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
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)
DescriptionCurator's Comment:: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/4244068
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.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL4462 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19700324 |
11.0 µM [IC50] | ||
Target ID: CHEMBL4506 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19700324 |
100.0 µM [IC50] | ||
Target ID: CHEMBL4461 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19700324 |
14.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Preventing | Niacinamide Approved UseTreatment and prevention of niacin deficiency, and certain conditions related to niacin deficiency such as pellagra. |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Dose | Population | Adverse 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... |
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 todiscontinuation/dose reduction: Nausea (20%) Sources: Page: p.69Toxicity renal (2.5%) |
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%) AEs leading toOliguria (50%) discontinuation/dose reduction: Nausea (severe, 50%) Sources: Page: p.1116Vomiting (severe, 50%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/15081432/ Page: 3.0 |
yes [Ki 13000 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/15081432/ Page: 3.0 |
yes [Ki 13000 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/15081432/ Page: 3.0 |
yes [Ki 3800 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/15081432/ Page: 3.0 |
yes [Ki 44000 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/15081432/ Page: 3.0 |
yes [Ki 51000 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/7508708/ |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/7508708/ |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
no | ||||
yes |
PubMed
Title | Date | PubMed |
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Induction of oxidative stress by homocyst(e)ine impairs endothelial function. | 2001 |
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Prevention of cyclophosphamide-induced accelerated diabetes in the NOD mouse by nicotinamide or a soy protein-based infant formula. | 2001 |
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Photodynamic therapy for malignant mesothelioma: preclinical studies for optimization of treatment protocols. | 2001 Apr |
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Improvement of tumor oxygenation by mild hyperthermia. | 2001 Apr |
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Photodynamic therapy with hypericin in a mouse P388 tumor model: vascular effects determine the efficacy. | 2001 Apr |
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Interligand Overhauser effects in type II dihydrofolate reductase. | 2001 Apr 10 |
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The activity of anandamide at vanilloid VR1 receptors requires facilitated transport across the cell membrane and is limited by intracellular metabolism. | 2001 Apr 20 |
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Enhanced maturation of porcine neonatal pancreatic cell clusters with growth factors fails to improve transplantation outcome. | 2001 Apr 27 |
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A leucine zipper protein of mitochondrial origin. | 2001 Apr 7 |
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Psychrophilic valine dehydrogenase of the antarctic psychrophile, Cytophaga sp. KUC-1: purification, molecular characterization and expression. | 2001 Aug |
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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 |
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Backbone dynamics in dihydrofolate reductase complexes: role of loop flexibility in the catalytic mechanism. | 2001 Aug 21 |
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NADPH-cytochrome P450 oxidoreductase. Structural basis for hydride and electron transfer. | 2001 Aug 3 |
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Cannabinoid receptors are absent in insects. | 2001 Aug 6 |
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Canine symmetrical lupoid onychodystrophy: a retrospective study with particular reference to management. | 2001 Feb |
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Human platelets bind and degrade 2-arachidonoylglycerol, which activates these cells through a cannabinoid receptor. | 2001 Feb |
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Farnesol oxidation in insects: evidence that the biosynthesis of insect juvenile hormone is mediated by a specific alcohol oxidase. | 2001 Feb |
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Methanol solvent may cause increased apparent metabolic instability in in vitro assays. | 2001 Feb |
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NAD+ inhibits the self-splicing of the group I intron. | 2001 Feb 16 |
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Kinetic and mechanistic properties of biotin sulfoxide reductase. | 2001 Feb 6 |
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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 |
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Nicotinamide-N-methyltransferase is higher in the lumbar cerebrospinal fluid of patients with Parkinson's disease. | 2001 Jan 26 |
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Molecular dynamics simulation of class 3 aldehyde dehydrogenase. | 2001 Jan 30 |
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Allosteric activation of pyruvate kinase via NAD+ in rat liver cells. | 2001 Jul |
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Characterization of poly(ADP-ribose)polymerase from Crithidia fasciculata: enzyme inhibition by beta-lapachone. | 2001 Jul |
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Increased plasma tryptophan in HIV-infected patients treated with pharmacologic doses of nicotinamide. | 2001 Jul-Aug |
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Significance of interferon-gamma in coronary artery bypass surgery. | 2001 Jul-Sep |
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[Effect of feeding with a poisonous mushroom Clitocybe acromelalga on the metabolism of tryptophan-niacin in rats]. | 2001 Jun |
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Effects of dietary pyrazinamide, an antituberculosis agent, on the metabolism of tryptophan to niacin and of tryptophan to serotonin in rats. | 2001 Jun |
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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 |
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Role of fatty acid amide hydrolase in the transport of the endogenous cannabinoid anandamide. | 2001 Jun |
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Characterization of multicomponent monosaccharide solutions using an enzyme-based sensor array. | 2001 Jun 15 |
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Progesterone up-regulates anandamide hydrolase in human lymphocytes: role of cytokines and implications for fertility. | 2001 Jun 15 |
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alpha-Keto heterocycle inhibitors of fatty acid amide hydrolase: carbonyl group modification and alpha-substitution. | 2001 Jun 18 |
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Evolution of the aldose reductase-related gecko eye lens protein rhoB-crystallin: a sheep in wolf's clothing. | 2001 Mar |
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Effects of nicotinamide, an inhibitor of PARS activity, on gut and liver O2 exchange and energy metabolism during hyperdynamic porcine endotoxemia. | 2001 Mar |
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Characterization of secretory and morphologic properties of primary cultured endocrine cells from porcine pancreata. | 2001 Mar |
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The neurobiology and evolution of cannabinoid signalling. | 2001 Mar 29 |
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Characterization of recombinant human nicotinamide mononucleotide adenylyl transferase (NMNAT), a nuclear enzyme essential for NAD synthesis. | 2001 Mar 9 |
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Purification and structure of the major product obtained by reaction of NADPH and NMNH with the myeloperoxidase/hydrogen peroxide/chloride system. | 2001 May |
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Effects of the interaction between carbogen and nicotinamide on R3230 Ac tumor blood flow in Fischer 344 rats. | 2001 May |
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Antinociceptive activity of the endogenous fatty acid amide, palmitylethanolamide. | 2001 May 11 |
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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 |
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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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26970333
10 mM Niacinamide inhibited Resveratrol-mediated ROS suppression in B16F1 melanoma cells
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Classification Tree | Code System | Code | ||
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WHO-ATC |
A11HA01
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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
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NCI_THESAURUS |
C26017
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LIVERTOX |
681
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WHO-ESSENTIAL MEDICINES LIST |
27
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NCI_THESAURUS |
C275
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DSLD |
1097 (Number of products:12)
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CFR |
21 CFR 184.1535
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DSLD |
204 (Number of products:661)
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WHO-VATC |
QA11HA01
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Code System | Code | Type | Description | ||
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202-713-4
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PRIMARY | |||
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7405
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1237
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PRIMARY | |||
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D009536
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404
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936
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C2327
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NICOTINAMIDE
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1462006
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PRIMARY | USP-RS | ||
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98-92-0
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98-92-0
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DB02701
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1906
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NIACINAMIDE
Created by
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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. | ||
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M7878
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PRIMARY | Merck Index | ||
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25X51I8RD4
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SUB09246MIG
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CHEMBL1140
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ACTIVE MOIETY
METABOLITE ACTIVE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)