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Atiprimod

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Pharmaceutical compound
Atiprimod
Clinical data
ATC code
  • none
Identifiers
IUPAC name
  • 3-(8,8-dipropyl-3-azaspirodecan-3-yl)-N,N- diethylpropan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC22H44N2
Molar mass336.598 g/mol g·mol
3D model (JSmol)
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

Atiprimod (INN, codenamed SK&F106615; also known as azaspirane, although this more properly refers to the class of chemicals to which atiprimod belongs) is a substance being studied in the treatment of certain multiple myelomas and other advanced cancers. Atiprimod may block the growth of tumors and the growth of blood vessels from surrounding tissue to the tumor. Atiprimod is a type of signal transduction inhibitor. It was first developed by SmithKline Beecham (now part of GlaxoSmithKline) as a potential treatment for rheumatoid arthritis.

January 7, 2008 Callisto Pharmaceuticals, Inc. announced that it has restructured its license agreement with Genzyme Corporation for Atiprimod. In August 2002, Callisto’s wholly owned subsidiary, Synergy, acquired from AnorMED Inc. worldwide exclusive rights to develop, manufacture and commercialize Atiprimod. AnorMED was acquired by Genzyme in November 2006.

The restructured agreement eliminates all milestone payments and reduces royalties owed to Genzyme to single digits. In return for the reduced future payments to Genzyme, Callisto is paying an upfront fee in 2008

Synergy Pharmaceuticals, Inc. (a wholly owned subsidiary of Callisto) entered into a license agreement with AnorMED Inc. to license Atiprimod from AnorMED. Atiprimod is a macrophage-targeting oral cytokine inhibitor which is being developed by AnorMED as a potential treatment for rheumatoid arthritis and other autoimmune diseases. Phase I trials have been successfully completed and Phase II multicenter trials have been approved by the FDA. The compound was discovered in a joint research and development program with SmithKline and French (now SmithKline Beecham, SB) but following acceptance of the Phase II protocol by the FDA, SB decided not to proceed with further development of atiprimod as a result of an internal restructuring program. All rights to atiprimod and other azaspiranes developed in this program have reverted to AnorMED. The compound was originally disclosed in European patent, EP-00310321, entitled 'Preparation of N-aminoalkyl-2-azaspirodecanes and analogs as immunosuppressants', while a cost-effective, efficacious pilot plant synthesis has also been described.

Synthesis

Dagger, R. E.; Grady, C. W.; 1999, U.S. patent 5,952,365.

References

  1. Jacobs GS (Spring 2004). "Atiprimod: A New Drug Candidate in Early-Stage Development for Myeloma" (). Myeloma Today. 5 (10). International Myeloma Foundation. Retrieved on September 14, 200.

Further reading

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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