PF-562271 HCl
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MedKoo CAT#: 206808

CAS#: 939791-41-0 (HCl)

Description: PF-562271, also known as PF-562,271 and PF-271, is an orally bioavailable small molecule and ATP-competitive focal adhesion kinase (FAK) inhibitor with potential antineoplastic and antiangiogenic activities. PF-562271 inhibits the tyrosine kinase FAK, and to a lesser extent, proline-rich tyrosine kinase (PYK2), which may inhibit tumor cell migration, proliferation, and survival.


Price and Availability

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1g
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2g
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Size
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5g
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PF-562271 HCl, purity > 98%, is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 206808
Name: PF-562271 HCl
CAS#: 939791-41-0 (HCl)
Chemical Formula: C21H21ClF3N7O3S
Exact Mass:
Molecular Weight: 543.9502
Elemental Analysis: C, 46.37; H, 3.89; Cl, 6.52; F, 10.48; N, 18.03; O, 8.82; S, 5.89


Related CAS #: 939791-38-5 (besylate)   717907-75-0 (free base)   939791-39-6 (mesylate)   939791-41-0 (HCl)   939791-40-9 (tosylate)    

Synonym: PF562271; PF562271; PF-562271; PF562,271; PF562,271; PF-562,271; PF-00562271; PF00562271; PF 00562271; PF562271 hydrochloride. PF271, PF-271, PF 271

IUPAC/Chemical Name: N-methyl-N-(3-(((2-((2-oxoindolin-5-yl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)amino)methyl)pyridin-2-yl)methanesulfonamide hydrochloride

InChi Key: RQEBZJWSAAWCAV-UHFFFAOYSA-N

InChi Code: InChI=1S/C21H20F3N7O3S.ClH/c1-31(35(2,33)34)19-12(4-3-7-25-19)10-26-18-15(21(22,23)24)11-27-20(30-18)28-14-5-6-16-13(8-14)9-17(32)29-16;/h3-8,11H,9-10H2,1-2H3,(H,29,32)(H2,26,27,28,30);1H

SMILES Code: CS(=O)(N(C)C1=NC=CC=C1CNC2=NC(NC3=CC4=C(NC(C4)=O)C=C3)=NC=C2C(F)(F)F)=O.[H]Cl


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Certificate of Analysis:

Safety Data Sheet (MSDS):

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:
>2 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


References

1: Fang Y, Wang D, Xu X, Liu J, Wu A, Li X, Xue Q, Wang H, Wang H, Zhang H. Synthesis, biological evaluation, and molecular dynamics (MD) simulation studies of three novel F-18 labeled and focal adhesion kinase (FAK) targeted 5-bromo pyrimidines as radiotracers for tumor. Eur J Med Chem. 2017 Feb 15;127:493-508. doi: 10.1016/j.ejmech.2017.01.015. Epub 2017 Jan 11. PubMed PMID: 28109944.

2: Kessler BE, Sharma V, Zhou Q, Jing X, Pike LA, Kerege AA, Sams SB, Schweppe RE. FAK Expression, Not Kinase Activity, Is a Key Mediator of Thyroid Tumorigenesis and Protumorigenic Processes. Mol Cancer Res. 2016 Sep;14(9):869-82. doi: 10.1158/1541-7786.MCR-16-0007. Epub 2016 Jun 3. PubMed PMID: 27259715; PubMed Central PMCID: PMC5025360.

3: Howe GA, Xiao B, Zhao H, Al-Zahrani KN, Hasim MS, Villeneuve J, Sekhon HS, Goss GD, Sabourin LA, Dimitroulakos J, Addison CL. Focal Adhesion Kinase Inhibitors in Combination with Erlotinib Demonstrate Enhanced Anti-Tumor Activity in Non-Small Cell Lung Cancer. PLoS One. 2016 Mar 10;11(3):e0150567. doi: 10.1371/journal.pone.0150567. eCollection 2016 Mar 10. PubMed PMID: 26962872; PubMed Central PMCID: PMC4786279.

4: Fan GP, Wang W, Zhao H, Cai L, Zhang PD, Yang ZH, Zhang J, Wang X. Pharmacological Inhibition of Focal Adhesion Kinase Attenuates Cardiac Fibrosis in Mice Cardiac Fibroblast and Post-Myocardial-Infarction Models. Cell Physiol Biochem. 2015;37(2):515-26. PubMed PMID: 26330161.

5: Rolón-Reyes K, Kucheryavykh YV, Cubano LA, Inyushin M, Skatchkov SN, Eaton MJ, Harrison JK, Kucheryavykh LY. Microglia Activate Migration of Glioma Cells through a Pyk2 Intracellular Pathway. PLoS One. 2015 Jun 22;10(6):e0131059. doi: 10.1371/journal.pone.0131059. eCollection 2015 Jun 22. PubMed PMID: 26098895; PubMed Central PMCID: PMC4476590.

6: Shelef MA, Bennin DA, Yasmin N, Warner TF, Ludwig T, Beggs HE, Huttenlocher A. Focal adhesion kinase is required for synovial fibroblast invasion, but not murine inflammatory arthritis. Arthritis Res Ther. 2014 Oct 4;16(5):464. doi: 10.1186/s13075-014-0464-6. PubMed PMID: 25280866; PubMed Central PMCID: PMC4203874.

7: Stone RL, Baggerly KA, Armaiz-Pena GN, Kang Y, Sanguino AM, Thanapprapasr D, Dalton HJ, Bottsford-Miller J, Zand B, Akbani R, Diao L, Nick AM, DeGeest K, Lopez-Berestein G, Coleman RL, Lutgendorf S, Sood AK. Focal adhesion kinase: an alternative focus for anti-angiogenesis therapy in ovarian cancer. Cancer Biol Ther. 2014 Jul;15(7):919-29. doi: 10.4161/cbt.28882. Epub 2014 Apr 23. PubMed PMID: 24755674; PubMed Central PMCID: PMC4100993.

8: Yoon H, Choi YL, Song JY, Do I, Kang SY, Ko YH, Song S, Kim BG. Targeted inhibition of FAK, PYK2 and BCL-XL synergistically enhances apoptosis in ovarian clear cell carcinoma cell lines. PLoS One. 2014 Feb 11;9(2):e88587. doi: 10.1371/journal.pone.0088587. eCollection 2014 Feb 11. PubMed PMID: 24523919; PubMed Central PMCID: PMC3921183.

9: Grädler U, Bomke J, Musil D, Dresing V, Lehmann M, Hölzemann G, Greiner H, Esdar C, Krier M, Heinrich T. Fragment-based discovery of focal adhesion kinase inhibitors. Bioorg Med Chem Lett. 2013 Oct 1;23(19):5401-9. doi: 10.1016/j.bmcl.2013.07.050. Epub 2013 Jul 31. PubMed PMID: 23973211.

10: Wiemer AJ, Wernimont SA, Cung TD, Bennin DA, Beggs HE, Huttenlocher A. The focal adhesion kinase inhibitor PF-562,271 impairs primary CD4+ T cell activation. Biochem Pharmacol. 2013 Sep 15;86(6):770-81. doi: 10.1016/j.bcp.2013.07.024. Epub 2013 Aug 5. PubMed PMID: 23928188; PubMed Central PMCID: PMC3762933.

11: Lagares D, Busnadiego O, García-Fernández RA, Lamas S, Rodríguez-Pascual F. Adenoviral gene transfer of endothelin-1 in the lung induces pulmonary fibrosis through the activation of focal adhesion kinase. Am J Respir Cell Mol Biol. 2012 Dec;47(6):834-42. doi: 10.1165/rcmb.2011-0446OC. Epub 2012 Sep 6. PubMed PMID: 22962065.

12: Lagares D, Busnadiego O, García-Fernández RA, Kapoor M, Liu S, Carter DE, Abraham D, Shi-Wen X, Carreira P, Fontaine BA, Shea BS, Tager AM, Leask A, Lamas S, Rodríguez-Pascual F. Inhibition of focal adhesion kinase prevents experimental lung fibrosis and myofibroblast formation. Arthritis Rheum. 2012 May;64(5):1653-64. doi: 10.1002/art.33482. PubMed PMID: 22492165; PubMed Central PMCID: PMC3338902.

13: Stokes JB, Adair SJ, Slack-Davis JK, Walters DM, Tilghman RW, Hershey ED, Lowrey B, Thomas KS, Bouton AH, Hwang RF, Stelow EB, Parsons JT, Bauer TW. Inhibition of focal adhesion kinase by PF-562,271 inhibits the growth and metastasis of pancreatic cancer concomitant with altering the tumor microenvironment. Mol Cancer Ther. 2011 Nov;10(11):2135-45. doi: 10.1158/1535-7163.MCT-11-0261. Epub 2011 Sep 8. PubMed PMID: 21903606; PubMed Central PMCID: PMC3213273.

14: Serrels A, McLeod K, Canel M, Kinnaird A, Graham K, Frame MC, Brunton VG. The role of focal adhesion kinase catalytic activity on the proliferation and migration of squamous cell carcinoma cells. Int J Cancer. 2012 Jul 15;131(2):287-97. doi: 10.1002/ijc.26351. Epub 2011 Aug 30. PubMed PMID: 21823119.

15: Schultze A, Fiedler W. Clinical importance and potential use of small molecule inhibitors of focal adhesion kinase. Anticancer Agents Med Chem. 2011 Sep;11(7):593-9. Review. PubMed PMID: 21787277.

16: Wendt MK, Smith JA, Schiemann WP. Transforming growth factor-β-induced epithelial-mesenchymal transition facilitates epidermal growth factor-dependent breast cancer progression. Oncogene. 2010 Dec 9;29(49):6485-98. doi: 10.1038/onc.2010.377. Epub 2010 Aug 30. PubMed PMID: 20802523; PubMed Central PMCID: PMC3076082.

17: Sun H, Pisle S, Gardner ER, Figg WD. Bioluminescent imaging study: FAK inhibitor, PF-562,271, preclinical study in PC3M-luc-C6 local implant and metastasis xenograft models. Cancer Biol Ther. 2010 Jul 1;10(1):38-43. Epub 2010 Jul 9. PubMed PMID: 20495381; PubMed Central PMCID: PMC3087944.

18: Hao H, Naomoto Y, Bao X, Watanabe N, Sakurama K, Noma K, Motoki T, Tomono Y, Fukazawa T, Shirakawa Y, Yamatsuji T, Matsuoka J, Wang ZG, Takaoka M. Focal adhesion kinase as potential target for cancer therapy (Review). Oncol Rep. 2009 Nov;22(5):973-9. Review. PubMed PMID: 19787209.

19: Wendt MK, Schiemann WP. Therapeutic targeting of the focal adhesion complex prevents oncogenic TGF-beta signaling and metastasis. Breast Cancer Res. 2009;11(5):R68. doi: 10.1186/bcr2360. PubMed PMID: 19740433; PubMed Central PMCID: PMC2790843.

20: Slack-Davis JK, Hershey ED, Theodorescu D, Frierson HF, Parsons JT. Differential requirement for focal adhesion kinase signaling in cancer progression in the transgenic adenocarcinoma of mouse prostate model. Mol Cancer Ther. 2009 Aug;8(8):2470-7. doi: 10.1158/1535-7163.MCT-09-0262. Epub 2009 Aug 11. PubMed PMID: 19671741; PubMed Central PMCID: PMC2728172.