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
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 |
11.0 µM [IC50] | ||
Target ID: CHEMBL4506 |
100.0 µM [IC50] | ||
Target ID: CHEMBL4461 |
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 |
|---|---|---|---|---|
Page: 3.0 |
yes [Ki 13000 uM] | |||
Page: 3.0 |
yes [Ki 13000 uM] | |||
Page: 3.0 |
yes [Ki 3800 uM] | |||
Page: 3.0 |
yes [Ki 44000 uM] | |||
Page: 3.0 |
yes [Ki 51000 uM] | |||
| yes | ||||
| 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 |
|
| Induction of oxidative stress by homocyst(e)ine impairs endothelial 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 |
|
| Characterization of palmitoylethanolamide transport in mouse Neuro-2a neuroblastoma and rat RBL-2H3 basophilic leukaemia cells: comparison with anandamide. | 2001 Apr |
|
| Photodynamic therapy with hypericin in a mouse P388 tumor model: vascular effects determine the efficacy. | 2001 Apr |
|
| Psychrophilic valine dehydrogenase of the antarctic psychrophile, Cytophaga sp. KUC-1: purification, molecular characterization and expression. | 2001 Aug |
|
| Backbone dynamics in dihydrofolate reductase complexes: role of loop flexibility in the catalytic mechanism. | 2001 Aug 21 |
|
| 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 |
|
| Escherichia coli O18:K1:H7 isolates from patients with acute cystitis and neonatal meningitis exhibit common phylogenetic origins and virulence factor profiles. | 2001 Feb 1 |
|
| Oxidative changes in brain pyridine nucleotides and neuroprotection using nicotinamide. | 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 |
|
| Purines inhibit poly(ADP-ribose) polymerase activation and modulate oxidant-induced cell death. | 2001 Jan |
|
| The nicotinamide biosynthetic pathway is a by-product of the RNA world. | 2001 Jan |
|
| Nicotinamide-N-methyltransferase is higher in the lumbar cerebrospinal fluid of patients with Parkinson's disease. | 2001 Jan 26 |
|
| The reactive oxygen species--and Michael acceptor-inducible human aldo-keto reductase AKR1C1 reduces the alpha,beta-unsaturated aldehyde 4-hydroxy-2-nonenal to 1,4-dihydroxy-2-nonene. | 2001 Jan 26 |
|
| Allosteric activation of pyruvate kinase via NAD+ in rat liver cells. | 2001 Jul |
|
| 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 |
|
| Role of fatty acid amide hydrolase in the transport of the endogenous cannabinoid anandamide. | 2001 Jun |
|
| 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 |
|
| [Successful therapy with tetracycline and nicotinamide in cicatricial pemphigoid]. | 2001 Mar |
|
| On the enzymatic activation of NADH. | 2001 Mar 23 |
|
| Crystal structure of paprika ferredoxin-NADP+ reductase. Implications for the electron transfer pathway. | 2001 Mar 23 |
|
| Effects of the interaction between carbogen and nicotinamide on R3230 Ac tumor blood flow in Fischer 344 rats. | 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 |
|
| 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 |
|
| Oxidation of NADH by chloramines and chloramides and its activation by iodide and by tertiary amines. | 2001 Sep 15 |
|
| 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
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| Code System | Code | Type | Description | ||
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6UNY448CMZ
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DTXSID401340281
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317251
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3726-23-6
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77316
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223-081-6
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PARENT (SALT/SOLVATE)
SUBSTANCE RECORD
