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=CN=CC=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

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

8.6996163E11
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

8.6996163E11
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

8.7004801E11
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
The effect of niceritrol (pentaerythritoltetranicotinate) and clofibrate upon hyperlipemia and atherosclerosis induced in rabbits by cholesterol-free semisynthetic diets.
1974 Nov-Dec
Action of niceritrol (pentaerythritoltetranicotinate) on lipid accumulation in aortas of cholesterol-fed rabbits independent of contemporary reduction of serum lipids.
1974 Nov-Dec
Cholestyramine, clofibrate and nicotinic acid as single or combined treatment of type IIa and IIb hyperlipoproteinaemia.
1975
Differential drug therapy of the hyperlipoproteinaemias. The efficacy of lipid lowering drugs alone and in combination.
1975
The effect of niceritrol (pentaerythritoltetranicotinate) on experimental atherosclerosis in cholesterol-fed rabbits at different levels of plasma cholesterol.
1975 Jan
The effects of different dose regimens of niceritrol of serum lipid concentrations in man.
1976
Biliary lipid composition during treatment with different hypolipidaemic drugs.
1979 Jun
Do breastfed infants need supplemental vitamins?
2001 Apr
Treatment of hyperlipidemia in HIV-infected patients.
2001 Apr 1
Niacin, poly(ADP-ribose) polymerase-1 and genomic stability.
2001 Apr 18
Ion interaction reagent reversed-phase high-performance liquid chromatography determination of anti-tuberculosis drugs and metabolites in biological fluids.
2001 Apr 25
Perchlorate stimulates insulin secretion by shifting the gating of L-type Ca2+ currents in mouse pancreatic B-cells towards negative potentials.
2001 Feb
Etofibrate but not controlled-release niacin decreases LDL cholesterol and lipoprotein (a) in type IIb dyslipidemic subjects.
2001 Feb
Common hepatic lipase gene promoter variant determines clinical response to intensive lipid-lowering treatment.
2001 Feb 13
Chronic nicotine alters NO signaling of Ca(2+) channels in cerebral arterioles.
2001 Feb 16
Differential effects of agonists of aldosterone secretion on steroidogenic acute regulatory phosphorylation.
2001 Feb 28
Effects of nicotinamide coenzymes on the stability of enzyme activities and proteins in niacin-deficient quail tissues against trypsin treatment.
2001 Jan
[The role of HDL in the prevention of cardiovascular events].
2001 Jan 21
Downregulation of the voltage-dependent calcium channel (VDCC) beta-subunit mRNAs in pancreatic islets of type 2 diabetic rats.
2001 Jan 26
Use of vitamin supplements and cataract: the Blue Mountains Eye Study.
2001 Jul
Neural regulation of in vitro giant contractions in the rat colon.
2001 Jul
Role of calcium channels in the spinal transmission of nociceptive information from the mesentery.
2001 Jul
Parathyroid cells express dihydropyridine-sensitive cation currents and L-type calcium channel subunits.
2001 Jul
An animal model of nicotinic-acid-induced vasodilation: effect of haloperidol, caffeine and nicotine upon nicotinic acid response.
2001 Jul 1
H+-ATPase-mediated cytoplasmic pH-responses associated with elevation of cytoplasmic calcium in cultured rabbit nonpigmented ciliary epithelium.
2001 Jul 1
5-Hydroxytryptamine stimulates net Ca2+ flux in the ventricular muscle of a mollusc (Busycon canaliculatum) during cardioexcitation.
2001 Jun
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 Jun
[Energy and nutrient intake in compulsory high school students].
2001 Jun
Adsorption and degradation of thiazopyr in compost-amended and non-amended soils.
2001 Jun
Randomized clinical trials and recent patterns in the use of statins.
2001 Jun
Hormonal regulation of the human ghrelin receptor gene transcription.
2001 Jun 15
Adsorption of imidazolinone herbicides on ferrihydrite-humic acid associations.
2001 Mar
[Nicotinic acid and the derivative].
2001 Mar
[Drug combination therapies for patients with hyperlipidemia and its significance].
2001 Mar
Disturbance of peristalsis in the guinea-pig isolated small intestine by indomethacin, but not cyclo-oxygenase isoform-selective inhibitors.
2001 Mar
Mechanism of CGRP-induced relaxation in rat intramural coronary arteries.
2001 Mar
The effects of gabapentin on different ligand- and voltage-gated currents in isolated cortical neurons.
2001 Mar
Pellagra in 2 homeless men.
2001 Mar
Regulation of Ca2+-sensitive adenylyl cyclase in gonadotropin-releasing hormone neurons.
2001 Mar
Novel approaches to lipid lowering: what is on the horizon?
2001 Mar 8
[Mycobacterium xenopi: epidemiological and bacteriological features].
2001 Mar-Apr
Vitamin and mineral supplement use by healthy teenagers in Korea: motivating factors and dietary consequences.
2001 May
(C-rac-5,5,7,12,12,14-Hexamethyl-1,4,8,11-tetraazacyclotetradecane-kappa4N)(nicotinato-O,O')nickel(II) perchlorate.
2001 May
New recommendations from the 1999 American College of Cardiology/American Heart Association acute myocardial infarction guidelines.
2001 May
Sites and ionic mechanisms of hypoxic vasoconstriction in frog skin.
2001 May
Effects of dextromethorphan on the seizures induced by kainate and the calcium channel agonist BAY k-8644: comparison with the effects of dextrorphan.
2001 May
Angiotensin II priming of aldosterone secretion with agents that enhance Ca(2+) influx.
2001 May 25
Determination of niacin in infant formula by solid-phase extraction and anion-exchange liquid chromatography.
2001 May-Jun
Structural investigation of the biosynthesis of alternative lower ligands for cobamides by nicotinate mononucleotide: 5,6-dimethylbenzimidazole phosphoribosyltransferase from Salmonella enterica.
2001 Oct 5
Methylnicotinate stimulated prostaglandin synthesis in patients with schizophrenia: A preliminary investigation.
2018 Sep
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.
Name Type Language
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
Nicotinic acid
EMA EPAR   EP   INN   MART.   MI   VANDF   WHO-DD   WHO-IP  
INN  
Official 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 COMPONENT OF ADVICOR
Common Name English
NIACIN [INCI]
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
NIACIN COMPONENT OF SIMCOR
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 Thu Jul 06 00:01:10 UTC 2023 , Edited by admin on Thu Jul 06 00:01:10 UTC 2023
LIVERTOX NBK548176
Created by admin on Thu Jul 06 00:01:10 UTC 2023 , Edited by admin on Thu Jul 06 00:01:10 UTC 2023
LIVERTOX NBK548710
Created by admin on Thu Jul 06 00:01:10 UTC 2023 , Edited by admin on Thu Jul 06 00:01:10 UTC 2023
NDF-RT N0000175594
Created by admin on Thu Jul 06 00:01:10 UTC 2023 , Edited by admin on Thu Jul 06 00:01:10 UTC 2023
WHO-VATC QC04AC01
Created by admin on Thu Jul 06 00:01:10 UTC 2023 , Edited by admin on Thu Jul 06 00:01:10 UTC 2023
CFR 21 CFR 184.1530
Created by admin on Thu Jul 06 00:01:10 UTC 2023 , Edited by admin on Thu Jul 06 00:01:10 UTC 2023
LOINC 10836-5
Created by admin on Thu Jul 06 00:01:10 UTC 2023 , Edited by admin on Thu Jul 06 00:01:10 UTC 2023
EPA PESTICIDE CODE 56701
Created by admin on Thu Jul 06 00:01:10 UTC 2023 , Edited by admin on Thu Jul 06 00:01:10 UTC 2023
WHO-VATC QC10AD02
Created by admin on Thu Jul 06 00:01:10 UTC 2023 , Edited by admin on Thu Jul 06 00:01:10 UTC 2023
DSLD 2544 (Number of products:3520)
Created by admin on Thu Jul 06 00:01:10 UTC 2023 , Edited by admin on Thu Jul 06 00:01:10 UTC 2023
NDF-RT N0000007641
Created by admin on Thu Jul 06 00:01:10 UTC 2023 , Edited by admin on Thu Jul 06 00:01:10 UTC 2023
WHO-ATC C10AD52
Created by admin on Thu Jul 06 00:01:10 UTC 2023 , Edited by admin on Thu Jul 06 00:01:10 UTC 2023
LOINC 34342-6
Created by admin on Thu Jul 06 00:01:10 UTC 2023 , Edited by admin on Thu Jul 06 00:01:10 UTC 2023
WHO-VATC QC10BA01
Created by admin on Thu Jul 06 00:01:10 UTC 2023 , Edited by admin on Thu Jul 06 00:01:10 UTC 2023
DSLD 1570 (Number of products:100)
Created by admin on Thu Jul 06 00:01:10 UTC 2023 , Edited by admin on Thu Jul 06 00:01:10 UTC 2023
NCI_THESAURUS C45812
Created by admin on Thu Jul 06 00:01:10 UTC 2023 , Edited by admin on Thu Jul 06 00:01:10 UTC 2023
WHO-ATC C10BA01
Created by admin on Thu Jul 06 00:01:10 UTC 2023 , Edited by admin on Thu Jul 06 00:01:10 UTC 2023
CFR 21 CFR 102.23
Created by admin on Thu Jul 06 00:01:10 UTC 2023 , Edited by admin on Thu Jul 06 00:01:10 UTC 2023
NDF-RT N0000007641
Created by admin on Thu Jul 06 00:01:10 UTC 2023 , Edited by admin on Thu Jul 06 00:01:10 UTC 2023
LOINC 18244-4
Created by admin on Thu Jul 06 00:01:10 UTC 2023 , Edited by admin on Thu Jul 06 00:01:10 UTC 2023
LOINC 2656-7
Created by admin on Thu Jul 06 00:01:10 UTC 2023 , Edited by admin on Thu Jul 06 00:01:10 UTC 2023
WHO-ATC C04AC01
Created by admin on Thu Jul 06 00:01:10 UTC 2023 , Edited by admin on Thu Jul 06 00:01:10 UTC 2023
DSLD 204 (Number of products:661)
Created by admin on Thu Jul 06 00:01:10 UTC 2023 , Edited by admin on Thu Jul 06 00:01:10 UTC 2023
WHO-ATC C10AD02
Created by admin on Thu Jul 06 00:01:10 UTC 2023 , Edited by admin on Thu Jul 06 00:01:10 UTC 2023
LOINC 79402-4
Created by admin on Thu Jul 06 00:01:10 UTC 2023 , Edited by admin on Thu Jul 06 00:01:10 UTC 2023
Code System Code Type Description
DRUG CENTRAL
2835
Created by admin on Thu Jul 06 00:01:10 UTC 2023 , Edited by admin on Thu Jul 06 00:01:10 UTC 2023
PRIMARY
NCI_THESAURUS
C689
Created by admin on Thu Jul 06 00:01:10 UTC 2023 , Edited by admin on Thu Jul 06 00:01:10 UTC 2023
PRIMARY
MESH
D009525
Created by admin on Thu Jul 06 00:01:10 UTC 2023 , Edited by admin on Thu Jul 06 00:01:10 UTC 2023
PRIMARY
ChEMBL
CHEMBL573
Created by admin on Thu Jul 06 00:01:10 UTC 2023 , Edited by admin on Thu Jul 06 00:01:10 UTC 2023
PRIMARY
EVMPD
SUB09247MIG
Created by admin on Thu Jul 06 00:01:10 UTC 2023 , Edited by admin on Thu Jul 06 00:01:10 UTC 2023
PRIMARY
MERCK INDEX
M7880
Created by admin on Thu Jul 06 00:01:10 UTC 2023 , Edited by admin on Thu Jul 06 00:01:10 UTC 2023
PRIMARY Merck Index
WIKIPEDIA
NIACIN
Created by admin on Thu Jul 06 00:01:10 UTC 2023 , Edited by admin on Thu Jul 06 00:01:10 UTC 2023
PRIMARY
CHEBI
176839
Created by admin on Thu Jul 06 00:01:10 UTC 2023 , Edited by admin on Thu Jul 06 00:01:10 UTC 2023
PRIMARY
PUBCHEM
938
Created by admin on Thu Jul 06 00:01:10 UTC 2023 , Edited by admin on Thu Jul 06 00:01:10 UTC 2023
PRIMARY
FDA UNII
2679MF687A
Created by admin on Thu Jul 06 00:01:10 UTC 2023 , Edited by admin on Thu Jul 06 00:01:10 UTC 2023
PRIMARY
CHEBI
17154
Created by admin on Thu Jul 06 00:01:10 UTC 2023 , Edited by admin on Thu Jul 06 00:01:10 UTC 2023
PRIMARY
EPA CompTox
DTXSID1020932
Created by admin on Thu Jul 06 00:01:10 UTC 2023 , Edited by admin on Thu Jul 06 00:01:10 UTC 2023
PRIMARY
CHEBI
15940
Created by admin on Thu Jul 06 00:01:10 UTC 2023 , Edited by admin on Thu Jul 06 00:01:10 UTC 2023
PRIMARY
RS_ITEM_NUM
1461003
Created by admin on Thu Jul 06 00:01:10 UTC 2023 , Edited by admin on Thu Jul 06 00:01:10 UTC 2023
PRIMARY
SMS_ID
100000092214
Created by admin on Thu Jul 06 00:01:10 UTC 2023 , Edited by admin on Thu Jul 06 00:01:10 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-441-0
Created by admin on Thu Jul 06 00:01:10 UTC 2023 , Edited by admin on Thu Jul 06 00:01:10 UTC 2023
PRIMARY
NSC
169454
Created by admin on Thu Jul 06 00:01:10 UTC 2023 , Edited by admin on Thu Jul 06 00:01:10 UTC 2023
PRIMARY
INN
373
Created by admin on Thu Jul 06 00:01:10 UTC 2023 , Edited by admin on Thu Jul 06 00:01:10 UTC 2023
PRIMARY
HSDB
3134
Created by admin on Thu Jul 06 00:01:10 UTC 2023 , Edited by admin on Thu Jul 06 00:01:10 UTC 2023
PRIMARY
DRUG BANK
DB00627
Created by admin on Thu Jul 06 00:01:10 UTC 2023 , Edited by admin on Thu Jul 06 00:01:10 UTC 2023
PRIMARY
RXCUI
7393
Created by admin on Thu Jul 06 00:01:10 UTC 2023 , Edited by admin on Thu Jul 06 00:01:10 UTC 2023
PRIMARY RxNorm
WHO INTERNATIONAL PHARMACOPEIA
NIACIN
Created by admin on Thu Jul 06 00:01:10 UTC 2023 , Edited by admin on Thu Jul 06 00:01:10 UTC 2023
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 Thu Jul 06 00:01:10 UTC 2023 , Edited by admin on Thu Jul 06 00:01:10 UTC 2023
PRIMARY
DAILYMED
2679MF687A
Created by admin on Thu Jul 06 00:01:10 UTC 2023 , Edited by admin on Thu Jul 06 00:01:10 UTC 2023
PRIMARY