NAV

Inositol nicotinate

Identification

Summary

Inositol nicotinate is a vasodilator and source of niacin found in dietary supplements.

Generic Name
Inositol nicotinate
DrugBank Accession Number
DB08949
Background

Inositol nicotinate, also known as Inositol hexaniacinate/hexanicotinate or "no-flush niacin", is a niacin ester and vasodilator. It is used in food supplements as a source of niacin (vitamin B3), where hydrolysis of 1 g (1.23 mmol) inositol hexanicotinate yields 0.91 g nicotinic acid and 0.22 g inositol. Niacin exists in different forms including nicotinic acid, nicotinamide and other derivatives such as inositol nicotinate. It is associated with reduced flushing compared to other vasodilators by being broken down into the metabolites and inositol at a slower rate. Nicotinic acid plays an essential role in many important metabolic processes and has been used as lipid-lowering agent. Inositol nicotinate is prescribed in Europe under the name Hexopal as a symptomatic treatment for severe intermittent claudication and Raynaud’s phenomenon.

Type
Small Molecule
Groups
Approved, Withdrawn
Structure
Similar Structures
Weight
Average: 810.732
Monoisotopic: 810.19217043
Chemical Formula
C42H30N6O12
Synonyms
  • hexanicotol
  • Inositol hexanicotinate
  • Inositol niacinate
  • Inositol nicotinate
  • mesoinositol hexanicotinate
  • myo-inositol hexanicotinate
External IDs
  • NSC-49506
  • WIN 9154
  • WIN-9154
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Pharmacology

Indication

Indicated as a dietary supplement for the source of niacin. Has been investigated for potential beneficial effects on serum lipids. In Europe, inositol hexanicotinate is indicated as a patented drug known as Hexopal, which is therapeutically indicated for the symptomatic relief of severe intermittent claudication and Raynaud’s phenomenon.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Inositol nicotinate mediates a vasodilatory, lipid-lowering and fibrinolytic effect on the cardiovascular system. Like other niacins, inositol nicotinate is a lipid-regulating agent that reduces the levels of plasma triglycerides, atherogenic apolipoprotein B (apoB)-containing lipoproteins (VLDL, LDL and lipoprotein a) while increasing antiatherogenic apoA-I-containing HDL levels 10.

Mechanism of action

Inositol nicotinate and other niacins directly and noncompetitively inhibit microsomal enzyme diacylglycerol acyltransferase 2 (DGAT2) responsible for esterification of fatty acids to form triglycerides, resulting in decreased triglyceride synthesis and hepatic atherogenic lipoprotein secretion. Inhibitied triglyceride synthesis results in accelerated intracellular hepatic apo B degradation and the decreased secretion of VLDL and LDL particles 6. Niacin also inhibits hepatic expression of beta-chain adenosine triphosphate synthase which inhibits the removal or uptake of HDL–apo A-I. It is also suggested that niacin increases vascular endothelial cell redox state, resulting in the inhibition of oxidative stress and vascular inflammatory genes or key cytokines involved in atherosclerosis. It acts as a ligand on G-protein coupled receptor 109A (HCAR2/HM74A) and 109B (HCAR3/HM74) which mediates the anti-lipolytic and lipid-lowering effects of nicotinic acid. Niacin-mediated signalling of GPR109A expressed on adipocytes and G(i)-mediated decrease in cAMP levels result in decreased lipolysis, fatty acid mobilization, and triglyceride synthesis. The action of inositol nicotinate on GPR109A expressed on skin and macrophages to cause increased prostaglandin D2/E2 activity is thought to be less significant compared to other niacin molecules as it involves sustained release that leads to less flushing 6.

TargetActionsOrganism
AHydroxycarboxylic acid receptor 3
agonist
Humans
AHydroxycarboxylic acid receptor 2
agonist
Humans
Absorption

Gastrointestinal absorption of inositol hexanicotinate varies widely, with an average of 70% of an orally ingested dose absorbed from stomach and upper small intestines into the bloodstream as intact form. The maximum serum levels of nicotinic acid is reached approximately 6-10 hours after oral ingestion. At low concentrations, the absorption of nicotinic acid and nicotinamide is mediated by sodium ion-dependent facilitated diffusion. At higher concentrations, passive diffusion predominates with doses of 3 to 4 g of niacin being almost completely absorbed 12.

Volume of distribution

Mean Vd following intravenous administration of 50mg/kg of inositol nicotinate in rats is 1051±250 mL/kg 2.

Protein binding

Not Available

Metabolism

Inositol nicotinate undergoes hydrolysis by plasma esterases, releasing free nicotinic acid and inositol in a sustained manner. The process takes more than 48hours, where the bloodstream enzymatic hydrolysis of inositol hexanicotinate was found to be slower in the first ester linkage of inositol hexanicotinate than in subsequent linkages 12. Sequential hydrolytic steps of inositol nicotinate forms one nicotinic acid molecule in each step, producing eventually six molecules of nicotinic acid and one inositol moiety 2.

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Route of elimination

Unabsorbed inositol nicotinate is detected in feces.

Half-life

Mean elimination half life in healthy human adults is approximately one hour 2.

Clearance

Mean clearance rate following intravenous administration of 50mg/kg of inositol nicotinate in rats is 65.4±19 mL/min/kg 2.

Adverse Effects
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Toxicity

NOAEL is 4000mg. Inositol nicotinate can cause muscle pain, headache, redness of face, nausea, vomiting, edema and rash.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
Integrate drug-drug
interactions in your software
IloprostIloprost may increase the hypotensive activities of Inositol nicotinate.
Isosorbide mononitrateInositol nicotinate may increase the vasodilatory activities of Isosorbide mononitrate.
Patent BlueThe therapeutic efficacy of Inositol nicotinate can be decreased when used in combination with Patent Blue.
Food Interactions
No interactions found.

Products

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International/Other Brands
Hexaniton (Ni-The) / Hexazin (Johnson) / Hexin (New Chemical) / Hexopal (Clonmel) / Iexaniton (Ni-The) / Nicoxatin (Fuso Pharmaceutical)
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Flush Free Niacin With InositolInositol nicotinate (125 mg) + Niacin (500 mg)CapsuleOralNutraceutical Corporation2003-09-022006-08-02Canada flag
Inositol Nicotinate 250 mgInositol nicotinate (51 mg) + Inositol nicotinate (186 mg)TabletOralGeneral Nutrition Canada Inc.1997-11-272009-08-05Canada flag
Inositol Nicotinate 250 mgInositol nicotinate (51 mg) + Inositol nicotinate (186 mg)TabletOralGeneral Nutrition Canada Inc.1997-11-272009-08-05Canada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
DermaNICInositol nicotinate (328 mg/1) + Acetylcysteine zinc (69.5 mg/1) + Chromium nicotinate (0.57 mg/1) + Ferrous cysteine glycinate (1.5 mg/1) + Folic acid (500 ug/1) + Hydroxocobalamin (15 ug/1) + Niacin (1.5 mg/1) + Nicotinamide (498 mg/1)TabletOralAllegis Pharmaceuticals, LLC2014-02-032016-12-01US flag
Tricare Prenatal DHA OneInositol nicotinate (20 mg/1) + Ascorbic acid (60 mg/1) + Biotin (300 ug/1) + Cholecalciferol (800 [iU]/1) + Cupric sulfate (2 mg/1) + Cyanocobalamin (100 ug/1) + Doconexent (215 mg/1) + Docusate sodium (25 mg/1) + Ferrous fumarate (27 mg/1) + Fish oil (500 mg/1) + Folic acid (1 mg/1) + Icosapent (45 mg/1) + Pyridoxine hydrochloride (25 mg/1) + Riboflavin (3.4 mg/1) + Thiamine mononitrate (3 mg/1) + Vitamin E (30 [iU]/1) + Zinc sulfate monohydrate (10 mg/1)Capsule, gelatin coatedOralMedecor Pharma, Llc2012-01-01Not applicableUS flag
Tricare Prenatal DHA One Rx MultivitaminInositol nicotinate (20 mg/1) + Ascorbic acid (60 mg/1) + Biotin (300 ug/1) + Cholecalciferol (800 [iU]/1) + Cupric sulfate (2 mg/1) + Cyanocobalamin (100 ug/1) + Doconexent (215 mg/1) + Docusate sodium (25 ug/1) + Ferrous fumarate (27 mg/1) + Fish oil (500 mg/1) + Folic acid (1 mg/1) + Icosapent (45 mg/1) + Potassium Iodide (150 ug/1) + Pyridoxine hydrochloride (25 mg/1) + Riboflavin (3.4 mg/1) + Thiamine mononitrate (3 mg/1) + Vitamin E (30 [iU]/1) + Zinc sulfate monohydrate (10 mg/1)Capsule, gelatin coatedOralMedecor Pharma, Llc2019-03-15Not applicableUS flag

Categories

ATC Codes
C04AC03 — Inositol nicotinate
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as hexacarboxylic acids and derivatives. These are carboxylic acids containing exactly six carboxyl groups.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Hexacarboxylic acids and derivatives
Direct Parent
Hexacarboxylic acids and derivatives
Alternative Parents
Pyridinecarboxylic acids / Cyclitols and derivatives / Heteroaromatic compounds / Carboxylic acid esters / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
Aromatic heteromonocyclic compound / Azacycle / Carboxylic acid ester / Cyclitol or derivatives / Heteroaromatic compound / Hexacarboxylic acid or derivatives / Hydrocarbon derivative / Organic nitrogen compound / Organic oxide / Organic oxygen compound
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
inositol hexanicotinate (CHEBI:31699)
Affected organisms
Not Available

Chemical Identifiers

UNII
A99MK953KZ
CAS number
6556-11-2
InChI Key
MFZCIDXOLLEMOO-GYSGTQPESA-N
InChI
InChI=1S/C42H30N6O12/c49-37(25-7-1-13-43-19-25)55-31-32(56-38(50)26-8-2-14-44-20-26)34(58-40(52)28-10-4-16-46-22-28)36(60-42(54)30-12-6-18-48-24-30)35(59-41(53)29-11-5-17-47-23-29)33(31)57-39(51)27-9-3-15-45-21-27/h1-24,31-36H/t31-,32-,33-,34+,35-,36-
IUPAC Name
(1R,2S,3R,4R,5S,6s)-2,3,4,5,6-pentakis(pyridine-3-carbonyloxy)cyclohexyl pyridine-3-carboxylate
SMILES
O=C(O[C@H]1[C@H](OC(=O)C2=CC=CN=C2)[C@@H](OC(=O)C2=CC=CN=C2)[C@H](OC(=O)C2=CC=CN=C2)[C@H](OC(=O)C2=CC=CN=C2)[C@@H]1OC(=O)C1=CC=CN=C1)C1=CC=CN=C1

References

General References
  1. Dib JG, Dedeyan S: Purported benefits of inositol niacinate. Am J Health Syst Pharm. 2004 Feb 1;61(3):307-8. [Article]
  2. Milton SG, Robinson K, Ma J, Wei B, Poon IO, Liang D: Biotransformation and pharmacokinetics of inositol hexanicotinate in rats. Xenobiotica. 2013 Sep;43(9):817-22. doi: 10.3109/00498254.2012.762591. Epub 2013 Jan 24. [Article]
  3. Canner PL, Furberg CD, Terrin ML, McGovern ME: Benefits of niacin by glycemic status in patients with healed myocardial infarction (from the Coronary Drug Project). Am J Cardiol. 2005 Jan 15;95(2):254-7. [Article]
  4. Karpe F, Frayn KN: The nicotinic acid receptor--a new mechanism for an old drug. Lancet. 2004 Jun 5;363(9424):1892-4. [Article]
  5. Harthon L, Brattsand R: Enzymatic hydrolysis of pentaerythritoltetranicotinate and meso-inositolhexanicotinate in blood and tissues. Arzneimittelforschung. 1979;29(12):1859-62. [Article]
  6. Kamanna VS, Kashyap ML: Mechanism of action of niacin. Am J Cardiol. 2008 Apr 17;101(8A):20B-26B. doi: 10.1016/j.amjcard.2008.02.029. [Article]
  7. Kamanna VS, Kashyap ML: Mechanism of action of niacin on lipoprotein metabolism. Curr Atheroscler Rep. 2000 Jan;2(1):36-46. [Article]
  8. Ganji SH, Kamanna VS, Kashyap ML: Niacin and cholesterol: role in cardiovascular disease (review). J Nutr Biochem. 2003 Jun;14(6):298-305. [Article]
  9. Garg A, Sharma A, Krishnamoorthy P, Garg J, Virmani D, Sharma T, Stefanini G, Kostis JB, Mukherjee D, Sikorskaya E: Role of Niacin in Current Clinical Practice: A Systematic Review. Am J Med. 2017 Feb;130(2):173-187. doi: 10.1016/j.amjmed.2016.07.038. Epub 2016 Oct 26. [Article]
  10. Ganji SH, Tavintharan S, Zhu D, Xing Y, Kamanna VS, Kashyap ML: Niacin noncompetitively inhibits DGAT2 but not DGAT1 activity in HepG2 cells. J Lipid Res. 2004 Oct;45(10):1835-45. Epub 2004 Jul 16. [Article]
  11. 23. (2012). In Rang and Dale's Pharmacology (7th ed., pp. 291). Edinburgh: Elsevier/Churchill Livingstone. [ISBN:978-0-7020-3471-8]
  12. SCIENTIFIC OPINION Inositol hexanicotinate [Link]
  13. Vitamin and Mineral Safety 3rd Edition (2013) Council for Responsible Nutrition (CRN); Niacin: Nicotinic Acid, Nicotinamide, and Inositol Hexanicotinate [Link]
KEGG Drug
D01813
PubChem Compound
3720
PubChem Substance
347827813
ChemSpider
16736141
RxNav
27604
ChEBI
31699
ChEMBL
CHEMBL1094982
ZINC
ZINC000150338506
Drugs.com
Drugs.com Drug Page
Wikipedia
Inositol_nicotinate
MSDS
Download (69.3 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
TabletOral
CapsuleOral
Capsule, gelatin coatedOral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubilityInsolubleSCIENTIFIC OPINION Inositol hexanicotinate
Predicted Properties
PropertyValueSource
Water Solubility0.0174 mg/mLALOGPS
logP3.49ALOGPS
logP3.88Chemaxon
logS-4.7ALOGPS
pKa (Strongest Basic)4.02Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count12Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area235.14 Å2Chemaxon
Rotatable Bond Count18Chemaxon
Refractivity201.77 m3·mol-1Chemaxon
Polarizability76.08 Å3Chemaxon
Number of Rings7Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0000003090-c7df261c3f2c098d67d3
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-01q9-0000092000-ea752b95d7d29ecbc560
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0bt9-0900000780-ef70a355e867a98f5540
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ac0-2030956040-8d599ee002d7d7530de8
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-4900803060-851d3c9bf700081d1dd3
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000010000-56a513e4a90e19eab253
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-279.6612537
predicted
DarkChem Lite v0.1.0
[M-H]-251.62541
predicted
DeepCCS 1.0 (2019)
[M+H]+277.8519537
predicted
DarkChem Lite v0.1.0
[M+H]+253.42409
predicted
DeepCCS 1.0 (2019)
[M+Na]+280.3417537
predicted
DarkChem Lite v0.1.0
[M+Na]+259.6781
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Hydroxycarboxylic acid receptor 3
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
G-protein coupled receptor activity
Specific Function
Receptor for 3-OH-octanoid acid mediates a negative feedback regulation of adipocyte lipolysis to counteract prolipolytic influences under conditions of physiological or pathological increases in b...
Gene Name
HCAR3
Uniprot ID
P49019
Uniprot Name
Hydroxycarboxylic acid receptor 3
Molecular Weight
44477.93 Da
References
  1. 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. [Article]
  2. 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. [Article]
  3. 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. [Article]
Details2. Hydroxycarboxylic acid receptor 2
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Nicotinic acid receptor activity
Specific Function
Acts as a high affinity receptor for both nicotinic acid (also known as niacin) and (D)-beta-hydroxybutyrate and mediates increased adiponectin secretion and decreased lipolysis through G(i)-protei...
Gene Name
HCAR2
Uniprot ID
Q8TDS4
Uniprot Name
Hydroxycarboxylic acid receptor 2
Molecular Weight
41849.08 Da
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. [Article]
  2. 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. [Article]
  3. 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. [Article]

Enzymes

Details1. ATP synthase subunit beta, mitochondrial
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Transporter activity
Specific Function
Mitochondrial membrane ATP synthase (F(1)F(0) ATP synthase or Complex V) produces ATP from ADP in the presence of a proton gradient across the membrane which is generated by electron transport comp...
Gene Name
ATP5B
Uniprot ID
P06576
Uniprot Name
ATP synthase subunit beta, mitochondrial
Molecular Weight
56559.42 Da
References
  1. Zhang LH, Kamanna VS, Zhang MC, Kashyap ML: Niacin inhibits surface expression of ATP synthase beta chain in HepG2 cells: implications for raising HDL. J Lipid Res. 2008 Jun;49(6):1195-201. doi: 10.1194/jlr.M700426-JLR200. Epub 2008 Mar 3. [Article]
Details2. Diacylglycerol O-acyltransferase 2
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Essential acyltransferase that catalyzes the terminal and only committed step in triacylglycerol synthesis by using diacylglycerol and fatty acyl CoA as substrates. Required for synthesis and storage of intracellular triglycerides. Probably plays a central role in cytosolic lipid accumulation. In liver, is primarily responsible for incorporating endogenously synthesized fatty acids into triglycerides (By similarity). Functions also as an acyl-CoA retinol acyltransferase (ARAT).
Specific Function
2-acylglycerol o-acyltransferase activity
Gene Name
DGAT2
Uniprot ID
Q96PD7
Uniprot Name
Diacylglycerol O-acyltransferase 2
Molecular Weight
43830.475 Da
References
  1. Ganji SH, Tavintharan S, Zhu D, Xing Y, Kamanna VS, Kashyap ML: Niacin noncompetitively inhibits DGAT2 but not DGAT1 activity in HepG2 cells. J Lipid Res. 2004 Oct;45(10):1835-45. Epub 2004 Jul 16. [Article]

Transporters

Details1. Sodium-coupled monocarboxylate transporter 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Symporter activity
Specific Function
Acts as an electrogenic sodium (Na(+)) and chloride (Cl-)-dependent sodium-coupled solute transporter, including transport of monocarboxylates (short-chain fatty acids including L-lactate, D-lactat...
Gene Name
SLC5A8
Uniprot ID
Q8N695
Uniprot Name
Sodium-coupled monocarboxylate transporter 1
Molecular Weight
66577.005 Da
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. [Article]

Drug created at May 27, 2014 18:49 / Updated at April 24, 2024 14:30