MedKoo Cat#: 532472 | Name: PKI166
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Description:

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

PKI166 is an experimental, reversible inhibitor of epidermal growth factor receptor tyrosine kinase which has anti-proliferative and apoptotic properties. PKI-166 prevented the stimulation of NF-kappaB by axonal membranes.

Chemical Structure

PKI166
PKI166
CAS#187724-61-4

Theoretical Analysis

MedKoo Cat#: 532472

Name: PKI166

CAS#: 187724-61-4

Chemical Formula: C20H18N4O

Exact Mass: 330.1481

Molecular Weight: 330.39

Elemental Analysis: C, 72.71; H, 5.49; N, 16.96; O, 4.84

Price and Availability

Size Price Availability Quantity
5mg USD 300.00 2 Weeks
10mg USD 550.00 2 Weeks
25mg USD 850.00 2 Weeks
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Related CAS #
No Data
Synonym
PKI166; PKI 166; PKI-166.
IUPAC/Chemical Name
4-[4-[[(1R)-1-phenylethyl]amino]-7H-pyrrolo[4,5-e]pyrimidin-6-yl]phenol
InChi Key
XRYJULCDUUATMC-CYBMUJFWSA-N
InChi Code
InChI=1S/C20H18N4O/c1-13(14-5-3-2-4-6-14)23-19-17-11-18(24-20(17)22-12-21-19)15-7-9-16(25)10-8-15/h2-13,25H,1H3,(H2,21,22,23,24)/t13-/m1/s1
SMILES Code
OC1=CC=C(C2=CC3=C(N[C@@H](C4=CC=CC=C4)C)N=CN=C3N2)C=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
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).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 330.39 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
1: Lee SH, Moon SJ, Paeng J, Kang HY, Nam BY, Kim S, Kim CH, Lee MJ, Oh HJ, Park JT, Han SH, Yoo TH, Kang SW. Podocyte hypertrophy precedes apoptosis under experimental diabetic conditions. Apoptosis. 2015 Aug;20(8):1056-71. doi: 10.1007/s10495-015-1134-0. PMID: 25953318. 2: Kaspersen SJ, Han J, Nørsett KG, Rydså L, Kjøbli E, Bugge S, Bjørkøy G, Sundby E, Hoff BH. Identification of new 4-N-substituted 6-aryl-7H-pyrrolo[2,3-d]pyrimidine-4-amines as highly potent EGFR-TK inhibitors with Src-family activity. Eur J Pharm Sci. 2014 Aug 1;59:69-82. doi: 10.1016/j.ejps.2014.04.011. Epub 2014 Apr 24. PMID: 24769040. 3: Behera R, Thomas SM, Mensa-Wilmot K. New chemical scaffolds for human african trypanosomiasis lead discovery from a screen of tyrosine kinase inhibitor drugs. Antimicrob Agents Chemother. 2014;58(4):2202-10. doi: 10.1128/AAC.01691-13. Epub 2014 Jan 27. PMID: 24468788; PMCID: PMC4023774. 4: Ulu N, Mulder GM, Vavrinec P, Landheer SW, Duman-Dalkilic B, Gurdal H, Goris M, Duin M, van Dokkum RP, Buikema H, van Goor H, Henning RH. Epidermal growth factor receptor inhibitor PKI-166 governs cardiovascular protection without beneficial effects on the kidney in hypertensive 5/6 nephrectomized rats. J Pharmacol Exp Ther. 2013 Jun;345(3):393-403. doi: 10.1124/jpet.113.203497. Epub 2013 Mar 25. PMID: 23528611. 5: Saad S, Zhang J, Yong R, Yaghobian D, Wong MG, Kelly DJ, Chen XM, Pollock CA. Role of the EGF receptor in PPARγ-mediated sodium and water transport in human proximal tubule cells. Diabetologia. 2013 May;56(5):1174-82. doi: 10.1007/s00125-013-2835-y. Epub 2013 Jan 31. PMID: 23370527. 6: Das S, Dey KK, Bharti R, MaitiChoudhury S, Maiti S, Mandal M. PKI 166 induced redox signalling and apoptosis through activation of p53, MAP kinase and caspase pathway in epidermoid carcinoma. J Exp Ther Oncol. 2012;10(2):139-53. PMID: 23350354. 7: Advani A, Wiggins KJ, Cox AJ, Zhang Y, Gilbert RE, Kelly DJ. Inhibition of the epidermal growth factor receptor preserves podocytes and attenuates albuminuria in experimental diabetic nephropathy. Nephrology (Carlton). 2011 Aug;16(6):573-81. doi: 10.1111/j.1440-1797.2011.01451.x. PMID: 21342330. 8: Limpert AS, Carter BD. Axonal neuregulin 1 type III activates NF-kappaB in Schwann cells during myelin formation. J Biol Chem. 2010 May 28;285(22):16614-22. doi: 10.1074/jbc.M109.098780. Epub 2010 Apr 1. PMID: 20360002; PMCID: PMC2878070. 9: Mulder GM, Nijboer WN, Seelen MA, Sandovici M, Bos EM, Melenhorst WB, Trzpis M, Kloosterhuis NJ, Visser L, Henning RH, Leuvenink HG, Ploeg RJ, Sunnarborg SW, van Goor H. Heparin binding epidermal growth factor in renal ischaemia/reperfusion injury. J Pathol. 2010 Jun;221(2):183-92. doi: 10.1002/path.2698. PMID: 20225242. 10: McGuire JF, Rouen S, Siegfreid E, Wright DE, Dobrowsky RT. Caveolin-1 and altered neuregulin signaling contribute to the pathophysiological progression of diabetic peripheral neuropathy. Diabetes. 2009 Nov;58(11):2677-86. doi: 10.2337/db09-0594. Epub 2009 Aug 12. PMID: 19675140; PMCID: PMC2768162. 11: Park SJ, Kim MJ, Kim HB, Sohn HY, Bae JH, Kang CD, Kim SH. Trichostatin A sensitizes human ovarian cancer cells to TRAIL-induced apoptosis by down- regulation of c-FLIPL via inhibition of EGFR pathway. Biochem Pharmacol. 2009 Apr 15;77(8):1328-36. doi: 10.1016/j.bcp.2008.12.027. Epub 2009 Jan 24. PMID: 19426671. 12: Pentassuglia L, Graf M, Lane H, Kuramochi Y, Cote G, Timolati F, Sawyer DB, Zuppinger C, Suter TM. Inhibition of ErbB2 by receptor tyrosine kinase inhibitors causes myofibrillar structural damage without cell death in adult rat cardiomyocytes. Exp Cell Res. 2009 Apr 15;315(7):1302-12. doi: 10.1016/j.yexcr.2009.02.001. Epub 2009 Feb 12. PMID: 19331811; PMCID: PMC4991362. 13: Pignon JC, Koopmansch B, Nolens G, Delacroix L, Waltregny D, Winkler R. Androgen receptor controls EGFR and ERBB2 gene expression at different levels in prostate cancer cell lines. Cancer Res. 2009 Apr 1;69(7):2941-9. doi: 10.1158/0008-5472.CAN-08-3760. Epub 2009 Mar 24. PMID: 19318561. 14: Barlesi F, Breen D. Thérapeutiques ciblant la voie des HER dans les cancers ORL et thoraciques [Targeting HER pathway in head and neck and thoracic cancers]. Bull Cancer. 2009;96 Suppl 1:S35-43. French. doi: 10.1684/bdc.2008.0774. PMID: 19433372. 15: Croyle M, Akeno N, Knauf JA, Fabbro D, Chen X, Baumgartner JE, Lane HA, Fagin JA. RET/PTC-induced cell growth is mediated in part by epidermal growth factor receptor (EGFR) activation: evidence for molecular and functional interactions between RET and EGFR. Cancer Res. 2008 Jun 1;68(11):4183-91. doi: 10.1158/0008-5472.CAN-08-0413. PMID: 18519677; PMCID: PMC4341915. 16: Kuwai T, Nakamura T, Sasaki T, Kim SJ, Fan D, Villares GJ, Zigler M, Wang H, Bar-Eli M, Kerbel RS, Fidler IJ. Phosphorylated epidermal growth factor receptor on tumor-associated endothelial cells is a primary target for therapy with tyrosine kinase inhibitors. Neoplasia. 2008 May;10(5):489-500. doi: 10.1593/neo.08200. PMID: 18472966; PMCID: PMC2373870. 17: Forsberg S, Ostman A, Rollman O. Regeneration of human epidermis on acellular dermis is impeded by small-molecule inhibitors of EGF receptor tyrosine kinase. Arch Dermatol Res. 2008 Oct;300(9):505-16. doi: 10.1007/s00403-008-0853-2. Epub 2008 Apr 30. PMID: 18446355. 18: Palayekar MJ, Herzog TJ. The emerging role of epidermal growth factor receptor inhibitors in ovarian cancer. Int J Gynecol Cancer. 2008 Sep- Oct;18(5):879-90. doi: 10.1111/j.1525-1438.2007.01144.x. Epub 2007 Dec 5. PMID: 18053062. 19: Rocha-Lima CM, Soares HP, Raez LE, Singal R. EGFR targeting of solid tumors. Cancer Control. 2007 Jul;14(3):295-304. doi: 10.1177/107327480701400313. PMID: 17615536. 20: Toffoli G, De Mattia E, Cecchin E, Biason P, Masier S, Corona G. Pharmacology of epidermal growth factor inhibitors. Int J Biol Markers. 2007 Jan-Mar;22(1 Suppl 4):S24-39. PMID: 17520578.