NicorandilA small molecule KATP (Kir6) channel opener and NO donor

Nicorandil (CAS 65141-46-0)

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Application: A small molecule KATP (Kir6) channel opener and NO donor
CAS Number: 65141-46-0
Purity: ≥98%
Molecular Weight: 211.17
Molecular Formula: C8H9N3O4
* Refer to Certificate of Analysis for lot specific data (including water content).
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Nicorandil is a small molecule KATP (Kir6) channel opener, producing relaxation of coronary vascular smooth muscle. Specific binding of Nicorandil to the C-terminus of the SUR2B K(ATP) channel generates K+ flux and hyperpolarization of the surface membrane, producing consequent closure of voltage-dependent ion channels and reduction of intracellular free Ca2+. Nicorandil stimulates guanylate cyclase and increases cyclic GMP levels in correlation with the activation of K(ATP) channels. Nicorandil is also described to suppress mitochondrial permeability transition triggered by oxidative stress resulting from ischemia-reperfusion, preventing mitochondrial calcium uptake/overload and oxidative damage. Nicorandil has also been shown to serve as a nitric oxide donor.


References

1. Kukovetz, W R., et al., 1992. Molecular mechanism of action of nicorandil. Journal of cardiovascular pharmacology. 20 Suppl 3(): S1-7. PMID: 1282168
2. Yoneyama, F., et al., 1990. Nicorandil increases coronary blood flow predominantly by K-channel opening mechanism. Cardiovascular drugs and therapy / sponsored by the International Society of Cardiovascular Pharmacotherapy. 4(4): 1119-26. PMID: 2150593
3. Miyazaki, Y., et al., 1985. Vasodilative effect of nicorandil on coronary artery. Arzneimittel-Forschung. 35(2): 504-7. PMID: 3158319
4. Haeusler, G., et al., 1994. Therapeutic potential of potassium channel activators in coronary heart disease. European heart journal. 15 Suppl C(): 82-8. PMID: 7995277
5. Shindo, T., et al., 1998. SUR2 subtype (A and B)-dependent differential activation of the cloned ATP-sensitive K+ channels by pinacidil and nicorandil. British journal of pharmacology. 124(5): 985-91. PMID: 9692785
6. Horinaka, Shigeo., et al., 2004. Nicorandil protects against lethal ischemic ventricular arrhythmias and up-regulates endothelial nitric oxide synthase expression and sulfonylurea receptor 2 mRNA in conscious rats with acute myocardial infarction. Cardiovascular drugs and therapy / sponsored by the International Society of Cardiovascular Pharmacotherapy. 18(1): 13-22. PMID: 15115899
7. Fujiwara, Takayuki., et al., 2007. Nicorandil suppresses the increases in plasma level of matrix metalloproteinase activity and attenuates left ventricular remodeling in patients with acute myocardial infarction. Heart and vessels. 22(5): 303-9. PMID: 17879021
8. Carreira, Raquel S., et al., 2008. Nicorandil protects cardiac mitochondria against permeability transition induced by ischemia-reperfusion. Journal of bioenergetics and biomembranes. 40(2): 95-102. PMID: 18415669

Physical State :
Solid
Solubility :
Soluble in water (4 mg/ml), DMSO (>25 mg/ml), ethanol, ether, and methanol.
Storage :
Store at -20° C
Melting Point :
92-93° C
Boiling Point :
~456.7° C at 760 mmHg (Predicted)
Density :
~1.3 g/cm3 (Predicted)
Refractive Index :
n20D 1.55 (Predicted)
IC50 :
SUR2B-containing KATP channel: EC5050 = 10 µM; SUR2A-containing KATP channel: EC5050 = >500 µM; Oryctolagus cuniculus: IC50 = 1100 nM; Sus scrofa: IC50 = 3200 nM
pK Values :
pKa: 12.70 (Predicted), pKb: 3.49 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
US4667600
PubChem CID :
47528
Merck Index :
14: 6521
MDL Number :
MFCD00186520
EC Number :
265-514-1
SMILES :
C1=CC(=CN=C1)C(=O)NCCO[N+](=O)[O-]

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Nicorandil  Product Citations

See how others have used Nicorandil. Click on the entry to view the PubMed entry .

Citations 1 to 3 of 3 total

PMID: # 25932125  Kong, JJ. et al. 2015. Int J Clin Exp Med. 8: 1966-75.

PMID: # 18415669  Carreira, RS. et al. 2008. J. Bioenerg. Biomembr. 40: 95-102.

PMID: # 9692785  Shindo, T. et al. 1998. Br. J. Pharmacol. 124: 985-991.

Citations 1 to 3 of 3 total
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Rated 5 out of 5 by from worked fine worked fine
Date published: 2015-04-08
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