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

Details

Stereochemistry ACHIRAL
Molecular Formula C6H6N2O.ClH
Molecular Weight 158.586
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NIACINAMIDE HYDROCHLORIDE

SMILES

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

InChI

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

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Lessons to be learned from studying Vibrio cholerae in model systems.
2001
Prevention of cyclophosphamide-induced accelerated diabetes in the NOD mouse by nicotinamide or a soy protein-based infant formula.
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
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
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
NADPH-cytochrome P450 oxidoreductase. Structural basis for hydride and electron transfer.
2001 Aug 3
Cannabinoid receptors are absent in insects.
2001 Aug 6
In vitro and in vivo inhibition of telomerase activity from Chinese hamster V79 cells.
2001 Feb-Apr
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
Effects of dietary pyrazinamide, an antituberculosis agent, on the metabolism of tryptophan to niacin and of tryptophan to serotonin in rats.
2001 Jun
Delayed multidose treatment with nicotinamide extends the degree and duration of neuroprotection by reducing infarction and improving behavioral scores up to two weeks following transient focal cerebral ischemia in Wistar rats.
2001 Jun
[Ring cleavage of N-arylpyridinium salts by nucleophiles--regioselectivity and stereochemistry of the products. 2].
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
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
Dose-dependent prophylactic effect of nicorandil, an ATP-sensitive potassium channel opener, on intra-operative myocardial ischaemia in patients undergoing major abdominal surgery.
2001 Mar
Evolution of the aldose reductase-related gecko eye lens protein rhoB-crystallin: a sheep in wolf's clothing.
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
Antinociceptive activity of the endogenous fatty acid amide, palmitylethanolamide.
2001 May 11
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
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
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
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
Oxidation of NADH by chloramines and chloramides and its activation by iodide and by tertiary amines.
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
Mycobacterium tuberculosis lipoamide dehydrogenase is encoded by Rv0462 and not by the lpdA or lpdB genes.
2001 Sep 25
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 15:38:12 GMT 2023
Edited
by admin
on Fri Dec 15 15:38:12 GMT 2023
Record UNII
4D16EOF1QW
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NIACINAMIDE HYDROCHLORIDE
Common Name English
NICOTINAMIDE HYDROCHLORIDE
Systematic Name English
NICOTINAMIDE HCL
Common Name English
3-PYRIDINECARBOXAMIDE HYDROCHLORIDE
Systematic Name English
Code System Code Type Description
DRUG BANK
DBSALT002262
Created by admin on Fri Dec 15 15:38:12 GMT 2023 , Edited by admin on Fri Dec 15 15:38:12 GMT 2023
PRIMARY
FDA UNII
4D16EOF1QW
Created by admin on Fri Dec 15 15:38:12 GMT 2023 , Edited by admin on Fri Dec 15 15:38:12 GMT 2023
PRIMARY
PUBCHEM
91408
Created by admin on Fri Dec 15 15:38:12 GMT 2023 , Edited by admin on Fri Dec 15 15:38:12 GMT 2023
PRIMARY
EPA CompTox
DTXSID00179982
Created by admin on Fri Dec 15 15:38:12 GMT 2023 , Edited by admin on Fri Dec 15 15:38:12 GMT 2023
PRIMARY
CAS
25334-23-0
Created by admin on Fri Dec 15 15:38:12 GMT 2023 , Edited by admin on Fri Dec 15 15:38:12 GMT 2023
PRIMARY
ECHA (EC/EINECS)
246-862-3
Created by admin on Fri Dec 15 15:38:12 GMT 2023 , Edited by admin on Fri Dec 15 15:38:12 GMT 2023
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PARENT -> SALT/SOLVATE
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ACTIVE MOIETY