T150

(−)-Thalidomide

>98%, solid

• Synonym(s): S(−)-2-(2,6-Dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione
• Empirical Formula (Hill Notation): C₁₃H₁₀N₂O₄
• CAS Number: 841-67-8
• Molecular Weight: 258.23
• NACRES: NA.77
• PubChem Substance ID: 24899969
• UNSPSC Code: 12352207
• MDL number: MFCD00210219

Properties

• Product Name: (−)-Thalidomide, >98%, solid
• 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
• SMILES string: O=C1CC[C@H](N2C(=O)c3ccccc3C2=O)C(=O)N1
• InChI key: UEJJHQNACJXSKW-VIFPVBQESA-N
• ligand: thalidomide
• assay: >98%
• form: solid
• optical activity: [α]23/D −62.6°, c = 2 in DMF(lit.)
• reaction suitability: reagent type: ligand
• technique(s): cell culture | embryo: suitable
• color: white
• solubility: DMSO: soluble; H₂O: insoluble; ethanol: insoluble
• originator: Celgene
• Gene Information: human ... LITAF(9516), TNF(7124) ; mouse ... Nos2(18126) ; rat ... Nos1(24598)

Description

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[1]. Thalidomide has also been used for studying glutathione mediated teratogenic resistance in mouse embryos[2].

Biochem/physiol Actions

(-)-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.[3] It is associated with several diseases such as, peripheral neuropathy, facial palsies, Duane syndrome and autism.[3][4]

Features and Benefits

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

General description

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.[3]

Preparation Note

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

Safety Information

• pictograms: GHS08,GHS07
• signalword: Danger
• hcodes: H302,H360
• pcodes: P201 - P301 + P312 + P330 - P308 + P313
• Hazard Classifications: Acute Tox. 4 Oral - Repr. 1B
• Storage Class: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• wgk: WGK 3
• ppe: Eyeshields, Gloves, type P3 (EN 143) respirator cartridges