Atiprimod

Atiprimod

Clinical data
ATC code	none
Identifiers
IUPAC name 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 Y
UNII	MG7D3QD743
KEGG	D03003 N
ChEMBL	ChEMBL103735 Y
CompTox Dashboard (EPA)	DTXSID10153834
Chemical and physical data
Formula	C22H44N2
Molar mass	336.608 g·mol−1
3D model (JSmol)	Interactive image
SMILES 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 Y Key:SERHTTSLBVGRBY-UHFFFAOYSA-N Y
NY (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. 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.

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.

Chemistry

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

Synthesis

Atiprimod synthesis: Anormed Inc. Dagger, R. E.; Grady, C. W.; 1999, U.S. Patent 5,952,365.

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

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