(S)-Thalidomide
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 597944

CAS#: 841-67-8

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

Chemical Structure

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

Theoretical Analysis

MedKoo Cat#: 597944
Name: (S)-Thalidomide
CAS#: 841-67-8
Chemical Formula: C13H10N2O4
Exact Mass: 258.06
Molecular Weight: 258.230
Elemental Analysis: C, 60.47; H, 3.90; N, 10.85; O, 24.78

Price and Availability

Size Price Availability Quantity
10mg USD 280
25mg USD 490
100mg USD 1000
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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:

Biological target:
In vitro activity:
In vivo activity:

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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Fischer ES, Böhm K, Lydeard JR, Yang H, Stadler MB, Cavadini S, Nagel J, Serluca F, Acker V, Lingaraju GM, Tichkule RB, Schebesta M, Forrester WC, Schirle M, Hassiepen U, Ottl J, Hild M, Beckwith RE, Harper JW, Jenkins JL, Thomä NH. Structure of the DDB1-CRBN E3 ubiquitin ligase in complex with thalidomide. Nature. 2014 Aug 7;512(7512):49-53. doi: 10.1038/nature13527. Epub 2014 Jul 16. PubMed PMID: 25043012; PubMed Central PMCID: PMC4423819.

2: Hui JY, Hoffmann M, Kumar G. Embryo-fetal exposure and developmental outcome of thalidomide following oral and intravaginal administration to pregnant rabbits. Reprod Toxicol. 2014 Sep;48:115-23. doi: 10.1016/j.reprotox.2014.05.002. Epub 2014 May 22. PubMed PMID: 24859269.

3: Chowdhury G, Shibata N, Yamazaki H, Guengerich FP. Human cytochrome P450 oxidation of 5-hydroxythalidomide and pomalidomide, an amino analogue of thalidomide. Chem Res Toxicol. 2014 Jan 21;27(1):147-56. doi: 10.1021/tx4004215. Epub 2013 Dec 24. PubMed PMID: 24350712; PubMed Central PMCID: PMC3929586.

4: Winter GE, Buckley DL, Paulk J, Roberts JM, Souza A, Dhe-Paganon S, Bradner JE. DRUG DEVELOPMENT. Phthalimide conjugation as a strategy for in vivo target protein degradation. Science. 2015 Jun 19;348(6241):1376-81. doi: 10.1126/science.aab1433. Epub 2015 May 21. PubMed PMID: 25999370; PubMed Central PMCID: PMC4937790.

5: Chamberlain PP, Lopez-Girona A, Miller K, Carmel G, Pagarigan B, Chie-Leon B, Rychak E, Corral LG, Ren YJ, Wang M, Riley M, Delker SL, Ito T, Ando H, Mori T, Hirano Y, Handa H, Hakoshima T, Daniel TO, Cathers BE. Structure of the human Cereblon-DDB1-lenalidomide complex reveals basis for responsiveness to thalidomide analogs. Nat Struct Mol Biol. 2014 Sep;21(9):803-9. doi: 10.1038/nsmb.2874. Epub 2014 Aug 10. PubMed PMID: 25108355.

6: Li Y, Zhou S, Hoffmann M, Kumar G, Palmisano M. Modeling and simulation to probe the pharmacokinetic disposition of pomalidomide R- and S-enantiomers. J Pharmacol Exp Ther. 2014 Aug;350(2):265-72. doi: 10.1124/jpet.114.215251. Epub 2014 May 15. PubMed PMID: 24833703.

7: Diamanti A, Capriati T, Papadatou B, Knafelz D, Bracci F, Corsetti T, Elia D, Torre G. The clinical implications of thalidomide in inflammatory bowel diseases. Expert Rev Clin Immunol. 2015 Jun;11(6):699-708. doi: 10.1586/1744666X.2015.1027687. Epub 2015 Apr 11. Review. PubMed PMID: 25865355.

8: Xu M, Hou Y, Sheng L, Peng J. Therapeutic effects of thalidomide in hematologic disorders: a review. Front Med. 2013 Sep;7(3):290-300. doi: 10.1007/s11684-013-0277-z. Epub 2013 Jul 15. Review. PubMed PMID: 23856973.

9: Koeppen S. Treatment of multiple myeloma: thalidomide-, bortezomib-, and lenalidomide-induced peripheral neuropathy. Oncol Res Treat. 2014;37(9):506-13. doi: 10.1159/000365534. Epub 2014 Aug 14. Review. PubMed PMID: 25231692.

10: Nishiyama S, Suemizu H, Shibata N, Guengerich FP, Yamazaki H. Simulation of Human Plasma Concentrations of Thalidomide and Primary 5-Hydroxylated Metabolites Explored with Pharmacokinetic Data in Humanized TK-NOG Mice. Chem Res Toxicol. 2015 Nov 16;28(11):2088-90. doi: 10.1021/acs.chemrestox.5b00381. Epub 2015 Oct 26. PubMed PMID: 26492539.

11: Ito T, Ando H, Handa H. Teratogenic effects of thalidomide: molecular mechanisms. Cell Mol Life Sci. 2011 May;68(9):1569-79. doi: 10.1007/s00018-010-0619-9. Epub 2011 Jan 5. Review. PubMed PMID: 21207098.

12: Muscal JA, Sun Y, Nuchtern JG, Dauser RC, McGuffey LH, Gibson BW, Berg SL. Plasma and cerebrospinal fluid pharmacokinetics of thalidomide and lenalidomide in nonhuman primates. Cancer Chemother Pharmacol. 2012 Apr;69(4):943-7. doi: 10.1007/s00280-011-1781-y. Epub 2011 Nov 23. PubMed PMID: 22109830; PubMed Central PMCID: PMC3685292.

13: Zahran MA, Abdin YG, Osman AM, Gamal-Eldeen AM, Talaat RM, Pedersen EB. Synthesis and evaluation of thalidomide and phthalimide esters as antitumor agents. Arch Pharm (Weinheim). 2014 Sep;347(9):642-9. doi: 10.1002/ardp.201400073. Epub 2014 Jun 18. PubMed PMID: 24943104.

14: Yamazaki H, Suemizu H, Murayama N, Utoh M, Shibata N, Nakamura M, Guengerich FP. In vivo drug interactions of the teratogen thalidomide with midazolam: heterotropic cooperativity of human cytochrome P450 in humanized TK-NOG mice. Chem Res Toxicol. 2013 Mar 18;26(3):486-9. doi: 10.1021/tx400008g. Epub 2013 Mar 1. PubMed PMID: 23419139; PubMed Central PMCID: PMC4049203.

15: Fialho SL, Souza PA, Fulgêncio GO, Miranda MM, Pereira BG, Haddad A, Messias A, Jorge R, Silva-Cunha A. In vivo release and retinal safety of intravitreal implants of thalidomide in rabbit eyes and antiangiogenic effect on the chorioallantoic membrane. J Drug Target. 2013 Nov;21(9):837-45. doi: 10.3109/1061186X.2013.829074. Epub 2013 Aug 19. PubMed PMID: 23952807.

16: Schafer PH, Parton A, Capone L, Cedzik D, Brady H, Evans JF, Man HW, Muller GW, Stirling DI, Chopra R. Apremilast is a selective PDE4 inhibitor with regulatory effects on innate immunity. Cell Signal. 2014 Sep;26(9):2016-29. doi: 10.1016/j.cellsig.2014.05.014. Epub 2014 May 29. PubMed PMID: 24882690.

17: Fink EC, Ebert BL. The novel mechanism of lenalidomide activity. Blood. 2015 Nov 19;126(21):2366-9. doi: 10.1182/blood-2015-07-567958. Epub 2015 Oct 5. Review. PubMed PMID: 26438514; PubMed Central PMCID: PMC4653765.

18: Smith SL, Singh P, Harding D, Lun D, Chambers JP. Thalidomide pharmacokinetics in sheep. N Z Vet J. 2016 Jul;64(4):238-42. doi: 10.1080/00480169.2015.1130663. Epub 2016 Feb 5. PubMed PMID: 26727254.

19: Lee SW, Park YB, Yang J, Park KH, Lee SK, Choi KH, Kim BS. Attenuation of nephritis in lupus-prone mice by thalidomide. Rheumatology (Oxford). 2012 Dec;51(12):2131-40. doi: 10.1093/rheumatology/kes227. Epub 2012 Aug 25. PubMed PMID: 22923758.

20: Yang C, Singh P, Singh H, Le ML, El-Matary W. Systematic review: thalidomide and thalidomide analogues for treatment of inflammatory bowel disease. Aliment Pharmacol Ther. 2015 Jun;41(11):1079-93. doi: 10.1111/apt.13181. Epub 2015 Apr 8. Review. PubMed PMID: 25858208.