U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C6H5NO2
Molecular Weight 123.1094
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Niacin

SMILES

OC(=O)C1=CC=CN=C1

InChI

InChIKey=PVNIIMVLHYAWGP-UHFFFAOYSA-N
InChI=1S/C6H5NO2/c8-6(9)5-2-1-3-7-4-5/h1-4H,(H,8,9)

HIDE SMILES / InChI

Molecular Formula C6H5NO2
Molecular Weight 123.1094
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including http://reference.medscape.com/drug/vitamin-b3-niacor-niacin-344422 https://www.ncbi.nlm.nih.gov/pubmed/16099840

Niacin (also known as vitamin B3 and nicotinic acid) is bio converted to nicotinamide which is further converted to nicotinamide adenine dinucleotide (NAD+) and the hydride equivalent (NADH) which are coenzymes necessary for tissue metabolism, lipid metabolism, and glycogenolysis. Niacin (but not nicotinamide) in gram doses reduces LDL-C, Apo B, Lp(a), TG, and TC, and increases HDL-C. The increase in HDL-C is associated with an increase in apolipoprotein A-I (Apo A-I) and a shift in the distribution of HDL subfractions. These shifts include an increase in the HDL2:HDL3 ratio, and an elevation in lipoprotein A-I (Lp A-I, an HDL-C particle containing only Apo A-I). The mechanism by which niacin alters lipid profiles is not completely understood and may involve several actions, including partial inhibition of release of free fatty acids from adipose tissue, and increased lipoprotein lipase activity (which may increase the rate of chylomicron triglyceride removal from plasma). Niacin decreases the rate of hepatic synthesis of VLDL-C and LDL-C, and does not appear to affect fecal excretion of fats, sterols, or bile acids. As an adjunct to diet, the efficacy of niacin and lovastatin in improving lipid profiles (either individually, or in combination with each other, or niacin in combination with other statins) for the treatment of dyslipidemia has been well documented. The effect of combined therapy with niacin and lovastatin on cardiovascular morbidity and mortality has not been determined. In addition, preliminary reports suggest that niacin causes favorable LDL particle size transformations, although the clinical relevance of this effect is not yet clear. April 15, 2016: Based on several large cardiovascular outcome trials including AIM-HIGH, ACCORD, and HPS2-THRIVE, the FDA decided that "scientific evidence no longer supports the conclusion that a drug-induced reduction in triglyceride levels and/or increase in HDL-cholesterol levels in statin-treated patients results in a reduction in the risk of cardiovascular events" Consistent with this conclusion, the FDA has determined that the benefits of niacin ER tablets for coadministration with statins no longer outweigh the risks, and the approval for this indication should be withdrawn.

CNS Activity

Curator's Comment: Niacin penetration into CSF and the extracellular space of brain from plasma as well as regulation of entry into brain cells by a saturable accumulation system are two distinct parts of the homeostatic system. In vivo, niacin that enters the central nervous system is converted to the principal plasma vitamer, niacinamide, in its free or bound forms such as NAD.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
NIASPAN

Approved Use

To reduce the risk of recurrent nonfatal myocardial infarction in patients with a history of myocardial infarction and hyperlipidemia.

Launch Date

1997
Palliative
NIASPAN

Approved Use

In combination with a bile acid binding resin slows progression or promotes regression of atherosclerotic disease in patients with a history of coronary artery disease (CAD) and hyperlipidemia.

Launch Date

1997
Primary
NIASPAN

Approved Use

NIASPAN contains extended-release niacin (nicotinic acid), and is indicated to reduce elevated TC, LDL-C, Apo B and TG, and to increase HDL-C in patients with primary hyperlipidemia and mixed dyslipidemia.

Launch Date

1997
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
5.39 μg/mL
2000 mg single, oral
dose: 2000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
NIACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1150 μg × min/mL
2000 mg single, oral
dose: 2000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
NIACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
30 min
2000 mg single, oral
dose: 2000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
NIACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [Ki 114 uM]
yes [Ki 19 uM]
yes [Ki 237 uM]
yes [Ki 44 uM]
yes [Ki 541 uM]
Drug as victim
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Structural investigation of the biosynthesis of alternative lower ligands for cobamides by nicotinate mononucleotide: 5,6-dimethylbenzimidazole phosphoribosyltransferase from Salmonella enterica.
2001-10-05
An animal model of nicotinic-acid-induced vasodilation: effect of haloperidol, caffeine and nicotine upon nicotinic acid response.
2001-07-01
H+-ATPase-mediated cytoplasmic pH-responses associated with elevation of cytoplasmic calcium in cultured rabbit nonpigmented ciliary epithelium.
2001-07-01
Use of vitamin supplements and cataract: the Blue Mountains Eye Study.
2001-07
Use of nicotinic acid in the management of recurrent hypoglycemic episodes in diabetes.
2001-07
Complex intracellular messenger pathways regulate one type of neuronal alpha-bungarotoxin-resistant nicotinic acetylcholine receptors expressed in insect neurosecretory cells (dorsal unpaired median neurons).
2001-07
Neural regulation of in vitro giant contractions in the rat colon.
2001-07
Role of calcium channels in the spinal transmission of nociceptive information from the mesentery.
2001-07
Parathyroid cells express dihydropyridine-sensitive cation currents and L-type calcium channel subunits.
2001-07
Hypoxia-induced upregulation of eNOS gene expression is redox-sensitive: a comparison between hypoxia and inhibitors of cell metabolism.
2001-07
Voltage-activated Ca2+ channels and ionotropic GABA receptors localized at axon terminals of mammalian retinal bipolar cells.
2001-06-22
Determination of niacin in infant formula by solid-phase extraction and anion-exchange liquid chromatography.
2001-06-22
Hormonal regulation of the human ghrelin receptor gene transcription.
2001-06-15
5-Hydroxytryptamine stimulates net Ca2+ flux in the ventricular muscle of a mollusc (Busycon canaliculatum) during cardioexcitation.
2001-06
Does the condition of the mouth and teeth affect the ability to eat certain foods, nutrient and dietary intake and nutritional status amongst older people?
2001-06
[Energy and nutrient intake in compulsory high school students].
2001-06
Adsorption and degradation of thiazopyr in compost-amended and non-amended soils.
2001-06
Randomized clinical trials and recent patterns in the use of statins.
2001-06
Choice of lipid-regulating drugs.
2001-05-28
Angiotensin II priming of aldosterone secretion with agents that enhance Ca(2+) influx.
2001-05-25
Niacin in patients with diabetes mellitus and coronary artery disease.
2001-05-01
Calcium buffering of resting, voltage-dependent Ca2+ influx by sarcoplasmic reticulum in femoral arteries from spontaneously hypertensive rats at prehypertensive stage.
2001-05
Determination by capillary electrophoresis of total and available niacin in different development stage of raw and processed legumes: comparison with high-performance liquid chromatography.
2001-05
The application of capillary electrophoresis to the analysis of vitamins in food and beverages.
2001-05
Determination of additives in food by capillary electrophoresis.
2001-05
Vitamin and mineral supplement use by healthy teenagers in Korea: motivating factors and dietary consequences.
2001-05
Contents of vitamins, mineral elements, and some phenolic compounds in cultivated mushrooms.
2001-05
(C-rac-5,5,7,12,12,14-Hexamethyl-1,4,8,11-tetraazacyclotetradecane-kappa4N)(nicotinato-O,O')nickel(II) perchlorate.
2001-05
Poor adherence with hypolipidemic drugs: a lost opportunity.
2001-05
New recommendations from the 1999 American College of Cardiology/American Heart Association acute myocardial infarction guidelines.
2001-05
The bio operon on the acquired symbiosis island of Mesorhizobium sp. strain R7A includes a novel gene involved in pimeloyl-CoA synthesis.
2001-05
Ion interaction reagent reversed-phase high-performance liquid chromatography determination of anti-tuberculosis drugs and metabolites in biological fluids.
2001-04-25
Pharmacology of H 394/84, a dihydropyridine neuropeptide Y Y(1) receptor antagonist, in vivo.
2001-04-20
A new niacin. Vitamin with an HDL kick.
2001-04-16
[Cardiology 2000].
2001-04-12
Lack of association between schizophrenia and the phospholipase-A(2) genes cPLA2 and sPLA2.
2001-04-08
Homocysteine elevation with fibrates: is it a class effect?
2001-04
Do breastfed infants need supplemental vitamins?
2001-04
Utility of PCR assays for rapid diagnosis of BCG infection in children.
2001-04
L-type calcium currents in atrial myocytes from patients with persistent and non-persistent atrial fibrillation.
2001-04
Adsorption of imidazolinone herbicides on ferrihydrite-humic acid associations.
2001-03
Interaction of imidazolinone herbicides with soil humic acids. Experimental results and molecular modeling.
2001-03
Relationships between dietary intake and cognitive function level in Korean elderly people.
2001-03
[Nicotinic acid and the derivative].
2001-03
[Drug combination therapies for patients with hyperlipidemia and its significance].
2001-03
Lipids and atherosclerosis: clinical management of hypercholesterolaemia.
2001-03
Nutritional status of vitamin A, E, C, B1, B2, B6, nicotinic acid, B12, folate, and beta-carotene in young women.
2001-02
The relationship among dental status, nutrient intake, and nutritional status in older people.
2001-02
Advancing our knowledge in biochemistry, genetics, and microbiology through studies on tryptophan metabolism.
2001
Biliary lipid composition during treatment with different hypolipidaemic drugs.
1979-06
Patents

Sample Use Guides

Patients not currently on NIASPAN must start ADVICOR at the lowest initial ADVICOR dose, a single 500 mg/20 mg tablet once daily at bedtime. The dose of ADVICOR should not be increased by more than 500 mg daily (based on the NIASPAN component) every 4 weeks. The dose of ADVICOR should be individualized based on targeted goals for cholesterol and triglycerides, and on patient response. Doses of ADVICOR greater than 2000 mg/40 mg daily are not recommended.
Route of Administration: Oral
HepG2 cells were preincubated for 48 hours with varying concentrations of niacin (0 to 3.0 mmol/L) in DMEM containing 10% FBS media. Incubation of HepG2 cells with niacin significantly inhibited (by 12% to 15%) fatty acid esterification to produce TG as assessed by the incorporation of 3H-oleic acid into TG. 14C-acetate incorporation into cholesterol and phospholipids was unchanged. The activity of microsomal triglyceride transfer protein MTP), a carrier protein for lipids, was not altered by pretreatment of cells with niacin.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:32:12 GMT 2025
Edited
by admin
on Mon Mar 31 18:32:12 GMT 2025
Record UNII
2679MF687A
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Nicotinic acid
EMA EPAR   EP   INN   MART.   MI   VANDF   WHO-DD   WHO-IP  
INN  
Preferred Name English
Niacin
FCC   HSDB   INCI   ORANGE BOOK   USP   USP-RS   VANDF  
INCI  
Official Name English
ADVICOR COMPONENT NIACIN
Common Name English
WAMPOCAP
Brand Name English
VITAMIN B3 [VANDF]
Common Name English
3-PYRIDINECARBOXYLIC ACID
Systematic Name English
NICOTINIC ACID [MI]
Common Name English
SIMCOR COMPONENT NIACIN
Common Name English
NIACIN [USP MONOGRAPH]
Common Name English
METHYL NICOTINATE IMPURITY A [EP IMPURITY]
Common Name English
NICOTINIC ACID [EMA EPAR]
Common Name English
NSC-169454
Code English
nicotinic acid [INN]
Common Name English
NICOTINIC ACID [EP MONOGRAPH]
Common Name English
NICOTINIC ACID [MART.]
Common Name English
NIACIN [ORANGE BOOK]
Common Name English
NICOLAR
Brand Name English
ACIDUM NICOTINICUM [WHO-IP LATIN]
Common Name English
NICOTINIC ACID [WHO-IP]
Common Name English
NIACIN [HSDB]
Common Name English
NIACIN [FCC]
Common Name English
NICOTINIC ACID [JAN]
Common Name English
NIACIN [VANDF]
Common Name English
NIACIN [USP-RS]
Common Name English
Nicotinic acid [WHO-DD]
Common Name English
VITAMIN B3
VANDF  
Common Name English
NIASPAN
Brand Name English
NICOTINIC ACID [EP IMPURITY]
Common Name English
NICOTINIC ACID [VANDF]
Common Name English
NIACOR
Brand Name English
NIACIN EXTENDED RELEASE
Common Name English
VITAMIN B-3
Systematic Name English
Classification Tree Code System Code
WHO-VATC QC10AD52
Created by admin on Mon Mar 31 18:32:12 GMT 2025 , Edited by admin on Mon Mar 31 18:32:12 GMT 2025
LIVERTOX NBK548176
Created by admin on Mon Mar 31 18:32:12 GMT 2025 , Edited by admin on Mon Mar 31 18:32:12 GMT 2025
LIVERTOX NBK548710
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NDF-RT N0000175594
Created by admin on Mon Mar 31 18:32:12 GMT 2025 , Edited by admin on Mon Mar 31 18:32:12 GMT 2025
WHO-VATC QC04AC01
Created by admin on Mon Mar 31 18:32:12 GMT 2025 , Edited by admin on Mon Mar 31 18:32:12 GMT 2025
CFR 21 CFR 184.1530
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LOINC 10836-5
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EPA PESTICIDE CODE 56701
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WHO-VATC QC10AD02
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DSLD 2544 (Number of products:3520)
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NDF-RT N0000007641
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WHO-ATC C10AD52
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LOINC 34342-6
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WHO-VATC QC10BA01
Created by admin on Mon Mar 31 18:32:12 GMT 2025 , Edited by admin on Mon Mar 31 18:32:12 GMT 2025
DSLD 1570 (Number of products:100)
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NCI_THESAURUS C45812
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WHO-ATC C10BA01
Created by admin on Mon Mar 31 18:32:12 GMT 2025 , Edited by admin on Mon Mar 31 18:32:12 GMT 2025
CFR 21 CFR 102.23
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NDF-RT N0000007641
Created by admin on Mon Mar 31 18:32:12 GMT 2025 , Edited by admin on Mon Mar 31 18:32:12 GMT 2025
LOINC 18244-4
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LOINC 2656-7
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WHO-ATC C04AC01
Created by admin on Mon Mar 31 18:32:12 GMT 2025 , Edited by admin on Mon Mar 31 18:32:12 GMT 2025
DSLD 204 (Number of products:661)
Created by admin on Mon Mar 31 18:32:12 GMT 2025 , Edited by admin on Mon Mar 31 18:32:12 GMT 2025
WHO-ATC C10AD02
Created by admin on Mon Mar 31 18:32:12 GMT 2025 , Edited by admin on Mon Mar 31 18:32:12 GMT 2025
LOINC 79402-4
Created by admin on Mon Mar 31 18:32:12 GMT 2025 , Edited by admin on Mon Mar 31 18:32:12 GMT 2025
Code System Code Type Description
DRUG CENTRAL
2835
Created by admin on Mon Mar 31 18:32:12 GMT 2025 , Edited by admin on Mon Mar 31 18:32:12 GMT 2025
PRIMARY
NCI_THESAURUS
C689
Created by admin on Mon Mar 31 18:32:12 GMT 2025 , Edited by admin on Mon Mar 31 18:32:12 GMT 2025
PRIMARY
MESH
D009525
Created by admin on Mon Mar 31 18:32:12 GMT 2025 , Edited by admin on Mon Mar 31 18:32:12 GMT 2025
PRIMARY
ChEMBL
CHEMBL573
Created by admin on Mon Mar 31 18:32:12 GMT 2025 , Edited by admin on Mon Mar 31 18:32:12 GMT 2025
PRIMARY
EVMPD
SUB09247MIG
Created by admin on Mon Mar 31 18:32:12 GMT 2025 , Edited by admin on Mon Mar 31 18:32:12 GMT 2025
PRIMARY
MERCK INDEX
m7880
Created by admin on Mon Mar 31 18:32:12 GMT 2025 , Edited by admin on Mon Mar 31 18:32:12 GMT 2025
PRIMARY Merck Index
WIKIPEDIA
NIACIN
Created by admin on Mon Mar 31 18:32:12 GMT 2025 , Edited by admin on Mon Mar 31 18:32:12 GMT 2025
PRIMARY
CHEBI
176839
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PRIMARY
PUBCHEM
938
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PRIMARY
FDA UNII
2679MF687A
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PRIMARY
CHEBI
17154
Created by admin on Mon Mar 31 18:32:12 GMT 2025 , Edited by admin on Mon Mar 31 18:32:12 GMT 2025
PRIMARY
EPA CompTox
DTXSID1020932
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PRIMARY
CHEBI
15940
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PRIMARY
RS_ITEM_NUM
1461003
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PRIMARY
SMS_ID
100000092214
Created by admin on Mon Mar 31 18:32:12 GMT 2025 , Edited by admin on Mon Mar 31 18:32:12 GMT 2025
PRIMARY
ECHA (EC/EINECS)
200-441-0
Created by admin on Mon Mar 31 18:32:12 GMT 2025 , Edited by admin on Mon Mar 31 18:32:12 GMT 2025
PRIMARY
NSC
169454
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PRIMARY
INN
373
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PRIMARY
HSDB
3134
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PRIMARY
DRUG BANK
DB00627
Created by admin on Mon Mar 31 18:32:12 GMT 2025 , Edited by admin on Mon Mar 31 18:32:12 GMT 2025
PRIMARY
RXCUI
7393
Created by admin on Mon Mar 31 18:32:12 GMT 2025 , Edited by admin on Mon Mar 31 18:32:12 GMT 2025
PRIMARY RxNorm
WHO INTERNATIONAL PHARMACOPEIA
NIACIN
Created by admin on Mon Mar 31 18:32:12 GMT 2025 , Edited by admin on Mon Mar 31 18:32:12 GMT 2025
PRIMARY Description: Colourless crystals or a white, crystalline powder; odourless or almost odourless. Solubility: Sparingly soluble in water; freely soluble in boiling water; soluble in 100 parts of ethanol (~750 g/l) TS; practicallyinsoluble in ether R. Category: Component of vitamin B complex; vasodilator. Storage: Nicotinic acid should be kept in a well-closed container, protected from light. Definition: Nicotinic acid contains not less than 99.0% and not more than 101.0% of C6H5NO2, calculated with reference to thedried substance.
CAS
59-67-6
Created by admin on Mon Mar 31 18:32:12 GMT 2025 , Edited by admin on Mon Mar 31 18:32:12 GMT 2025
PRIMARY
DAILYMED
2679MF687A
Created by admin on Mon Mar 31 18:32:12 GMT 2025 , Edited by admin on Mon Mar 31 18:32:12 GMT 2025
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
EXCRETED UNCHANGED
URINE
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
PARENT -> CONSTITUENT ALWAYS PRESENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
TARGET -> AGONIST
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METABOLITE -> PARENT
METABOLITE -> PARENT
administered niacin dose was recovered in urine as niacin metabolites, NUA, N-methylnicotinamide (MNA), and N-methyl-2-pyridone-5-carboxamide (2PY), respectively.
MAJOR
URINE
METABOLITE -> PARENT
Oral administration of niacin (2 g of extended released form), the urine recovery of niacin and metabolites accounted for 69.5% of the administered dose
URINE
METABOLITE TOXIC -> PARENT
Promotes vascular inflammation and contributes to cardiovascular disease risk.
METABOLITE -> PARENT
Oral administration of niacin (2 g of extended released form), the urine recovery of niacin and metabolites accounted for 69.5% of the administered dose.
MAJOR
URINE
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PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC Elimination
PHARMACOKINETIC