurezza

• Pittogrammi: GHS08,GHS07
• Avvertenze: Danger
• Indicazioni di pericolo: H302,H360
• Consigli di prudenza: P201 - P301 + P312 + P330 - P308 + P313
• Classi di pericolo: Acute Tox. 4 Oral - Repr. 1B
• Codice della classe di stoccaggio: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• Classe di pericolosità dell'acqua (WGK): WGK 3
• Dispositivi di protezione individuale: Eyeshields, Gloves, type P3 (EN 143) respirator cartridges