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N3539

Sigma-Aldrich

Nicorandil

≥98% (HPLC)

Synonym(s):

2-(Pyridine-3-carbonylamino)ethyl nitrate, 2-Nicotinamidoethyl nitrate, Ikorel, N-[2-(Nitrooxy)ethyl]-3-pyridinecarboxamide, SG-75, Sigmart, Zynicor

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About This Item

Empirical Formula (Hill Notation):
C8H9N3O4
CAS Number:
65141-46-0
Molecular Weight:
211.17
EC Number:
265-514-1
MDL number:
MFCD00186520
UNSPSC Code:
12352200
PubChem Substance ID:
329818637
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to off-white

solubility

DMSO: >10 mg/mL

storage temp.

room temp

SMILES string

[O-][N+](=O)OCCNC(=O)c1cccnc1

InChI

1S/C8H9N3O4/c12-8(7-2-1-3-9-6-7)10-4-5-15-11(13)14/h1-3,6H,4-5H2,(H,10,12)

InChI key

LBHIOVVIQHSOQN-UHFFFAOYSA-N

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Application

Nicorandil has been used as an activator of potassium (K+) channel and inhibitor of voltage-gated calcium channel to study its effects on action potentials in long QT syndrome 2 (LQTS2) human induced pluripotent stem cell (hiPSCs)-derived cardiomyocytes.

Biochem/physiol Actions

Nicorandil exhibits cardio-protective effects.
Nicorandil is a hybrid ATP-sensitive K+ (KATP) channel opener and nicotinamide nitrate NO donor. Nicorandil selectively activates SUR2B- versus SUR2A-containing KATP channels. It enhances endothelial NO synthase expression and protects against ischemic ventricular arrhythmias. By activating potassium channels, and donating nitric oxide to activate the enzyme guanylate cyclase, Nicorandil causes activation of GMP leading to both arterial and venous vasodilatation. Nicorandil is selective for vascular potassium channels, but has no significant action on cardiac contractility and conduction.

Features and Benefits

This compound is featured on the Potassium Channels page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H242,H302

Hazard Classifications

Acute Tox. 4 Oral - Org. Perox. D

Storage Class Code

5.2 - Organic peroxides and self-reacting hazardous materials

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A Markham et al.
Drugs, 60(4), 955-974 (2000-11-21)
Nicorandil is a drug with both nitrate-like and ATP-sensitive potassium-channel (K+ ATP) activating properties. By virtue of this dual mechanism of action, the drug acts as a balanced coronary and peripheral vasodilator and reduces both preload and afterload. The K+
Lamiaa A Ahmed et al.
Biochemical pharmacology, 86(9), 1301-1310 (2013-07-23)
Despite of its known cardiotoxicity, doxorubicin is still a highly effective anti-neoplastic agent in the treatment of several cancers. In the present study, the cardioprotective effect of nicorandil was investigated on hemodynamic alterations and mitochondrial dysfunction induced by cumulative administration
L Toquero et al.
Colorectal disease : the official journal of the Association of Coloproctology of Great Britain and Ireland, 8(8), 717-720 (2006-09-15)
Use of Nicorandil in the treatment of ischaemic heart disease has been associated with oral, ileal and more recently anal ulceration. We report a series of six cases of peri-anal ulceration in patients on nicorandil therapy, their response to withdrawal
Clinical trials update: The Heart Protection Study, IONA, CARISA, ENRICHD, ACUTE, ALIVE, MADIT II and REMATCH. Impact Of Nicorandil on Angina. Combination Assessment of Ranolazine In Stable Angina. ENhancing Recovery In Coronary Heart Disease patients. Assessment of Cardioversion Using Transoesophageal Echocardiography. AzimiLide post-Infarct surVival Evaluation. Randomised Evaluation of Mechanical Assistance for Treatment of Chronic Heart failure.
Amala A Louis et al.
European journal of heart failure, 4(1), 111-116 (2002-01-29)
V M Smith et al.
The British journal of dermatology, 167(5), 1048-1052 (2012-10-09)
Nicorandil has been available in the U.K. since 1994 for the prophylaxis and treatment of angina. Since the first reported case of nicorandil-associated oral ulceration in 1997 complications elsewhere in the gastrointestinal tract have been reported. Our case series highlights
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