Buparlisib (BKM120)

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

Description:Buparlisib, also known as BKM120, is an orally bioavailable specific oral inhibitor of the pan-class I phosphatidylinositol 3-kinase (PI3K) family of lipid kinases with potential antineoplastic activity. PI3K inhibitor BKM120 specifically inhibits class I PIK3 in the PI3K/AKT kinase (or protein kinase B) signaling pathway in an ATP-competitive manner, thereby inhibiting the production of the secondary messenger phosphatidylinositol-3,4,5-trisphosphate and activation of the PI3K signaling pathway.

Price and Availability

Buparlisib, purity > 98%, is in stock. The same day shipping out after order is received.

Chemical Structure

Theoretical Analysis

MedKoo Cat#: 204690Name: Buparlisib (BKM120)CAS#: 944396-07-0 (free base)Chemical Formula: C18H21F3N6O2Exact Mass: 410.16781Molecular Weight: 410.39Elemental Analysis:C, 52.68; H, 5.16; F, 13.89; N, 20.48; O, 7.80

Related CAS #:944396-07-0 (free base)1312445-63-8 (HCl)

Synonym:NVPBKM120; NVP BKM120; NV- BKM120; BKM120; BKM-120; BKM 120; Buparlisib.

IUPAC/Chemical Name:5-[2,6-Di(4-morpholinyl)-4-pyrimidinyl]-4-(trifluoromethyl)-2-pyridinamine.

InChi Key:CWHUFRVAEUJCEF-UHFFFAOYSA-N

InChi Code:InChI=1S/C18H21F3N6O2/c19-18(20,21)13-9-15(22)23-11-12(13)14-10-16(26-1-5-28-6-2-26)25-17(24-14)27-3-7-29-8-4-27/h9-11H,1-8H2,(H2,22,23)

SMILES Code:NC1=NC=C(C2=NC(N3CCOCC3)=NC(N4CCOCC4)=C2)C(C(F)(F)F)=C1

Technical Data

Additional Information

Related:944396-07-0 (free base)1312445-63-8 (HCl).

NVP-BKM120 is a selective pan class 1 PI3 Kinase inhibitor.  It was found that NVP-BKM120 inhibited the PI3 signaling pathways, leading to different forms of cell death based on P53 statuses. Further studies are warranted to determine if NVP-BKM120 has potential as a glioma treatment. (source: http://www.ncbi.nlm.nih.gov/pubmed/22065080 ).    

References

1: Rodon J, Braña I, Siu LL, De Jonge MJ, Homji N,Mills D, Di Tomaso E, Sarr C, Trandafir L, Massacesi C, Eskens F,Bendell JC. Phase I dose-escalation and -expansion study of buparlisib(BKM120), an oral pan-Class I PI3K inhibitor, in patients with advancedsolid tumors. Invest New Drugs. 2014 Mar 21. [Epub ahead of print]PubMed PMID: 24652201.

2: Ando Y, Inada-Inoue M, Mitsuma A, Yoshino T, Ohtsu A, Suenaga N, SatoM, Kakizume T, Robson M, Quadt C, Doi T. Phase I dose-escalation studyof buparlisib (BKM120), an oral pan-class I PI3K inhibitor, in Japanesepatients with advanced solid tumors. Cancer Sci. 2014 Mar;105(3):347-53.doi: 10.1111/cas.12350. Epub 2014 Feb 13. PubMed PMID: 24405565.

3: Liang YC, Wu HG, Xue HJ, Liu Q, Shi LL, Liu T, Wu G. Effects of PI3Kinhibitor NVP-BKM120 on acquired resistance to gefitinib of human lungadenocarcinoma H1975 cells. J Huazhong Univ Sci Technolog Med Sci. 2013Dec;33(6):845-51. doi: 10.1007/s11596-013-1209-5. Epub 2013 Dec 13.PubMed PMID: 24337846.

4: Lonetti A, Antunes IL, Chiarini F, Orsini E, Buontempo F, Ricci F,Tazzari PL, Pagliaro P, Melchionda F, Pession A, Bertaina A, LocatelliF, McCubrey JA, Barata JT, Martelli AM. Activity of the pan-class Iphosphoinositide 3-kinase inhibitor NVP-BKM120 in T-cell acutelymphoblastic leukemia. Leukemia. 2013 Nov 6. doi: 10.1038/leu.2013.369.[Epub ahead of print] PubMed PMID: 24310736.

5: Geisthoff UW, Nguyen HL, Hess D. Improvement in hereditaryhemorrhagic telangiectasia after treatment with the phosphoinositide3-kinase inhibitor BKM120. Ann Hematol. 2014 Apr;93(4):703-4. doi:10.1007/s00277-013-1845-7. Epub 2013 Jul 27. PubMed PMID: 23892886.

6: Rosich L, Saborit-Villarroya I, López-Guerra M, Xargay-Torrent S,Montraveta A, Aymerich M, Villamor N, Campo E, Pérez-Galán P, Roué G,Colomer D. The phosphatidylinositol-3-kinase inhibitor NVP-BKM120overcomes resistance signals derived from microenvironment by regulatingthe Akt/FoxO3a/Bim axis in chronic lymphocytic leukemia cells.Haematologica. 2013 Nov;98(11):1739-47. doi:10.3324/haematol.2013.088849. Epub 2013 Jul 12. PubMed PMID: 23850807;PubMed Central PMCID: PMC3815175.

7: Zang C, Eucker J, Liu H, Coordes A, Lenarz M, Possinger K, Scholz CW.Inhibition of pan-class I phosphatidyl-inositol-3-kinase by NVP-BKM120effectively blocks proliferation and induces cell death in diffuse largeB-cell lymphoma. Leuk Lymphoma. 2014 Feb;55(2):425-34. doi:10.3109/10428194.2013.806800. Epub 2013 Jul 25. PubMed PMID: 23721513.

8: Ren H, Zhao L, Li Y, Yue P, Deng X, Owonikoko TK, Chen M, Khuri FR,Sun SY. The PI3 kinase inhibitor NVP-BKM120 induces GSK3/FBXW7-dependentMcl-1 degradation, contributing to induction of apoptosis andenhancement of TRAIL-induced apoptosis. Cancer Lett. 2013 Sep28;338(2):229-38. doi: 10.1016/j.canlet.2013.03.032. Epub 2013 Apr 2.PubMed PMID: 23562472; PubMed Central PMCID: PMC3750077.

9: Kirstein MM, Boukouris AE, Pothiraju D, Buitrago-Molina LE, MarhenkeS, Schütt J, Orlik J, Kühnel F, Hegermann J, Manns MP, Vogel A. Activityof the mTOR inhibitor RAD001, the dual mTOR and PI3-kinase inhibitorBEZ235 and the PI3-kinase inhibitor BKM120 in hepatocellular carcinoma.Liver Int. 2013 May;33(5):780-93. doi: 10.1111/liv.12126. Epub 2013 Mar15. PubMed PMID: 23489999.

10: Amrein L, Shawi M, Grenier J, Aloyz R, Panasci L. Thephosphatidylinositol-3 kinase I inhibitor BKM120 induces cell death inB-chronic lymphocytic leukemia cells in vitro. Int J Cancer. 2013Jul;133(1):247-52. doi: 10.1002/ijc.27989. Epub 2013 Jan 15. PubMedPMID: 23238639; PubMed Central PMCID: PMC3847963.