(−)-Thalidomide
SIGMA/T150 - >98%, solid
Synonym: S(−)-2-(2,6-Dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione
CAS Number: 841-67-8
Empirical Formula (Hill Notation): C13H10N2O4
Molecular Weight: 258.23
MDL Number: MFCD00210219
Linear Formula: C13H10N2O4
Product Type: Chemical
| assay | >98% |
| color | white |
| form | solid |
| InChI | 1S/C13H10N2O4/c16-10-6-5- |
| InChI key | UEJJHQNACJXSKW-VIFPVBQESA |
| optical activity | [α]23/D −62.6°, c = 2 in DMF(lit.) |
| originator | Celgene |
| SMILES string | O=C1CC[C@H](N2C(=O)c3cccc |
| solubility | DMSO: soluble |
| ethanol: insoluble | |
| H2O: insoluble | |
| technique(s) | cell culture | embryo: suitable |
| 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 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. |
| 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. |
| Packaging: | 10 mg in poly bottle |
| Packaging: | 25, 100 mg in glass bottle |
| Preparation Note: | (-)-Thalidomide is soluble in DMSO, but is insoluble in water and ethanol. |
| Symbol |   GHS07,GHS08 |
| Signal word | Danger |
| Hazard statements | H302 - H360 |
| Precautionary statements | P201 - P301 + P312 + P330 - P308 + P313 |
| Hazard Codes | T |
| Risk Statements | 61-22 |
| Safety Statements | 53-36/37/39-45 |
| RIDADR | NONH for all modes of transport |
| WGK Germany | WGK 3 |
| Purity | >98% |
| UNSPSC | 12352200 |