nicotinic acid 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 ┬ÁM/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 438.32 12.45 268 14854 64346 46606594
Drug hypersensitivity 190.53 12.45 307 14815 243518 46427422
Pruritus 133.40 12.45 262 14860 242090 46428850
Skin burning sensation 111.85 12.45 59 15063 10633 46660307
Feeling hot 42.83 12.45 57 15065 37871 46633069
Product residue present 42.24 12.45 22 15100 3860 46667080
Paraesthesia 39.80 12.45 105 15017 117332 46553608
Erythema 36.14 12.45 115 15007 142705 46528235
Urticaria 34.58 12.45 100 15022 117792 46553148
Burning sensation 29.26 12.45 52 15070 44359 46626581
Myalgia 28.33 12.45 96 15026 122992 46547948
Blood triglycerides increased 27.72 12.45 26 15096 11757 46659183
Completed suicide 26.95 12.45 7 15115 145913 46525027
Femoral artery dissection 25.32 12.45 5 15117 31 46670909
Therapy cessation 24.09 12.45 36 15086 26593 46644347
Low density lipoprotein increased 24.02 12.45 18 15104 5982 46664958
Sinoatrial block 23.00 12.45 9 15113 809 46670131
Drug ineffective 22.23 12.45 129 14993 677709 45993231
Rhabdomyolysis 21.35 12.45 44 15078 41865 46629075
Coronary artery disease 20.30 12.45 38 15084 33714 46637226
Rheumatoid arthritis 20.27 12.45 29 15093 240186 46430754
Off label use 18.67 12.45 62 15060 379779 46291161
Febrile neutropenia 16.61 12.45 5 15117 94622 46576318
Myopathy 16.09 12.45 17 15105 8864 46662076
Product dose omission issue 15.81 12.45 101 15021 168419 46502521
Pyrexia 15.75 12.45 59 15063 348743 46322197
Neutropenia 15.65 12.45 14 15108 143190 46527750
Cyst 14.92 12.45 19 15103 12081 46658859
General physical health deterioration 14.31 12.45 10 15112 115759 46555181
Blood cholesterol abnormal 14.26 12.45 9 15113 2268 46668672
Bicytopenia 14.12 12.45 8 15114 1656 46669284
Blood glucose increased 13.85 12.45 53 15069 71960 46598980
Coronary artery occlusion 13.78 12.45 15 15107 8087 46662853
Blood cholesterol increased 13.76 12.45 36 15086 39977 46630963
High density lipoprotein decreased 13.56 12.45 8 15114 1786 46669154
Hyperlipidaemia 12.58 12.45 22 15100 18517 46652423
Stress 12.55 12.45 41 15081 51510 46619430
Maternal exposure during pregnancy 12.48 12.45 9 15113 102540 46568400

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 914.51 12.44 427 19382 29065 29903604
Product residue present 226.76 12.44 80 19729 2598 29930071
High density lipoprotein decreased 119.72 12.44 53 19756 3157 29929512
Pruritus 116.06 12.44 247 19562 117957 29814712
Myalgia 96.65 12.44 178 19631 76489 29856180
Skin burning sensation 73.44 12.44 40 19769 3740 29928929
Drug hypersensitivity 53.57 12.44 131 19678 68388 29864281
Blood creatine phosphokinase increased 46.84 12.44 95 19714 43753 29888916
Feeling hot 46.02 12.44 54 19755 15450 29917219
Blood glucose increased 45.30 12.44 115 19694 61415 29871254
Toxicity to various agents 45.15 12.44 31 19778 177152 29755517
Drug abuse 42.66 12.44 3 19806 82069 29850600
Myocardial infarction 41.71 12.44 179 19630 125446 29807223
Off label use 40.57 12.44 64 19745 249226 29683443
Coronary artery disease 38.78 12.44 95 19714 49617 29883052
Blood triglycerides increased 38.60 12.44 47 19762 13970 29918699
Burning sensation 37.12 12.44 50 19759 16424 29916245
Paraesthesia 35.36 12.44 97 19712 54230 29878439
Coronary artery occlusion 33.34 12.44 39 19770 11118 29921551
Low density lipoprotein increased 31.50 12.44 24 19785 3992 29928677
Rhabdomyolysis 29.64 12.44 101 19708 63479 29869190
Neutropenia 27.13 12.44 27 19782 128513 29804156
Product use in unapproved indication 26.32 12.44 8 19801 73685 29858984
Death 23.78 12.44 139 19670 357144 29575525
Muscle spasms 22.73 12.44 94 19715 64744 29867925
Dyspepsia 22.63 12.44 57 19752 30272 29902397
General physical health deterioration 22.24 12.44 20 19789 99924 29832745
Hot flush 22.23 12.44 37 19772 14643 29918026
Erythema 21.66 12.44 105 19704 77346 29855323
Pyrexia 20.97 12.44 112 19697 294377 29638292
Myopathy 20.67 12.44 30 19779 10556 29922113
Dizziness 20.11 12.44 207 19602 194702 29737967
Transaminases abnormal 19.50 12.44 7 19802 239 29932430
Injury 18.52 12.44 43 19766 21688 29910981
Hypoaesthesia 18.51 12.44 78 19731 54152 29878517
Urticaria 18.22 12.44 78 19731 54528 29878141
Pain in extremity 18.19 12.44 130 19679 110091 29822578
Glycosylated haemoglobin increased 17.24 12.44 26 19783 9465 29923204
Blood cholesterol increased 17.20 12.44 36 19773 16934 29915735
Febrile neutropenia 16.73 12.44 28 19781 106665 29826004
Product use issue 16.42 12.44 5 19804 46011 29886658
Asthenia 15.35 12.44 218 19591 221072 29711597
Pain 14.88 12.44 177 19632 172464 29760205
Interstitial lung disease 14.68 12.44 11 19798 60186 29872483
Abnormal clotting factor 14.15 12.44 3 19806 12 29932657
Impaired work ability 14.06 12.44 18 19791 5625 29927044
Contusion 13.96 12.44 49 19760 31231 29901438
Cardiac failure 13.92 12.44 21 19788 83397 29849272
Renal impairment 13.28 12.44 22 19787 84162 29848507
Malignant neoplasm progression 13.25 12.44 17 19792 72270 29860399
Therapy cessation 12.95 12.44 30 19779 15107 29917562
Intentional product use issue 12.93 12.44 4 19805 36436 29896233
Chest pain 12.61 12.44 126 19683 117501 29815168
Hepatic function abnormal 12.57 12.44 6 19803 41939 29890730
Sepsis 12.55 12.44 52 19757 146343 29786326
Blood testosterone decreased 12.52 12.44 15 19794 4381 29928288

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
CHEBI has role CHEBI:35679 hypolipidemic agent
CHEBI has role CHEBI:50247 antidotes
CHEBI has role CHEBI:75769 vitamin b
CHEBI has role CHEBI:75771 mus musculus metabolite
CHEBI has role CHEBI:76971 e.coli metabolites
CHEBI has role CHEBI:84264 yndase inhibitors
CHEBI has role CHEBI:22586 antioxidants
CHEBI has role CHEBI:23357 cofactor
CHEBI has role CHEBI:61115 hdac inhibitor
CHEBI has role CHEBI:62913 poly(adp-ribose) polymerase inhibitors
CHEBI has role CHEBI:63726 neuroprotective agents
CHEBI has role CHEBI:67079 antiinflammatory agents
CHEBI has role CHEBI:71181 sir2 inhibitors
CHEBI has role CHEBI:75772 baker's yeast metabolite

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

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
Nicotinate-nucleotide pyrophosphorylase [carboxylating] Enzyme WOMBAT-PK
Nicotinamide N-methyltransferase Enzyme WOMBAT-PK
Hydroxycarboxylic acid receptor 3 GPCR AGONIST EC50 6.52 IUPHAR
Nicotinamide phosphoribosyltransferase Enzyme WOMBAT-PK
Hydroxycarboxylic acid receptor 2 GPCR Ki 7.48 CHEMBL
Hydroxycarboxylic acid receptor 2 GPCR IC50 6.85 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
938 PUBCHEM_CID
DB00627 DRUGBANK_ID
CHEMBL573 ChEMBL_ID
D009525 MESH_DESCRIPTOR_UI
1588 IUPHAR_LIGAND_ID
373 INN_ID
2679MF687A UNII
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

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Niaspan HUMAN PRESCRIPTION DRUG LABEL 1 0074-3074 TABLET, FILM COATED, EXTENDED RELEASE 500 mg ORAL NDA 25 sections
Niaspan HUMAN PRESCRIPTION DRUG LABEL 1 0074-3079 TABLET, FILM COATED, EXTENDED RELEASE 750 mg ORAL NDA 25 sections
Niaspan HUMAN PRESCRIPTION DRUG LABEL 1 0074-3080 TABLET, FILM COATED, EXTENDED RELEASE 1000 mg ORAL NDA 25 sections
Niaspan HUMAN PRESCRIPTION DRUG LABEL 1 0074-3265 TABLET, FILM COATED, EXTENDED RELEASE 500 mg ORAL NDA 25 sections
Niaspan HUMAN PRESCRIPTION DRUG LABEL 1 0074-3274 TABLET, FILM COATED, EXTENDED RELEASE 750 mg ORAL NDA 25 sections
Niaspan HUMAN PRESCRIPTION DRUG LABEL 1 0074-3275 TABLET, FILM COATED, EXTENDED RELEASE 1000 mg ORAL NDA 25 sections
VitafolOne HUMAN PRESCRIPTION DRUG LABEL 16 0642-0070 CAPSULE, GELATIN COATED 15 mg ORAL unapproved drug other 7 sections
Vitafol Caplet HUMAN PRESCRIPTION DRUG LABEL 12 0642-0072 CAPSULE 15 mg ORAL UNULLPPROVED DRUG OTHER 13 sections
Select OB HUMAN PRESCRIPTION DRUG LABEL 15 0642-0077 TABLET, CHEWABLE 15 mg ORAL UNULLPPROVED 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 UNULLPPROVED DRUG OTHER 13 sections
Strovite Forte Caplet HUMAN PRESCRIPTION DRUG LABEL 19 0642-0204 TABLET, COATED 100 mg ORAL UNULLPPROVED 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 UNULLPPROVED 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 UNULLPPROVED 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
Prenatal Vitamins Plus Low Iron HUMAN PRESCRIPTION DRUG LABEL 15 39328-106 TABLET 20 mg ORAL Unapproved drug other 9 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 47335-613 TABLET, FILM COATED, EXTENDED RELEASE 1000 mg ORAL ANDA 27 sections
NIACIN Human Prescription Drug Label 1 47335-614 TABLET, FILM COATED, EXTENDED RELEASE 750 mg ORAL ANDA 27 sections
Multivitamin with fluoride HUMAN PRESCRIPTION DRUG LABEL 11 50090-0356 TABLET, CHEWABLE 13.50 mg ORAL UNULLPPROVED DRUG OTHER 8 sections
Multivitamin with fluoride HUMAN PRESCRIPTION DRUG LABEL 11 50090-0435 TABLET, CHEWABLE 13.50 mg ORAL UNULLPPROVED DRUG OTHER 8 sections
Prenatal Vitamins Plus Low Iron HUMAN PRESCRIPTION DRUG LABEL 15 50090-0616 TABLET 20 mg ORAL Unapproved drug other 9 sections
Multivitamin with Fluoride HUMAN PRESCRIPTION DRUG LABEL 12 50090-4475 TABLET, CHEWABLE 13.50 mg ORAL unapproved drug other 10 sections
Niacin HUMAN PRESCRIPTION DRUG LABEL 1 50268-584 TABLET, EXTENDED RELEASE 500 mg ORAL ANDA 19 sections
Niacin HUMAN PRESCRIPTION DRUG LABEL 1 50268-586 TABLET, EXTENDED RELEASE 1000 mg ORAL ANDA 19 sections