Atiprimod

Chemical compound
  • none
Identifiers
  • 3-(8,8-dipropyl-3-azaspiro[4.5]decan-3-yl)-N,N- diethylpropan-1-amine
CAS Number
  • 123018-47-3 ☒N
PubChem CID
  • 129869
ChemSpider
  • 114962 checkY
UNII
  • MG7D3QD743
KEGG
  • D03003 ☒N
ChEMBL
  • ChEMBL103735 checkY
CompTox Dashboard (EPA)
  • DTXSID10153834 Edit this at Wikidata
Chemical and physical dataFormulaC22H44N2Molar mass336.608 g·mol−13D model (JSmol)
  • Interactive image
  • N(CC)(CC)CCCN2CCC1(CCC(CC1)(CCC)CCC)C2
InChI
  • InChI=1S/C22H44N2/c1-5-10-21(11-6-2)12-14-22(15-13-21)16-19-24(20-22)18-9-17-23(7-3)8-4/h5-20H2,1-4H3 checkY
  • Key:SERHTTSLBVGRBY-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Atiprimod (INN, codenamed SK&F106615) is a substance being studied in the treatment of certain multiple myelomas and other advanced cancers. It may block the growth of tumors and the growth of blood vessels from surrounding tissue to the tumor. This drug is also being researched as a potential treatment for various autoimmune diseases. It was first developed by GlaxoSmithKline as a potential treatment for rheumatoid arthritis.[1] The substance is also known as azaspirane, although this more properly refers to the class of chemicals to which atiprimod belongs.

This compound has also been shown to kill mantle cell lymphoma cells in vitro.[2]

Mechanism of action

Atiprimod has been shown to inhibit angiogenesis (growth of blood vessels) in a blood vessel model using chicken eggs. It is thought to inhibit the secretion of vascular endothelial growth factor (VEGF), a growth factor that promotes angiogenesis.[citation needed]

Chemistry

Atiprimod is an amphiphilic compound and a cation at neutral pH.

Synthesis

Atiprimod synthesis[3]

References

  1. ^ Jacobs GS (Spring 2004). "Atiprimod: A New Drug Candidate in Early-Stage Development for Myeloma". Myeloma Today. 5 (10). International Myeloma Foundation. Archived from the original on 2011-07-18. Retrieved 2010-09-30.
  2. ^ Wang M, Zhang L, Han X, Yang J, Qian J, Hong S, et al. (June 2007). "Atiprimod inhibits the growth of mantle cell lymphoma in vitro and in vivo and induces apoptosis via activating the mitochondrial pathways". Blood. 109 (12): 5455–5462. doi:10.1182/blood-2006-12-063958. PMID 17317853.
  3. ^ US 5952365, Dagger RE, Grady CW, "2-[2-(dimethylaminoehtyl]-8,8-diproply-2-azaspiro[4.5]decane dimaleate", issued 4 September 1999, assigned to Anormed Inc. 

Further reading

  • Hamasaki M, Hideshima T, Tassone P, et al. (June 2005). "Azaspirane (N-N-diethyl-8,8-dipropyl-2-azaspiro 4.5 decane-2-propanamine) inhibits human multiple myeloma cell growth in the bone marrow milieu in vitro and in vivo". Blood. 105 (11): 4470–6. doi:10.1182/blood-2004-09-3794. PMC 1895034. PMID 15705788.

External links

  • Atiprimod entry in the public domain NCI Dictionary of Cancer Terms

Public Domain This article incorporates public domain material from Dictionary of Cancer Terms. U.S. National Cancer Institute.

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