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MedKoo Cat#: 597944 | Name: (S)-Thalidomide
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Chemical Structure

(S)-Thalidomide
(S)-Thalidomide
CAS#841-67-8

Theoretical Analysis

MedKoo Cat#: 597944

Name: (S)-Thalidomide

CAS#: 841-67-8

Chemical Formula: C13H10N2O4

Exact Mass: 258.0641

Molecular Weight: 258.23

Elemental Analysis: C, 60.47; H, 3.90; N, 10.85; O, 24.78

Price and Availability

Size Price Availability Quantity
10mg USD 350.00
25mg USD 600.00
100mg USD 1,200.00
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Related CAS #
No Data
Synonym
(S)-Thalidomide; l-Thalidomide; NSC 91730; NSC-91730; NSC91730;
IUPAC/Chemical Name
(S)-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione
InChi Key
UEJJHQNACJXSKW-VIFPVBQESA-N
InChi Code
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 Code
O=C1N([C@@H](CC2)C(NC2=O)=O)C(C3=C1C=CC=C3)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 258.23 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Watson ER, Novick S, Matyskiela ME, Chamberlain PP, H de la Peña A, Zhu J, Tran E, Griffin PR, Wertz IE, Lander GC. Molecular glue CELMoD compounds are regulators of cereblon conformation. Science. 2022 Nov 4;378(6619):549-553. doi: 10.1126/science.add7574. Epub 2022 Nov 3. PMID: 36378961; PMCID: PMC9714526. 2: Baranowska-Łączkowska A, Banaszak-Piechowska A, Donarska B, Łączkowski KZ. Towards understanding the interaction of (S)-thalidomide with nucleobases. Arch Biochem Biophys. 2020 Oct 30;693:108566. doi: 10.1016/j.abb.2020.108566. Epub 2020 Sep 5. PMID: 32896516. 3: Kowalczyk A, Lipiński PFJ, Karoń K, Rode JE, Lyczko K, Dobrowolski JC, Donten M, Kaczorek D, Poszytek J, Kawęcki R, Łapkowski M, Malkowska A, Grudzinski IP, Nowicka AM. Enantioselective sensing of (S)-Thalidomide in blood plasma with a chiral naphthalene diimide derivative. Biosens Bioelectron. 2020 Nov 1;167:112446. doi: 10.1016/j.bios.2020.112446. Epub 2020 Jul 25. PMID: 32818748. 4: Liu WM, Strauss SJ, Chaplin T, Shahin S, Propper DJ, Young BD, Joel SP, Malpas JS. s-thalidomide has a greater effect on apoptosis than angiogenesis in a multiple myeloma cell line. Hematol J. 2004;5(3):247-54. doi: 10.1038/sj.thj.6200351. PMID: 15167912. 5: Eriksson T, Björkman S, Höglund P. Clinical pharmacology of thalidomide. Eur J Clin Pharmacol. 2001 Aug;57(5):365-76. doi: 10.1007/s002280100320. PMID: 11599654. 6: Bosch ME, Sánchez AJ, Rojas FS, Ojeda CB. Recent advances in analytical determination of thalidomide and its metabolites. J Pharm Biomed Anal. 2008 Jan 7;46(1):9-17. doi: 10.1016/j.jpba.2007.10.003. Epub 2007 Oct 9. PMID: 18023317. 7: Meyring M, Mühlbacher J, Messer K, Kastner-Pustet N, Bringmann G, Mannschreck A, Blaschke G. In vitro biotransformation of (R)- and (S)-thalidomide: application of circular dichroism spectroscopy to the stereochemical characterization of the hydroxylated metabolites. Anal Chem. 2002 Aug 1;74(15):3726-35. doi: 10.1021/ac0203138. PMID: 12175160. 8: Stephens TD. The effect of thalidomide in chicken embryos. Birth Defects Res A Clin Mol Teratol. 2009 Aug;85(8):725-31. doi: 10.1002/bdra.20597. PMID: 19645049. 9: Blanco S, Macario A, López JC. The structure of isolated thalidomide as reference for its chirality-dependent biological activity: a laser-ablation rotational study. Phys Chem Chem Phys. 2021 Jun 23;23(24):13705-13713. doi: 10.1039/d1cp01691a. PMID: 34128013. 10: Wnendt S, Finkam M, Winter W, Ossig J, Raabe G, Zwingenberger K. Enantioselective inhibition of TNF-alpha release by thalidomide and thalidomide- analogues. Chirality. 1996;8(5):390-6. doi: 10.1002/(SICI)1520-636X(1996)8:5<390::AID-CHIR6>3.0.CO;2-I. PMID: 8900028. 11: Dharia SP, Steinkampf MP, Cater C. Thalidomide-induced amenorrhea: case report and literature review. Fertil Steril. 2004 Aug;82(2):460-2. doi: 10.1016/j.fertnstert.2003.12.038. PMID: 15302302. 12: Höglund P, Eriksson T, Björkman S. A double-blind study of the sedative effects of the thalidomide enantiomers in humans. J Pharmacokinet Biopharm. 1998 Aug;26(4):363-83. doi: 10.1023/a:1021008016719. PMID: 10214558. 13: Sembongi K, Tanaka M, Sakurada K, Kobayashi M, Itagaki S, Hirano T, Iseki K. A new method for determination of both thalidomide enantiomers using HPLC systems. Biol Pharm Bull. 2008 Mar;31(3):497-500. doi: 10.1248/bpb.31.497. PMID: 18310917. 14: Murphy S, Boyle FM, Davey RA, Gu XQ, Mather LE. Enantioselectivity of thalidomide serum and tissue concentrations in a rat glioma model and effects of combination treatment with cisplatin and BCNU. J Pharm Pharmacol. 2007 Jan;59(1):105-14. doi: 10.1211/jpp.59.1.0014. PMID: 17227627. 15: Hashimoto Y. Structural development of biological response modifiers based on retinoids and thalidomide. Mini Rev Med Chem. 2002 Dec;2(6):543-51. doi: 10.2174/1389557023405576. PMID: 12370039. 16: Murphy-Poulton SF, Boyle F, Gu XQ, Mather LE. Thalidomide enantiomers: determination in biological samples by HPLC and vancomycin-CSP. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Feb 2;831(1-2):48-56. doi: 10.1016/j.jchromb.2005.11.023. PMID: 16321578. 17: Shoji A, Kuwahara M, Ozaki H, Sawai H. Modified DNA aptamer that binds the (R)-isomer of a thalidomide derivative with high enantioselectivity. J Am Chem Soc. 2007 Feb 7;129(5):1456-64. doi: 10.1021/ja067098n. PMID: 17263432. 18: Cooper-Shepherd DA, Olivos HJ, Wu Z, Palmer ME. Exploiting Self-Association to Evaluate Enantiomeric Composition by Cyclic Ion Mobility-Mass Spectrometry. Anal Chem. 2022 Jun 14;94(23):8441-8448. doi: 10.1021/acs.analchem.2c01212. Epub 2022 Jun 3. PMID: 35657797; PMCID: PMC9201813. 19: Eriksson T, Björkman S, Roth B, Fyge A, Höglund P. Stereospecific determination, chiral inversion in vitro and pharmacokinetics in humans of the enantiomers of thalidomide. Chirality. 1995;7(1):44-52. doi: 10.1002/chir.530070109. PMID: 7702998. 20: Matsuzawa N, Nakamura K, Matsuda M, Ishida F, Ohmori S. Influence of cytochrome P450 2C19 gene variations on pharmacokinetic parameters of thalidomide in Japanese patients. Biol Pharm Bull. 2012;35(3):317-20. doi: 10.1248/bpb.35.317. PMID: 22382316.