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
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
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 |
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 |
---|---|---|
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
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 15:02:48 GMT 2023
by
admin
on
Fri Dec 15 15:02:48 GMT 2023
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Record UNII |
6UNY448CMZ
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Record Status |
Validated (UNII)
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Record Version |
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6UNY448CMZ
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DTXSID401340281
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223-081-6
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Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE |