Details
Stereochemistry | ACHIRAL |
Molecular Formula | C6H5NO2 |
Molecular Weight | 123.1094 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)C1=CN=CC=C1
InChI
InChIKey=PVNIIMVLHYAWGP-UHFFFAOYSA-N
InChI=1S/C6H5NO2/c8-6(9)5-2-1-3-7-4-5/h1-4H,(H,8,9)
Molecular Formula | C6H5NO2 |
Molecular Weight | 123.1094 |
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
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/158635
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) Sources: https://www.drugbank.ca/drugs/DB08949 |
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Target ID: P49019 Gene ID: 8843.0 Gene Symbol: HCAR3 Target Organism: Homo sapiens (Human) Sources: https://www.drugbank.ca/drugs/DB08949 |
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Target ID: P06576 Gene ID: 506.0 Gene Symbol: ATP5B Target Organism: Homo sapiens (Human) Sources: https://www.drugbank.ca/drugs/DB08949 |
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Target ID: CHEMBL4421 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15580557 |
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Target ID: CHEMBL3785 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15580557 |
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Target ID: GO:0032310 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28552466 |
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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 |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/15081432/ Page: 3.0 |
yes [Ki 114 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/15081432/ Page: 3.0 |
yes [Ki 19 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/15081432/ Page: 3.0 |
yes [Ki 237 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/15081432/ Page: 3.0 |
yes [Ki 44 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/15081432/ 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 |
---|---|---|
The effect of niceritrol (pentaerythritoltetranicotinate) and clofibrate upon hyperlipemia and atherosclerosis induced in rabbits by cholesterol-free semisynthetic diets. | 1974 Nov-Dec |
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Action of niceritrol (pentaerythritoltetranicotinate) on lipid accumulation in aortas of cholesterol-fed rabbits independent of contemporary reduction of serum lipids. | 1974 Nov-Dec |
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Actions of vitamins A and E and some nicotinic acid derivatives on plasma lipids and on lipid infiltration of aorta in cholesterol-fed rabbits. | 1975 Jul-Aug |
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Biliary lipid composition during treatment with different hypolipidaemic drugs. | 1979 Jun |
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Homocysteine elevation with fibrates: is it a class effect? | 2001 Apr |
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Treatment of hyperlipidemia in HIV-infected patients. | 2001 Apr 1 |
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A new niacin. Vitamin with an HDL kick. | 2001 Apr 16 |
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Pharmacology of H 394/84, a dihydropyridine neuropeptide Y Y(1) receptor antagonist, in vivo. | 2001 Apr 20 |
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Ion interaction reagent reversed-phase high-performance liquid chromatography determination of anti-tuberculosis drugs and metabolites in biological fluids. | 2001 Apr 25 |
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Nutritional status of vitamin A, E, C, B1, B2, B6, nicotinic acid, B12, folate, and beta-carotene in young women. | 2001 Feb |
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The relationship among dental status, nutrient intake, and nutritional status in older people. | 2001 Feb |
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Etofibrate but not controlled-release niacin decreases LDL cholesterol and lipoprotein (a) in type IIb dyslipidemic subjects. | 2001 Feb |
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Characterization of a G protein-coupled receptor for nicotinic acid. | 2001 Feb |
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Biophysical properties, pharmacology, and modulation of human, neuronal L-type (alpha(1D), Ca(V)1.3) voltage-dependent calcium currents. | 2001 Feb |
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Down-regulation of L-type calcium channels in inflamed circular smooth muscle cells of the canine colon. | 2001 Feb |
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Common hepatic lipase gene promoter variant determines clinical response to intensive lipid-lowering treatment. | 2001 Feb 13 |
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Safety and effectiveness of Niaspan when added sequentially to a statin for treatment of dyslipidemia. | 2001 Feb 15 |
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Chronic nicotine alters NO signaling of Ca(2+) channels in cerebral arterioles. | 2001 Feb 16 |
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Effects of nicotinamide coenzymes on the stability of enzyme activities and proteins in niacin-deficient quail tissues against trypsin treatment. | 2001 Jan |
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[The role of HDL in the prevention of cardiovascular events]. | 2001 Jan 21 |
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Downregulation of the voltage-dependent calcium channel (VDCC) beta-subunit mRNAs in pancreatic islets of type 2 diabetic rats. | 2001 Jan 26 |
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Use of vitamin supplements and cataract: the Blue Mountains Eye Study. | 2001 Jul |
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Use of nicotinic acid in the management of recurrent hypoglycemic episodes in diabetes. | 2001 Jul |
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Complex intracellular messenger pathways regulate one type of neuronal alpha-bungarotoxin-resistant nicotinic acetylcholine receptors expressed in insect neurosecretory cells (dorsal unpaired median neurons). | 2001 Jul |
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An animal model of nicotinic-acid-induced vasodilation: effect of haloperidol, caffeine and nicotine upon nicotinic acid response. | 2001 Jul 1 |
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H+-ATPase-mediated cytoplasmic pH-responses associated with elevation of cytoplasmic calcium in cultured rabbit nonpigmented ciliary epithelium. | 2001 Jul 1 |
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5-Hydroxytryptamine stimulates net Ca2+ flux in the ventricular muscle of a mollusc (Busycon canaliculatum) during cardioexcitation. | 2001 Jun |
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Does the condition of the mouth and teeth affect the ability to eat certain foods, nutrient and dietary intake and nutritional status amongst older people? | 2001 Jun |
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[Energy and nutrient intake in compulsory high school students]. | 2001 Jun |
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Adsorption of imidazolinone herbicides on ferrihydrite-humic acid associations. | 2001 Mar |
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Interaction of imidazolinone herbicides with soil humic acids. Experimental results and molecular modeling. | 2001 Mar |
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[Nicotinic acid and the derivative]. | 2001 Mar |
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[Drug combination therapies for patients with hyperlipidemia and its significance]. | 2001 Mar |
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Disturbance of peristalsis in the guinea-pig isolated small intestine by indomethacin, but not cyclo-oxygenase isoform-selective inhibitors. | 2001 Mar |
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Mechanism of CGRP-induced relaxation in rat intramural coronary arteries. | 2001 Mar |
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Activation of purified cardiac ryanodine receptors by dihydropyridine agonists. | 2001 Mar |
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Effect of nicotinic acid administration on hepatic very low density lipoprotein-triglyceride production. | 2001 Mar |
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Voltage-activated Ca2+ channels and ionotropic GABA receptors localized at axon terminals of mammalian retinal bipolar cells. | 2001 Mar-Apr |
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Calcium buffering of resting, voltage-dependent Ca2+ influx by sarcoplasmic reticulum in femoral arteries from spontaneously hypertensive rats at prehypertensive stage. | 2001 May |
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The application of capillary electrophoresis to the analysis of vitamins in food and beverages. | 2001 May |
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(C-rac-5,5,7,12,12,14-Hexamethyl-1,4,8,11-tetraazacyclotetradecane-kappa4N)(nicotinato-O,O')nickel(II) perchlorate. | 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 |
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The bio operon on the acquired symbiosis island of Mesorhizobium sp. strain R7A includes a novel gene involved in pimeloyl-CoA synthesis. | 2001 May |
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Effects of dextromethorphan on the seizures induced by kainate and the calcium channel agonist BAY k-8644: comparison with the effects of dextrorphan. | 2001 May |
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Niacin in patients with diabetes mellitus and coronary artery disease. | 2001 May 1 |
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Angiotensin II priming of aldosterone secretion with agents that enhance Ca(2+) influx. | 2001 May 25 |
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Determination of niacin in infant formula by solid-phase extraction and anion-exchange liquid chromatography. | 2001 May-Jun |
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Structural investigation of the biosynthesis of alternative lower ligands for cobamides by nicotinate mononucleotide: 5,6-dimethylbenzimidazole phosphoribosyltransferase from Salmonella enterica. | 2001 Oct 5 |
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Methylnicotinate stimulated prostaglandin synthesis in patients with schizophrenia: A preliminary investigation. | 2018 Sep |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10195935
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.
Substance Class |
Chemical
Created
by
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on
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Record UNII |
2679MF687A
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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WHO-VATC |
QC10AD52
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LIVERTOX |
NBK548176
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LIVERTOX |
NBK548710
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NDF-RT |
N0000175594
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WHO-VATC |
QC04AC01
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CFR |
21 CFR 184.1530
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LOINC |
10836-5
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EPA PESTICIDE CODE |
56701
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WHO-VATC |
QC10AD02
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DSLD |
2544 (Number of products:3520)
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NDF-RT |
N0000007641
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WHO-ATC |
C10AD52
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LOINC |
34342-6
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WHO-VATC |
QC10BA01
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DSLD |
1570 (Number of products:100)
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NCI_THESAURUS |
C45812
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WHO-ATC |
C10BA01
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CFR |
21 CFR 102.23
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NDF-RT |
N0000007641
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LOINC |
18244-4
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LOINC |
2656-7
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WHO-ATC |
C04AC01
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DSLD |
204 (Number of products:661)
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WHO-ATC |
C10AD02
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LOINC |
79402-4
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2835
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C689
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D009525
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CHEMBL573
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m7880
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PRIMARY | Merck Index | ||
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NIACIN
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176839
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938
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2679MF687A
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1461003
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100000092214
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200-441-0
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169454
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373
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3134
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DB00627
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7393
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NIACIN
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PRIMARY | Description: Colourless crystals or a white, crystalline powder; odourless or almost odourless. Solubility: Sparingly soluble in water; freely soluble in boiling water; soluble in 100 parts of ethanol (~750 g/l) TS; practicallyinsoluble in ether R. Category: Component of vitamin B complex; vasodilator. Storage: Nicotinic acid should be kept in a well-closed container, protected from light. Definition: Nicotinic acid contains not less than 99.0% and not more than 101.0% of C6H5NO2, calculated with reference to thedried substance. | ||
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59-67-6
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2679MF687A
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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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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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PARENT -> CONSTITUENT ALWAYS PRESENT |
Nutritional value per 100 g (3.5 oz) - 0.639 mg (4%)
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SALT/SOLVATE -> PARENT |
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TARGET -> AGONIST |
AGONIST
EC50
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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Elimination PHARMACOKINETIC |
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