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.

Chemical Structure

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Atiprimod (free base)
CAS# 123018-47-3
Instruction

Theoretical Analysis

MedKoo Cat#: 200340
Name: Atiprimod (free base)
CAS#: 123018-47-3
Chemical Formula: C22H44N2
Exact Mass: 336.35
Molecular Weight: 336.610
Elemental Analysis: C, 78.50; H, 13.18; N, 8.32

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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

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).

HS Tariff Code: 2934.99.9001

Product Data:
Product Data
Instruction:
View handling instruction
Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 336.610000000000000000000000000000 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.

Recalculate based on batch purity %
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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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  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.