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 ;
PubChem CID	129869;
ChemSpider	114962 ;
UNII	MG7D3QD743;
KEGG	D03003 ;
ChEMBL	ChEMBL103735 ;
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 ; Key:SERHTTSLBVGRBY-UHFFFAOYSA-N ;
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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.

Chemistry

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

Synthesis

Atiprimod synthesis[3]

References

Jacobs GS (Spring 2004). "Atiprimod: A New Drug Candidate in Early-Stage Development for Myeloma". Myeloma Today. International Myeloma Foundation. 5 (10). Archived from the original on 2011-07-18. Retrieved 2010-09-30.
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.
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.

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.

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.

[1] Jacobs GS (Spring 2004). "Atiprimod: A New Drug Candidate in Early-Stage Development for Myeloma". Myeloma Today. International Myeloma Foundation. 5 (10). 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.