T151

(+)-Thalidomide

≥98% (HPLC), powder

• Synonym(s): R-(+)-2-(2,6-Dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione
• Empirical Formula (Hill Notation): C₁₃H₁₀N₂O₄
• CAS Number: 2614-06-4
• Molecular Weight: 258.23
• NACRES: NA.77
• PubChem Substance ID: 24899975
• UNSPSC Code: 12352200
• MDL number: MFCD00210220
• Assay: ≥98% (HPLC)
• Form: powder

Properties

• ligand: thalidomide
• Quality Segment: 200
• assay: ≥98% (HPLC)
• form: powder
• reaction suitability: reagent type: ligand
• technique(s): targeted protein degradation: suitable
• color: white to beige
• solubility: DMSO: 15 mg/mL, clear
• originator: Celgene
• storage temp.: room temp
• 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-/m1/s1
• InChI key: UEJJHQNACJXSKW-SECBINFHSA-N
• 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. Thalidomide has also been used for studying glutathione mediated teratogenic resistance in mouse embryos.

Biochem/physiol Actions

(-)-Thalidomide selectively inhibits biosynthesis of tumor necrosis factor α (TNF-α). (R)-Thalidomide is called "safe enantiomer", but it can be converted in the body to (S)-isomer.

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.

Preparation Note

Thalidomide is soluble in DMSO at a concentration that is greater than or equal to 20 mg/ml. It is insoluble in ethanol and water.

Safety Information

• Pictograms: GHS08,GHS07
• Signal Word: Danger
• Hazard Codes: H302,H360
• Precautionary Statements: 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
• Flash Point (°F): Not applicable
• Flash Point (°C): Not applicable
• PPE (personal protective equipment): Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges