ChemicalBook > CAS DataBase List > Nicorandil

Nicorandil

Product Name
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;Nicodil;Nicordil;PERISALOL
CBNumber
CB1291140
Molecular Formula
C8H9N3O4
Formula Weight
211.17
MOL File
65141-46-0.mol
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Nicorandil Property

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
form 
powder
pka
12.70±0.46(Predicted)
color 
white to off-white
Merck 
14,6521
CAS DataBase Reference
65141-46-0
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Safety

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)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H242Heating may cause a fire

H302Harmful if swallowed

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P235Keep cool.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P370+P378In case of fire: Use … for extinction.

P410Protect from sunlight.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
N3539
Product name
Nicorandil
Purity
≥98% (HPLC)
Packaging
50mg
Price
$86
Updated
2024/03/01
Sigma-Aldrich
Product number
N3539
Product name
Nicorandil
Purity
≥98% (HPLC)
Packaging
250mg
Price
$347
Updated
2024/03/01
TCI Chemical
Product number
N0837
Product name
Nicorandil
Purity
>98.0%(HPLC)(T)
Packaging
100mg
Price
$66
Updated
2024/03/01
TCI Chemical
Product number
N0837
Product name
Nicorandil
Purity
>98.0%(HPLC)(T)
Packaging
1g
Price
$124
Updated
2024/03/01
Alfa Aesar
Product number
J60879
Product name
Nicorandil, 98+%
Packaging
250mg
Price
$81.65
Updated
2024/03/01
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Nicorandil Chemical Properties,Usage,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.

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.

Preparation

Nicorandil is obtained by treating nicotinic acid chloride hydrochloride with nitro-oxy-ethyl-amine nitrate in an organic solvent.

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

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.

Nicorandil Preparation Products And Raw materials

Raw materials

2-N-BUTOXYETHYL METHACRYLATE Methyl nicotinate Monoethanolamine Nicotinoyl chloride hydrochloride Nitric acid

Preparation Products

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View Lastest Price from Nicorandil manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Nicorandil 65141-46-0
Price
US $0.00/G
Min. Order
100G
Purity
98%min
Supply Ability
30KG/month
Release date
2023-01-31
Hebei Yanxi Chemical Co., Ltd.
Product
nicorandil 65141-46-0
Price
US $0.00/kg
Min. Order
1kg
Purity
0.99
Supply Ability
20tons
Release date
2023-10-10
Hebei Weibang Biotechnology Co., Ltd
Product
Nicorandil 65141-46-0
Price
US $1.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10 mt
Release date
2024-10-24

65141-46-0, NicorandilRelated Search:

Nicotinamide Ethanol Ethylparaben Ethyl acrylate Ethyl vanillin Ethyl 4-hydroxy-3-methoxycinnamate Ethyl acetate Ethyl nitrate 1-(2,6-Dimethylphenoxy)-2-propanamine Ethyl nitrite Aminoethyl nitrate N-(2-HYDROXYETHYL)NITOTINAMIDE 2-HYDROXYETHYL N-PENTYL SULPHIDE, 95 NICORANDIL-D4,NICORANDIL-D4 (PYRIDYL-D4) 3-Pyridinecarboxaldehyde-D4 NICOTINAMIDE-2,4,5,6-D4 Nicorandil Nicorandil fumaric acid salt

  • n-[2-(nitroxy)ethyl]-3-pyridinecarboxamide
  • N-[2-(NITROOXY)ETHYL]-3-PYRIDINECARBOXAMIDE
  • 2-[(Pyridin-3-ylcarbonyl)amino]ethyl nitrate, N-[2-(Nitroxy)ethyl]pyridine-3-carboxamide
  • 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)
  • Nicorandil, 98%, a potassium channel activator
  • 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)
  • 2-[(3-pyridinylcarbonyl)amino]ethyl nitrate
  • Nicorandil&gt
  • 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
  • Nicorandil Impurity 45
  • Nicordil
  • Nicorandil IP/BP
  • Nicorandi
  • Nicorandil, ≥ 98.0%
  • Nicorandil CAS
  • Nicodil
  • 65141-46-0
  • Pharmaceutical
  • Ikorel
  • reagent
  • Cardiovascular APIs
  • Potassium channel
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Aromatics
  • Heterocycles
  • 65141-46-0