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Identification
NameNiacin
Accession NumberDB00627  (APRD00536, NUTR00042)
Typesmall molecule
Groupsapproved, investigational, 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
Synonyms
SynonymLanguageCode
3-carboxypyridineNot AvailableNot Available
3-Pyridinecarboxylic acidNot AvailableNot Available
3-Pyridylcarboxylic acidNot AvailableNot Available
Acide NicotiniqueNot AvailableINN
Acidum NicotinicumNot AvailableINN
M-Pyridinecarboxylic AcidNot AvailableNot Available
Nicotinic AcidNot AvailableINN
pyridine-β-carboxylic acidNot AvailableNot Available
Vitamin B3Not AvailableNot Available
β-pyridinecarboxylic acidNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
NiacorNot Available
NiaspanNot Available
Brand mixtures
Brand NameIngredients
Chromium with Niacin and Niacinamide-LiqChromium (Chromic Chloride) + Nicotinamide + Nicotinic Acid
FF Formula Niacin & InositolInositol + Nicotinic Acid
Flush Free Niacin with InositolInositol (Inositol Hexanicotinate) + Nicotinic Acid
Lipofactors & NiacinCholine (Choline Bitartrate) + Inositol + Nicotinic Acid
My Favorite Niacin and Inositol TabInositol + Nicotinic Acid
Niacin 500 Mg and InositolInositol + Nicotinic Acid
Niacin and InositolInositol + Nicotinic Acid
Niacin Capsules with ChromiumChromium + Nicotinic Acid
Niacin-Niacinamide TabNicotinamide + Nicotinic Acid
No Flush Niacin with InositolInositol (Inositol Hexanicotinate) + Nicotinic Acid
One a Day Advance High Pot.B Complex and CBeta-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 CBeta-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 TabChromium (Chromium Hvp Chelate) + Gamma-Linolenic Acid (Borage Oil) + Nicotinic Acid
SimcorNiacin + Simvastatin
Vitamin C with Niacin and Niacinamide-LiqNicotinamide + Nicotinic Acid + Vitamin C
Categories
CAS number59-67-6
WeightAverage: 123.1094
Monoisotopic: 123.032028409
Chemical FormulaC6H5NO2
InChI KeyPVNIIMVLHYAWGP-UHFFFAOYSA-N
InChI
InChI=1S/C6H5NO2/c8-6(9)5-2-1-3-7-4-5/h1-4H,(H,8,9)
IUPAC Name
pyridine-3-carboxylic acid
SMILES
OC(=O)C1=CN=CC=C1
Mass Specshow(7.87 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassPyridines and Derivatives
SubclassPyridinecarboxylic Acids and Derivatives
Direct parentPyridinecarboxylic Acids
Alternative parentsPolyamines; Enolates; Carboxylic Acids
Substituentscarboxylic acid derivative; enolate; carboxylic acid; polyamine; organonitrogen compound
Classification descriptionThis compound belongs to the pyridinecarboxylic acids. These are compounds containing a pyridine ring bearing a carboxylic acid group.
Pharmacology
IndicationFor the treatment of type IV and V hyperlipidemia. It is indicated as ajunctive therapy.
PharmacodynamicsNiacin 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 actionNiacin 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.
AbsorptionBoth nicotinic acid and nicotinamide are efficiently absorbed from the stomach and small intestine.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic

Route of eliminationNot Available
Half life20-45 minutes.
ClearanceNot Available
ToxicityNicotinic 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
PathwayCategorySMPDB ID
Nicotinate and Nicotinamide MetabolismMetabolicSMP00048
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9672
Blood Brain Barrier + 0.9648
Caco-2 permeable + 0.8701
P-glycoprotein substrate Non-substrate 0.8683
P-glycoprotein inhibitor I Non-inhibitor 0.9935
P-glycoprotein inhibitor II Non-inhibitor 1.0
Renal organic cation transporter Non-inhibitor 0.8938
CYP450 2C9 substrate Non-substrate 0.8246
CYP450 2D6 substrate Non-substrate 0.9231
CYP450 3A4 substrate Non-substrate 0.8381
CYP450 1A2 substrate Non-inhibitor 0.9045
CYP450 2C9 substrate Non-inhibitor 0.907
CYP450 2D6 substrate Non-inhibitor 0.923
CYP450 2C19 substrate Non-inhibitor 0.94
CYP450 3A4 substrate Non-inhibitor 0.912
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9875
Ames test Non AMES toxic 0.9939
Carcinogenicity Non-carcinogens 0.8566
Biodegradation Ready biodegradable 0.9437
Rat acute toxicity 1.2760 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9557
hERG inhibition (predictor II) Non-inhibitor 0.9829
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
FormRouteStrength
CapsuleOral
Capsule, extended releaseOral
PowderOral
SolutionIntramuscular
TabletOral
Tablet, extended releaseOral
Prices
Unit descriptionCostUnit
Niaspan 1000 mg Controlled Release Tabs4.67USDtab
Simcor 1000-20 mg 24 Hour tablet4.67USDtablet
Niaspan er 1000 mg tablet4.49USDtablet
Simcor 1000-20 mg tablet4.49USDtablet
Niaspan 1000 mg tablet er4.04USDtablet
Niaspan 750 mg Controlled Release Tabs3.76USDtab
Niaspan er 750 mg tablet3.62USDtablet
Simcor 750-20 mg tablet3.62USDtablet
Niaspan 750 mg tablet er3.25USDtablet
Niaspan 500 mg Controlled Release Tabs2.65USDtab
Simcor 500-20 mg 24 Hour tablet2.64USDtablet
Niaspan er 500 mg tablet2.54USDtablet
Simcor 500-20 mg tablet2.54USDtablet
Niaspan 500 mg tablet er2.28USDtablet
Nicomide-t 4% cream1.1USDg
Niacinamide ascorbate powder0.57USDg
Niacin flush free 750 mg capsule0.35USDcapsule
Niacinamide powder0.24USDg
Slo-niacin 750 mg tablet0.19USDtablet
Niacin 500 mg capsule0.16USDcapsule
Slo-niacin 500 mg tablet0.14USDtablet
Niacin 500 mg tablet0.1USDtablet
Slo-niacin 250 mg tablet0.09USDtablet
Niacin 1000 mg tablet sa0.08USDtablet
No flush niacin capsule0.08USDcapsule
Niacin 250 mg tablet sa0.06USDtablet
Niacin flush free 500 mg capsule0.06USDcapsule
Niacin 250 mg tablet0.03USDtablet
Niacinamide 500 mg tablet0.03USDtablet
Niacin 100 mg caplet0.02USDcaplet
Niacin 100 mg tablet0.02USDtablet
Niacin 50 mg tablet0.02USDtablet
Niacinamide 100 mg tablet0.02USDtablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
CountryPatent NumberApprovedExpires (estimated)
United States64690351998-03-152018-03-15
United States61299301993-09-202013-09-20
Canada22831592007-06-192018-03-06
Canada22985492006-01-102018-07-31
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point236.6 °CPhysProp
water solubility1.8E+004 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP0.36SANGSTER (1993)
logS-0.84ADME Research, USCD
pKa4.75 (at 25 °C)DEAN,JA (1985)
Predicted Properties
PropertyValueSource
water solubility8.31e+01 g/lALOGPS
logP0.29ALOGPS
logP-0.17ChemAxon
logS-0.17ALOGPS
pKa (strongest acidic)2.79ChemAxon
pKa (strongest basic)4.19ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count1ChemAxon
polar surface area50.19ChemAxon
rotatable bond count1ChemAxon
refractivity31.16ChemAxon
polarizability11.3ChemAxon
number of rings1ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraGC-MSMS/MSLC-MS1D NMR2D NMR
References
Synthesis Reference

Joseph E. Toomey, Jr., “Electrochemical synthesis of niacin and other N-heterocyclic compounds.” U.S. Patent US5002641, issued 1914.

US5002641
General Reference
  1. Gopal E, Fei YJ, Miyauchi S, Zhuang L, Prasad PD, Ganapathy V: Sodium-coupled and electrogenic transport of B-complex vitamin nicotinic acid by slc5a8, a member of the Na/glucose co-transporter gene family. Biochem J. 2005 May 15;388(Pt 1):309-16. Pubmed
External Links
ResourceLink
KEGG DrugD00049
KEGG CompoundC00253
PubChem Compound938
PubChem Substance46507508
ChemSpider913
BindingDB23515
ChEBI15940
ChEMBLCHEMBL573
PharmGKBPA450617
IUPHAR1594
Guide to Pharmacology1594
HETNIO
Drug Product Database2245265
RxListhttp://www.rxlist.com/cgi/generic3/niacor.htm
Drugs.comhttp://www.drugs.com/niacin.html
WikipediaNiacin
ATC CodesNot Available
AHFS Codes
  • 24:06.92
  • 88:08.00
PDB Entries
FDA labelshow(330 KB)
MSDSshow(73.2 KB)
Interactions
Drug Interactions
Drug
ColesevelamBile Acid Sequestrants may decrease the absorption of Niacin. It may be prudent to separate the administration times of niacin and bile acid sequestrants by a few hours in order to reduce the potential for reduced efficacy of these agents. The manufacturer of colesevelam recommends that drugs should be administered at least 1 hour before or 4 hours after colesevelam.
LovastatinRisk of severe myopathy/rhabdomyolysis with this combination
PitavastatinIncreased incidence of adverse drug reactions (ie. rhabdomyolysis) of both niacin and pitavastatin via pharmacodynamic synergism. Use alternative therapy.
Food Interactions
  • Avoid alcohol.
  • Take with food.

Targets

1. Hydroxycarboxylic acid receptor 3

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Hydroxycarboxylic acid receptor 3 P49019 Details

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. Hydroxycarboxylic acid receptor 2

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Hydroxycarboxylic acid receptor 2 Q8TDS4 Details

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]

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: binder

Components

Name UniProt ID Details
Nicotinate-nucleotide pyrophosphorylase [carboxylating] Q15274 Details

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

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: binder

Components

Name UniProt ID Details
Nicotinamide N-methyltransferase P40261 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2D6 P10635 Details

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. Solute carrier family 22 member 5

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 5 O76082 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier organic anion transporter family member 2B1 O94956 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Monocarboxylate transporter 1 P53985 Details

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

4. Sodium-coupled monocarboxylate transporter 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Sodium-coupled monocarboxylate transporter 1 Q8N695 Details

References:

  1. Gopal E, Fei YJ, Miyauchi S, Zhuang L, Prasad PD, Ganapathy V: Sodium-coupled and electrogenic transport of B-complex vitamin nicotinic acid by slc5a8, a member of the Na/glucose co-transporter gene family. Biochem J. 2005 May 15;388(Pt 1):309-16. Pubmed

5. Monocarboxylate transporter 4

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Monocarboxylate transporter 4 O15427 Details

References:

  1. Shimada A, Nakagawa Y, Morishige H, Yamamoto A, Fujita T: Functional characteristics of H+ -dependent nicotinate transport in primary cultures of astrocytes from rat cerebral cortex. Neurosci Lett. 2006 Jan 16;392(3):207-12. Epub 2005 Oct 5. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:11