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Basic information

  • Name:
  • Nicorandil

  • CAS No.:
  • 65141-46-0

  • Molecular Structure:
  • Formula:
  • C8H9N3O4
  • Molecular Weight:
  • 211.18
  • Synonyms:
  • 2-Nicotinamidoethylnitrate;Dancor;Ikorel;N-(2-Hydroxyethyl)nicotinamide nitrate;N-(2-Hydroxyethyl)nicotinamide nitrate ester;N-(2-Nitrooxyethyl)nicotinamide;3-Pyridinecarboxamide,N-[2-(nitrooxy)ethyl]-;Perisalol;SG 75;Sigmart;U 64417;
  • EINECS:
  • 265-514-1
  • Density:
  • 1.331 g/cm3
  • Melting Point:
  • 92 °C
  • Boiling Point:
  • 456.7 °C at 760 mmHg
  • Flash Point:
  • 230 °C
  • Appearance:
  • White solid

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  • Livzon
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Chemistry

Structure of Nicorandil (CAS NO.65141-46-0):

IUPAC Name: 2-(pyridine-3-carbonylamino)ethyl nitrate 
Empirical Formula: C8H9N3O4
Molecular Weight: 211.1748 
EINECS: 265-514-1 
Index of Refraction: 1.547
Molar Refractivity: 50.36 cm3
Molar Volume: 158.6 cm3
Polarizability: 19.96×10-24cm3
Surface Tension: 55.2 dyne/cm
Density: 1.331 g/cm3
Flash Point: 230 °C
Enthalpy of Vaporization: 71.67 kJ/mol 
Melting Point: 92°C
Boiling Point: 456.7 °C at 760 mmHg
Vapour Pressure: 1.58E-08 mmHg at 25°C 
Physical Appearance: White solid 
Product Categories: Pharmaceutical;Intermediates & Fine Chemicals;Pharmaceuticals;Potassium channel 
Synonyms of Nicorandil (CAS NO.65141-46-0): 2-(Nicotinamido)ethyl nitrat ; 2-Nicotinamidoethyl nitrate ; 3-Pyridinecarboxamide, N-(2-(nitroxy)ethyl)- ; N-(2-Hydroxyethyl)nicotinamide nitrate ; Nicorandilum

Uses

 Nicorandil (CAS NO.65141-46-0) is used as an antianginal .

Production

 Nicorandil acts by relaxing the smooth muscle of the blood vessels, especially those of the venous system. It does this through two methods. Firstly, by activating potassium channels, and secondly by donating nitric oxide to activate the enzyme guanylate cyclase. Guanylate cyclase causes activation of GMP leading to both arterial and venous vasodilatation. As it is selective for vascular potassium channels, it has no significant action on cardiac contractility and conduction.
Although it can dilate the coronary vessels of a healthy individual, its effects on the coronary vessels of someone with ischaemic heart disease will be little as they will already be completely dilated. Instead, it dilates the venous system, reducing preload and the work of the heart.

Toxicity Data With Reference

1.    

orl-rat LD50:1220 mg/kg

    YKYUA6    Yakkyoku. Pharmacy. 35 (1984),1627.
2.    

ipr-rat LD50:1100 mg/kg

    YKYUA6    Yakkyoku. Pharmacy. 35 (1984),1627.
3.    

scu-rat LD50:1200 mg/kg

    YKYUA6    Yakkyoku. Pharmacy. 35 (1984),1627.
4.    

orl-mus LD50:1150 mg/kg

    YKYUA6    Yakkyoku. Pharmacy. 35 (1984),1627.
5.    

ipr-mus LD50:990 mg/kg

    YKYUA6    Yakkyoku. Pharmacy. 35 (1984),1627.
6.    

scu-mus LD50:1350 mg/kg

    YKYUA6    Yakkyoku. Pharmacy. 35 (1984),1627.
7.    

orl-dog LD50:62,500 µg/kg

    YKYUA6    Yakkyoku. Pharmacy. 35 (1984),1627.

Safety Profile

Poison by ingestion. Moderately toxic by intraperitoneal and subcutaneous routes. When heated to decomposition it emits toxic fumes of NOx. See also NITRATES.

Specification

 Common side effects include flushing, palpitation, weakness, headache, mouth ulcers, nausea and vomiting. More recently peri-anal, ileal and peri-stomal ulceration has been reported as a side effect. Anal ulceration is now included in the British National Formulary as a reported side effect. It can also give the feeling of severe toothache, and nasal congestion.

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