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N3539

Sigma-Aldrich

Nicorandil

≥98% (HPLC)

Synonym(e):

N-[2-(Nitrooxy)-ethyl]-3-pyridincarbamid

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About This Item

Empirische Formel (Hill-System):
C8H9N3O4
CAS-Nummer:
65141-46-0
Molekulargewicht:
211.17
EG-Nummer:
265-514-1
MDL-Nummer:
MFCD00186520
UNSPSC-Code:
12352200
PubChem Substanz-ID:
329818637
NACRES:
NA.77

Qualitätsniveau

100

Assay

≥98% (HPLC)

Form

powder

Farbe

white to off-white

Löslichkeit

DMSO: >10 mg/mL

Lagertemp.

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)

InChIKey

LBHIOVVIQHSOQN-UHFFFAOYSA-N

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Anwendung

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. Wirkung

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.

Leistungsmerkmale und Vorteile

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.

Piktogramme

FlameExclamation mark
GHS02,GHS07

Signalwort

Danger

H-Sätze

H242,H302

Gefahreneinstufungen

Acute Tox. 4 Oral - Org. Perox. D

Lagerklassenschlüssel

5.2 - Organic peroxides and self-reacting hazardous materials

WGK

WGK 1

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves

Analysenzertifikate (COA)

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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
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
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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