Atiprimod dihydrochloride | CAS#130065-61-1 | Anti-Arthritic

MedKoo Cat#: 593018 | Name: Atiprimod dihydrochloride

Description:

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

Atiprimod is a macrophage-targeting oral cytokine inhibitor which was developed by AnorMED as a potential treatment for rheumatoid arthritis and other autoimmune diseases.

Chemical Structure

Atiprimod dihydrochloride

CAS#130065-61-1 (2HCl)

Theoretical Analysis

MedKoo Cat#: 593018

Name: Atiprimod dihydrochloride

CAS#: 130065-61-1 (2HCl)

Chemical Formula: C22H46Cl2N2

Exact Mass: 408.3038

Molecular Weight: 409.52

Elemental Analysis: C, 64.52; H, 11.32; Cl, 17.31; N, 6.84

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Related CAS #

123018-47-3 (free base) 130065-61-1 (2HCl) 183063-72-1 (dimaleate)

Synonym

Atiprimod dihydrochloride, Atiprimod 2HCl

IUPAC/Chemical Name

2-Azaspiro(4.5)decane-2-propanamine, N,N-diethyl-8,8-dipropyl-, dihydrochloride

InChi Key

MOUZYBYTICOTFQ-UHFFFAOYSA-N

InChi Code

InChI=1S/C22H44N2.2ClH/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;2*1H

SMILES Code

CCCC(CC1)(CCC)CCC21CCN(CCCN(CC)CC)C2.[H]Cl.[H]Cl

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

Shelf Life

>3 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).

HS Tariff Code

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 409.52 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Coker-Gurkan A, Can E, Sahin S, Obakan-Yerlikaya P, Arisan ED. Atiprimod triggered apoptotic cell death via acting on PERK/eIF2α/ATF4/CHOP and STAT3/NF- ΚB axis in MDA-MB-231 and MDA-MB-468 breast cancer cells. Mol Biol Rep. 2021 Jun;48(6):5233-5247. doi: 10.1007/s11033-021-06528-1. Epub 2021 Jul 9. PMID: 34244887. 2: Coker-Gurkan A, Ayhan-Sahin B, Keceloglu G, Obakan-Yerlikaya P, Arisan ED, Palavan-Unsal N. Atiprimod induce apoptosis in pituitary adenoma: Endoplasmic reticulum stress and autophagy pathways. J Cell Biochem. 2019 Dec;120(12):19749-19763. doi: 10.1002/jcb.29281. Epub 2019 Jul 3. PMID: 31270852. 3: Lakings DB. Atiprimod (AnorMED). IDrugs. 2000 Mar;3(3):329-35. PMID: 16103943. 4: Shailubhai K. Atiprimod: a multi-functional drug candidate for myeloid and other malignancies. Leuk Res. 2007 Jan;31(1):9-10. doi: 10.1016/j.leukres.2006.06.007. Epub 2006 Jul 24. PMID: 16860863. 5: 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. doi: 10.1016/j.leukres.2006.05.027. Epub 2006 Jul 7. PMID: 16828865. 6: 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. doi: 10.1038/sj.bjc.6602637. PMID: 15970928; PMCID: PMC2361492. 7: 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. doi: 10.1182/blood-2006-12-063958. Epub 2007 Feb 22. PMID: 17317853. 8: Badger AM, Handler JA, Genell CA, Herzyk D, Gore E, Polsky R, Webb L, Bugelski PJ. Atiprimod (SK&F 106615), a novel macrophage targeting agent, enhances alveolar macrophage candidacidal activity and is not immunosuppressive in Candida-infected mice. Int J Immunopharmacol. 1999 Mar;21(3):161-76. doi: 10.1016/s0192-0561(98)00076-9. PMID: 10348366. 9: 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. 2011 Oct;29(5):818-26. doi: 10.1007/s10637-010-9429-z. Epub 2010 Apr 7. PMID: 20372971; PMCID: PMC4170651. 10: Shailubhai K, Dheer S, Picker D, Kaur G, Sausville EA, Jacob GS. Atiprimod is an inhibitor of cancer cell proliferation and angiogenesis. J Exp Ther Oncol. 2004 Dec;4(4):267-79. PMID: 15844657. 11: Coker-Gurkan A, Ozakaltun B, Akdeniz BS, Ergen B, Obakan-Yerlikaya P, Akkoc T, Arisan ED. Proinflammatory cytokine profile is critical in autocrine GH- triggered curcumin resistance engulf by atiprimod cotreatment in MCF-7 and MDA- MB-231 breast cancer cells. Mol Biol Rep. 2020 Nov;47(11):8797-8808. doi: 10.1007/s11033-020-05928-z. Epub 2020 Oct 31. PMID: 33130987. 12: Sun L, Zhang L, Qian J, Yang J, Yi Q, Dong W, Wang M. Combination of atiprimod and the proteasome inhibitor bortezomib induces apoptosis of mantle cell lymphoma in vitro and in vivo. Leuk Res. 2012 Mar;36(3):363-8. doi: 10.1016/j.leukres.2011.09.014. Epub 2011 Oct 13. PMID: 22000823. 13: 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. doi: 10.1038/sj.leu.2404912. Epub 2007 Sep 20. PMID: 17882285. 14: 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. doi: 10.1158/1535-7163.MCT-06-0561. PMID: 17237271. 15: Handler JA, Badger A, Genell CA, Klinkner AM, Kassis S, Waites CR, Bugelski PJ. Selective inhibition of phospholipases by atiprimod, a macrophage targeting antiarthritic compound. Toxicol Appl Pharmacol. 1999 Aug 15;159(1):9-17. doi: 10.1006/taap.1999.8732. PMID: 10448120. 16: Hamasaki M, Hideshima T, Tassone P, Neri P, Ishitsuka K, Yasui H, Shiraishi N, Raje N, Kumar S, Picker DH, Jacob GS, Richardson PG, Munshi NC, Anderson KC. 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. 2005 Jun 1;105(11):4470-6. doi: 10.1182/blood-2004-09-3794. Epub 2005 Feb 10. PMID: 15705788; PMCID: PMC1895034. 17: Manshouri T, Estrov Z, Quintás-Cardama A, Burger J, Zhang Y, Livun A, Knez L, Harris D, Creighton CJ, Kantarjian HM, Verstovsek S. Bone marrow stroma- secreted cytokines protect JAK2(V617F)-mutated cells from the effects of a JAK2 inhibitor. Cancer Res. 2011 Jun 1;71(11):3831-40. doi: 10.1158/0008-5472.CAN-10-4002. Epub 2011 Apr 21. PMID: 21512135; PMCID: PMC4067142. 18: Tomillero A, Moral MA. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2008 Sep;30(7):543-88. PMID: 18985183. 19: Wang M, Zhang L, Han X, Yang J, Qian J, Hong S, Lin P, Shi Y, Romaguera J, Kwak LW, Yi Q. A severe combined immunodeficient-hu in vivo mouse model of human primary mantle cell lymphoma. Clin Cancer Res. 2008 Apr 1;14(7):2154-60. doi: 10.1158/1078-0432.CCR-07-4409. Erratum in: Clin Cancer Res. 2014 Oct 1;20(19):5142-3. PMID: 18381957. 20: Tassone P, Neri P, Carrasco DR, Burger R, Goldmacher VS, Fram R, Munshi V, Shammas MA, Catley L, Jacob GS, Venuta S, Anderson KC, Munshi NC. A clinically relevant SCID-hu in vivo model of human multiple myeloma. Blood. 2005 Jul 15;106(2):713-6. doi: 10.1182/blood-2005-01-0373. Epub 2005 Apr 7. PMID: 15817674; PMCID: PMC1895174.