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Chemistry

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Also known as: 65141-46-0, Ikorel, 2-nicotinamidoethyl nitrate, Sigmart, Sg-75, Dancor
Molecular Formula
C8H9N3O4
Molecular Weight
211.17  g/mol
InChI Key
LBHIOVVIQHSOQN-UHFFFAOYSA-N
FDA UNII
260456HAM0

Nicorandil
A derivative of the NIACINAMIDE that is structurally combined with an organic nitrate. It is a potassium-channel opener that causes vasodilatation of arterioles and large coronary arteries. Its nitrate-like properties produce venous vasodilation through stimulation of guanylate cyclase.
1 2D Structure

Nicorandil

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-(pyridine-3-carbonylamino)ethyl nitrate
2.1.2 InChI
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)
2.1.3 InChI Key
LBHIOVVIQHSOQN-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC(=CN=C1)C(=O)NCCO[N+](=O)[O-]
2.2 Other Identifiers
2.2.1 UNII
260456HAM0
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2 Nicotinamidethyl Nitrate

2. 2 Nicotinamidoethyl Nitrate

3. 2-nicotinamidethyl Nitrate

4. 2-nicotinamidoethyl Nitrate

5. Adancor

6. Dancor

7. Ikorel

8. Nitrate, 2-nicotinamidethyl

9. Nitrate, 2-nicotinamidoethyl

10. Sg 75

11. Sg-75

12. Sg75

2.3.2 Depositor-Supplied Synonyms

1. 65141-46-0

2. Ikorel

3. 2-nicotinamidoethyl Nitrate

4. Sigmart

5. Sg-75

6. Dancor

7. Nicorandilum

8. Adancor

9. 2-(pyridine-3-carbonylamino)ethyl Nitrate

10. 2-(nicotinamido)ethyl Nitrate

11. Sg 75

12. N-(2-hydroxyethyl)nicotinamide Nitrate

13. N-(2-hydroxyethyl)nicotinamide Nitrate (ester)

14. Nicorandil (ikorel)

15. Chebi:31905

16. N-[2-(nitrooxy)ethyl]-3-pyridinecarboxamide

17. 3-pyridinecarboxamide, N-(2-(nitroxy)ethyl)-

18. 3-pyridinecarboxamide, N-[2-(nitrooxy)ethyl]-

19. 260456ham0

20. Ncgc00025357-01

21. 2-(pyridin-3-ylformamido)ethyl Nitrate

22. 3-pyridinecarboxamide, N-(2-(nitrooxy)ethyl)-

23. Dsstox_cid_25692

24. Dsstox_rid_81064

25. Dsstox_gsid_45692

26. Nicorandilum [inn-latin]

27. 2-[(pyridin-3-ylcarbonyl)amino]ethyl Nitrate

28. 2-(nicotinamido)ethyl Nitrat

29. Smr000466365

30. Sigmart (tn)

31. Cas-65141-46-0

32. Perisalol

33. N-(2-(nitrooxy)ethyl)-3-pyridinecarboxamide

34. Sr-01000597534

35. Einecs 265-514-1

36. Brn 0481451

37. Nicorandilo

38. Unii-260456ham0

39. Nicorandil [usan:inn:ban:jan]

40. Nicorandil- Bio-x

41. Mfcd00186520

42. 2-(pyridine-3-carboxamido)ethyl Nitrate

43. Cpd000466365

44. Rp-46417

45. Nicorandil [mi]

46. Nicorandil [inn]

47. Nicorandil [jan]

48. Nicorandil [usan]

49. N-[2-(nitrooxy)ethyl]pyridine-3-carboxamide

50. Nicorandil [mart.]

51. Nicorandil [who-dd]

52. Schembl34547

53. Mls000759488

54. Mls001424162

55. Mls002222323

56. Mls006010701

57. Chembl284906

58. Gtpl2411

59. Dtxsid8045692

60. Nicorandil (jp17/usan/inn)

61. Nicorandil [ep Monograph]

62. Hms2051n16

63. Hms2089l12

64. Hms2095e14

65. Hms2232a06

66. Hms3268l19

67. Hms3371n18

68. Hms3393n16

69. Hms3413g17

70. Hms3655p05

71. Hms3677g17

72. Hms3712e14

73. Bcp09434

74. Hy-b0341

75. Zinc1533102

76. Tox21_110968

77. Bdbm50247908

78. S1971

79. Stl445540

80. Akos001589705

81. Akos015855406

82. Akos025149378

83. Tox21_110968_1

84. Ab04467

85. Ac-4690

86. Ccg-101045

87. Db09220

88. Hs-0049

89. Nc00295

90. Ncgc00025357-02

91. Ncgc00025357-04

92. 2-(pyridine-3-carbylamino) Ethyl Nitrate

93. Bn164649

94. Ft-0602677

95. N0837

96. Sw197675-3

97. D01810

98. T72780

99. Ab00639978-08

100. Ab00639978-09

101. Ab00639978_10

102. Ab00639978_11

103. A834984

104. Q862989

105. Sr-01000597534-1

106. Sr-01000597534-5

107. Brd-k97752965-001-01-6

108. F0005-2298

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 211.17 g/mol
Molecular Formula C8H9N3O4
XLogP30.8
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count5
Rotatable Bond Count4
Exact Mass211.05930578 g/mol
Monoisotopic Mass211.05930578 g/mol
Topological Polar Surface Area97 Ų
Heavy Atom Count15
Formal Charge0
Complexity228
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Indicated for the prevention and treatment of chronic stable angina pectoris and reduction in the risk of acute coronary syndromes.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Nicorandil is a potassium channel opener with nitrovasodilator (NO donor) actions, making it both an arterial and a venous dilator. It causes sustained dilation of both the arterial resistance and conductive vessels that increases coronary blood flow, however the effect of the drug on coronary arteries does not involve the coronary steal phenomenon. Activation of potassium channels lead to hyperpolarization of the smooth muscle cells, followed by arterial dilation and afterload reduction. Nicorandil is shown to increase pooling in the capacitance vessels with a decrease in preload through relaxing the venous vascular system. Overall, improved blood flow and reduced infarct size are achieved through reduction of end-diastolix pressure and decreased extravascular component of vascular resistance. Open studies showed the effectiveness of nicorandil treatment on various types of angina pectoris.


5.2 MeSH Pharmacological Classification

Antihypertensive Agents

Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS. (See all compounds classified as Antihypertensive Agents.)


Vasodilator Agents

Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)


Vitamin B Complex

A group of water-soluble vitamins, some of which are COENZYMES. (See all compounds classified as Vitamin B Complex.)


Anti-Arrhythmia Agents

Agents used for the treatment or prevention of cardiac arrhythmias. They may affect the polarization-repolarization phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibers. Anti-arrhythmia agents are often classed into four main groups according to their mechanism of action: sodium channel blockade, beta-adrenergic blockade, repolarization prolongation, or calcium channel blockade. (See all compounds classified as Anti-Arrhythmia Agents.)


5.3 ATC Code

C - Cardiovascular system

C01 - Cardiac therapy

C01D - Vasodilators used in cardiac diseases

C01DX - Other vasodilators used in cardiac diseases

C01DX16 - Nicorandil


5.4 Absorption, Distribution and Excretion

Absorption

Following oral administration, nicorandil is well absorbed from the gastrointestinal tract with the oral bioavailability of 75% with the maximum peak plasma concentration (Cmax) reached within 30-60 minutes. The mean Cmax is Cmax then is approximately 300 ng/ml. Steady-state plasma concentrations of nicorandil usually are reached within approximately 96-120 h after twice daily dosing (10 or 20mg).


Route of Elimination

The main route of elimination is the kidney with more than 60% of the administered dose was eliminated in the urine 24 hours after dosing. Only approximately 1% of nicorandil is excreted unchanged in the urine, and the remaining compounds are mainly the denitrated metabolite (9%) and its derivatives (e.g. nicotinuric acid 6%, nicotinamide 1%, N-methylnicotinamide < 1% and nicotinic acid < 1%). Less than 2% of administered dose is excreted through the biliary system.


Volume of Distribution

After oral (and i.v.) administration of the drug, the apparent volume of distribution is approximately 1.0-1.4 L/kg body weight.


Clearance

The total body clearance is approximately 1.15 L/min.


5.5 Metabolism/Metabolites

Nicorandil undergoes extensive hepatic metabolism. The main biotransformation pathways of nicorandil are denitration, followed by subsequent nicotinamide metabolism. The main pharmacologically inactive denitrated metabolite 2-nicotinamidoethanol can be detected in the urine. The derivatives formed from the nicotinamide metabolism of denitrated products are nicotinuric acid, nicotinamide, N-methylnicotinamide and nicotinic acid.


5.6 Biological Half-Life

The elimination half life is approximately 1 hour.


5.7 Mechanism of Action

Nicorandil mediates its therapeutic efficacy via two main mechanisms. Nicorandil is an activator and opener of ATP-sensitive (ATP-dependent) potassium channels (KATP channels) that are composed of Kir6.x-type subunits and sulfonylurea receptor (SUR) subunits. Nicorandil binding sites are located in the sulfonylurea receptor 2 (SUR2) in the ATP-sensitive potassium channel, which are regulatory subunits of the channel that exhibit an ATPase activitiy. There are 2 types of SUR2 subunits (2A/2B) that have identical nucleotide binding domains (NBD), where SUR2A is more predominantly expressed in skeletal and cardiac myocytes and SUR2B in smooth muscle cells. Nicorandil more potently activates SUR2B/Kir6.2 than SUR2A/Kir6.2 channels to cause hyperpolarization. ATP-NBD1 interaction influences the channel signalling by nicorandil, and the response of the channel to nicorandil is also facilitated and heightened by the interaction of ATP or ADP with NBD2. Potentiated activity of ATP-sensitive channels have cardioprotective role by limiting the duration of action potentials and preventing intraceullar calcium overload. This attenuates cellular injury by preserving cellular energetics and ultimately cell survival. KATP channel-dependent membrane hyperpolarization can also lead to vasodilation via reduction in Ca2+ influx through the voltage-gated Ca2+ channels and regulation of intracellular Ca2+ mobilization in smooth muscle cells. Nicorandil contain a nitrate moiety in its structure, making it a good dilator of vascular smooth muscle like other nitroglycerin esters. Direct relaxation of venous vascular system arises from NO-donor mediated stimulation of guanylyl cyclase and increased levels of intracellular cyclic GMP (cGMP). Elevated levels of cGMP contributes to the total relaxing effect of nicorandil at higher concentrations of the drug.


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18-Jan-2021
09-Sep-2024
KGS
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Average Price (USD/KGS)

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Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

Importing Country Total Quantity
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(USD/KGS)
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