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
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
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 |
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 |
|||
Primary | Unknown Approved UseUnknown |
|||
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 |
---|---|---|
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
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
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:38:12 GMT 2023
by
admin
on
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Record UNII |
4D16EOF1QW
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Record Status |
Validated (UNII)
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Record Version |
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |