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Details

Stereochemistry ACHIRAL
Molecular Formula C13H11NO2
Molecular Weight 213.2319
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BENZYL NICOTINATE

SMILES

O=C(OCC1=CC=CC=C1)C2=CN=CC=C2

InChI

InChIKey=KVYGGMBOZFWZBQ-UHFFFAOYSA-N
InChI=1S/C13H11NO2/c15-13(12-7-4-8-14-9-12)16-10-11-5-2-1-3-6-11/h1-9H,10H2

HIDE SMILES / InChI

Description
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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
NIASPAN

Approved Use

To reduce the risk of recurrent nonfatal myocardial infarction in patients with a history of myocardial infarction and hyperlipidemia.

Launch Date

1997
Palliative
NIASPAN

Approved Use

In 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 Date

1997
Primary
NIASPAN

Approved Use

NIASPAN 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 Date

1997
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
5.39 μg/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
1150 μg × min/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
30 min
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

Overview

CYP3A4CYP2C9CYP2D6hERG



Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [Ki 114 uM]
yes [Ki 19 uM]
yes [Ki 237 uM]
yes [Ki 44 uM]
yes [Ki 541 uM]
Drug as victim
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Biliary lipid composition during treatment with different hypolipidaemic drugs.
1979 Jun
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
Do breastfed infants need supplemental vitamins?
2001 Apr
L-type calcium currents in atrial myocytes from patients with persistent and non-persistent atrial fibrillation.
2001 Apr
Carbohydrate metabolism during exercise in females: effect of reduced fat availability.
2001 Apr
Treatment of hyperlipidemia in HIV-infected patients.
2001 Apr 1
[Cardiology 2000].
2001 Apr 12
A new niacin. Vitamin with an HDL kick.
2001 Apr 16
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
Lack of association between schizophrenia and the phospholipase-A(2) genes cPLA2 and sPLA2.
2001 Apr 8
Nutritional status of vitamin A, E, C, B1, B2, B6, nicotinic acid, B12, folate, and beta-carotene in young women.
2001 Feb
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
Perchlorate stimulates insulin secretion by shifting the gating of L-type Ca2+ currents in mouse pancreatic B-cells towards negative potentials.
2001 Feb
Abnormality of calcium channel inhibitor released from fetal membranes in preterm labor.
2001 Feb
Chronic nicotine alters NO signaling of Ca(2+) channels in cerebral arterioles.
2001 Feb 16
Differential effects of agonists of aldosterone secretion on steroidogenic acute regulatory phosphorylation.
2001 Feb 28
[The role of HDL in the prevention of cardiovascular events].
2001 Jan 21
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
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
Adsorption of imidazolinone herbicides on ferrihydrite-humic acid associations.
2001 Mar
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
[Nicotinic acid and the derivative].
2001 Mar
[Drug combination therapies for patients with hyperlipidemia and its significance].
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
Pellagra in 2 homeless men.
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
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
The application of capillary electrophoresis to the analysis of vitamins in food and beverages.
2001 May
Contents of vitamins, mineral elements, and some phenolic compounds in cultivated mushrooms.
2001 May
(C-rac-5,5,7,12,12,14-Hexamethyl-1,4,8,11-tetraazacyclotetradecane-kappa4N)(nicotinato-O,O')nickel(II) perchlorate.
2001 May
Poor adherence with hypolipidemic drugs: a lost opportunity.
2001 May
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
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
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
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
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.
Name Type Language
BENZYL NICOTINATE
INCI   JAN   MART.   WHO-DD  
INCI  
Official Name English
NICOTINIC ACID BENZYL ESTER [MI]
Common Name English
BENZYL NICOTINATE [INCI]
Common Name English
BENZYL NICOTINATE [JAN]
Common Name English
Benzyl nicotinate [WHO-DD]
Common Name English
BENZYL NICOTINATE [MART.]
Common Name English
NICOTINIC ACID BENZYL ESTER
MI  
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C29707
Created by admin on Fri Dec 15 15:18:20 GMT 2023 , Edited by admin on Fri Dec 15 15:18:20 GMT 2023
Code System Code Type Description
RXCUI
31767
Created by admin on Fri Dec 15 15:18:20 GMT 2023 , Edited by admin on Fri Dec 15 15:18:20 GMT 2023
PRIMARY RxNorm
MESH
C025653
Created by admin on Fri Dec 15 15:18:20 GMT 2023 , Edited by admin on Fri Dec 15 15:18:20 GMT 2023
PRIMARY
NCI_THESAURUS
C83549
Created by admin on Fri Dec 15 15:18:20 GMT 2023 , Edited by admin on Fri Dec 15 15:18:20 GMT 2023
PRIMARY
DRUG CENTRAL
3379
Created by admin on Fri Dec 15 15:18:20 GMT 2023 , Edited by admin on Fri Dec 15 15:18:20 GMT 2023
PRIMARY
CAS
94-44-0
Created by admin on Fri Dec 15 15:18:20 GMT 2023 , Edited by admin on Fri Dec 15 15:18:20 GMT 2023
PRIMARY
SMS_ID
100000092407
Created by admin on Fri Dec 15 15:18:20 GMT 2023 , Edited by admin on Fri Dec 15 15:18:20 GMT 2023
PRIMARY
EPA CompTox
DTXSID7046542
Created by admin on Fri Dec 15 15:18:20 GMT 2023 , Edited by admin on Fri Dec 15 15:18:20 GMT 2023
PRIMARY
PUBCHEM
7191
Created by admin on Fri Dec 15 15:18:20 GMT 2023 , Edited by admin on Fri Dec 15 15:18:20 GMT 2023
PRIMARY
EVMPD
SUB13026MIG
Created by admin on Fri Dec 15 15:18:20 GMT 2023 , Edited by admin on Fri Dec 15 15:18:20 GMT 2023
PRIMARY
ChEMBL
CHEMBL209744
Created by admin on Fri Dec 15 15:18:20 GMT 2023 , Edited by admin on Fri Dec 15 15:18:20 GMT 2023
PRIMARY
CHEBI
31268
Created by admin on Fri Dec 15 15:18:20 GMT 2023 , Edited by admin on Fri Dec 15 15:18:20 GMT 2023
PRIMARY
FDA UNII
S497LCF9C9
Created by admin on Fri Dec 15 15:18:20 GMT 2023 , Edited by admin on Fri Dec 15 15:18:20 GMT 2023
PRIMARY
DAILYMED
S497LCF9C9
Created by admin on Fri Dec 15 15:18:20 GMT 2023 , Edited by admin on Fri Dec 15 15:18:20 GMT 2023
PRIMARY
MERCK INDEX
m7881
Created by admin on Fri Dec 15 15:18:20 GMT 2023 , Edited by admin on Fri Dec 15 15:18:20 GMT 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
202-332-3
Created by admin on Fri Dec 15 15:18:20 GMT 2023 , Edited by admin on Fri Dec 15 15:18:20 GMT 2023
PRIMARY