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T150 Sigma-Aldrich

(−)-Thalidomide

>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

  •  PubChem Substance ID 24899969

  •  NACRES NA.77

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Properties

Related Categories Angiogenesis Regulators, Application Index, Approved Therapeutics/Drug Candidates, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules,
assay   >98%
form   solid
optical activity   [α]23/D −62.6°, c = 2 in DMF(lit.)
application(s)   cell culture | embryo: suitable
color   white
solubility   DMSO: soluble
  H2O: insoluble
  ethanol: insoluble
originator   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
InChI key   UEJJHQNACJXSKW-VIFPVBQESA-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.

Packaging

10 mg in poly bottle

25, 100 mg in glass bottle

Biochem/physiol Actions

(-)-Thalidomide selectively inhibits biosynthesis of tumor necrosis factor α (TNF-α); inhibitor of angiogenesis. (S)-Thalidomide is a teratogenic enatiomer.

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, but is insoluble in water and ethanol.

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
TI4925050

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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