Atiprimod (free base)
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.
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.
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.
| Chemical | |
|---|---|
| CAS Num | 123018-47-3 |
| Chemical Formula | C22H44N2 |
| Molecular Weight | 336.61 |
| IUPAC Chemical Name | 3-(8,8-dipropyl-3-azaspiro[4.5]decan-3-yl)-N,N- diethylpropan-1-amine |
| Exact Mass | 336.35 |
| 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 |
| Solubility | Soluble in DMSO, not in water |
| SMILES Code | CCN(CC)CCCN1CCC2(CCC(CCC)(CCC)CC2)C1 |
| Biological | |
| Targets and Effects | N/A |
| Pathways | Apoptosis |
| Physical | |
| 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). |
| Shelf Life | >5 years if stored properly |
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