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ChemicalBook >> CAS DataBase List >>Nicorandil

Nicorandil

CAS No.
65141-46-0
Chemical Name:
Nicorandil
Synonyms
2-[(Pyridin-3-ylcarbonyl)amino]ethyl nitrate, N-[2-(Nitroxy)ethyl]pyridine-3-carboxamide;SG-75;Dancor;IKOREL;Zynicor;SIGMART;ADANCOR;Nicordil;PERISALOL;Nicorandi
CBNumber:
CB1291140
Molecular Formula:
C8H9N3O4
Molecular Weight:
211.17
MDL Number:
MFCD00186520
MOL File:
65141-46-0.mol
MSDS File:
SDS
Last updated:2024-10-30 18:52:02

Nicorandil Properties

Melting point 92°C
Boiling point 350.85°C (rough estimate)
Density 1.4271 (rough estimate)
refractive index 1.7400 (estimate)
RTECS US4667600
storage temp. 2-8°C
solubility DMSO: >10mg/mL
pka 12.70±0.46(Predicted)
form powder
color white to off-white
Merck 14,6521
CAS DataBase Reference 65141-46-0
FDA UNII 260456HAM0
NCI Drug Dictionary nicorandil
ATC code C01DX16

Pharmacokinetic data

Protein binding Slightly
Excreted unchanged in urine 1%
Biological half-life 1 / Unchanged

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS02,GHS07
Signal word  Danger
Hazard statements  H242-H302
Precautionary statements  P210-P235-P280-P301+P312-P370+P378-P410
Hazard Codes  Xn
Risk Statements  22-41
Safety Statements  26-39
WGK Germany  3
HS Code  29333990
Toxicity LD50 in rats (mg/kg): 1200-1300 orally; 800-1000 i.v. (Nagano)
NFPA 704
0
3 0

Nicorandil price More Price(46)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich N3539 Nicorandil ≥98% (HPLC) 65141-46-0 50mg $86 2024-03-01 Buy
Sigma-Aldrich N3539 Nicorandil ≥98% (HPLC) 65141-46-0 250mg $347 2024-03-01 Buy
TCI Chemical N0837 Nicorandil >98.0%(HPLC)(T) 65141-46-0 100mg $66 2024-03-01 Buy
TCI Chemical N0837 Nicorandil >98.0%(HPLC)(T) 65141-46-0 1g $124 2024-03-01 Buy
Alfa Aesar J60879 Nicorandil, 98+% 65141-46-0 250mg $81.65 2024-03-01 Buy
Product number Packaging Price Buy
N3539 50mg $86 Buy
N3539 250mg $347 Buy
N0837 100mg $66 Buy
N0837 1g $124 Buy
J60879 250mg $81.65 Buy

Nicorandil Chemical Properties,Uses,Production

Chemical Properties

Nicorandil is N-(2-hydroxyethyl)-nicotinamide nitrate (ester). It is a white crystalline powder or white needles with a faint, characteristic odour. It is freely soluble in methanol, ethanol, acetone or glacial acetic acid, slightly soluble in chloroform or water, almost insoluble in ether or benzene. Melting point 88.5-93.5 ℃. Acute toxicity LD50 rat (mg/kg): 1200-1300 orally, 800-1000 intravenously.

Originator

Chugai (Japan)

Uses

Nicorandil is a vasodilator used for the prophylaxis and treatment of angina. This medication widens blood vessels thus increasing the blood and oxygen flow to the heart. It is not currently available in the US.
Nicorandil is a nitric oxide donor and ATP-sensitive potassium channel opener. A study showed that Nicorandil is able to protect against stress-induced cell death in dystrophin-deficient cardiomyocytes and also preserve cardiac function in the mdx mouse heart subjected to ischemia and reperfusion injury.

Preparation

Nicorandil is obtained by treating nicotinic acid chloride hydrochloride with nitro-oxy-ethyl-amine nitrate in an organic solvent.
synthesis of Nicorandil
Nicorandil was synthesized from 2-aminoethanol by a four step process. In order to protect the amino group during nitration, 2-aminoethanol was first treated with phthalic anhydride. The amide formed was then nitrated using a nitrating mixture and was subsequently deprotected by reacting with hydrazine hydrate. The 2- nitroxyethylamine obtained was condensed with nicotinoyl chloride in pyridine. Treatment with aqueous sodium bicarbonate solution gave nicorandil as free base.
synthesis of Nicorandil

Definition

ChEBI: Nicorandil is a pyrimidinecarboxamide that is nicotinamide in which one of the hydrogens attached to the carboxamide nitrogen is replaced by a 2-(nitrooxy)ethyl group. It has both nitrate-like and ATP-sensitive potassium channel activator properties, and is used for the prevention and treatment of angina pectoris. It has a role as a vasodilator agent and a potassium channel opener. It is a pyridinecarboxamide and a nitrate ester. It derives from a nicotinamide.

brand name

SIGMART; PERISALOL

Biochem/physiol Actions

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.

Clinical Use

Nicorandil is used for the prevention and treatment of chronic stable angina. It is usually used when angina becomes difficult to control by other drugs and is given as an additional treatment.

Drug interactions

Potentially hazardous interactions with other drugs
Avanafil, sildenafil, tadalafil and vardenafil: enhanced hypotensive effect - avoid.
Riociguat: possible enhanced hypotensive effect - avoid.

Metabolism

Metabolism of nicorandil is mainly by denitration of the molecule into the nicotinamide pathway. About 20% of a dose is excreted in the urine mainly as metabolites

Mode of action

The coronary vasodilating activity of nicorandil is considered to be the consequence of the increasing cyclic GMP production by stimulating guanylyl cyclase in the coronary vascular smooth muscle, similar to other nitrates/nitrites (in vitro). In addition, other mechanisms such as hyperpolarization of the cell membrane were investigated concerning its coronary blood flowincreasing and coronary vasospasmolytic effects.
The vasorelaxant effect of nicorandil in isolated blood vessels is suppressed by an ATP-sensitive K channel blocker or a guanylate cyclase inhibitor. Moreover, in a canine model of acute heart failure, the cardiac haemodynamics-improving effect of the drug (e.g. effect of increasing the aortic blood flow) was suppressed by an ATP-sensitive K channel blocker. Furthermore, the drug caused an increase in the cGMP content in isolated blood vessels. These facts suggest that the vasodilating effect of the drug is related to the effect of opening the ATP-sensitive K channel, as well as to the effect of increasing production of cGMP.

6265-73-2
65141-46-0
Synthesis of Nicorandil from N-(2-HYDROXYETHYL)NITOTINAMIDE

Nicorandil Preparation Products And Raw materials

Global( 441)Suppliers
Supplier Tel Email Country ProdList Advantage
Hebei Weibang Biotechnology Co., Ltd
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View Lastest Price from Nicorandil manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Nicorandil pictures 2024-10-30 Nicorandil
65141-46-0
US $51.00-36.00 / mg 99.44% 10g TargetMol Chemicals Inc.
Nicorandil pictures 2024-10-30 Nicorandil
65141-46-0
US $51.00-36.00 / mg 99.44% 10g TargetMol Chemicals Inc.
Nicorandil pictures 2024-10-30 Nicorandil
65141-46-0
US $0.00 / G 100G 98%min 30KG/month WUHAN FORTUNA CHEMICAL CO., LTD
  • Nicorandil pictures
  • Nicorandil
    65141-46-0
  • US $51.00-36.00 / mg
  • 99.44%
  • TargetMol Chemicals Inc.
  • Nicorandil pictures
  • Nicorandil
    65141-46-0
  • US $51.00-36.00 / mg
  • 99.44%
  • TargetMol Chemicals Inc.
  • Nicorandil pictures
  • Nicorandil
    65141-46-0
  • US $0.00 / G
  • 98%min
  • WUHAN FORTUNA CHEMICAL CO., LTD

Nicorandil Spectrum

n-[2-(nitroxy)ethyl]-3-pyridinecarboxamide N-[2-(NITROOXY)ETHYL]-3-PYRIDINECARBOXAMIDE 3-Pyridinecarboxamide, N-[2-(nitrooxy)ethyl]- SG-75 Dancor Nitric acid 2-nicotinoylaminoethyl ester 2-(pyridin-3-ylcarbonylamino)ethyl nitrate 2-(pyridine-3-carbonylamino)ethyl nitrate nitric acid 2-(pyridine-3-carbonylamino)ethyl ester N-(2-Hydroxyethyl)nieotimmide nitrate(ester) 2-(pyridin-3-ylforMaMido)ethyl nitrate Nicorandil(Ikorel) N-(2-Nitrooxyethyl)nicotinaMide 2-(Pyridine-3-carboxamido)ethyl Nitrate N-[2-(Nitrooxy)ethyl]pyridine-3-carboxamide Zynicor NICORANDIL PERISALOL SIGMART N-[2-Hydroxyethyl] nicotinamide nitrate Adancor, Ikorel, Perisalol, Sigmart IKOREL ADANCOR 2-nicotinamidoethylnitrate n-(2-(nitrooxy)ethyl)-3-pyridinecarboxamid n-(2-hydroxyethyl)nicotinamidenitrate(ester) Nicorandil, 98%, a potassium channel activator 2-[(3-pyridinylcarbonyl)amino]ethyl nitrate Nicorandil> Nicorandil CRS 2-(Pyridine-3-carboxamido)ethyl Nitrate N-[2-(Nitrooxy)ethyl]pyridine-3-carboxamide Nicorandil USP/EP/BP Nicorandil (SG-75) Nicorandil, ≥98% (HPLC) NicorandilQ: What is Nicorandil Q: What is the CAS Number of Nicorandil Q: What is the storage condition of Nicorandil Q: What are the applications of Nicorandil 2-[(Pyridin-3-ylcarbonyl)amino]ethyl nitrate, N-[2-(Nitroxy)ethyl]pyridine-3-carboxamide Nicorandil Impurity 45 Nicordil Nicorandil IP/BP Nicorandi Nicorandil, ≥ 98.0% Nicorandil CAS 65141-46-0 Pharmaceutical Ikorel reagent Cardiovascular APIs Potassium channel Intermediates & Fine Chemicals Pharmaceuticals Aromatics Heterocycles 65141-46-0