(±)-Thalidomide

  • CAT Number: A000994
  • CAS Number: 50-35-1
  • Molecular Formula: C₁₃H₁₀N₂O₄
  • Molecular Weight: 258.23
  • Purity: ≥95%
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Thalidomide is a synthetic derivative of glutamic acid (alpha-phthalimido-glutarimide) with teratogenic, immunomodulatory, anti-inflammatory and anti-angiogenic properties. Thalidomide acts primarily by inhibiting both the production of tumor necrosis factor alpha (TNF-alpha) in stimulated peripheral monocytes and the activities of interleukins and interferons. This agent also inhibits polymorphonuclear chemotaxis and monocyte phagocytosis. In addition, thalidomide inhibits pro-angiogenic factors such as vascular endothelial growth factor (VEGF) and basic fibroblast growth factor (bFGF), thereby inhibiting angiogenesis.

Catalog Number A000994
CAS Number 50-35-1
Molecular Formula

C₁₃H₁₀N₂O₄

Purity 95%
Target TNF-α
Solubility >11.8mg/mL in DMSO
Storage -20°C
InChI 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)
InChIKey UEJJHQNACJXSKW-UHFFFAOYSA-N
SMILES C1CC(=O)NC(=O)C1N2C(=O)C3=CC=CC=C3C2=O
Reference

1: Liu T, Guo F, Zhu X, He X, Xie L. Thalidomide and its analogues: A review of
the potential for immunomodulation of fibrosis diseases and opthalmopathy. Exp
Ther Med. 2017 Dec;14(6):5251-5257. doi: 10.3892/etm.2017.5209. Epub 2017 Sep 27.
PubMed PMID: 29285050; PubMed Central PMCID: PMC5740745.
<br>

2: Haraf R, Flora AS, Assaly R. Thalidomide as a Cough Suppressant in Idiopathic
Pulmonary Fibrosis. Am J Ther. 2017 Nov 22. doi: 10.1097/MJT.0000000000000695.
[Epub ahead of print] PubMed PMID: 29232284.
<br>

3: Khan MI, Momeny M, Ostadhadi S, Jahanabadi S, Ejtemaei-Mehr S, Sameem B,
Zarrinrad G, Dehpour AR. Thalidomide attenuates development of morphine
dependence in mice by inhibiting PI3K/Akt and nitric oxide signaling pathways.
Prog Neuropsychopharmacol Biol Psychiatry. 2017 Dec 6. pii:
S0278-5846(17)30288-9. doi: 10.1016/j.pnpbp.2017.12.002. [Epub ahead of print]
PubMed PMID: 29223784.
<br>

4: Tamzaourte M, Zajjari Y. Efficacy of Thalidomide for Recurrent
Gastrointestinal Bleeding due to angiodysplasias in a Hemodialysis Patient.
Indian J Nephrol. 2017 Nov-Dec;27(6):489-490. doi: 10.4103/ijn.IJN_32_17. PubMed
PMID: 29217895; PubMed Central PMCID: PMC5704423.
<br>

5: Bray JP, Orbell G, Cave N, Munday JS. Does thalidomide prolong survival in
dogs with splenic haemangiosarcoma? J Small Anim Pract. 2017 Dec 6. doi:
10.1111/jsap.12796. [Epub ahead of print] PubMed PMID: 29210452.
<br>

6: Passos GR, Camargo JA, Ferrari KL, Saad MJA, de Mattos AC, Reis LO.
Intravesical Thalidomide boosts bacillus Calmette-Guérin (BCG) in non-muscle
invasive bladder cancer treatment. Med Oncol. 2017 Dec 4;35(1):3. doi:
10.1007/s12032-017-1067-2. PubMed PMID: 29209984.
<br>

7: Wang L, Hong Y, Wu J, Leung YK, Huang Y. Efficacy of thalidomide therapy in
pediatric Crohn/’s disease with evidence of tuberculosis. World J Gastroenterol.
2017 Nov 21;23(43):7727-7734. doi: 10.3748/wjg.v23.i43.7727. PubMed PMID:
29209113; PubMed Central PMCID: PMC5703932.

<br>
8: Gomes JDA, Kowalski TW, Fraga LR, Tovo-Rodrigues L, Sanseverino MTV,
Schuler-Faccini L, Vianna FSL. Genetic susceptibility to thalidomide embryopathy
in humans: Study of candidate development genes. Birth Defects Res. 2017 Nov 28.
doi: 10.1002/bdr2.1163. [Epub ahead of print] PubMed PMID: 29193903.
<br>

9: Salemi M, Mohammadi S, Ghavamzadeh A, Nikbakht M. Anti-Vascular Endothelial
Growth Factor Targeting by Curcumin and Thalidomide in Acute Myeloid Leukemia
Cells. Asian Pac J Cancer Prev. 2017 Nov 26;18(11):3055-3061. PubMed PMID:
29172279.
<br>

10: Liu X, Wang H, Wu X, Hong X, Luo Z. Phase II study of doxorubicin and
thalidomide in patients with refractory aggressive fibromatosis. Invest New
Drugs. 2017 Nov 23. doi: 10.1007/s10637-017-0542-0. [Epub ahead of print] PubMed
PMID: 29170886.

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