KN-92 free base
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MedKoo CAT#: 530547

CAS#: 176708-42-2 (free base)

Description: KN-92 is an inactive analog of the CaM kinase II inhibitor KN 93.

Chemical Structure

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KN-92 free base
CAS# 176708-42-2 (free base)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 530547
Name: KN-92 free base
CAS#: 176708-42-2 (free base)
Chemical Formula: C24H25ClN2O3S
Exact Mass: 456.13
Molecular Weight: 456.985
Elemental Analysis: C, 63.08; H, 5.51; Cl, 7.76; N, 6.13; O, 10.50; S, 7.02

Price and Availability

Size Price Availability Quantity
100mg USD 850
200mg USD 1250
500mg USD 1950
1g USD 2950
2g USD 4250
5g USD 6650
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Related CAS #: 1431698-47-3 (HCl)   176708-42-2 (free base)   1135280-28-2 (phosphate)    

Synonym: KN-92 free base; K92; K 92.

IUPAC/Chemical Name: (E)-N-(2-(((3-(4-chlorophenyl)allyl)(methyl)amino)methyl)phenyl)-4-methoxybenzenesulfonamide

InChi Key: RUAOVVIUGUOYHA-AATRIKPKSA-N

InChi Code: InChI=1S/C24H25ClN2O3S/c1-27(17-5-6-19-9-11-21(25)12-10-19)18-20-7-3-4-8-24(20)26-31(28,29)23-15-13-22(30-2)14-16-23/h3-16,26H,17-18H2,1-2H3/b6-5+

SMILES Code: CN(C/C=C/C1=CC=C(Cl)C=C1)CC2=CC=CC=C2NS(=O)(C3=CC=C(OC)C=C3)=O

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:

Product Data:
Product Data
Instruction:
View handling instruction
Biological target: KN-92 is an inactive derivative of KN-93, without CaM kinase inhibitory activity.
In vitro activity: However, KN-92, an inactive derivative of KN-93, did not inhibit cell proliferation effectively. Moreover, analysis of cell cycle regulator expression revealed that KN-93 rather than KN-92 reduced the expression of p53 and p21. Reference: World J Gastroenterol. 2007 Mar 7;13(9):1445-8. https://pubmed.ncbi.nlm.nih.gov/17457979/
In vivo activity: KN-93 treatment preserved rat normal myocyte contraction, relaxation, [Ca2+]iT, and β-adrenergic reserve, whereas KN-92 treatment failed to improve LV and myocyte function, and plasma norepinephrine remained high in CHF. Reference: J Pharmacol Exp Ther. 2021 Jun;377(3):316-325. https://pubmed.ncbi.nlm.nih.gov/33722881/

Preparing Stock Solutions

The following data is based on the product molecular weight 456.99 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: 1. An P, Zhu JY, Yang Y, Lv P, Tian YH, Chen MK, Luo HS. KN-93, a specific inhibitor of CaMKII inhibits human hepatic stellate cell proliferation in vitro. World J Gastroenterol. 2007 Mar 7;13(9):1445-8. doi: 10.3748/wjg.v13.i9.1445. PMID: 17457979; PMCID: PMC4146932. 2. Smyth JT, Abbott AL, Lee B, Sienaert I, Kasri NN, De Smedt H, Ducibella T, Missiaen L, Parys JB, Fissore RA. Inhibition of the inositol trisphosphate receptor of mouse eggs and A7r5 cells by KN-93 via a mechanism unrelated to Ca2+/calmodulin-dependent protein kinase II antagonism. J Biol Chem. 2002 Sep 20;277(38):35061-70. doi: 10.1074/jbc.M202928200. Epub 2002 Jul 16. PMID: 12121980. 3. Liu Y, Shao Q, Cheng HJ, Li T, Zhang X, Callahan MF, Herrington D, Kitzman D, Zhao D, Cheng CP. Chronic Ca2+/Calmodulin-Dependent Protein Kinase II Inhibition Rescues Advanced Heart Failure. J Pharmacol Exp Ther. 2021 Jun;377(3):316-325. doi: 10.1124/jpet.120.000361. Epub 2021 Mar 15. PMID: 33722881; PMCID: PMC8140392. 4. Kong L, Xiong F, Sun N, Xu C, Chen Y, Yang J, Su X. CaMKIIδ inhibition protects against myocardial ischemia/reperfusion injury: Role of Beclin-1-dependent autophagy. Eur J Pharmacol. 2020 Nov 5;886:173539. doi: 10.1016/j.ejphar.2020.173539. Epub 2020 Sep 9. PMID: 32918874.
In vitro protocol: 1. An P, Zhu JY, Yang Y, Lv P, Tian YH, Chen MK, Luo HS. KN-93, a specific inhibitor of CaMKII inhibits human hepatic stellate cell proliferation in vitro. World J Gastroenterol. 2007 Mar 7;13(9):1445-8. doi: 10.3748/wjg.v13.i9.1445. PMID: 17457979; PMCID: PMC4146932. 2. Smyth JT, Abbott AL, Lee B, Sienaert I, Kasri NN, De Smedt H, Ducibella T, Missiaen L, Parys JB, Fissore RA. Inhibition of the inositol trisphosphate receptor of mouse eggs and A7r5 cells by KN-93 via a mechanism unrelated to Ca2+/calmodulin-dependent protein kinase II antagonism. J Biol Chem. 2002 Sep 20;277(38):35061-70. doi: 10.1074/jbc.M202928200. Epub 2002 Jul 16. PMID: 12121980.
In vivo protocol: 1. Liu Y, Shao Q, Cheng HJ, Li T, Zhang X, Callahan MF, Herrington D, Kitzman D, Zhao D, Cheng CP. Chronic Ca2+/Calmodulin-Dependent Protein Kinase II Inhibition Rescues Advanced Heart Failure. J Pharmacol Exp Ther. 2021 Jun;377(3):316-325. doi: 10.1124/jpet.120.000361. Epub 2021 Mar 15. PMID: 33722881; PMCID: PMC8140392. 2. Kong L, Xiong F, Sun N, Xu C, Chen Y, Yang J, Su X. CaMKIIδ inhibition protects against myocardial ischemia/reperfusion injury: Role of Beclin-1-dependent autophagy. Eur J Pharmacol. 2020 Nov 5;886:173539. doi: 10.1016/j.ejphar.2020.173539. Epub 2020 Sep 9. PMID: 32918874.

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1: Takeuchi M, Yamamoto T. Apoptosis induced by NAD depletion is inhibited by KN-93 in a CaMKII-independent manner. Exp Cell Res. 2015 Jul 1;335(1):62-7. doi: 10.1016/j.yexcr.2015.05.019. PubMed PMID: 26024774.

2: Ke J, Chen F, Zhang C, Xiao X, Tu J, Dai M, Wang X, Chen B, Chen M. Effects of calmodulin-dependent protein kinase II inhibitor, KN-93, on electrophysiological features of rabbit hypertrophic cardiac myocytes. J Huazhong Univ Sci Technolog Med Sci. 2012 Aug;32(4):485-9. doi: 10.1007/s11596-012-0084-9. PubMed PMID: 22886958.

3: Popovic MA, Stojilkovic SS, Gonzalez-Iglesias AE. Effects of isoquinolonesulfonamides on action potential secretion coupling in pituitary cells. Horm Mol Biol Clin Investig. 2010 Jan;1(1):35-42. doi: 10.1515/HMBCI.2010.005. PubMed PMID: 25961970.

4: An P, Zhu JY, Yang Y, Lv P, Tian YH, Chen MK, Luo HS. KN-93, a specific inhibitor of CaMKII inhibits human hepatic stellate cell proliferation in vitro. World J Gastroenterol. 2007 Mar 7;13(9):1445-8. PubMed PMID: 17457979; PubMed Central PMCID: PMC4146932.

5: Ke J, Zhang CT, Ma YX, Liu J, Zhang QY, Liu N, Ruan YF, Lin L. [The effects of calmodulin kinase II inhibitor on ventricular arrhythmias in rabbits with cardiac hypertrophy]. Zhonghua Xin Xue Guan Bing Za Zhi. 2007 Jan;35(1):33-6. Chinese. PubMed PMID: 17386161.

6: Banerjee C, Khatri P, Raman R, Bhatia H, Datta M, Mazumder S. Role of calmodulin-calmodulin kinase II, cAMP/protein kinase A and ERK 1/2 on Aeromonas hydrophila-induced apoptosis of head kidney macrophages. PLoS Pathog. 2014 Apr 24;10(4):e1004018. doi: 10.1371/journal.ppat.1004018. PubMed PMID: 24763432; PubMed Central PMCID: PMC3999153.

7: Ninan I, Jardemark KE, Liang X, Wang RY. Calcium/calmodulin-dependent kinase II is involved in the facilitating effect of clozapine on NMDA- and electrically evoked responses in the medial prefrontal cortical pyramidal cells. Synapse. 2003 Mar 15;47(4):285-94. PubMed PMID: 12539202.

8: Brooks IM, Tavalin SJ. Ca2+/calmodulin-dependent protein kinase II inhibitors disrupt AKAP79-dependent PKC signaling to GluA1 AMPA receptors. J Biol Chem. 2011 Feb 25;286(8):6697-706. doi: 10.1074/jbc.M110.183558. PubMed PMID: 21156788; PubMed Central PMCID: PMC3057809.

9: Lisachev PD, Pustyl'nik VO, Shtark MB. [Regulation of S100B expression during long term potentiation]. Ross Fiziol Zh Im I M Sechenova. 2014 Aug;100(8):953-63. Russian. PubMed PMID: 25682687.

10: Chiluiza D, Krishna S, Schumacher VA, Schlöndorff J. Gain-of-function mutations in transient receptor potential C6 (TRPC6) activate extracellular signal-regulated kinases 1/2 (ERK1/2). J Biol Chem. 2013 Jun 21;288(25):18407-20. doi: 10.1074/jbc.M113.463059. PubMed PMID: 23645677; PubMed Central PMCID: PMC3689983.

11: Groth RD, Lindskog M, Thiagarajan TC, Li L, Tsien RW. Beta Ca2+/CaM-dependent kinase type II triggers upregulation of GluA1 to coordinate adaptation to synaptic inactivity in hippocampal neurons. Proc Natl Acad Sci U S A. 2011 Jan 11;108(2):828-33. doi: 10.1073/pnas.1018022108. PubMed PMID: 21187407; PubMed Central PMCID: PMC3021030.

12: Liu N, Ruan Y, Denegri M, Bachetti T, Li Y, Colombi B, Napolitano C, Coetzee WA, Priori SG. Calmodulin kinase II inhibition prevents arrhythmias in RyR2(R4496C+/-) mice with catecholaminergic polymorphic ventricular tachycardia. J Mol Cell Cardiol. 2011 Jan;50(1):214-22. doi: 10.1016/j.yjmcc.2010.10.001. PubMed PMID: 20937285.

13: Song YH, Cho H, Ryu SY, Yoon JY, Park SH, Noh CI, Lee SH, Ho WK. L-type Ca(2+) channel facilitation mediated by H(2)O(2)-induced activation of CaMKII in rat ventricular myocytes. J Mol Cell Cardiol. 2010 Apr;48(4):773-80. doi: 10.1016/j.yjmcc.2009.10.020. PubMed PMID: 19883656.

14: Silva-Neto MA, Atella GC, Shahabuddin M. Inhibition of Ca2+/calmodulin-dependent protein kinase blocks morphological differentiation of plasmodium gallinaceum zygotes to ookinetes. J Biol Chem. 2002 Apr 19;277(16):14085-91. PubMed PMID: 11827960.

15: Anderson ME, Braun AP, Wu Y, Lu T, Wu Y, Schulman H, Sung RJ. KN-93, an inhibitor of multifunctional Ca++/calmodulin-dependent protein kinase, decreases early afterdepolarizations in rabbit heart. J Pharmacol Exp Ther. 1998 Dec;287(3):996-1006. PubMed PMID: 9864285.

16: Pezhouman A, Singh N, Song Z, Nivala M, Eskandari A, Cao H, Bapat A, Ko CY, Nguyen TP, Qu Z, Karagueuzian HS, Weiss JN. Molecular Basis of Hypokalemia-Induced Ventricular Fibrillation. Circulation. 2015 Oct 20;132(16):1528-37. doi: 10.1161/CIRCULATIONAHA.115.016217. PubMed PMID: 26269574; PubMed Central PMCID: PMC4618042.

17: Rezazadeh S, Claydon TW, Fedida D. KN-93 (2-[N-(2-hydroxyethyl)]-N-(4-methoxybenzenesulfonyl)]amino-N-(4-chlorocinnamyl)-N -methylbenzylamine), a calcium/calmodulin-dependent protein kinase II inhibitor, is a direct extracellular blocker of voltage-gated potassium channels. J Pharmacol Exp Ther. 2006 Apr;317(1):292-9. PubMed PMID: 16368898.

18: Kostic S, Pan B, Guo Y, Yu H, Sapunar D, Kwok WM, Hudmon A, Wu HE, Hogan QH. Regulation of voltage-gated Ca(2+) currents by Ca(2+)/calmodulin-dependent protein kinase II in resting sensory neurons. Mol Cell Neurosci. 2014 Sep;62:10-8. doi: 10.1016/j.mcn.2014.07.004. PubMed PMID: 25064143; PubMed Central PMCID: PMC4187344.

19: Mitsuyama H, Yokoshiki H, Watanabe M, Mizukami K, Shimokawa J, Tsutsui H. Ca2+/calmodulin-dependent protein kinase II increases the susceptibility to the arrhythmogenic action potential alternans in spontaneously hypertensive rats. Am J Physiol Heart Circ Physiol. 2014 Jul 15;307(2):H199-206. doi: 10.1152/ajpheart.00387.2012. PubMed PMID: 24858851.

20: Lim NR, Thomas CJ, Silva LS, Yeap YY, Yap S, Bell JR, Delbridge LM, Bogoyevitch MA, Woodman OL, Williams SJ, May CN, Ng DC. Cardioprotective 3',4'-dihydroxyflavonol attenuation of JNK and p38(MAPK) signalling involves CaMKII inhibition. Biochem J. 2013 Dec 1;456(2):149-61. doi: 10.1042/BJ20121538. PubMed PMID: 24032640.