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

Details

Stereochemistry ACHIRAL
Molecular Formula C6H6N2O
Molecular Weight 122.1246
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NIACINAMIDE

SMILES

NC(=O)C1=CN=CC=C1

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

Molecular Formula C6H6N2O
Molecular Weight 122.1246
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 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
Tetracycline and nicotinamide for the treatment of bullous pemphigoid: our experience in Singapore.
2000 Jul
Elevation of blood NAD level after moderate exercise in young women and mice.
2001 Apr
The metabolism of nicotinamide in human liver cirrhosis: a study on N-methylnicotinamide and 2-pyridone-5-carboxamide production.
2001 Apr
Interligand Overhauser effects in type II dihydrofolate reductase.
2001 Apr 10
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
Nicotinamide adenine dinucleotide (NAD) and its metabolites inhibit T lymphocyte proliferation: role of cell surface NAD glycohydrolase and pyrophosphatase activities.
2001 Aug 15
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
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
Oxidative changes in brain pyridine nucleotides and neuroprotection using nicotinamide.
2001 Feb 16
Kinetic and mechanistic properties of biotin sulfoxide reductase.
2001 Feb 6
The crystal structure of an asymmetric complex of the two nucleotide binding components of proton-translocating transhydrogenase.
2001 Feb 7
Purines inhibit poly(ADP-ribose) polymerase activation and modulate oxidant-induced cell death.
2001 Jan
The nicotinamide biosynthetic pathway is a by-product of the RNA world.
2001 Jan
Homoserine dehydrogenase from Saccharomyces cerevisiae: kinetic mechanism and stereochemistry of hydride transfer.
2001 Jan 12
The reactive oxygen species--and Michael acceptor-inducible human aldo-keto reductase AKR1C1 reduces the alpha,beta-unsaturated aldehyde 4-hydroxy-2-nonenal to 1,4-dihydroxy-2-nonene.
2001 Jan 26
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 poly(ADP-ribose) polymerase inhibitors on the ischemia-reperfusion-induced oxidative cell damage and mitochondrial metabolism in Langendorff heart perfusion system.
2001 Jun
An NMR-based metabonomic approach to the investigation of coelomic fluid biochemistry in earthworms under toxic stress.
2001 Jun 29
Probing catalysis by Escherichia coli dTDP-glucose-4,6-dehydratase: identification and preliminary characterization of functional amino acid residues at the active site.
2001 Jun 5
Effects of nicotinamide, an inhibitor of PARS activity, on gut and liver O2 exchange and energy metabolism during hyperdynamic porcine endotoxemia.
2001 Mar
ARIP cells as a model for pancreatic beta cell growth and development.
2001 Mar
Characterization of secretory and morphologic properties of primary cultured endocrine cells from porcine pancreata.
2001 Mar
[A case of pemphigus foliaceus associated with bullous impetigo successfully treated with tetracycline and nicotinamide].
2001 Mar 1
The neurobiology and evolution of cannabinoid signalling.
2001 Mar 29
Inducible protective processes in animal systems: VIII. Enhancement of adaptive response by nicotinamide.
2001 May
Effects of the interaction between carbogen and nicotinamide on R3230 Ac tumor blood flow in Fischer 344 rats.
2001 May
Fatty acid amide hydrolase inhibition by neurotoxic organophosphorus pesticides.
2001 May 15
Characterization and manipulation of the acyl chain selectivity of fatty acid amide hydrolase.
2001 May 22
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
Identification of a new class of molecules, the arachidonyl amino acids, and characterization of one member that inhibits pain.
2001 Nov 16
Fast hydride transfer in proton-translocating transhydrogenase revealed in a rapid mixing continuous flow device.
2001 Nov 30
Molecular targets for cannabidiol and its synthetic analogues: effect on vanilloid VR1 receptors and on the cellular uptake and enzymatic hydrolysis of anandamide.
2001 Oct
Contributions of valine-292 in the nicotinamide binding site of liver alcohol dehydrogenase and dynamics to catalysis.
2001 Oct 23
A dinucleotide repeat polymorphism at the poly(ADP-ribose) polymerase gene is not associated with predisposition to type 1 diabetes in French Caucasians.
2001 Sep
A possible role of lipoxygenase in the activation of vanilloid receptors by anandamide in the guinea-pig bronchus.
2001 Sep
Fatty acid amide hydrolase: biochemistry, pharmacology, and therapeutic possibilities for an enzyme hydrolyzing anandamide, 2-arachidonoylglycerol, palmitoylethanolamide, and oleamide.
2001 Sep 1
Lipopolysaccharide downregulates fatty acid amide hydrolase expression and increases anandamide levels in human peripheral lymphocytes.
2001 Sep 15
Oxidation of NADH by chloramines and chloramides and its activation by iodide and by tertiary amines.
2001 Sep 15
NAD+-dependent DNA ligase encoded by a eukaryotic virus.
2001 Sep 28
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
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:23:22 GMT 2023
Edited
by admin
on Fri Dec 15 15:23:22 GMT 2023
Record UNII
25X51I8RD4
Record Status Validated (UNII)
Record Version
  • Download
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 [JAN]
Common Name English
Nicotinamide [WHO-DD]
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
NIACINAMIDE [USP MONOGRAPH]
Common Name English
NICOTINAMIDE [EP MONOGRAPH]
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
NICOTINAMIDE [EP IMPURITY]
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 [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 Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
DSLD 2664 (Number of products:4764)
Created by admin on Fri Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
NCI_THESAURUS C26017
Created by admin on Fri Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
LIVERTOX 681
Created by admin on Fri Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
WHO-ESSENTIAL MEDICINES LIST 27
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NCI_THESAURUS C275
Created by admin on Fri Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
DSLD 1097 (Number of products:12)
Created by admin on Fri Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
CFR 21 CFR 184.1535
Created by admin on Fri Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
DSLD 204 (Number of products:661)
Created by admin on Fri Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
WHO-VATC QA11HA01
Created by admin on Fri Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
Code System Code Type Description
ECHA (EC/EINECS)
202-713-4
Created by admin on Fri Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
PRIMARY
NSC
13128
Created by admin on Fri Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
PRIMARY
RXCUI
7405
Created by admin on Fri Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
PRIMARY RxNorm
HSDB
1237
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PRIMARY
DAILYMED
25X51I8RD4
Created by admin on Fri Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
PRIMARY
MESH
D009536
Created by admin on Fri Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
PRIMARY
INN
404
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PRIMARY
NSC
27452
Created by admin on Fri Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
PRIMARY
PUBCHEM
936
Created by admin on Fri Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
PRIMARY
NCI_THESAURUS
C2327
Created by admin on Fri Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
PRIMARY
WIKIPEDIA
NICOTINAMIDE
Created by admin on Fri Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
PRIMARY
CAS
98-92-0
Created by admin on Fri Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
PRIMARY
EPA CompTox
DTXSID2020929
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PRIMARY
DRUG BANK
DB02701
Created by admin on Fri Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
PRIMARY
DRUG CENTRAL
1906
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PRIMARY
SMS_ID
100000092193
Created by admin on Fri Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
NIACINAMIDE
Created by admin on Fri Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
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 Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
PRIMARY Merck Index
RS_ITEM_NUM
1462006
Created by admin on Fri Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
PRIMARY
FDA UNII
25X51I8RD4
Created by admin on Fri Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
PRIMARY
EVMPD
SUB09246MIG
Created by admin on Fri Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
PRIMARY
CHEBI
17154
Created by admin on Fri Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
PRIMARY
ChEMBL
CHEMBL1140
Created by admin on Fri Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
NAD-dependent lysine desuccinylase activity is inhibited by physiological nicotinamide concentrations, while deacetylase activity is not.
Related Record Type Details
METABOLITE ACTIVE -> PARENT
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ACTIVE MOIETY