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
Lessons to be learned from studying Vibrio cholerae in model systems.
2001
Update on major trials for the prevention of type 1 diabetes mellitus: the American Diabetes Prevention Trial (DPT-1) and the European Nicotinamide Diabetes Intervention Trial (ENDIT).
2001
The nitrilase superfamily: classification, structure and function.
2001
Elevation of blood NAD level after moderate exercise in young women and mice.
2001 Apr
The IL-8 release from cultured human keratinocytes, mediated by antibodies to bullous pemphigoid autoantigen 180, is inhibited by dapsone.
2001 Apr
Photodynamic therapy for malignant mesothelioma: preclinical studies for optimization of treatment protocols.
2001 Apr
Characterization of palmitoylethanolamide transport in mouse Neuro-2a neuroblastoma and rat RBL-2H3 basophilic leukaemia cells: comparison with anandamide.
2001 Apr
Enhanced maturation of porcine neonatal pancreatic cell clusters with growth factors fails to improve transplantation outcome.
2001 Apr 27
Ca(2+)-calmodulin antagonist chlorpromazine and poly(ADP-ribose) polymerase modulators 4-aminobenzamide and nicotinamide influence hepatic expression of BCL-XL and P53 and protect against acetaminophen-induced programmed and unprogrammed cell death in mice.
2001 Aug 1
NADPH-cytochrome P450 oxidoreductase. Structural basis for hydride and electron transfer.
2001 Aug 3
Cannabinoid receptors are absent in insects.
2001 Aug 6
Oxidative changes in brain pyridine nucleotides and neuroprotection using nicotinamide.
2001 Feb 16
Homoserine dehydrogenase from Saccharomyces cerevisiae: kinetic mechanism and stereochemistry of hydride transfer.
2001 Jan 12
Ternary complexes of liver alcohol dehydrogenase.
2001 Jan 30
Molecular dynamics simulation of class 3 aldehyde dehydrogenase.
2001 Jan 30
Anandamide degradation and N-acylethanolamines level in wild-type and CB1 cannabinoid receptor knockout mice of different ages.
2001 Jul
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
[Ring cleavage of N-arylpyridinium salts by nucleophiles--regioselectivity and stereochemistry of the products. 2].
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
Erythromycin biosynthesis. The 4-pro-S hydride of NADPH is utilized for ketoreduction by both module 5 and module 6 of the 6-deoxyerythronolide B synthase.
2001 Jun 18
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
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
Dietary vitamin K1 requirement and comparison of biopotency of different vitamin K sources for young turkeys.
2001 May
Purification and structure of the major product obtained by reaction of NADPH and NMNH with the myeloperoxidase/hydrogen peroxide/chloride system.
2001 May
Potential for creatine and other therapies targeting cellular energy dysfunction in neurological disorders.
2001 May
Antinociceptive activity of the endogenous fatty acid amide, palmitylethanolamide.
2001 May 11
Fatty acid amide hydrolase inhibition by neurotoxic organophosphorus pesticides.
2001 May 15
Characterization of the hydroxypropylmethylcellulose-nicotinamide binary system.
2001 May 21
Characterization and manipulation of the acyl chain selectivity of fatty acid amide hydrolase.
2001 May 22
Identification of a new class of molecules, the arachidonyl amino acids, and characterization of one member that inhibits pain.
2001 Nov 16
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
Behavioral evidence for the interaction of oleamide with multiple neurotransmitter systems.
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
Prospects for predicting and stopping the development of type 1 of diabetes.
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
Effect of nicotinamide on the properties of aqueous HPMC solutions.
2001 Sep 11
Lipopolysaccharide downregulates fatty acid amide hydrolase expression and increases anandamide levels in human peripheral lymphocytes.
2001 Sep 15
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
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
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