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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+
Shigeo Horinaka
Drugs, 71(9), 1105-1119 (2011-06-30)
Nicorandil, a unique dual pharmacological mechanism anti-anginal agent with adenosine triphosphate sensitive potassium (K(ATP)) channel agonist and nitrate-like properties, provides cardiologists with a means of managing angina pectoris patients effectively and provides long-term cardioprotection. The aim of this review is
Makoto Sahara et al.
PloS one, 7(3), e33367-e33367 (2012-04-06)
An antianginal K(ATP) channel opener nicorandil has various beneficial effects on cardiovascular systems; however, its effects on pulmonary vasculature under pulmonary arterial hypertension (PAH) have not yet been elucidated. Therefore, we attempted to determine whether nicorandil can attenuate monocrotaline (MCT)-induced
Neil J Cahoon et al.
Plastic and reconstructive surgery, 131(3), 473-485 (2013-03-01)
In autogenous muscle transplantation, unpredictable complications can cause prolonged ischemia, resulting in ischemia-reperfusion injury. The authors investigated the efficacy and mechanism of nicorandil, a nitrovasodilator and adenosine triphosphate-sensitive potassium channel opener, in inducing perioperative protection of muscle flaps from ischemia-reperfusion
Nicorandil: a drug for many purposes: too good to be true?
Eric Eeckhout
European heart journal, 24(14), 1282-1284 (2003-07-23)
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