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(S)-(−)-Thalidomide (CAS 841-67-8)

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Alternate Names:
(S)-Thalidomide
Application:
(S)-(−)-Thalidomide is an optically active isomer of Thalidomide
CAS Number:
841-67-8
Molecular Weight:
258.23
Molecular Formula:
C13H10N2O4
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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(S)-(−)-Thalidomide is an optically active isomer of Thalidomide. Inhibits FGF-induced angiogenesis and replication of human immunodeficiency virus type 1. (S)-thalidomide is a 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione that has S-configuration at the chiral centre. It has a role as a teratogenic agent. It is an enantiomer of a (R)-thalidomide. It enhances TNF-α production induced by phorbol 12-myristate 13-acetate (TPA). Understanding how (S)-(−)-thalidomide interacts with biological targets, such as proteins or DNA, can provide valuable insights into the molecular mechanisms underlying its effects. This research can contribute to the broader knowledge of how small molecules influence cellular processes and lead to the discovery of new targets. The synthesis of pure enantiomers like (S)-(−)-thalidomide is a significant challenge in organic chemistry. Developing methods for the enantioselective synthesis or the resolution of racemic mixtures into their individual enantiomers is for producing compounds with the desired biological activity.


(S)-(−)-Thalidomide (CAS 841-67-8) References

  1. In vitro biotransformation of (R)- and (S)-thalidomide: application of circular dichroism spectroscopy to the stereochemical characterization of the hydroxylated metabolites.  |  Meyring, M., et al. 2002. Anal Chem. 74: 3726-35. PMID: 12175160
  2. s-thalidomide has a greater effect on apoptosis than angiogenesis in a multiple myeloma cell line.  |  Liu, WM., et al. 2004. Hematol J. 5: 247-54. PMID: 15167912
  3. Chiral discrimination between thalidomide enantiomers using a solid surface with two-dimensional chirality.  |  Nakanishi, T., et al. 2004. Chirality. 16 Suppl: S36-9. PMID: 15239071
  4. Recent advances in analytical determination of thalidomide and its metabolites.  |  Bosch, ME., et al. 2008. J Pharm Biomed Anal. 46: 9-17. PMID: 18023317
  5. A new method for determination of both thalidomide enantiomers using HPLC systems.  |  Sembongi, K., et al. 2008. Biol Pharm Bull. 31: 497-500. PMID: 18310917
  6. Thalidomide-a notorious sedative to a wonder anticancer drug.  |  Zhou, S., et al. 2013. Curr Med Chem. 20: 4102-8. PMID: 23931282
  7. Towards understanding the interaction of (S)-thalidomide with nucleobases.  |  Baranowska-Łączkowska, A., et al. 2020. Arch Biochem Biophys. 693: 108566. PMID: 32896516
  8. The structure of isolated thalidomide as reference for its chirality-dependent biological activity: a laser-ablation rotational study.  |  Blanco, S., et al. 2021. Phys Chem Chem Phys. 23: 13705-13713. PMID: 34128013
  9. A comparison of the teratogenic activity of thalidomide in rabbits and rats.  |  Schumacher, H., et al. 1968. J Pharmacol Exp Ther. 160: 189-200. PMID: 5639104
  10. Thalidomide is an inhibitor of angiogenesis.  |  D'Amato, RJ., et al. 1994. Proc Natl Acad Sci U S A. 91: 4082-5. PMID: 7513432
  11. Thalidomide inhibits the replication of human immunodeficiency virus type 1.  |  Makonkawkeyoon, S., et al. 1993. Proc Natl Acad Sci U S A. 90: 5974-8. PMID: 8327469
  12. Enantiomers of thalidomide: blood distribution and the influence of serum albumin on chiral inversion and hydrolysis.  |  Eriksson, T., et al. 1998. Chirality. 10: 223-8. PMID: 9499573
  13. Evaluation of stability difference between asymmetric homochiral dimer in (S)-thalidomide crystal and symmetric heterochiral dimer in (RS)-thalidomide crystal  |  Toshiya Suzuki, Masahito Tanaka, Motoo Shiro, Norio Shibata, Tetsuya Osaka & Toru Asahi. 2010. Phase Transitions. 83: 223-234.

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

(S)-(−)-Thalidomide, 10 mg

sc-208337
10 mg
$203.00

(S)-(−)-Thalidomide, 50 mg

sc-208337A
50 mg
$681.00