NS-11021
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MedKoo CAT#: 555184

CAS#: 956014-19-0

Description: NS-11021 is an activator of large-conductance Ca2+-activated potassium channels (BKCa, KCa1.1). BK channel activation by NS11021 decreases excitability and contractility of urinary bladder smooth muscle. NS11021 enhances erectile responses in rats.

Chemical Structure

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NS-11021
CAS# 956014-19-0
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 555184
Name: NS-11021
CAS#: 956014-19-0
Chemical Formula: C16H9BrF6N6S
Exact Mass: 509.97
Molecular Weight: 511.244
Elemental Analysis: C, 37.59; H, 1.77; Br, 15.63; F, 22.30; N, 16.44; S, 6.27

Price and Availability

Size Price Availability Quantity
50mg USD 450
100mg USD 750
200mg USD 1250
500mg USD 2150
1g USD 2950
2g USD 3950
5g USD 6250
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Synonym: NS-11021; NS 11021; NS11021.

IUPAC/Chemical Name: N'-[3,5-bis(trifluoromethyl)phenyl]-N-[4-bromo-2-(2H-tetrazol-5-yl)phenyl]-thiourea

InChi Key: MDKAFDIKYQMOMF-UHFFFAOYSA-N

InChi Code: InChI=1S/C16H9BrF6N6S/c17-9-1-2-12(11(6-9)13-26-28-29-27-13)25-14(30)24-10-4-7(15(18,19)20)3-8(5-10)16(21,22)23/h1-6H,(H2,24,25,30)(H,26,27,28,29)

SMILES Code: S=C(NC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1)NC2=CC=C(Br)C=C2C3=NNN=N3

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:
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Biological target: NS 11021 is a potent and specific Ca2+-activated big-conductance K+ Channels (KCa1.1 channels) activator.
In vitro activity: In the present study, the effect of a novel NeuroSearch compound, 1-(3,5-bis-trifluoromethyl-phenyl)-3-[4-bromo-2-(1H-tetrazol-5-yl)-phenyl]-thiourea (NS11021), was investigated on cloned KCa1.1 expressed in Xenopus laevis oocytes and mammalian cells using electrophysiological methods. NS11021 at concentrations above 0.3 microM activated KCa1.1 in a concentration-dependent manner by parallel-shifting the channel activation curves to more negative potentials. Single-channel analysis revealed that NS11021 increased the open probability of the channel by altering gating kinetics without affecting the single-channel conductance. Reference: Mol Pharmacol. 2007 Oct;72(4):1033-44. https://pubmed.ncbi.nlm.nih.gov/17636045/
In vivo activity: Erectile responses in anaesthetized rats were significantly increased after injection of both 0.1 and 1 mg·kg−1 NS11021 (Figure 9C, n= 5). NS11021 (0.1 mg·kg−1) did not change MAP, but a higher dose (1 mg·kg−1) induced a transient drop in MAP (maximum fall of 9.0 ± 2.5 mmHg, n= 5), which recovered to pre-injection values after 41.8 ± 15.2 s (data not shown). Reference: Br J Pharmacol. 2009 Nov;158(6):1465-76. https://pubmed.ncbi.nlm.nih.gov/19845682/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 15.0 29.34
DMF:PBS (pH 7.2) (1:3) 0.3 0.49
DMSO 53.7 105.05
Ethanol 25.7 50.29

Preparing Stock Solutions

The following data is based on the product molecular weight 511.24 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. Shrum S, Rusch NJ, MacMillan-Crow LA. Specific BK Channel Activator NS11021 Protects Rat Renal Proximal Tubular Cells from Cold Storage-Induced Mitochondrial Injury In Vitro. Biomolecules. 2019 Dec 4;9(12):825. doi: 10.3390/biom9120825. PMID: 31817165; PMCID: PMC6995623. 2. Bentzen BH, Nardi A, Calloe K, Madsen LS, Olesen SP, Grunnet M. The small molecule NS11021 is a potent and specific activator of Ca2+-activated big-conductance K+ channels. Mol Pharmacol. 2007 Oct;72(4):1033-44. doi: 10.1124/mol.107.038331. Epub 2007 Jul 16. PMID: 17636045. 3. Kun A, Matchkov VV, Stankevicius E, Nardi A, Hughes AD, Kirkeby HJ, Demnitz J, Simonsen U. NS11021, a novel opener of large-conductance Ca(2+)-activated K(+) channels, enhances erectile responses in rats. Br J Pharmacol. 2009 Nov;158(6):1465-76. doi: 10.1111/j.1476-5381.2009.00404.x. Epub 2009 Oct 20. PMID: 19845682; PMCID: PMC2795213.
In vitro protocol: 1. Shrum S, Rusch NJ, MacMillan-Crow LA. Specific BK Channel Activator NS11021 Protects Rat Renal Proximal Tubular Cells from Cold Storage-Induced Mitochondrial Injury In Vitro. Biomolecules. 2019 Dec 4;9(12):825. doi: 10.3390/biom9120825. PMID: 31817165; PMCID: PMC6995623. 2. Bentzen BH, Nardi A, Calloe K, Madsen LS, Olesen SP, Grunnet M. The small molecule NS11021 is a potent and specific activator of Ca2+-activated big-conductance K+ channels. Mol Pharmacol. 2007 Oct;72(4):1033-44. doi: 10.1124/mol.107.038331. Epub 2007 Jul 16. PMID: 17636045.
In vivo protocol: 1. Kun A, Matchkov VV, Stankevicius E, Nardi A, Hughes AD, Kirkeby HJ, Demnitz J, Simonsen U. NS11021, a novel opener of large-conductance Ca(2+)-activated K(+) channels, enhances erectile responses in rats. Br J Pharmacol. 2009 Nov;158(6):1465-76. doi: 10.1111/j.1476-5381.2009.00404.x. Epub 2009 Oct 20. PMID: 19845682; PMCID: PMC2795213.

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1: Frankenreiter S, Groneberg D, Kuret A, Krieg T, Ruth P, Friebe A, Lukowski R. Cardioprotection by ischemic postconditioning and cGMP-elevating agents involves cardiomyocyte nitric oxide-sensitive guanylyl cyclase. Cardiovasc Res. 2018 Feb 9. doi: 10.1093/cvr/cvy039. [Epub ahead of print] PubMed PMID: 29438488.

2: Zaidman NA, Panoskaltsis-Mortari A, O'Grady SM. Large-conductance Ca(2+) -activated K(+) channel activation by apical P2Y receptor agonists requires hydrocortisone in differentiated airway epithelium. J Physiol. 2017 Jul 15;595(14):4631-4645. doi: 10.1113/JP274200. Epub 2017 Jun 11. PubMed PMID: 28481415; PubMed Central PMCID: PMC5509885.

3: Su F, Guo AC, Li WW, Zhao YL, Qu ZY, Wang YJ, Wang Q, Zhu YL. Low-Dose Ethanol Preconditioning Protects Against Oxygen-Glucose Deprivation/Reoxygenation-Induced Neuronal Injury By Activating Large Conductance, Ca(2+)-Activated K(+) Channels In Vitro. Neurosci Bull. 2017 Feb;33(1):28-40. doi: 10.1007/s12264-016-0080-3. Epub 2016 Nov 16. PubMed PMID: 27854008; PubMed Central PMCID: PMC5567547.

4: Zhong XZ, Sun X, Cao Q, Dong G, Schiffmann R, Dong XP. BK channel agonist represents a potential therapeutic approach for lysosomal storage diseases. Sci Rep. 2016 Sep 27;6:33684. doi: 10.1038/srep33684. PubMed PMID: 27670435; PubMed Central PMCID: PMC5037385.

5: Wakle-Prabagaran M, Lorca RA, Ma X, Stamnes SJ, Amazu C, Hsiao JJ, Karch CM, Hyrc KL, Wright ME, England SK. BKCa channel regulates calcium oscillations induced by alpha-2-macroglobulin in human myometrial smooth muscle cells. Proc Natl Acad Sci U S A. 2016 Apr 19;113(16):E2335-44. doi: 10.1073/pnas.1516863113. Epub 2016 Apr 4. PubMed PMID: 27044074; PubMed Central PMCID: PMC4843459.

6: Yan XH, Guo XY, Jiao FY, Liu X, Liu Y. Activation of large-conductance Ca(2+)-activated K(+) channels inhibits glutamate-induced oxidative stress through attenuating ER stress and mitochondrial dysfunction. Neurochem Int. 2015 Nov;90:28-35. doi: 10.1016/j.neuint.2015.07.004. Epub 2015 Jul 7. PubMed PMID: 26163046.

7: Fernandes VS, Xin W, Petkov GV. Novel mechanism of hydrogen sulfide-induced guinea pig urinary bladder smooth muscle contraction: role of BK channels and cholinergic neurotransmission. Am J Physiol Cell Physiol. 2015 Jul 15;309(2):C107-16. doi: 10.1152/ajpcell.00021.2015. Epub 2015 May 6. PubMed PMID: 25948731; PubMed Central PMCID: PMC4504942.

8: Laskowski M, Kicinska A, Szewczyk A, Jarmuszkiewicz W. Mitochondrial large-conductance potassium channel from Dictyostelium discoideum. Int J Biochem Cell Biol. 2015 Mar;60:167-75. doi: 10.1016/j.biocel.2015.01.006. Epub 2015 Jan 14. PubMed PMID: 25596489.

9: Shi L, Zhang H, Chen Y, Liu Y, Lu N, Zhao T, Zhang L. Chronic exercise normalizes changes in Cav 1.2 and KCa 1.1 channels in mesenteric arteries from spontaneously hypertensive rats. Br J Pharmacol. 2015 Apr;172(7):1846-58. doi: 10.1111/bph.13035. Epub 2015 Jan 23. PubMed PMID: 25440572; PubMed Central PMCID: PMC4376461.

10: Soltysinska E, Bentzen BH, Barthmes M, Hattel H, Thrush AB, Harper ME, Qvortrup K, Larsen FJ, Schiffer TA, Losa-Reyna J, Straubinger J, Kniess A, Thomsen MB, Brüggemann A, Fenske S, Biel M, Ruth P, Wahl-Schott C, Boushel RC, Olesen SP, Lukowski R. KCNMA1 encoded cardiac BK channels afford protection against ischemia-reperfusion injury. PLoS One. 2014 Jul 29;9(7):e103402. doi: 10.1371/journal.pone.0103402. eCollection 2014. PubMed PMID: 25072914; PubMed Central PMCID: PMC4114839.

11: Liu H, Xin T, He W, Li F, Su ZQ. Myelinated Ah-type trigeminal ganglion neurons in female rats: neuroexcitability, chemosensitivity to histamine, and potential clinical impact. Neurosci Lett. 2014 May 1;567:74-9. doi: 10.1016/j.neulet.2014.03.039. Epub 2014 Mar 28. PubMed PMID: 24686179.

12: Wojtovich AP, Nadtochiy SM, Urciuoli WR, Smith CO, Grunnet M, Nehrke K, Brookes PS. A non-cardiomyocyte autonomous mechanism of cardioprotection involving the SLO1 BK channel. PeerJ. 2013 Mar 5;1:e48. doi: 10.7717/peerj.48. Print 2013. PubMed PMID: 23638385; PubMed Central PMCID: PMC3628382.

13: Borchert GH, Hlaváčková M, Kolář F. Pharmacological activation of mitochondrial BK(Ca) channels protects isolated cardiomyocytes against simulated reperfusion-induced injury. Exp Biol Med (Maywood). 2013 Feb;238(2):233-41. doi: 10.1177/1535370212474596. PubMed PMID: 23576804.

14: Bednarczyk P, Koziel A, Jarmuszkiewicz W, Szewczyk A. Large-conductance Ca²⁺-activated potassium channel in mitochondria of endothelial EA.hy926 cells. Am J Physiol Heart Circ Physiol. 2013 Jun 1;304(11):H1415-27. doi: 10.1152/ajpheart.00976.2012. Epub 2013 Mar 29. PubMed PMID: 23542921.

15: Király I, Pataricza J, Bajory Z, Simonsen U, Varro A, Papp JG, Pajor L, Kun A. Involvement of large-conductance Ca(2+) -activated K(+) channels in both nitric oxide and endothelium-derived hyperpolarization-type relaxation in human penile small arteries. Basic Clin Pharmacol Toxicol. 2013 Jul;113(1):19-24. doi: 10.1111/bcpt.12059. Epub 2013 Mar 21. PubMed PMID: 23414060.

16: Roy S, Morayo Akande A, Large RJ, Webb TI, Camarasu C, Sergeant GP, McHale NG, Thornbury KD, Hollywood MA. Structure-activity relationships of a novel group of large-conductance Ca(2+)-activated K(+) (BK) channel modulators: the GoSlo-SR family. ChemMedChem. 2012 Oct;7(10):1763-9. doi: 10.1002/cmdc.201200321. Epub 2012 Aug 28. PubMed PMID: 22930560.

17: Venglovecz V, Hegyi P, Rakonczay Z Jr, Tiszlavicz L, Nardi A, Grunnet M, Gray MA. Pathophysiological relevance of apical large-conductance Ca²+-activated potassium channels in pancreatic duct epithelial cells. Gut. 2011 Mar;60(3):361-9. doi: 10.1136/gut.2010.214213. Epub 2010 Oct 12. PubMed PMID: 20940280.

18: Wulf-Johansson H, Amrutkar DV, Hay-Schmidt A, Poulsen AN, Klaerke DA, Olesen J, Jansen-Olesen I. Localization of large conductance calcium-activated potassium channels and their effect on calcitonin gene-related peptide release in the rat trigemino-neuronal pathway. Neuroscience. 2010 Jun 2;167(4):1091-102. doi: 10.1016/j.neuroscience.2010.02.063. Epub 2010 Mar 6. PubMed PMID: 20211697.

19: Layne JJ, Nausch B, Olesen SP, Nelson MT. BK channel activation by NS11021 decreases excitability and contractility of urinary bladder smooth muscle. Am J Physiol Regul Integr Comp Physiol. 2010 Feb;298(2):R378-84. doi: 10.1152/ajpregu.00458.2009. Epub 2009 Nov 18. PubMed PMID: 19923353; PubMed Central PMCID: PMC2828174.

20: Kun A, Matchkov VV, Stankevicius E, Nardi A, Hughes AD, Kirkeby HJ, Demnitz J, Simonsen U. NS11021, a novel opener of large-conductance Ca(2+)-activated K(+) channels, enhances erectile responses in rats. Br J Pharmacol. 2009 Nov;158(6):1465-76. doi: 10.1111/j.1476-5381.2009.00404.x. Epub 2009 Oct 20. PubMed PMID: 19845682; PubMed Central PMCID: PMC2795213.