nicotinic acid ๐Ÿถ Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
nicotinic acid or nicotinoyl alcohol derivatives 2835 59-67-6

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • niacin potassium
  • niacin magnesium
  • nicotinic acid
  • vitamin b3 (niacin)
  • 3-pyridinecarboxylic acid
  • niaspan
  • niacin
  • niacor
  • Vitamin B3
A water-soluble vitamin of the B complex occurring in various animal and plant tissues. It is required by the body for the formation of coenzymes NAD and NADP. It has PELLAGRA-curative, vasodilating, and antilipemic properties.
  • Molecular weight: 123.11
  • Formula: C6H5NO2
  • CLOGP: 0.80
  • LIPINSKI: 0
  • HAC: 3
  • HDO: 1
  • TPSA: 50.19
  • ALOGS: -0.17
  • ROTB: 1

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.20 g O
0.20 g P
2 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 16.66 mg/mL Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 101.53 ยตM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD

Approvals:

DateAgencyCompanyOrphan
July 24, 1957 FDA MEDPOINTE PHARM HLC

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
Flushing 445.86 12.80 260 13819 66755 50524290
Drug hypersensitivity 206.09 12.80 298 13781 250712 50340333
Skin burning sensation 123.07 12.80 59 14020 10126 50580919
Pruritus 117.12 12.80 249 13830 283319 50307726
Paraesthesia 49.89 12.80 106 13973 120137 50470908
Product residue present 46.57 12.80 22 14057 3650 50587395
Feeling hot 43.35 12.80 54 14025 39148 50551897
Urticaria 41.35 12.80 103 13976 129458 50461587
Myalgia 39.85 12.80 99 13980 124220 50466825
Erythema 36.26 12.80 106 13973 146308 50444737
Rhabdomyolysis 35.75 12.80 49 14030 38978 50552067
Burning sensation 31.44 12.80 50 14029 45396 50545649
Infusion related reaction 31.01 12.80 5 14074 169552 50421493
Coronary artery disease 26.74 12.80 37 14042 29689 50561356
Femoral artery dissection 26.22 12.80 5 14074 30 50591015
Drug ineffective 25.29 12.80 130 13949 819203 49771842
Low density lipoprotein increased 25.07 12.80 17 14062 5629 50585416
Sinoatrial block 24.80 12.80 9 14070 766 50590279
Completed suicide 23.87 12.80 4 14075 131885 50459160
Off label use 23.32 12.80 62 14017 474364 50116681
Blood triglycerides increased 22.02 12.80 21 14058 11291 50579754
Systemic lupus erythematosus 21.91 12.80 6 14073 140616 50450429
Maternal exposure during pregnancy 21.12 12.80 9 14070 159769 50431276
Blood glucose increased 19.95 12.80 54 14025 71270 50519775
Glossodynia 19.84 12.80 4 14075 115565 50475480
Myopathy 19.78 12.80 18 14061 9121 50581924
Neutropenia 18.52 12.80 9 14070 147956 50443089
Blood cholesterol abnormal 18.27 12.80 10 14069 2258 50588787
Cyst 17.15 12.80 19 14060 12168 50578877
Lower respiratory tract infection 16.97 12.80 3 14076 95198 50495847
Pyrexia 16.96 12.80 52 14027 380151 50210894
Febrile neutropenia 15.53 12.80 4 14075 97663 50493382
High density lipoprotein decreased 15.10 12.80 8 14071 1692 50589353
Treatment failure 14.89 12.80 10 14069 137627 50453418
Swelling face 14.88 12.80 40 14039 52555 50538490
Hyperlipidaemia 14.58 12.80 21 14058 17469 50573576
General physical health deterioration 14.56 12.80 11 14068 142423 50448622
Product use in unapproved indication 14.56 12.80 7 14072 115812 50475233
Bicytopenia 14.13 12.80 8 14071 1928 50589117
Wound 13.91 12.80 6 14073 105788 50485257
Blood magnesium increased 13.57 12.80 9 14070 2871 50588174
Product use issue 13.50 12.80 13 14066 149462 50441583
Pain in extremity 13.34 12.80 125 13954 272740 50318305
Angina pectoris 13.12 12.80 25 14054 26163 50564882
Low turnover osteopathy 13.09 12.80 10 14069 3984 50587061
Condition aggravated 12.97 12.80 41 14038 297017 50294028

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
Flushing 911.24 12.90 420 18592 28572 29526943
Product residue present 229.27 12.90 79 18933 2460 29553055
Pruritus 116.97 12.90 242 18770 116607 29438908
Myalgia 93.17 12.90 169 18843 73850 29481665
High density lipoprotein decreased 80.49 12.90 39 18973 2940 29552575
Skin burning sensation 75.59 12.90 40 18972 3633 29551882
Myocardial infarction 68.56 12.90 190 18822 110106 29445409
Drug hypersensitivity 58.38 12.90 133 18879 68273 29487242
Off label use 50.63 12.90 72 18940 300728 29254787
Toxicity to various agents 47.95 12.90 26 18986 173635 29381880
Blood glucose increased 47.37 12.90 112 18900 58872 29496643
Feeling hot 47.31 12.90 54 18958 15434 29540081
Blood creatine phosphokinase increased 45.09 12.90 88 18924 40556 29514959
Coronary artery disease 44.63 12.90 92 18920 44098 29511417
Burning sensation 41.14 12.90 51 18961 15887 29539628
Paraesthesia 37.67 12.90 97 18915 53748 29501767
Coronary artery occlusion 35.68 12.90 38 18974 10056 29545459
Blood triglycerides increased 33.02 12.90 41 18971 12793 29542722
Low density lipoprotein increased 30.47 12.90 23 18989 3881 29551634
Rhabdomyolysis 30.34 12.90 97 18915 60711 29494804
Product use in unapproved indication 28.70 12.90 10 19002 86865 29468650
Neutropenia 28.06 12.90 26 18986 131685 29423830
Death 26.88 12.90 121 18891 341963 29213552
Completed suicide 25.62 12.90 13 18999 90233 29465282
Dyspepsia 23.94 12.90 57 18955 30068 29525447
Febrile neutropenia 22.92 12.90 23 18989 112217 29443298
Injury 22.04 12.90 42 18970 19004 29536511
Hot flush 21.31 12.90 36 18976 14834 29540681
Dizziness 21.06 12.90 200 18812 189484 29366031
Erythema 20.82 12.90 100 18912 75506 29480009
Product use issue 20.64 12.90 4 19008 51440 29504075
Muscle spasms 20.08 12.90 89 18923 64993 29490522
Myopathy 19.97 12.90 29 18983 10504 29545011
General physical health deterioration 19.96 12.90 22 18990 102835 29452680
Transaminases abnormal 19.39 12.90 7 19005 250 29555265
Pyrexia 18.45 12.90 109 18903 287513 29268002
Chest pain 17.74 12.90 128 18884 111845 29443670
Pain in extremity 16.79 12.90 125 18887 110308 29445207
Glycosylated haemoglobin increased 16.50 12.90 25 18987 9401 29546114
Blood cholesterol increased 16.36 12.90 33 18979 15562 29539953
Intentional product use issue 15.65 12.90 4 19008 42494 29513021
Angina pectoris 15.33 12.90 46 18966 27804 29527711
Asthenia 15.28 12.90 208 18804 215042 29340473
Hypoaesthesia 14.91 12.90 71 18941 53396 29502119
Gout 14.53 12.90 33 18979 16878 29538637
Impaired work ability 14.47 12.90 18 18994 5622 29549893
Pain 14.43 12.90 171 18841 171261 29384254
Blood testosterone decreased 14.25 12.90 15 18997 3915 29551600
Abnormal clotting factor 14.23 12.90 3 19009 12 29555503
Urticaria 14.11 12.90 71 18941 54589 29500926
Renal impairment 14.08 12.90 19 18993 81314 29474201
Flatulence 13.52 12.90 33 18979 17676 29537839
Cerebrovascular accident 13.40 12.90 90 18922 76821 29478694
Malignant neoplasm progression 13.04 12.90 17 18995 73842 29481673

FDA Adverse Event Reporting System (Geriatric)

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
Flushing 185.76 11.99 179 22160 78469 64397924
Drug hypersensitivity 115.07 11.99 254 22085 237561 64238832
Myocardial infarction 92.75 11.99 188 22151 165633 64310760
Coronary artery disease 87.05 11.99 106 22233 60327 64416066
Myalgia 81.86 11.99 174 22165 158443 64317950
Rhabdomyolysis 68.77 11.99 118 22221 91608 64384785
Blood creatine phosphokinase increased 48.78 11.99 79 22260 58479 64417914
High density lipoprotein decreased 46.15 11.99 24 22315 3922 64472471
Off label use 45.10 11.99 95 22244 632711 63843682
Blood triglycerides increased 44.58 11.99 43 22296 18823 64457570
Completed suicide 36.52 11.99 16 22323 224398 64251995
Coronary artery occlusion 29.73 11.99 30 22309 13861 64462532
Myopathy 27.05 11.99 32 22307 17648 64458745
Angina pectoris 26.20 11.99 52 22287 45029 64431364
Blood glucose increased 26.08 11.99 84 22255 97989 64378404
Low density lipoprotein increased 24.92 11.99 21 22318 7719 64468674
Contraindicated product administered 24.44 11.99 4 22335 107825 64368568
Femoral artery dissection 23.98 11.99 5 22334 39 64476354
Product use in unapproved indication 23.76 11.99 16 22323 176602 64299791
Neutropenia 23.57 11.99 29 22310 239595 64236798
Febrile neutropenia 22.68 11.99 19 22320 187638 64288755
Toxicity to various agents 22.28 11.99 59 22280 363454 64112939
Infusion related reaction 21.99 11.99 15 22324 164452 64311941
Acute myocardial infarction 20.64 11.99 62 22277 69656 64406737
Cardiac failure congestive 20.05 11.99 94 22245 130486 64345907
Product residue present 19.96 11.99 13 22326 3229 64473164
Sinoatrial block 19.34 11.99 9 22330 1157 64475236
Cerebrovascular accident 18.95 11.99 96 22243 137487 64338906
General physical health deterioration 18.80 11.99 26 22313 204399 64271994
Product use issue 18.77 11.99 15 22324 151700 64324693
Maternal exposure during pregnancy 18.76 11.99 5 22334 95879 64380514
Therapy cessation 18.31 11.99 37 22302 32452 64443941
Chest pain 18.25 11.99 142 22197 235838 64240555
Glycosylated haemoglobin increased 18.19 11.99 25 22314 15994 64460399
Dizziness 18.14 11.99 228 22111 429935 64046458
Treatment failure 17.95 11.99 9 22330 116807 64359586
Blood testosterone decreased 16.83 11.99 10 22329 2115 64474278
Pyrexia 16.77 11.99 119 22220 558525 63917868
Gastrointestinal haemorrhage 16.62 11.99 90 22249 132222 64344171
Hyperlipidaemia 16.47 11.99 29 22310 22947 64453446
Transaminases abnormal 16.26 11.99 7 22332 749 64475644
Angina unstable 15.88 11.99 23 22316 15444 64460949
Burning sensation 15.50 11.99 45 22294 49619 64426774
Muscle spasms 15.14 11.99 92 22247 140931 64335462
Blood cholesterol abnormal 14.70 11.99 10 22329 2671 64473722
Condition aggravated 14.50 11.99 73 22266 372353 64104040
Urticaria 14.50 11.99 94 22245 147223 64329170
Pruritus 14.20 11.99 168 22171 312232 64164161
Drug ineffective 14.01 11.99 206 22133 840041 63636352
International normalised ratio increased 13.65 11.99 59 22280 79108 64397285
C-reactive protein increased 13.58 11.99 8 22331 94901 64381492
Dyspnoea exertional 13.53 11.99 56 22283 73674 64402719
Lower respiratory tract infection 13.50 11.99 8 22331 94606 64381787
Metabolic syndrome 13.45 11.99 9 22330 2339 64474054
Pericardial haemorrhage 12.86 11.99 11 22328 4125 64472268
Oedema peripheral 12.80 11.99 120 22219 210197 64266196
Skin burning sensation 12.75 11.99 17 22322 10566 64465827
Paraesthesia 12.73 11.99 85 22254 134437 64341956
Coronary artery restenosis 12.65 11.99 7 22332 1295 64475098
Injury 12.29 11.99 45 22294 55947 64420446

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC C04AC01 CARDIOVASCULAR SYSTEM
PERIPHERAL VASODILATORS
PERIPHERAL VASODILATORS
Nicotinic acid and derivatives
ATC C10AD02 CARDIOVASCULAR SYSTEM
LIPID MODIFYING AGENTS
LIPID MODIFYING AGENTS, PLAIN
Nicotinic acid and derivatives
ATC C10AD52 CARDIOVASCULAR SYSTEM
LIPID MODIFYING AGENTS
LIPID MODIFYING AGENTS, PLAIN
Nicotinic acid and derivatives
ATC C10BA01 CARDIOVASCULAR SYSTEM
LIPID MODIFYING AGENTS
LIPID MODIFYING AGENTS, COMBINATIONS
Combinations of various lipid modifying agents
FDA CS M0014839 Nicotinic Acids
FDA EPC N0000175594 Nicotinic Acid
MeSH PA D000963 Antimetabolites
MeSH PA D002317 Cardiovascular Agents
MeSH PA D000960 Hypolipidemic Agents
MeSH PA D057847 Lipid Regulating Agents
MeSH PA D018977 Micronutrients
MeSH PA D014665 Vasodilator Agents
MeSH PA D014803 Vitamin B Complex
MeSH PA D014815 Vitamins
CHEBI has role CHEBI:25212 metabolites
CHEBI has role CHEBI:35620 vasodilator agents
CHEBI has role CHEBI:35679 antilipemic drugs
CHEBI has role CHEBI:50247 antidotes
CHEBI has role CHEBI:75771 Mus musculus metabolites
CHEBI has role CHEBI:76924 plant metabolites
CHEBI has role CHEBI:76971 Escherichia coli metabolites
CHEBI has role CHEBI:84087 human urinary metabolites
CHEBI has role CHEBI:84264 nicotinamide deaminase inhibitors
CHEBI has role CHEBI:22586 antioxidants
CHEBI has role CHEBI:23357 cofactor
CHEBI has role CHEBI:61115 histone deacetylase inhibitors
CHEBI has role CHEBI:62913 PARP
CHEBI has role CHEBI:63726 neuroprotective agents
CHEBI has role CHEBI:67079 anti-inflammatory agents
CHEBI has role CHEBI:71181 Sir2 inhibitors
CHEBI has role CHEBI:75772 S. cerevisiae metabolites
CHEBI has role CHEBI:176497 geroprotectors

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Hypercholesterolemia indication 13644009
Hyperlipidemia indication 55822004 DOID:1168
Vitamin deficiency indication 85670002
Familial hypercholesterolemia - heterozygous indication 238079002
Mixed hyperlipidemia indication 267434003
Hypertriglyceridemia indication 302870006




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 2.31 acidic
pKa2 4.85 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
Hydroxycarboxylic acid receptor 2 GPCR AGONIST Ki 7.30 CHEMBL SCIENTIFIC LITERATURE
Amyloid beta A4 protein Unclassified IC50 4.88 CHEMBL
Hydroxycarboxylic acid receptor 3 GPCR AGONIST EC50 6.52 IUPHAR
Nicotinamide N-methyltransferase Enzyme WOMBAT-PK
Nicotinate-nucleotide pyrophosphorylase [carboxylating] Enzyme WOMBAT-PK
Nicotinamide phosphoribosyltransferase Enzyme WOMBAT-PK
Hydroxycarboxylic acid receptor 2 GPCR IC50 6.85 CHEMBL
Hydroxycarboxylic acid receptor 2 GPCR Ki 7.48 CHEMBL

External reference:

IDSource
4019440 VUID
N0000147570 NUI
D00049 KEGG_DRUG
4017632 VANDF
4017661 VANDF
4017718 VANDF
4019440 VANDF
4020285 VANDF
4021898 VANDF
C0027996 UMLSCUI
CHEBI:15940 CHEBI
NIO PDB_CHEM_ID
CHEMBL573 ChEMBL_ID
938 PUBCHEM_CID
DB00627 DRUGBANK_ID
1588 IUPHAR_LIGAND_ID
218728 RXNORM
2275 MMSL
4947 MMSL
5169 MMSL
5170 MMSL
5684 MMSL
7159 MMSL
7161 MMSL
72420 MMSL
d00314 MMSL
d03739 MMSL
001052 NDDF
001055 NDDF
173196005 SNOMEDCT_US
273943001 SNOMEDCT_US
63639004 SNOMEDCT_US
D009525 MESH_DESCRIPTOR_UI
373 INN_ID
2679MF687A UNII

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Niaspan HUMAN PRESCRIPTION DRUG LABEL 1 0074-3074 TABLET, FILM COATED, EXTENDED RELEASE 500 mg ORAL NDA 29 sections
Niaspan HUMAN PRESCRIPTION DRUG LABEL 1 0074-3074 TABLET, FILM COATED, EXTENDED RELEASE 500 mg ORAL NDA 29 sections
Niaspan HUMAN PRESCRIPTION DRUG LABEL 1 0074-3079 TABLET, FILM COATED, EXTENDED RELEASE 750 mg ORAL NDA 29 sections
Niaspan HUMAN PRESCRIPTION DRUG LABEL 1 0074-3079 TABLET, FILM COATED, EXTENDED RELEASE 750 mg ORAL NDA 29 sections
Niaspan HUMAN PRESCRIPTION DRUG LABEL 1 0074-3080 TABLET, FILM COATED, EXTENDED RELEASE 1000 mg ORAL NDA 29 sections
Niaspan HUMAN PRESCRIPTION DRUG LABEL 1 0074-3080 TABLET, FILM COATED, EXTENDED RELEASE 1000 mg ORAL NDA 29 sections
Niaspan HUMAN PRESCRIPTION DRUG LABEL 1 0074-3265 TABLET, FILM COATED, EXTENDED RELEASE 500 mg ORAL NDA 29 sections
Niaspan HUMAN PRESCRIPTION DRUG LABEL 1 0074-3265 TABLET, FILM COATED, EXTENDED RELEASE 500 mg ORAL NDA 29 sections
Niaspan HUMAN PRESCRIPTION DRUG LABEL 1 0074-3274 TABLET, FILM COATED, EXTENDED RELEASE 750 mg ORAL NDA 29 sections
Niaspan HUMAN PRESCRIPTION DRUG LABEL 1 0074-3274 TABLET, FILM COATED, EXTENDED RELEASE 750 mg ORAL NDA 29 sections
Niaspan HUMAN PRESCRIPTION DRUG LABEL 1 0074-3275 TABLET, FILM COATED, EXTENDED RELEASE 1000 mg ORAL NDA 29 sections
Niaspan HUMAN PRESCRIPTION DRUG LABEL 1 0074-3275 TABLET, FILM COATED, EXTENDED RELEASE 1000 mg ORAL NDA 29 sections
VitafolOne HUMAN PRESCRIPTION DRUG LABEL 16 0642-0070 CAPSULE, GELATIN COATED 15 mg ORAL unapproved drug other 14 sections
Vitafol Caplet HUMAN PRESCRIPTION DRUG LABEL 12 0642-0072 CAPSULE 15 mg ORAL UNAPPROVED DRUG OTHER 13 sections
Select OB HUMAN PRESCRIPTION DRUG LABEL 15 0642-0077 TABLET, CHEWABLE 15 mg ORAL UNAPPROVED DRUG OTHER 14 sections
Vitafol OB Caplet HUMAN PRESCRIPTION DRUG LABEL 15 0642-0079 TABLET 18 mg ORAL Unapproved drug other 14 sections
Vitafol Plus HUMAN PRESCRIPTION DRUG LABEL 17 0642-0092 CAPSULE, LIQUID FILLED 15 mg ORAL UNAPPROVED DRUG OTHER 13 sections
Strovite Forte Caplet HUMAN PRESCRIPTION DRUG LABEL 19 0642-0204 TABLET, COATED 100 mg ORAL UNAPPROVED DRUG OTHER 15 sections
Reaphirm Plant Source DHA HUMAN PRESCRIPTION DRUG LABEL 16 0642-3010 CAPSULE, GELATIN COATED 15 mg ORAL unapproved drug other 7 sections
O-Cal Prenatal Vitamin HUMAN PRESCRIPTION DRUG LABEL 16 0813-0202 TABLET 17 mg ORAL UNAPPROVED DRUG OTHER 6 sections
Niacin HUMAN PRESCRIPTION DRUG LABEL 1 10135-612 TABLET, EXTENDED RELEASE 500 mg ORAL ANDA 25 sections
Niacin HUMAN PRESCRIPTION DRUG LABEL 1 10135-613 TABLET, EXTENDED RELEASE 750 mg ORAL ANDA 25 sections
Niacin HUMAN PRESCRIPTION DRUG LABEL 1 10135-614 TABLET, EXTENDED RELEASE 1000 mg ORAL ANDA 25 sections
TriStart DHA HUMAN PRESCRIPTION DRUG LABEL 15 15370-250 CAPSULE, LIQUID FILLED 5 mg ORAL UNAPPROVED DRUG OTHER 12 sections
Niaspan HUMAN PRESCRIPTION DRUG LABEL 1 21695-852 TABLET, FILM COATED, EXTENDED RELEASE 500 mg ORAL NDA 26 sections
Niaspan HUMAN PRESCRIPTION DRUG LABEL 1 21695-865 TABLET, FILM COATED, EXTENDED RELEASE 1000 mg ORAL NDA 26 sections
Niacin Human Prescription Drug Label 1 33342-187 TABLET 500 mg ORAL ANDA 25 sections
Niacin Human Prescription Drug Label 1 33342-189 TABLET 1000 mg ORAL ANDA 25 sections
NIACIN Human Prescription Drug Label 1 47335-539 TABLET, FILM COATED, EXTENDED RELEASE 500 mg ORAL ANDA 27 sections
NIACIN Human Prescription Drug Label 1 47335-539 TABLET, FILM COATED, EXTENDED RELEASE 500 mg ORAL ANDA 27 sections