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

Details

Stereochemistry ACHIRAL
Molecular Formula C6H6N2O
Molecular Weight 122.1249
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NIACINAMIDE

SMILES

c1cc(cnc1)C(=N)O

InChI

InChIKey=DFPAKSUCGFBDDF-UHFFFAOYSA-N
InChI=1S/C6H6N2O/c7-6(9)5-2-1-3-8-4-5/h1-4H,(H2,7,9)

HIDE SMILES / InChI

Description
Curator's Comment:: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/4244068

Niacinamide, known as nicotinamide, is an important compound functioning as a component of the coenzyme NAD. Its primary significance is in the prevention and/or cure of blacktongue and pellagra. Pellagra is a nutritional disease that occurs due to insufficient dietary amounts of vitamin B3 or the chemical it is made from (tryptophan). Symptoms of pellagra include skin disease, diarrhea, dementia, and depression. In addition, was experiments, revealed, that niacinamide hydroiodide might have role in ophthalmology and parenteral use of niacinamide hydroiodide can treat arteriosclerotic syndromes.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
11.0 µM [IC50]
100.0 µM [IC50]
14.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Preventing
Niacinamide

Approved Use

Treatment and prevention of niacin deficiency, and certain conditions related to niacin deficiency such as pellagra.
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
213.2 ng/mL
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered: LOVASTATIN
NIACINAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
2669 ng × h/mL
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered: LOVASTATIN
NIACINAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
15.9 h
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered: LOVASTATIN
NIACINAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
6 g single, oral
Highest studied dose
Dose: 6 g
Route: oral
Route: single
Dose: 6 g
Sources: Page: p.136
healthy, 27-45
n = 6
Health Status: healthy
Age Group: 27-45
Sex: M
Population Size: 6
Sources: Page: p.136
Other AEs: Vomiting...
Other AEs:
Vomiting
Sources: Page: p.136
80 mg/kg 1 times / day multiple, oral
MTD
Dose: 80 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 80 mg/kg, 1 times / day
Sources: Page: p.69
unhealthy, 41-82
n = 40
Health Status: unhealthy
Condition: Head and neck cancer
Age Group: 41-82
Sex: M+F
Population Size: 40
Sources: Page: p.69
DLT: Nausea...
Disc. AE: Nausea, Toxicity renal...
Dose limiting toxicities:
Nausea (severe, 17.5%)
AEs leading to
discontinuation/dose reduction:
Nausea (20%)
Toxicity renal (2.5%)
Sources: Page: p.69
80 mg/kg 1 times / day multiple, oral
MTD
Dose: 80 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 80 mg/kg, 1 times / day
Sources: Page: p.1116
unhealthy, 54-81
n = 7
Health Status: unhealthy
Condition: Head and neck cancer
Age Group: 54-81
Sex: M+F
Population Size: 7
Sources: Page: p.1116
100 mg/kg 1 times / day multiple, oral
Highest studied dose
Dose: 100 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg/kg, 1 times / day
Sources: Page: p.1116
unhealthy, 75-82
n = 2
Health Status: unhealthy
Condition: Head and neck cancer
Age Group: 75-82
Sex: F
Population Size: 2
Sources: Page: p.1116
DLT: Hypotension, Oliguria...
Disc. AE: Nausea, Vomiting...
Dose limiting toxicities:
Hypotension (severe, 50%)
Oliguria (50%)
AEs leading to
discontinuation/dose reduction:
Nausea (severe, 50%)
Vomiting (severe, 50%)
Sources: Page: p.1116
AEs

AEs

AESignificanceDosePopulation
Vomiting
6 g single, oral
Highest studied dose
Dose: 6 g
Route: oral
Route: single
Dose: 6 g
Sources: Page: p.136
healthy, 27-45
n = 6
Health Status: healthy
Age Group: 27-45
Sex: M
Population Size: 6
Sources: Page: p.136
Toxicity renal 2.5%
Disc. AE
80 mg/kg 1 times / day multiple, oral
MTD
Dose: 80 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 80 mg/kg, 1 times / day
Sources: Page: p.69
unhealthy, 41-82
n = 40
Health Status: unhealthy
Condition: Head and neck cancer
Age Group: 41-82
Sex: M+F
Population Size: 40
Sources: Page: p.69
Nausea 20%
Disc. AE
80 mg/kg 1 times / day multiple, oral
MTD
Dose: 80 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 80 mg/kg, 1 times / day
Sources: Page: p.69
unhealthy, 41-82
n = 40
Health Status: unhealthy
Condition: Head and neck cancer
Age Group: 41-82
Sex: M+F
Population Size: 40
Sources: Page: p.69
Nausea severe, 17.5%
DLT
80 mg/kg 1 times / day multiple, oral
MTD
Dose: 80 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 80 mg/kg, 1 times / day
Sources: Page: p.69
unhealthy, 41-82
n = 40
Health Status: unhealthy
Condition: Head and neck cancer
Age Group: 41-82
Sex: M+F
Population Size: 40
Sources: Page: p.69
Oliguria 50%
DLT
100 mg/kg 1 times / day multiple, oral
Highest studied dose
Dose: 100 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg/kg, 1 times / day
Sources: Page: p.1116
unhealthy, 75-82
n = 2
Health Status: unhealthy
Condition: Head and neck cancer
Age Group: 75-82
Sex: F
Population Size: 2
Sources: Page: p.1116
Hypotension severe, 50%
DLT
100 mg/kg 1 times / day multiple, oral
Highest studied dose
Dose: 100 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg/kg, 1 times / day
Sources: Page: p.1116
unhealthy, 75-82
n = 2
Health Status: unhealthy
Condition: Head and neck cancer
Age Group: 75-82
Sex: F
Population Size: 2
Sources: Page: p.1116
Nausea severe, 50%
Disc. AE
100 mg/kg 1 times / day multiple, oral
Highest studied dose
Dose: 100 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg/kg, 1 times / day
Sources: Page: p.1116
unhealthy, 75-82
n = 2
Health Status: unhealthy
Condition: Head and neck cancer
Age Group: 75-82
Sex: F
Population Size: 2
Sources: Page: p.1116
Vomiting severe, 50%
Disc. AE
100 mg/kg 1 times / day multiple, oral
Highest studied dose
Dose: 100 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg/kg, 1 times / day
Sources: Page: p.1116
unhealthy, 75-82
n = 2
Health Status: unhealthy
Condition: Head and neck cancer
Age Group: 75-82
Sex: F
Population Size: 2
Sources: Page: p.1116
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer






Drug as perpetrator​

Drug as perpetrator​

Drug as victim
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Induction of oxidative stress by homocyst(e)ine impairs endothelial function.
2001
Prevention of cyclophosphamide-induced accelerated diabetes in the NOD mouse by nicotinamide or a soy protein-based infant formula.
2001
Photodynamic therapy for malignant mesothelioma: preclinical studies for optimization of treatment protocols.
2001 Apr
Improvement of tumor oxygenation by mild hyperthermia.
2001 Apr
Photodynamic therapy with hypericin in a mouse P388 tumor model: vascular effects determine the efficacy.
2001 Apr
Interligand Overhauser effects in type II dihydrofolate reductase.
2001 Apr 10
The activity of anandamide at vanilloid VR1 receptors requires facilitated transport across the cell membrane and is limited by intracellular metabolism.
2001 Apr 20
Enhanced maturation of porcine neonatal pancreatic cell clusters with growth factors fails to improve transplantation outcome.
2001 Apr 27
A leucine zipper protein of mitochondrial origin.
2001 Apr 7
Psychrophilic valine dehydrogenase of the antarctic psychrophile, Cytophaga sp. KUC-1: purification, molecular characterization and expression.
2001 Aug
Palmitoylethanolamide inhibits the expression of fatty acid amide hydrolase and enhances the anti-proliferative effect of anandamide in human breast cancer cells.
2001 Aug 15
Backbone dynamics in dihydrofolate reductase complexes: role of loop flexibility in the catalytic mechanism.
2001 Aug 21
NADPH-cytochrome P450 oxidoreductase. Structural basis for hydride and electron transfer.
2001 Aug 3
Cannabinoid receptors are absent in insects.
2001 Aug 6
Canine symmetrical lupoid onychodystrophy: a retrospective study with particular reference to management.
2001 Feb
Human platelets bind and degrade 2-arachidonoylglycerol, which activates these cells through a cannabinoid receptor.
2001 Feb
Farnesol oxidation in insects: evidence that the biosynthesis of insect juvenile hormone is mediated by a specific alcohol oxidase.
2001 Feb
Methanol solvent may cause increased apparent metabolic instability in in vitro assays.
2001 Feb
NAD+ inhibits the self-splicing of the group I intron.
2001 Feb 16
Kinetic and mechanistic properties of biotin sulfoxide reductase.
2001 Feb 6
Validation of an HPLC method for the determination of urinary and plasma levels of N1-methylnicotinamide, an endogenous marker of renal cationic transport and plasma flow.
2001 Jan
Nicotinamide-N-methyltransferase is higher in the lumbar cerebrospinal fluid of patients with Parkinson's disease.
2001 Jan 26
Molecular dynamics simulation of class 3 aldehyde dehydrogenase.
2001 Jan 30
Allosteric activation of pyruvate kinase via NAD+ in rat liver cells.
2001 Jul
Characterization of poly(ADP-ribose)polymerase from Crithidia fasciculata: enzyme inhibition by beta-lapachone.
2001 Jul
Increased plasma tryptophan in HIV-infected patients treated with pharmacologic doses of nicotinamide.
2001 Jul-Aug
Significance of interferon-gamma in coronary artery bypass surgery.
2001 Jul-Sep
[Effect of feeding with a poisonous mushroom Clitocybe acromelalga on the metabolism of tryptophan-niacin in rats].
2001 Jun
Effects of dietary pyrazinamide, an antituberculosis agent, on the metabolism of tryptophan to niacin and of tryptophan to serotonin in rats.
2001 Jun
Effect of poly(ADP-ribose) polymerase inhibitors on the ischemia-reperfusion-induced oxidative cell damage and mitochondrial metabolism in Langendorff heart perfusion system.
2001 Jun
Role of fatty acid amide hydrolase in the transport of the endogenous cannabinoid anandamide.
2001 Jun
Characterization of multicomponent monosaccharide solutions using an enzyme-based sensor array.
2001 Jun 15
Progesterone up-regulates anandamide hydrolase in human lymphocytes: role of cytokines and implications for fertility.
2001 Jun 15
alpha-Keto heterocycle inhibitors of fatty acid amide hydrolase: carbonyl group modification and alpha-substitution.
2001 Jun 18
Evolution of the aldose reductase-related gecko eye lens protein rhoB-crystallin: a sheep in wolf's clothing.
2001 Mar
Effects of nicotinamide, an inhibitor of PARS activity, on gut and liver O2 exchange and energy metabolism during hyperdynamic porcine endotoxemia.
2001 Mar
Characterization of secretory and morphologic properties of primary cultured endocrine cells from porcine pancreata.
2001 Mar
The neurobiology and evolution of cannabinoid signalling.
2001 Mar 29
Characterization of recombinant human nicotinamide mononucleotide adenylyl transferase (NMNAT), a nuclear enzyme essential for NAD synthesis.
2001 Mar 9
Purification and structure of the major product obtained by reaction of NADPH and NMNH with the myeloperoxidase/hydrogen peroxide/chloride system.
2001 May
Effects of the interaction between carbogen and nicotinamide on R3230 Ac tumor blood flow in Fischer 344 rats.
2001 May
Antinociceptive activity of the endogenous fatty acid amide, palmitylethanolamide.
2001 May 11
Characterization of the hydroxypropylmethylcellulose-nicotinamide binary system.
2001 May 21
The structure of Escherichia coli nitroreductase complexed with nicotinic acid: three crystal forms at 1.7 A, 1.8 A and 2.4 A resolution.
2001 May 25
Molecularly imprinted polymers from nicotinamide and its positional isomers.
2001 May-Jun
Behavioral evidence for the interaction of oleamide with multiple neurotransmitter systems.
2001 Oct
Fatty acid amide hydrolase: biochemistry, pharmacology, and therapeutic possibilities for an enzyme hydrolyzing anandamide, 2-arachidonoylglycerol, palmitoylethanolamide, and oleamide.
2001 Sep 1
Effect of nicotinamide on the properties of aqueous HPMC solutions.
2001 Sep 11
13C NMR analysis of electrostatic interactions between NAD+ and active site residues of UDP-galactose 4-epimerase: implications for the activation induced by uridine nucleotides.
2001 Sep 18
Mycobacterium tuberculosis lipoamide dehydrogenase is encoded by Rv0462 and not by the lpdA or lpdB genes.
2001 Sep 25
Patents

Sample Use Guides

For mild vitamin B3 deficiency, niacin or niacinamide 50-100 mg per day is used. For pellagra in adults, niacin or niacinamide 300-500 mg daily is given in divided doses. For pellagra in children, niacin or niacinamide 100-300 mg daily is given in divided doses. For Hartnup disease, niacin or niacinamide 50-200 mg daily.
Route of Administration: Oral
10 mM Niacinamide inhibited Resveratrol-mediated ROS suppression in B16F1 melanoma cells
Name Type Language
NIACINAMIDE
FCC   HSDB   II   INCI   ORANGE BOOK   USP   USP-RS   VANDF  
INCI  
Official Name English
TPN COMPONENT NIACINAMIDE
Common Name English
NIACINAMIDE [HSDB]
Common Name English
NIACIN (AS NIACINAMIDE) [VANDF]
Common Name English
NICOTINAMIDE
EP   INN   MART.   MI   WHO-DD   WHO-IP  
INN  
Official Name English
NSC-13128
Code English
NICOTINAMIDUM
HPUS   WHO-IP LATIN  
Common Name English
NICOTINAMIDE [INN]
Common Name English
NICOTINAMIDE [EP MONOGRAPH]
Common Name English
NICOTINAMIDE [EP]
Common Name English
NICOTINAMIDE [WHO-DD]
Common Name English
NICOTINAMIDE [WHO-IP]
Common Name English
NIACINAMID
Common Name English
NICOTINAMIDE [MART.]
Common Name English
NIACINAMIDE COMPONENT OF TPN
Common Name English
NIACINAMIDE [INCI]
Common Name English
NSC-27452
Code English
NICOTINAMIDE [MI]
Common Name English
NIACINAMIDE [VANDF]
Common Name English
NIACINAMIDE [II]
Common Name English
NIACINAMIDE [USP-RS]
Common Name English
NIACINAMIDE [USP]
Common Name English
NIACINAMIDE [FCC]
Common Name English
NICOTINAMIDUM [WHO-IP LATIN]
Common Name English
NICOTINAMIDUM [HPUS]
Common Name English
NIACINAMIDE [ORANGE BOOK]
Common Name English
Classification Tree Code System Code
WHO-ATC A11HA01
Created by admin on Fri Jun 25 21:18:21 UTC 2021 , Edited by admin on Fri Jun 25 21:18:21 UTC 2021
DSLD 2664 (Number of products:4764)
Created by admin on Fri Jun 25 21:18:21 UTC 2021 , Edited by admin on Fri Jun 25 21:18:21 UTC 2021
NCI_THESAURUS C26017
Created by admin on Fri Jun 25 21:18:21 UTC 2021 , Edited by admin on Fri Jun 25 21:18:21 UTC 2021
LIVERTOX 681
Created by admin on Fri Jun 25 21:18:21 UTC 2021 , Edited by admin on Fri Jun 25 21:18:21 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 27
Created by admin on Fri Jun 25 21:18:21 UTC 2021 , Edited by admin on Fri Jun 25 21:18:21 UTC 2021
NCI_THESAURUS C275
Created by admin on Fri Jun 25 21:18:21 UTC 2021 , Edited by admin on Fri Jun 25 21:18:21 UTC 2021
DSLD 1097 (Number of products:12)
Created by admin on Fri Jun 25 21:18:21 UTC 2021 , Edited by admin on Fri Jun 25 21:18:21 UTC 2021
CFR 21 CFR 184.1535
Created by admin on Fri Jun 25 21:18:21 UTC 2021 , Edited by admin on Fri Jun 25 21:18:21 UTC 2021
DSLD 204 (Number of products:661)
Created by admin on Fri Jun 25 21:18:21 UTC 2021 , Edited by admin on Fri Jun 25 21:18:21 UTC 2021
WHO-VATC QA11HA01
Created by admin on Fri Jun 25 21:18:21 UTC 2021 , Edited by admin on Fri Jun 25 21:18:21 UTC 2021
Code System Code Type Description
ECHA (EC/EINECS)
202-713-4
Created by admin on Fri Jun 25 21:18:21 UTC 2021 , Edited by admin on Fri Jun 25 21:18:21 UTC 2021
PRIMARY
RXCUI
7405
Created by admin on Fri Jun 25 21:18:21 UTC 2021 , Edited by admin on Fri Jun 25 21:18:21 UTC 2021
PRIMARY RxNorm
HSDB
1237
Created by admin on Fri Jun 25 21:18:21 UTC 2021 , Edited by admin on Fri Jun 25 21:18:21 UTC 2021
PRIMARY
MESH
D009536
Created by admin on Fri Jun 25 21:18:21 UTC 2021 , Edited by admin on Fri Jun 25 21:18:21 UTC 2021
PRIMARY
INN
404
Created by admin on Fri Jun 25 21:18:21 UTC 2021 , Edited by admin on Fri Jun 25 21:18:21 UTC 2021
PRIMARY
PUBCHEM
936
Created by admin on Fri Jun 25 21:18:21 UTC 2021 , Edited by admin on Fri Jun 25 21:18:21 UTC 2021
PRIMARY
NCI_THESAURUS
C2327
Created by admin on Fri Jun 25 21:18:21 UTC 2021 , Edited by admin on Fri Jun 25 21:18:21 UTC 2021
PRIMARY
WIKIPEDIA
NICOTINAMIDE
Created by admin on Fri Jun 25 21:18:21 UTC 2021 , Edited by admin on Fri Jun 25 21:18:21 UTC 2021
PRIMARY
USP_CATALOG
1462006
Created by admin on Fri Jun 25 21:18:21 UTC 2021 , Edited by admin on Fri Jun 25 21:18:21 UTC 2021
PRIMARY USP-RS
CAS
98-92-0
Created by admin on Fri Jun 25 21:18:21 UTC 2021 , Edited by admin on Fri Jun 25 21:18:21 UTC 2021
PRIMARY
EPA CompTox
98-92-0
Created by admin on Fri Jun 25 21:18:21 UTC 2021 , Edited by admin on Fri Jun 25 21:18:21 UTC 2021
PRIMARY
DRUG BANK
DB02701
Created by admin on Fri Jun 25 21:18:21 UTC 2021 , Edited by admin on Fri Jun 25 21:18:21 UTC 2021
PRIMARY
DRUG CENTRAL
1906
Created by admin on Fri Jun 25 21:18:21 UTC 2021 , Edited by admin on Fri Jun 25 21:18:21 UTC 2021
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
NIACINAMIDE
Created by admin on Fri Jun 25 21:18:21 UTC 2021 , Edited by admin on Fri Jun 25 21:18:21 UTC 2021
PRIMARY Description: Colourless crystals or a white, crystalline powder; odourless or almost odourless. Solubility: Soluble in 1 part of water and 2 parts of ethanol (~750 g/l) TS; slightly soluble in ether R. Category: Vitamin. Storage: Nicotinamide should be kept in a well-closed container. Definition: Nicotinamide contains not less than 99.0% and not more than 101.0% of C6H6N2O, calculated with reference to thedried substance.
MERCK INDEX
M7878
Created by admin on Fri Jun 25 21:18:21 UTC 2021 , Edited by admin on Fri Jun 25 21:18:21 UTC 2021
PRIMARY Merck Index
FDA UNII
25X51I8RD4
Created by admin on Fri Jun 25 21:18:21 UTC 2021 , Edited by admin on Fri Jun 25 21:18:21 UTC 2021
PRIMARY
EVMPD
SUB09246MIG
Created by admin on Fri Jun 25 21:18:21 UTC 2021 , Edited by admin on Fri Jun 25 21:18:21 UTC 2021
PRIMARY
ChEMBL
CHEMBL1140
Created by admin on Fri Jun 25 21:18:21 UTC 2021 , Edited by admin on Fri Jun 25 21:18:21 UTC 2021
PRIMARY