Atiprimod (free base)

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 200340

CAS#: 123018-47-3

Description: Atiprimod is an orally bioavailable small molecule belonging to the azaspirane class of cationic amphiphilic agents with anti-inflammatory, antineoplastic, and antiangiogenic properties. Atiprimod inhibits the phosphorylation of signal transducer and activator of transcription 3 (STAT3), blocking the signalling pathways of interleukin-6 and vascular endothelial growth factor (VEGF) and downregulating the anti-apoptotic proteins Bcl-2, Bcl-XL, and Mcl-1, thereby inhibiting cell proliferation, inducing cell cycle arrest, and inducing apoptosis.


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Atiprimod, purity > 98%, is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 200340
Name: Atiprimod (free base)
CAS#: 123018-47-3
Chemical Formula: C22H44N2
Exact Mass: 336.35
Molecular Weight: 336.61
Elemental Analysis: C, 78.50; H, 13.18; N, 8.32


Synonym: azaspirane; SKF 106615SKF 106615SKF106615; SK&F-106615-A-2; SK&F-106615-I-2; SK&F106615A2; SK&F-106615I2

IUPAC/Chemical Name: 3-(8,8-dipropyl-3-azaspiro[4.5]decan-3-yl)-N,N- diethylpropan-1-amine

InChi Key: SERHTTSLBVGRBY-UHFFFAOYSA-N

InChi Code: 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

SMILES Code: CCN(CC)CCCN1CCC2(CCC(CCC)(CCC)CC2)C1


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>5 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


Additional Information

Atiprimod (INN, code named 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, CallistoÂ’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-azaspiro[4.5]decanes and analogs as immunosuppressants', while a cost-effective, efficacious pilot plant synthesis has also been described. (from http://en.wikipedia.org/wiki/Atiprimod).
 
Related CAS#
130065-61-1(Atiprimod dihydrochloride)
123018-47-3(Atiprimod free base)
 
 


References

  1: Quintás-Cardama A, Manshouri T, Estrov Z, Harris D, Zhang Y, Gaikwad A, Kantarjian HM, Verstovsek S. Preclinical characterization of atiprimod, a novel JAK2 AND JAK3 inhibitor. Invest New Drugs. 2010 Apr 7. [Epub ahead of print] PubMed PMID: 20372971.

2: Neri P, Tassone P, Shammas M, Yasui H, Schipani E, Batchu RB, Blotta S, Prabhala R, Catley L, Hamasaki M, Hideshima T, Chauhan D, Jacob GS, Picker D, Venuta S, Anderson KC, Munshi NC. Biological pathways and in vivo antitumor activity induced by Atiprimod in myeloma. Leukemia. 2007 Dec;21(12):2519-26. Epub 2007 Sep 20. PubMed PMID: 17882285.

3: Wang M, Zhang L, Han X, Yang J, Qian J, Hong S, Samaniego F, Romaguera J, Yi Q. Atiprimod inhibits the growth of mantle cell lymphoma in vitro and in vivo and induces apoptosis via activating the mitochondrial pathways. Blood. 2007 Jun 15;109(12):5455-62. Epub 2007 Feb 22. PubMed PMID: 17317853.

4: Choudhari SR, Khan MA, Harris G, Picker D, Jacob GS, Block T, Shailubhai K. Deactivation of Akt and STAT3 signaling promotes apoptosis, inhibits proliferation, and enhances the sensitivity of hepatocellular carcinoma cells to an anticancer agent, Atiprimod. Mol Cancer Ther. 2007 Jan;6(1):112-21. PubMed PMID: 17237271.

5: Kaden S, Reissig HU. Efficient approach to the Azaspirane core of FR 901483. Org Lett. 2006 Oct 12;8(21):4763-6. PubMed PMID: 17020297.

6: Shailubhai K. Atiprimod: a multi-functional drug candidate for myeloid and other malignancies. Leuk Res. 2007 Jan;31(1):9-10. Epub 2006 Jul 24. PubMed PMID: 16860863.

7: Lakings DB. Atiprimod (AnorMED). IDrugs. 2000 Mar;3(3):329-35. PubMed PMID: 16103943.

8: Amit-Vazina M, Shishodia S, Harris D, Van Q, Wang M, Weber D, Alexanian R, Talpaz M, Aggarwal BB, Estrov Z. Atiprimod blocks STAT3 phosphorylation and induces apoptosis in multiple myeloma cells. Br J Cancer. 2005 Jul 11;93(1):70-80. PubMed PMID: 15970928; PubMed Central PMCID: PMC2361492.

9: Faderl S, Ferrajoli A, Harris D, Van Q, Kantarjian HM, Estrov Z. Atiprimod blocks phosphorylation of JAK-STAT and inhibits proliferation of acute myeloid leukemia (AML) cells. Leuk Res. 2007 Jan;31(1):91-5. Epub 2006 Jul 7. PubMed PMID: 16828865.

10: Obniska J, Kamiński K. Lipophilicity characterization of new N-phenylamino-azaspiranes as potential anticonvulsant agents. Biomed Chromatogr. 2006 Nov;20(11):1185-91. PubMed PMID: 16799923.