MedKoo Cat#: 509120 Name: YM201636 CAS#: 371942-69-7 Chemical Formula: C25H21N7O3 Exact Mass: 467.17059 Molecular Weight: 467.48 Elemental Analysis: C, 64.23; H, 4.53; N, 20.97; O, 10.27

Synonym: YM201636 YM-201636 YM 201636.

IUPAC/Chemical Name: 6-amino-N-(3-(4-(4-morpholinyl)pyrido(3,2-4,5)furo(3,2-d)pyrimidin-2-yl)phenyl)-3-pyridinecarboxamide

InChi Key: YBPIBGNBHHGLEB-UHFFFAOYSA-N

InChi Code: InChI=1S/C25H21N7O3/c26-19-7-6-16(14-28-19)24(33)29-17-4-1-3-15(13-17)22-30-20-18-5-2-8-27-25(18)35-21(20)23(31-22)32-9-11-34-12-10-32/h1-8,13-14H,9-12H2,(H2,26,28)(H,29,33)

SMILES Code: O=C(C1=CC=C(N)N=C1)NC2=CC=CC(C3=NC(N4CCOCC4)=C(OC5=NC=CC=C56)C6=N3)=C2

Technical Data

Appearance: White to off-white 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

References

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2: Sbrissa D, Ikonomov OC, Filios C, Delvecchio K, Shisheva A. Functional dissociation between PIKfyve-synthesized PtdIns5P and PtdIns(3,5)P2 by means of the PIKfyve inhibitor YM201636. Am J Physiol Cell Physiol. 2012 May 23. [Epub ahead of print] PubMed PMID: 22621786.

3: Seebohm G, Neumann S, Theiss C, Novkovic T, Hill EV, Tavaré JM, Lang F, Hollmann M, Manahan-Vaughan D, Strutz-Seebohm N. Identification of a novel signaling pathway and its relevance for GluA1 recycling. PLoS One. 2012;7(3):e33889. Epub 2012 Mar 21. PubMed PMID: 22470488; PubMed Central PMCID: PMC3309939.

4: Dukes JD, Whitley P, Chalmers AD. The PIKfyve inhibitor YM201636 blocks the continuous recycling of the tight junction proteins claudin-1 and claudin-2 in MDCK cells. PLoS One. 2012;7(3):e28659. Epub 2012 Mar 1. PubMed PMID: 22396724; PubMed Central PMCID: PMC3291620.

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6: Dupuis-Coronas S, Lagarrigue F, Ramel D, Chicanne G, Saland E, Gaits-Iacovoni F, Payrastre B, Tronchère H. The nucleophosmin-anaplastic lymphoma kinase oncogene interacts, activates, and uses the kinase PIKfyve to increase invasiveness. J Biol Chem. 2011 Sep 16;286(37):32105-14. Epub 2011 Jul 7. PubMed PMID: 21737449; PubMed Central PMCID: PMC3173219.

7: Fernandes F, Chen K, Ehrlich LS, Jin J, Chen MH, Medina GN, Symons M, Montelaro R, Donaldson J, Tjandra N, Carter CA. Phosphoinositides direct equine infectious anemia virus gag trafficking and release. Traffic. 2011 Apr;12(4):438-51. doi: 10.1111/j.1600-0854.2010.01153.x. Epub 2011 Feb 1. PubMed PMID: 21176037; PubMed Central PMCID: PMC3064743.

8: Kerr MC, Wang JT, Castro NA, Hamilton NA, Town L, Brown DL, Meunier FA, Brown NF, Stow JL, Teasdale RD. Inhibition of the PtdIns(5) kinase PIKfyve disrupts intracellular replication of Salmonella. EMBO J. 2010 Apr 21;29(8):1331-47. Epub 2010 Mar 18. PubMed PMID: 20300065; PubMed Central PMCID: PMC2868569.

9: Ikonomov OC, Sbrissa D, Shisheva A. YM201636, an inhibitor of retroviral budding and PIKfyve-catalyzed PtdIns(3,5)P2 synthesis, halts glucose entry by insulin in adipocytes. Biochem Biophys Res Commun. 2009 May 8;382(3):566-70. Epub 2009 Mar 14. PubMed PMID: 19289105.

10: Jefferies HB, Cooke FT, Jat P, Boucheron C, Koizumi T, Hayakawa M, Kaizawa H, Ohishi T, Workman P, Waterfield MD, Parker PJ. A selective PIKfyve inhibitor blocks PtdIns(3,5)P(2) production and disrupts endomembrane transport and retroviral budding. EMBO Rep. 2008 Feb;9(2):164-70. Epub 2008 Jan 11. PubMed PMID: 18188180; PubMed Central PMCID: PMC2246419.