nicorandil Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
nicotinic acid or nicotinoyl alcohol derivatives 1919 65141-46-0

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • nicorandil
  • perisalol
  • sigmart
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.
  • Molecular weight: 211.18
  • Formula: C8H9N3O4
  • CLOGP: -1.80
  • LIPINSKI: 0
  • HAC: 7
  • HDO: 1
  • TPSA: 97.04
  • ALOGS: -2.25
  • ROTB: 5

Drug dosage:

DoseUnitRoute
40 mg O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 4.20 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0.50 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 4.06 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 75 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 1.40 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 8.90 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.76 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 3.60 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Jan. 1, 1984 YEAR INTRODUCED

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Rhabdomyolysis 121.17 19.87 71 5635 41838 46638518
Cardiac failure 90.06 19.87 76 5630 79872 46600484
Acute kidney injury 62.70 19.87 107 5599 235748 46444608
Angina pectoris 58.56 19.87 38 5668 26737 46653619
Hepatic function abnormal 54.41 19.87 40 5666 34381 46645975
Hyponatraemia 42.58 19.87 57 5649 101275 46579081
Fixed eruption 40.21 19.87 11 5695 854 46679502
Blood creatine phosphokinase increased 38.88 19.87 30 5676 27694 46652662
Blood pressure decreased 38.64 19.87 41 5665 57118 46623238
Drug interaction 37.54 19.87 79 5627 203015 46477341
Drug ineffective 36.23 19.87 19 5687 677819 46002537
Melaena 32.43 19.87 27 5679 27745 46652611
Renal impairment 31.47 19.87 42 5664 74330 46606026
Bradycardia 30.47 19.87 39 5667 66259 46614097
Interstitial lung disease 30.09 19.87 35 5671 53914 46626442
Hypotension 29.38 19.87 78 5628 232511 46447845
Hyperkalaemia 28.45 19.87 33 5673 50676 46629680
Fatigue 28.38 19.87 20 5686 608677 46071679
Prinzmetal angina 27.80 19.87 8 5698 747 46679609
Upper gastrointestinal haemorrhage 27.67 19.87 20 5686 16718 46663638
Gastrointestinal haemorrhage 27.23 19.87 40 5666 77333 46603023
Altered state of consciousness 25.82 19.87 22 5684 23326 46657030
Ischaemic stroke 25.43 19.87 19 5687 16703 46663653
Cerebral infarction 23.78 19.87 21 5685 23345 46657011
Gynaecomastia 23.30 19.87 5 5701 138 46680218
Disseminated intravascular coagulation 23.28 19.87 19 5687 18986 46661370
Myocardial infarction 22.90 19.87 42 5664 97486 46582870
Decreased appetite 21.47 19.87 62 5644 193774 46486582
Hypoglycaemia 20.43 19.87 29 5677 54320 46626036
Depressed level of consciousness 20.31 19.87 27 5679 47542 46632814
Acute myocardial infarction 19.98 19.87 22 5684 31902 46648454

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Angina pectoris 128.77 17.37 90 8802 29428 29914158
Interstitial lung disease 101.02 17.37 106 8786 60091 29883495
Hepatic function abnormal 60.06 17.37 68 8824 41877 29901709
Arteriospasm coronary 52.35 17.37 22 8870 2596 29940990
Cardiac failure 42.34 17.37 83 8809 83335 29860251
Acute myocardial infarction 41.72 17.37 64 8828 52875 29890711
Coronary artery restenosis 41.68 17.37 15 8877 1168 29942418
Rhabdomyolysis 39.46 17.37 69 8823 63511 29880075
Myocardial ischaemia 37.33 17.37 35 8857 17282 29926304
Chest pain 37.24 17.37 97 8795 117530 29826056
Acute kidney injury 35.67 17.37 168 8724 273674 29669912
Ventricular fibrillation 33.40 17.37 31 8861 15107 29928479
Altered state of consciousness 33.20 17.37 35 8857 19884 29923702
Drug interaction 32.49 17.37 131 8761 199437 29744149
Vascular stent stenosis 31.86 17.37 12 8880 1062 29942524
Cerebral infarction 31.51 17.37 39 8853 26334 29917252
Tonsillar ulcer 31.02 17.37 8 8884 199 29943387
Prinzmetal angina 29.83 17.37 11 8881 918 29942668
Melaena 29.55 17.37 42 8850 32395 29911191
Liver disorder 29.34 17.37 40 8852 29682 29913904
Drug ineffective 29.19 17.37 35 8857 340352 29603234
Malaise 29.09 17.37 112 8780 166850 29776736
Angina unstable 28.70 17.37 26 8866 12284 29931302
Pericardial haemorrhage 28.65 17.37 15 8877 2903 29940683
Death 26.34 17.37 41 8851 357242 29586344
Intraventricular haemorrhage 25.34 17.37 14 8878 3016 29940570
Disseminated intravascular coagulation 23.66 17.37 31 8861 22140 29921446
Coronary artery stenosis 22.81 17.37 20 8872 9050 29934536
Pulmonary alveolar haemorrhage 21.75 17.37 17 8875 6564 29937022
Insulin autoimmune syndrome 20.72 17.37 6 8886 232 29943354
Fatigue 20.69 17.37 40 8852 320633 29622953
Urticaria pigmentosa 20.18 17.37 4 8888 28 29943558
Nitritoid reaction 20.18 17.37 4 8888 28 29943558
International normalised ratio increased 20.07 17.37 44 8848 47695 29895891
Hypovitaminosis 19.94 17.37 7 8885 507 29943079
Off label use 19.91 17.37 27 8865 249263 29694323
Swollen tongue 19.90 17.37 22 8870 13170 29930416
Bradycardia 19.64 17.37 53 8839 65473 29878113
Prerenal failure 19.47 17.37 10 8882 1861 29941725
Catheter site cellulitis 18.68 17.37 5 8887 144 29943442
Myositis 18.66 17.37 19 8873 10358 29933228
Haemoptysis 18.32 17.37 33 8859 31045 29912541

Pharmacologic Action:

SourceCodeDescription
ATC C01DX16 CARDIOVASCULAR SYSTEM
CARDIAC THERAPY
VASODILATORS USED IN CARDIAC DISEASES
Other vasodilators used in cardiac diseases
MeSH PA D018977 Micronutrients
MeSH PA D000889 Anti-Arrhythmia Agents
MeSH PA D000959 Antihypertensive Agents
MeSH PA D002317 Cardiovascular Agents
MeSH PA D014665 Vasodilator Agents
MeSH PA D014803 Vitamin B Complex
MeSH PA D014815 Vitamins
CHEBI has role CHEBI:35620 vasodilator
CHEBI has role CHEBI:79085 potassium channel activator

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Angina pectoris indication 194828000

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 10.97 acidic
pKa2 3.07 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Atrial natriuretic peptide receptor 1 Enzyme EC50 7.20 WOMBAT-PK
ATP-sensitive inward rectifier potassium channel 1 Ion channel IC50 5.95 WOMBAT-PK
ATP-sensitive inward rectifier potassium channel 11 Ion channel IC50 5.89 WOMBAT-PK

External reference:

IDSource
N0000167327 NUI
D01810 KEGG_DRUG
C0068700 UMLSCUI
CHEBI:31905 CHEBI
CHEMBL284906 ChEMBL_ID
D020108 MESH_DESCRIPTOR_UI
DB09220 DRUGBANK_ID
2411 IUPHAR_LIGAND_ID
4933 INN_ID
260456HAM0 UNII
47528 PUBCHEM_CID
31748 RXNORM
005831 NDDF
319304004 SNOMEDCT_US
395809002 SNOMEDCT_US

Pharmaceutical products:

None