Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C8H9NO2 |
| Molecular Weight | 151.1626 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCOC(=O)C1=CN=CC=C1
InChI
InChIKey=XBLVHTDFJBKJLG-UHFFFAOYSA-N
InChI=1S/C8H9NO2/c1-2-11-8(10)7-4-3-5-9-6-7/h3-6H,2H2,1H3
DescriptionCurator's Comment: description was created based on several sources, including
http://reference.medscape.com/drug/vitamin-b3-niacor-niacin-344422
https://www.ncbi.nlm.nih.gov/pubmed/16099840
Curator's Comment: description was created based on several sources, including
http://reference.medscape.com/drug/vitamin-b3-niacor-niacin-344422
https://www.ncbi.nlm.nih.gov/pubmed/16099840
Niacin (also known as vitamin B3 and nicotinic acid) is bio converted to nicotinamide which is further converted to nicotinamide adenine dinucleotide (NAD+) and the hydride equivalent (NADH) which are coenzymes necessary for tissue metabolism, lipid metabolism, and glycogenolysis. Niacin (but not nicotinamide) in gram doses reduces LDL-C, Apo B, Lp(a), TG, and TC, and increases HDL-C. The increase in HDL-C is associated with an increase in apolipoprotein A-I (Apo A-I) and a shift in the distribution of HDL subfractions. These shifts include an increase in the HDL2:HDL3 ratio, and an elevation in lipoprotein A-I (Lp A-I, an HDL-C particle containing only Apo A-I). The mechanism by which niacin alters lipid profiles is not completely understood and may involve several actions, including partial inhibition of release of free fatty acids from adipose tissue, and increased lipoprotein lipase activity (which may increase the rate of chylomicron triglyceride removal from plasma). Niacin decreases the rate of hepatic synthesis of VLDL-C and LDL-C, and does not appear to affect fecal excretion of fats, sterols, or bile acids. As an adjunct to diet, the efficacy of niacin and lovastatin in improving lipid profiles (either individually, or in combination with each other, or niacin in combination with other statins) for the treatment of dyslipidemia has been well documented. The effect of combined therapy with niacin and lovastatin on cardiovascular morbidity and mortality has not been determined. In addition, preliminary reports suggest that niacin causes favorable LDL particle size transformations, although the clinical relevance of this effect is not yet clear. April 15, 2016: Based on several large cardiovascular outcome trials including AIM-HIGH, ACCORD, and HPS2-THRIVE, the FDA decided that "scientific evidence no longer supports the conclusion that a drug-induced reduction in triglyceride levels and/or increase in HDL-cholesterol levels in statin-treated patients results in a reduction in the risk of cardiovascular events" Consistent with this conclusion, the FDA has determined that the benefits of niacin ER tablets for coadministration with statins no longer outweigh the risks, and the approval for this indication should be withdrawn.
CNS Activity
Curator's Comment: Niacin penetration into CSF and the extracellular space of brain from plasma as well as regulation of entry into brain cells by a saturable accumulation system are two distinct parts of the homeostatic system. In vivo, niacin that enters the central nervous system is converted to the principal plasma vitamer, niacinamide, in its free or bound forms such as NAD.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: Q8TDS4 Gene ID: 338442.0 Gene Symbol: HCAR2 Target Organism: Homo sapiens (Human) |
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Target ID: P49019 Gene ID: 8843.0 Gene Symbol: HCAR3 Target Organism: Homo sapiens (Human) |
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Target ID: P06576 Gene ID: 506.0 Gene Symbol: ATP5B Target Organism: Homo sapiens (Human) |
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Target ID: CHEMBL4421 |
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Target ID: CHEMBL3785 |
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Target ID: GO:0032310 |
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Target ID: GO:0070527 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Preventing | NIASPAN Approved UseTo reduce the risk of recurrent nonfatal myocardial infarction in patients with a history of myocardial infarction and hyperlipidemia. Launch Date1997 |
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| Palliative | NIASPAN Approved UseIn combination with a bile acid binding resin slows progression or promotes regression of atherosclerotic disease in patients with a history of coronary artery disease (CAD) and hyperlipidemia. Launch Date1997 |
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| Primary | NIASPAN Approved UseNIASPAN contains extended-release niacin (nicotinic acid), and is indicated to reduce elevated TC, LDL-C, Apo B and TG, and to increase HDL-C in patients with primary hyperlipidemia and mixed dyslipidemia. Launch Date1997 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
5.39 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17463214/ |
2000 mg single, oral dose: 2000 mg route of administration: Oral experiment type: SINGLE co-administered: |
NIACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1150 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17463214/ |
2000 mg single, oral dose: 2000 mg route of administration: Oral experiment type: SINGLE co-administered: |
NIACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
30 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17463214/ |
2000 mg single, oral dose: 2000 mg route of administration: Oral experiment type: SINGLE co-administered: |
NIACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Page: 3.0 |
yes [Ki 114 uM] | |||
Page: 3.0 |
yes [Ki 19 uM] | |||
Page: 3.0 |
yes [Ki 237 uM] | |||
Page: 3.0 |
yes [Ki 44 uM] | |||
Page: 3.0 |
yes [Ki 541 uM] |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| yes |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Biliary lipid composition during treatment with different hypolipidaemic drugs. | 1979 Jun |
|
| Advancing our knowledge in biochemistry, genetics, and microbiology through studies on tryptophan metabolism. | 2001 |
|
| The solvent shells of cluster ions produced by direct electric field extraction from glycerol/water mixtures. | 2001 |
|
| Homocysteine elevation with fibrates: is it a class effect? | 2001 Apr |
|
| Utility of PCR assays for rapid diagnosis of BCG infection in children. | 2001 Apr |
|
| Effect of acute pharmacological modulation of plasma free fatty acids on GH secretion in acromegalic patients. | 2001 Apr |
|
| Carbohydrate metabolism during exercise in females: effect of reduced fat availability. | 2001 Apr |
|
| [Cardiology 2000]. | 2001 Apr 12 |
|
| Niacin, poly(ADP-ribose) polymerase-1 and genomic stability. | 2001 Apr 18 |
|
| DNA damage from micronutrient deficiencies is likely to be a major cause of cancer. | 2001 Apr 18 |
|
| Pharmacology of H 394/84, a dihydropyridine neuropeptide Y Y(1) receptor antagonist, in vivo. | 2001 Apr 20 |
|
| Ion interaction reagent reversed-phase high-performance liquid chromatography determination of anti-tuberculosis drugs and metabolites in biological fluids. | 2001 Apr 25 |
|
| Angiotensin II type I receptor modulates intracellular free Mg2+ in renally derived cells via Na+-dependent Ca2+-independent mechanisms. | 2001 Apr 27 |
|
| Lack of association between schizophrenia and the phospholipase-A(2) genes cPLA2 and sPLA2. | 2001 Apr 8 |
|
| Differential effects of agonists of aldosterone secretion on steroidogenic acute regulatory phosphorylation. | 2001 Feb 28 |
|
| Marginal vitamin and mineral intake of Costa Rican adolescents. | 2001 Jan-Feb |
|
| Vitamin requirements of the cultured flesh fly cells, Sarcophaga peregrina (Diptera, Sarcophagidae). | 2001 Jan-Feb |
|
| Use of vitamin supplements and cataract: the Blue Mountains Eye Study. | 2001 Jul |
|
| Use of nicotinic acid in the management of recurrent hypoglycemic episodes in diabetes. | 2001 Jul |
|
| Neural regulation of in vitro giant contractions in the rat colon. | 2001 Jul |
|
| Role of calcium channels in the spinal transmission of nociceptive information from the mesentery. | 2001 Jul |
|
| Hypoxia-induced upregulation of eNOS gene expression is redox-sensitive: a comparison between hypoxia and inhibitors of cell metabolism. | 2001 Jul |
|
| H+-ATPase-mediated cytoplasmic pH-responses associated with elevation of cytoplasmic calcium in cultured rabbit nonpigmented ciliary epithelium. | 2001 Jul 1 |
|
| [Energy and nutrient intake in compulsory high school students]. | 2001 Jun |
|
| Adsorption and degradation of thiazopyr in compost-amended and non-amended soils. | 2001 Jun |
|
| Randomized clinical trials and recent patterns in the use of statins. | 2001 Jun |
|
| Hormonal regulation of the human ghrelin receptor gene transcription. | 2001 Jun 15 |
|
| Interaction of imidazolinone herbicides with soil humic acids. Experimental results and molecular modeling. | 2001 Mar |
|
| Relationships between dietary intake and cognitive function level in Korean elderly people. | 2001 Mar |
|
| Lipids and atherosclerosis: clinical management of hypercholesterolaemia. | 2001 Mar |
|
| Role of ferrihydrite in adsorption of three imidazolinone herbicides. | 2001 Mar |
|
| Disturbance of peristalsis in the guinea-pig isolated small intestine by indomethacin, but not cyclo-oxygenase isoform-selective inhibitors. | 2001 Mar |
|
| Mechanism of CGRP-induced relaxation in rat intramural coronary arteries. | 2001 Mar |
|
| The effects of gabapentin on different ligand- and voltage-gated currents in isolated cortical neurons. | 2001 Mar |
|
| Signalling mechanisms underlying the myogenic response in human subcutaneous resistance arteries. | 2001 Mar |
|
| Regulation of Ca2+-sensitive adenylyl cyclase in gonadotropin-releasing hormone neurons. | 2001 Mar |
|
| Reduction of lipoprotein(a) in postmenopausal women. | 2001 Mar 12 |
|
| Novel approaches to lipid lowering: what is on the horizon? | 2001 Mar 8 |
|
| Voltage-activated Ca2+ channels and ionotropic GABA receptors localized at axon terminals of mammalian retinal bipolar cells. | 2001 Mar-Apr |
|
| [Mycobacterium xenopi: epidemiological and bacteriological features]. | 2001 Mar-Apr |
|
| Determination of additives in food by capillary electrophoresis. | 2001 May |
|
| Vitamin and mineral supplement use by healthy teenagers in Korea: motivating factors and dietary consequences. | 2001 May |
|
| Contents of vitamins, mineral elements, and some phenolic compounds in cultivated mushrooms. | 2001 May |
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| Poor adherence with hypolipidemic drugs: a lost opportunity. | 2001 May |
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| New recommendations from the 1999 American College of Cardiology/American Heart Association acute myocardial infarction guidelines. | 2001 May |
|
| Nifedipine-activated Ca(2+) permeability in newborn rat cortical collecting duct cells in primary culture. | 2001 May |
|
| Angiotensin II priming of aldosterone secretion with agents that enhance Ca(2+) influx. | 2001 May 25 |
|
| Choice of lipid-regulating drugs. | 2001 May 28 |
|
| Determination of niacin in infant formula by solid-phase extraction and anion-exchange liquid chromatography. | 2001 May-Jun |
|
| Use of niacin in the prevention and management of hyperlipidemia. | 2001 Winter |
Patents
Sample Use Guides
Patients not currently on NIASPAN must start ADVICOR at the lowest initial ADVICOR dose, a single 500 mg/20 mg tablet once daily at bedtime. The dose of ADVICOR should not be increased by more than 500 mg daily (based on the NIASPAN component) every 4 weeks. The dose of ADVICOR should be individualized based on targeted goals for cholesterol and triglycerides, and on patient response. Doses of ADVICOR greater than 2000 mg/40 mg daily are not
recommended.
Route of Administration:
Oral
HepG2 cells were preincubated for 48 hours with varying concentrations of niacin (0 to 3.0 mmol/L) in DMEM containing 10% FBS media. Incubation of HepG2 cells with niacin significantly inhibited (by 12% to 15%) fatty acid esterification to produce TG as assessed by the incorporation of 3H-oleic acid into TG. 14C-acetate incorporation into cholesterol and phospholipids was unchanged. The activity of microsomal triglyceride transfer protein MTP), a carrier protein for lipids, was not altered by pretreatment of cells with niacin.
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236122
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614-18-6
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SUB13747MIG
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8872
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NIJ3H353YH
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C037328
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DTXSID9046526
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210-370-7
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69188
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NIJ3H353YH
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100000079013
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ACTIVE MOIETY
SUBSTANCE RECORD
