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

Details

Stereochemistry ACHIRAL
Molecular Formula C6H6N2O.HI
Molecular Weight 250.0371
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NIACINAMIDE HYDRIODIDE

SMILES

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

InChI

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

HIDE SMILES / InChI

Molecular Formula HI
Molecular Weight 127.9124
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
Tetracycline and nicotinamide for the treatment of bullous pemphigoid: our experience in Singapore.
2000 Jul
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
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
Niacin, poly(ADP-ribose) polymerase-1 and genomic stability.
2001 Apr 18
The activity of anandamide at vanilloid VR1 receptors requires facilitated transport across the cell membrane and is limited by intracellular metabolism.
2001 Apr 20
A leucine zipper protein of mitochondrial origin.
2001 Apr 7
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
NADPH-cytochrome P450 oxidoreductase. Structural basis for hydride and electron transfer.
2001 Aug 3
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
The crystal structure of an asymmetric complex of the two nucleotide binding components of proton-translocating transhydrogenase.
2001 Feb 7
In vitro and in vivo inhibition of telomerase activity from Chinese hamster V79 cells.
2001 Feb-Apr
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
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
Allosteric activation of pyruvate kinase via NAD+ in rat liver cells.
2001 Jul
Increased plasma tryptophan in HIV-infected patients treated with pharmacologic doses of nicotinamide.
2001 Jul-Aug
Effects of dietary pyrazinamide, an antituberculosis agent, on the metabolism of tryptophan to niacin and of tryptophan to serotonin in rats.
2001 Jun
[Ring cleavage of N-arylpyridinium salts by nucleophiles--regioselectivity and stereochemistry of the products. 2].
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
Effects of nicotinamide, an inhibitor of PARS activity, on gut and liver O2 exchange and energy metabolism during hyperdynamic porcine endotoxemia.
2001 Mar
[Successful therapy with tetracycline and nicotinamide in cicatricial pemphigoid].
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
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
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
Characterization of the hydroxypropylmethylcellulose-nicotinamide binary system.
2001 May 21
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
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
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
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:02:48 GMT 2023
Edited
by admin
on Fri Dec 15 15:02:48 GMT 2023
Record UNII
6UNY448CMZ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NIACINAMIDE HYDRIODIDE
Common Name English
NICOTINAMIDE HYDRIODIDE [VANDF]
Common Name English
NICOTINAMIDE HYDRIODIDE
VANDF  
Systematic Name English
3-PYRIDINECARBOXAMIDE, MONOHYDRIODIDE
Common Name English
3-PYRIDINECARBOXAMIDE, HYDRIODIDE (1:1)
Common Name English
Code System Code Type Description
FDA UNII
6UNY448CMZ
Created by admin on Fri Dec 15 15:02:48 GMT 2023 , Edited by admin on Fri Dec 15 15:02:48 GMT 2023
PRIMARY
EPA CompTox
DTXSID401340281
Created by admin on Fri Dec 15 15:02:48 GMT 2023 , Edited by admin on Fri Dec 15 15:02:48 GMT 2023
PRIMARY
RXCUI
317251
Created by admin on Fri Dec 15 15:02:48 GMT 2023 , Edited by admin on Fri Dec 15 15:02:48 GMT 2023
PRIMARY RxNorm
CAS
3726-23-6
Created by admin on Fri Dec 15 15:02:48 GMT 2023 , Edited by admin on Fri Dec 15 15:02:48 GMT 2023
PRIMARY
PUBCHEM
77316
Created by admin on Fri Dec 15 15:02:48 GMT 2023 , Edited by admin on Fri Dec 15 15:02:48 GMT 2023
PRIMARY
ECHA (EC/EINECS)
223-081-6
Created by admin on Fri Dec 15 15:02:48 GMT 2023 , Edited by admin on Fri Dec 15 15:02:48 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE