T150

(−)-Thalidomide

>98%, solid

• Synonym(e): S(−)-2-(2,6-Dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione
• Empirische Formel (Hill-System): C₁₃H₁₀N₂O₄
• CAS-Nummer: 841-67-8
• Molekulargewicht: 258.23
• MDL-Nummer: MFCD00210219
• UNSPSC-Code: 12352207
• PubChem Substanz-ID: 24899969
• NACRES: NA.77

Eigenschaften

• ligand: thalidomide
• Assay: >98%
• Form: solid
• Optische Aktivität: [α]23/D −62.6°, c = 2 in DMF(lit.)
• Eignung der Reaktion: reagent type: ligand
• Methode(n): cell culture | embryo: suitable
• Farbe: white
• Löslichkeit: DMSO: soluble; H₂O: insoluble; ethanol: insoluble
• Ersteller: Celgene
• SMILES String: 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
• InChIKey: UEJJHQNACJXSKW-VIFPVBQESA-N
• Angaben zum Gen: human ... LITAF(9516) , TNF(7124) ; mouse ... Nos2(18126) ; rat ... Nos1(24598)

Beschreibung

Allgemeine Beschreibung

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.

Anwendung

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. Wirkung

(-)-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.

Leistungsmerkmale und Vorteile

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

Angaben zur Herstellung

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

Sicherheitshinweise

• Piktogramme: GHS08,GHS07
• Signalwort: Danger
• H-Sätze: H302,H360
• P-Sätze: P201 - P301 + P312 + P330 - P308 + P313
• Gefahreneinstufungen: Acute Tox. 4 Oral - Repr. 1B
• Lagerklassenschlüssel: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3
• Persönliche Schutzausrüstung: Eyeshields, Gloves, type P3 (EN 143) respirator cartridges