Details
Stereochemistry | ACHIRAL |
Molecular Formula | C6H5NO2 |
Molecular Weight | 123.1096 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
c1cc(cnc1)C(=O)O
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 | 123.1096 |
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 Date8.6996163E11 |
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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 Date8.6996163E11 |
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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 Date8.7004801E11 |
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 |
---|---|---|
Advancing our knowledge in biochemistry, genetics, and microbiology through studies on tryptophan metabolism. | 2001 |
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Homocysteine elevation with fibrates: is it a class effect? | 2001 Apr |
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Do breastfed infants need supplemental vitamins? | 2001 Apr |
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Dietary inadequacies observed in homeless men visiting an emergency night shelter in Paris. | 2001 Apr |
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Treatment of hyperlipidemia in HIV-infected patients. | 2001 Apr 1 |
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[Cardiology 2000]. | 2001 Apr 12 |
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A new niacin. Vitamin with an HDL kick. | 2001 Apr 16 |
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Niacin, poly(ADP-ribose) polymerase-1 and genomic stability. | 2001 Apr 18 |
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DNA damage from micronutrient deficiencies is likely to be a major cause of cancer. | 2001 Apr 18 |
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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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Lack of association between schizophrenia and the phospholipase-A(2) genes cPLA2 and sPLA2. | 2001 Apr 8 |
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The relationship among dental status, nutrient intake, and nutritional status in older people. | 2001 Feb |
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Comparative study of the molecular and functional expression of L-type Ca2+ channels and large-conductance, Ca2+-activated K+ channels in rabbit aorta and vas deferens smooth muscle. | 2001 Feb |
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Perchlorate stimulates insulin secretion by shifting the gating of L-type Ca2+ currents in mouse pancreatic B-cells towards negative potentials. | 2001 Feb |
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Marginal vitamin and mineral intake of Costa Rican adolescents. | 2001 Jan-Feb |
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Vitamin requirements of the cultured flesh fly cells, Sarcophaga peregrina (Diptera, Sarcophagidae). | 2001 Jan-Feb |
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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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Neural regulation of in vitro giant contractions in the rat colon. | 2001 Jul |
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Role of calcium channels in the spinal transmission of nociceptive information from the mesentery. | 2001 Jul |
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Parathyroid cells express dihydropyridine-sensitive cation currents and L-type calcium channel subunits. | 2001 Jul |
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Hypoxia-induced upregulation of eNOS gene expression is redox-sensitive: a comparison between hypoxia and inhibitors of cell metabolism. | 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 and degradation of thiazopyr in compost-amended and non-amended soils. | 2001 Jun |
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Hormonal regulation of the human ghrelin receptor gene transcription. | 2001 Jun 15 |
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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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Relationships between dietary intake and cognitive function level in Korean elderly people. | 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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Lipids and atherosclerosis: clinical management of hypercholesterolaemia. | 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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Determination by capillary electrophoresis of total and available niacin in different development stage of raw and processed legumes: comparison with high-performance liquid chromatography. | 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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Determination of additives in food by capillary electrophoresis. | 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 |
|
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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Nifedipine-activated Ca(2+) permeability in newborn rat cortical collecting duct cells in primary culture. | 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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Choice of lipid-regulating drugs. | 2001 May 28 |
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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 |
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
admin
on
Edited
Fri Jun 25 21:17:23 UTC 2021
by
admin
on
Fri Jun 25 21:17:23 UTC 2021
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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
Created by
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LIVERTOX |
680
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NDF-RT |
N0000175594
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WHO-VATC |
QC04AC01
Created by
admin on Fri Jun 25 21:17:23 UTC 2021 , Edited by admin on Fri Jun 25 21:17:23 UTC 2021
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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
Created by
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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)
Created by
admin on Fri Jun 25 21:17:23 UTC 2021 , Edited by admin on Fri Jun 25 21:17:23 UTC 2021
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NCI_THESAURUS |
C45812
Created by
admin on Fri Jun 25 21:17:23 UTC 2021 , Edited by admin on Fri Jun 25 21:17:23 UTC 2021
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WHO-ATC |
C10BA01
Created by
admin on Fri Jun 25 21:17:23 UTC 2021 , Edited by admin on Fri Jun 25 21:17:23 UTC 2021
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CFR |
21 CFR 102.23
Created by
admin on Fri Jun 25 21:17:23 UTC 2021 , Edited by admin on Fri Jun 25 21:17:23 UTC 2021
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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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Code System | Code | Type | Description | ||
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2835
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C689
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D009525
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PRIMARY | |||
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CHEMBL573
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SUB09247MIG
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PRIMARY | |||
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M7880
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PRIMARY | Merck Index | ||
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NIACIN
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PRIMARY | |||
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1461003
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PRIMARY | USP-RS | ||
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938
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PRIMARY | |||
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2679MF687A
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59-67-6
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200-441-0
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373
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3134
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DB00627
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7393
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PRIMARY | RxNorm | ||
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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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PRIMARY |
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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PARENT -> CONSTITUENT ALWAYS PRESENT |
Nutritional value per 100 g (3.5 oz) - 0.639 mg (4%)
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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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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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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT |
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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ACTIVE MOIETY |
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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