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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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Xiang-Rong Zuo et al.
PloS one, 7(9), e44485-e44485 (2012-09-13)
Most of the deaths among patients with severe pulmonary arterial hypertension (PAH) are caused by progressive right ventricular (RV) pathological remodeling, dysfunction, and failure. Nicorandil can inhibit the development of PAH by reducing pulmonary artery pressure and RV hypertrophy. However
A H Gomma et al.
Drugs, 61(12), 1705-1710 (2001-11-06)
Potassium channel openers or agonists represent a novel new class of compounds in the treatment of a range of cardiovascular disorders, particularly angina pectoris and hypertension. Nicorandil is the only clinically available potassium channel opener with antianginal effects, and with
Dene Simpson et al.
Drugs, 64(17), 1941-1955 (2004-08-27)
Nicorandil (Adancor, Angicor, Dancor, Nikoril [Europe], Ikorel [Europe and Oceania], Sigmart [Japan, Korea and Taiwan]) is an adenosine triphosphate (ATP)-sensitive potassium (KATP) channel agonist with nitrate-like properties used in the management of stable angina pectoris. With well established monotherapeutic antianginal
C M Healy et al.
Heart (British Cardiac Society), 90(7), e38-e38 (2004-06-18)
Four patients with nicorandil induced ulceration are described, and the literature on the subject is reviewed. Nicorandil induced ulcers are very painful and distressing for patients. Clinically they appear as large, deep, persistent ulcers that have punched out edges. They
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
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