Details
Stereochemistry | ACHIRAL |
Molecular Formula | C6H6N2O |
Molecular Weight | 122.1246 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NC(=O)C1=CN=CC=C1
InChI
InChIKey=DFPAKSUCGFBDDF-UHFFFAOYSA-N
InChI=1S/C6H6N2O/c7-6(9)5-2-1-3-8-4-5/h1-4H,(H2,7,9)
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 |
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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 |
---|---|---|
Tetracycline and nicotinamide for the treatment of bullous pemphigoid: our experience in Singapore. | 2000 Jul |
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Lessons to be learned from studying Vibrio cholerae in model systems. | 2001 |
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The nitrilase superfamily: classification, structure and function. | 2001 |
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The metabolism of nicotinamide in human liver cirrhosis: a study on N-methylnicotinamide and 2-pyridone-5-carboxamide production. | 2001 Apr |
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Characterization of palmitoylethanolamide transport in mouse Neuro-2a neuroblastoma and rat RBL-2H3 basophilic leukaemia cells: comparison with anandamide. | 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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Nicotinamide adenine dinucleotide (NAD) and its metabolites inhibit T lymphocyte proliferation: role of cell surface NAD glycohydrolase and pyrophosphatase activities. | 2001 Aug 15 |
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Cannabinoid receptors are absent in insects. | 2001 Aug 6 |
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Methanol solvent may cause increased apparent metabolic instability in in vitro assays. | 2001 Feb |
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The crystal structure of an asymmetric complex of the two nucleotide binding components of proton-translocating transhydrogenase. | 2001 Feb 7 |
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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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Homoserine dehydrogenase from Saccharomyces cerevisiae: kinetic mechanism and stereochemistry of hydride transfer. | 2001 Jan 12 |
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Ternary complexes of liver alcohol dehydrogenase. | 2001 Jan 30 |
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Increased plasma tryptophan in HIV-infected patients treated with pharmacologic doses of nicotinamide. | 2001 Jul-Aug |
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[Effect of feeding with a poisonous mushroom Clitocybe acromelalga on the metabolism of tryptophan-niacin in rats]. | 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 |
|
An NMR-based metabonomic approach to the investigation of coelomic fluid biochemistry in earthworms under toxic stress. | 2001 Jun 29 |
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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 |
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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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[Successful therapy with tetracycline and nicotinamide in cicatricial pemphigoid]. | 2001 Mar |
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On the enzymatic activation of NADH. | 2001 Mar 23 |
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Evidence for an endocannabinoid system in the central nervous system of the leech Hirudo medicinalis. | 2001 Mar 5 |
|
Potential for creatine and other therapies targeting cellular energy dysfunction in neurological disorders. | 2001 May |
|
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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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 |
|
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 |
|
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 |
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
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Record UNII |
25X51I8RD4
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WHO-ATC |
A11HA01
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DSLD |
2664 (Number of products:4764)
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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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13128
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7405
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1237
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25X51I8RD4
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D009536
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936
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C2327
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NICOTINAMIDE
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98-92-0
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DTXSID2020929
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DB02701
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1906
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100000092193
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NIACINAMIDE
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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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1462006
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25X51I8RD4
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SUB09246MIG
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17154
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CHEMBL1140
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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TARGET -> INHIBITOR |
NAD-dependent lysine desuccinylase activity is inhibited by physiological nicotinamide concentrations, while deacetylase activity is not.
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Related Record | Type | Details | ||
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METABOLITE ACTIVE -> PARENT |
Related Record | Type | Details | ||
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ACTIVE MOIETY |