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Identification
Name Niacin
Accession Number DB00627 (APRD00536, NUTR00042)
Type small molecule
Groups approved, nutraceutical
Description

A water-soluble vitamin of the B complex occurring in various animal and plant tissues. It is required by the body for the formation of coenzymes NAD and NADP. It has pellagra-curative, vasodilating, and antilipemic properties. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • 3-Pyridinecarboxylic acid
  • Acide Nicotinique
  • Acidum Nicotinicum
  • M-Pyridinecarboxylic Acid
  • NAH
  • niacin
  • Nicotine Acid
  • Nicotinic Acid
  • Pyridinecarboxylic Acid
  • Pyridylcarboxylic Acid
  • Vitamin B3
Brand names
  • Akotin
  • Anti-Pellagra Vitamin
  • Apelagrin
  • Bionic
  • Daskil
  • Davitamon PP
  • Diacin
  • Direktan
  • Efacin
  • Kyselina Nikotinova
  • Linic
  • Naotin
  • Niac
  • Niaspan
  • Nicacid
  • Nicangin
  • NICO
  • Nico-Span
  • Nicocidin
  • Nicocrisina
  • Nicodan
  • Nicodelmine
  • Nicodon
  • Niconacid
  • Niconat
  • Niconazid
  • Nicorol
  • Nicosan 3
  • Nicoside
  • Nicosyl
  • Nicotamin
  • Nicotene
  • Nicotil
  • Nicotinipca
  • Nicotinsaure
  • Nicovasan
  • Nicovasen
  • Nicovel
  • Nicyl
  • Nipellen
  • Nyclin
  • P.P. Factor
  • Pellagra Preventive Factor
  • Pellagramin
  • Pellagrin
  • Pelonin
  • Peviton
  • PP Factor
  • Simcor
  • Sk-Niacin
  • Tega-Span
  • Tinic
  • Vitaplex N
Brand name mixtures
  • Chromium with Niacin and Niacinamide-Liq (Chromium (Chromic Chloride) + Nicotinamide + Nicotinic Acid)
  • Ff Formula Niacin & Inositol (Inositol + Nicotinic Acid)
  • Flush Free Niacin with Inositol (Inositol (Inositol Hexanicotinate) + Nicotinic Acid)
  • Lipofactors & Niacin (Choline (Choline Bitartrate) + Inositol + Nicotinic Acid)
  • My Favorite Niacin and Inositol Tab (Inositol + Nicotinic Acid)
  • Niacin 500 Mg and Inositol (Inositol + Nicotinic Acid)
  • Niacin and Inositol (Inositol + Nicotinic Acid)
  • Niacin Capsules with Chromium (Chromium + Nicotinic Acid)
  • Niacin-Niacinamide Tab (Nicotinamide + Nicotinic Acid)
  • No Flush Niacin with Inositol (Inositol (Inositol Hexanicotinate) + Nicotinic Acid)
  • One a Day Advance High Pot.B Complex and C (Beta-Carotene + Copper (Cupric Oxide) + D-Pantothenic Acid (Calcium D-Pantothenate) + Dl-Alpha Tocopheryl Acetate + Folic Acid + Iron (Ferrous Fumarate) + Nicotinamide (Niacin Ascorbate) + Thiamine Mononitrate + Vitamin a Acetate + Vitamin B12 + Vitamin B2 + Vitamin B6 + Vitamin C + Vitamin D + Zinc (Zinc Oxide))
  • One Tablet Daily High Potency B Complex and C (Beta-Carotene + Copper (Cupric Oxide) + D-Pantothenic Acid (Calcium D-Pantothenate) + Folic Acid + Iron (Ferrous Fumarate) + Nicotinamide (Niacin Ascorbate) + Vitamin a (Vitamin a Acetate) + Vitamin B1 (Thiamine Mononitrate) + Vitamin B12 + Vitamin B2 + Vitamin B6 + Vitamin C + Vitamin D + Vitamin E (Dl-Alpha Tocopheryl Acetate) + Zinc (Zinc Oxide))
  • Primanol-Borage with Niacin and Chromium Tab (Chromium (Chromium Hvp Chelate) + Gamma-Linolenic Acid (Borage Oil) + Nicotinic Acid)
  • Vitamin C with Niacin and Niacinamide-Liq (Nicotinamide + Nicotinic Acid + Vitamin C)
Categories
  • Vitamins (Vitamin B Complex)
  • Vasodilator Agents
  • Antilipemic Agents
  • Vitamin B Complex
CAS number 59-67-6
Weight Average: 123.1094
Monoisotopic: 123.032028409
Chemical Formula C6H5NO2
InChI Key InChIKey=PVNIIMVLHYAWGP-UHFFFAOYSA-N
InChI
InChI=1S/C6H5NO2/c8-6(9)5-2-1-3-7-4-5/h1-4H,(H,8,9)
Plain Text
IUPAC Name
pyridine-3-carboxylic acid
SMILES
OC(=O)C1=CC=CN=C1
Plain Text
Mass Spec show (7.9 KB)
Taxonomy
Kingdom Organic
Classes
  • Amino Acids
  • Pyridines and Derivatives
Substructures
  • Amino Acids
  • Hydroxy Compounds
  • Acetates
  • Pyridines and Derivatives
  • Carboxylic Acids and Derivatives
  • Heterocyclic compounds
  • Aromatic compounds
Pharmacology
Indication For the treatment of type IV and V hyperlipidemia. It is indicated as ajunctive therapy.
Pharmacodynamics Niacin and niacinamide are indicated for prevention and treatment of vitamin B3 deficiency states. Vitamin B3 (Niacin) also acts to reduce LDL cholesterol, triglycerides, and HDL cholesterol. The magnitude of individual lipid and lipoprotein responses may be influenced by the severity and type of underlying lipid abnormality. The increase in total HDL is associated with a shift in the distribution of HDL subfractions (as defined by ultra-centrifugation) with an increase in the HDL2:HDL3 ratio and an increase in apolipoprotein A-I content. Vitamin B3 (Niacin) treatment also decreases the serum levels of apolipoprotein B-100 (apo B), the major protein component of the VLDL (very low-density lipoprotein) and LDL fractions, and of lipoprotein-a, a variant form of LDL independently associated with coronary risk.
Mechanism of action Niacin binds to Nicotinate D-ribonucleotide phyrophsopate phosphoribosyltransferase, Nicotinic acid phosphoribosyltransferase, Nicotinate N-methyltransferase and the Niacin receptor. Niacin is the precursor to nicotinamide adenine dinucleotide (NAD) and nicotinamide adenine dinucleotide phosphate (NADP), which are vital cofactors for dozens of enzymes. The mechanism by which niacin exerts its lipid lowering effects is not entirely understood, but may involve several actions, including a decrease in esterification of hepatic triglycerides. Niacin treatment also decreases the serum levels of apolipoprotein B-100 (apo B), the major protein component of the VLDL (very low-density lipoprotein) and LDL fractions.
Absorption Both nicotinic acid and nicotinamide are efficiently absorbed from the stomach and small intestine.
Volume of distribution Not Available
Protein binding Not Available
Metabolism

Hepatic
Route of elimination Not Available
Half life 20-45 minutes.
Clearance Not Available
Toxicity Nicotinic acid can cause vasodilation of cutaneous blood vessels resulting in increased blood flow, principally in the face, neck and chest. This produces the niacin- or nicotinic acid-flush. The niacin-flush is thought to be mediated via the prostaglandin prostacyclin. Histamine may also play a role in the niacin-flush. Flushing is the adverse reaction first observed after intake of a large dose of nicotinic acid, and the most bothersome one. LD50 7000 mg/kg (Rat)
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Medpointe pharmaceuticals medpointe healthcare inc
  • Barr laboratories inc
  • Abbott laboratories
  • Everylife
  • Halsey drug co inc
  • Impax laboratories inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Mk laboratories inc
  • Purepac pharmaceutical co
  • Sandoz inc
  • Tablicaps inc
  • Watson laboratories inc
  • West ward pharmaceutical corp
  • Wockhardt ltd
  • Upsher smith laboratories inc
  • Sanofi aventis us llc
Packagers
Dosage forms
Form Route Strength
Capsule Oral
Capsule, extended release Oral
Powder Oral
Solution Intramuscular
Tablet Oral
Tablet, extended release Oral
Prices
Unit description Cost Unit
Niaspan 1000 mg Controlled Release Tabs 4.67 USD tab
Simcor 1000-20 mg 24 Hour tablet 4.67 USD tablet
Niaspan er 1000 mg tablet 4.49 USD tablet
Simcor 1000-20 mg tablet 4.49 USD tablet
Niaspan 1000 mg tablet er 4.04 USD tablet
Niaspan 750 mg Controlled Release Tabs 3.76 USD tab
Niaspan er 750 mg tablet 3.62 USD tablet
Simcor 750-20 mg tablet 3.62 USD tablet
Niaspan 750 mg tablet er 3.25 USD tablet
Niaspan 500 mg Controlled Release Tabs 2.65 USD tab
Simcor 500-20 mg 24 Hour tablet 2.64 USD tablet
Niaspan er 500 mg tablet 2.54 USD tablet
Simcor 500-20 mg tablet 2.54 USD tablet
Niaspan 500 mg tablet er 2.28 USD tablet
Nicomide-t 4% cream 1.1 USD g
Niacinamide ascorbate powder 0.57 USD g
Niacin flush free 750 mg capsule 0.35 USD capsule
Niacinamide powder 0.24 USD g
Slo-niacin 750 mg tablet 0.19 USD tablet
Niacin 500 mg capsule 0.16 USD capsule
Slo-niacin 500 mg tablet 0.14 USD tablet
Niacin 500 mg tablet 0.1 USD tablet
Slo-niacin 250 mg tablet 0.09 USD tablet
Niacin 1000 mg tablet sa 0.08 USD tablet
No flush niacin capsule 0.08 USD capsule
Niacin 250 mg tablet sa 0.06 USD tablet
Niacin flush free 500 mg capsule 0.06 USD capsule
Niacin 250 mg tablet 0.03 USD tablet
Niacinamide 500 mg tablet 0.03 USD tablet
Niacin 100 mg caplet 0.02 USD caplet
Niacin 100 mg tablet 0.02 USD tablet
Niacin 50 mg tablet 0.02 USD tablet
Niacinamide 100 mg tablet 0.02 USD tablet
Patents
Country Patent Number Approved Expires
United States 6469035 1998-03-15 2018-03-15
United States 6129930 1993-09-20 2013-09-20
Canada 2283159 2007-06-19 2018-03-06
Canada 2298549 2006-01-10 2018-07-31
Properties
State solid
Melting point 237 oC
Experimental Properties
Property Value Source
water solubility 18 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)] PhysProp
logP 0.4 PhysProp
logS -0.84 [ADME Research, USCD] PhysProp
pKa 4.75 Various sources
Predicted Properties
Property Value Source
water solubility 8.31e+01 g/l ALOGPS
logP 0.29 ALOGPS
logP -0.19 ChemAxon Molconvert
logS -0.17 ALOGPS
pKa ChemAxon Molconvert
hydrogen acceptor count 3 ChemAxon Molconvert
hydrogen donor count 1 ChemAxon Molconvert
polar surface area 50.19 ChemAxon Molconvert
rotatable bond count 1 ChemAxon Molconvert
refractivity 31.16 ChemAxon Molconvert
polarizability 11.30 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00049 Link_out
KEGG Compound C00253 Link_out
PubChem Compound 938 Link_out
PubChem Substance 46507508 Link_out
ChemSpider 913 Link_out
BindingDB 23515 Link_out
ChEBI 15940 Link_out
ChEMBL 15940 Link_out
PharmGKB PA450617 Link_out
HET NIO Link_out
Drug Product Database 2245265 Link_out
RxList http://www.rxlist.com/cgi/generic3/niacor.htm Link_out
Drugs.com http://www.drugs.com/niacin.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Niacin Link_out
ATC Codes
  • C04AC01
  • C10AD02
AHFS Codes
  • 24:06.92
  • 88:08.00
PDB Entries
FDA label show (329.8 KB)
MSDS show (73.2 KB)
Interactions
Drug Interactions Not Available
Food Interactions
  • Avoid alcohol.
  • Take with food.
Targets

1. Nicotinic acid receptor 2

Pharmacological action: yes
Actions: agonist

Acts as a low affinity receptor for nicotinic acid and mediate its anti-lipolytic effect through a G(i)-protein-mediated inhibition of adenylyl cyclase. This pharmacological effect requires nicotinic acid doses that are much higher than those provided by a normal diet

Organism class: human
UniProt ID: P49019 Link_out
Gene: GPR109B Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Tunaru S, Kero J, Schaub A, Wufka C, Blaukat A, Pfeffer K, Offermanns S: PUMA-G and HM74 are receptors for nicotinic acid and mediate its anti-lipolytic effect. Nat Med. 2003 Mar;9(3):352-5. Epub 2003 Feb 3. Pubmed
  2. Taggart AK, Kero J, Gan X, Cai TQ, Cheng K, Ippolito M, Ren N, Kaplan R, Wu K, Wu TJ, Jin L, Liaw C, Chen R, Richman J, Connolly D, Offermanns S, Wright SD, Waters MG: (D)-beta-Hydroxybutyrate inhibits adipocyte lipolysis via the nicotinic acid receptor PUMA-G. J Biol Chem. 2005 Jul 22;280(29):26649-52. Epub 2005 Jun 1. Pubmed
  3. Zhang Y, Schmidt RJ, Foxworthy P, Emkey R, Oler JK, Large TH, Wang H, Su EW, Mosior MK, Eacho PI, Cao G: Niacin mediates lipolysis in adipose tissue through its G-protein coupled receptor HM74A. Biochem Biophys Res Commun. 2005 Aug 26;334(2):729-32. Pubmed
  4. Tunaru S, Lattig J, Kero J, Krause G, Offermanns S: Characterization of determinants of ligand binding to the nicotinic acid receptor GPR109A (HM74A/PUMA-G). Mol Pharmacol. 2005 Nov;68(5):1271-80. Epub 2005 Aug 11. Pubmed
  5. Benyo Z, Gille A, Kero J, Csiky M, Suchankova MC, Nusing RM, Moers A, Pfeffer K, Offermanns S: GPR109A (PUMA-G/HM74A) mediates nicotinic acid-induced flushing. J Clin Invest. 2005 Dec;115(12):3634-40. Pubmed
  6. Wise A, Foord SM, Fraser NJ, Barnes AA, Elshourbagy N, Eilert M, Ignar DM, Murdock PR, Steplewski K, Green A, Brown AJ, Dowell SJ, Szekeres PG, Hassall DG, Marshall FH, Wilson S, Pike NB: Molecular identification of high and low affinity receptors for nicotinic acid. J Biol Chem. 2003 Mar 14;278(11):9869-74. Epub 2003 Jan 9. Pubmed

2. Nicotinic acid receptor 1

Pharmacological action: yes
Actions: agonist

Acts as a high affinity receptor for nicotinic acid and mediates its anti-lipolytic effect through a G(i)-protein-mediated inhibition of adenylyl cyclase. This pharmacological effect requires nicotinic acid doses that are much higher than those provided by a normal diet

Organism class: human
UniProt ID: Q8TDS4 Link_out
Gene: GPR109A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Wise A, Foord SM, Fraser NJ, Barnes AA, Elshourbagy N, Eilert M, Ignar DM, Murdock PR, Steplewski K, Green A, Brown AJ, Dowell SJ, Szekeres PG, Hassall DG, Marshall FH, Wilson S, Pike NB: Molecular identification of high and low affinity receptors for nicotinic acid. J Biol Chem. 2003 Mar 14;278(11):9869-74. Epub 2003 Jan 9. Pubmed
  2. Soga T, Kamohara M, Takasaki J, Matsumoto S, Saito T, Ohishi T, Hiyama H, Matsuo A, Matsushime H, Furuichi K: Molecular identification of nicotinic acid receptor. Biochem Biophys Res Commun. 2003 Mar 28;303(1):364-9. Pubmed
  3. Zellner C, Pullinger CR, Aouizerat BE, Frost PH, Kwok PY, Malloy MJ, Kane JP: Variations in human HM74 (GPR109B) and HM74A (GPR109A) niacin receptors. Hum Mutat. 2005 Jan;25(1):18-21. Pubmed
  4. Zhang Y, Schmidt RJ, Foxworthy P, Emkey R, Oler JK, Large TH, Wang H, Su EW, Mosior MK, Eacho PI, Cao G: Niacin mediates lipolysis in adipose tissue through its G-protein coupled receptor HM74A. Biochem Biophys Res Commun. 2005 Aug 26;334(2):729-32. Pubmed
  5. Tunaru S, Lattig J, Kero J, Krause G, Offermanns S: Characterization of determinants of ligand binding to the nicotinic acid receptor GPR109A (HM74A/PUMA-G). Mol Pharmacol. 2005 Nov;68(5):1271-80. Epub 2005 Aug 11. Pubmed

3. Nicotinate-nucleotide pyrophosphorylase [carboxylating]

Pharmacological action: yes
Actions: binder
Organism class: human
UniProt ID: Q15274 Link_out
Gene: QPRT Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Fukuwatari T, Morikawa Y, Hayakawa F, Sugimoto E, Shibata K: Influence of adenine-induced renal failure on tryptophan-niacin metabolism in rats. Biosci Biotechnol Biochem. 2001 Oct;65(10):2154-61. Pubmed
  2. Shin DH, Oganesyan N, Jancarik J, Yokota H, Kim R, Kim SH: Crystal structure of a nicotinate phosphoribosyltransferase from Thermoplasma acidophilum. J Biol Chem. 2005 May 6;280(18):18326-35. Epub 2005 Mar 6. Pubmed
  3. Zheng XQ, Hayashibe E, Ashihara H: Changes in trigonelline (N-methylnicotinic acid) content and nicotinic acid metabolism during germination of mungbean (Phaseolus aureus) seeds. J Exp Bot. 2005 Jun;56(416):1615-23. Epub 2005 Apr 18. Pubmed

4. Nicotinamide N-methyltransferase

Pharmacological action: yes
Actions: binder

Catalyzes the N-methylation of nicotinamide and other pyridines to form pyridinium ions. This activity is important for biotransformation of many drugs and xenobiotic compounds

Organism class: human
UniProt ID: P40261 Link_out
Gene: NNMT Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Riederer M, Erwa W, Zimmermann R, Frank S, Zechner R: Adipose tissue as a source of nicotinamide N-methyltransferase and homocysteine. Atherosclerosis. 2009 Jun;204(2):412-7. Epub 2008 Sep 27. Pubmed
Enzymes

1. Cytochrome P450 2D6

Actions: inhibitor

Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants

UniProt ID: P10635 Link_out
Gene: CYP2D6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
Transporters

1. Organic cation/carnitine transporter 2

Actions: inhibitor

Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also Relative uptake activity ratio of carnitine to TEA is 11.3

UniProt ID: O76082 Link_out
Gene: SLC22A5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Ohashi R, Tamai I, Yabuuchi H, Nezu JI, Oku A, Sai Y, Shimane M, Tsuji A: Na(+)-dependent carnitine transport by organic cation transporter (OCTN2): its pharmacological and toxicological relevance. J Pharmacol Exp Ther. 1999 Nov;291(2):778-84. Pubmed

2. Solute carrier organic anion transporter family member 2B1

Actions: inhibitor

Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost

UniProt ID: O94956 Link_out
Gene: SLCO2B1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Kobayashi D, Nozawa T, Imai K, Nezu J, Tsuji A, Tamai I: Involvement of human organic anion transporting polypeptide OATP-B (SLC21A9) in pH-dependent transport across intestinal apical membrane. J Pharmacol Exp Ther. 2003 Aug;306(2):703-8. Epub 2003 Apr 30. Pubmed

3. Monocarboxylate transporter 1

Actions: substrate

Proton-linked monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucine, valine and isoleucine, and the ketone bodies acetoacetate, beta-hydroxybutyrate and acetate

UniProt ID: P53985 Link_out
Gene: SLC16A1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Tamai I, Sai Y, Ono A, Kido Y, Yabuuchi H, Takanaga H, Satoh E, Ogihara T, Amano O, Izeki S, Tsuji A: Immunohistochemical and functional characterization of pH-dependent intestinal absorption of weak organic acids by the monocarboxylic acid transporter MCT1. J Pharm Pharmacol. 1999 Oct;51(10):1113-21. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 23, 2011 08:11

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.