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Inositol Niacinate

Inositol niacinate

Synopsis, Chemistry

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Also known as: Inositol nicotinate, 6556-11-2, Inositol hexanicotinate, Mesotal, Dilexpal, Hexanicotol

Molecular Formula

C₄₂H₃₀N₆O₁₂

Molecular Weight

810.7 g/mol

InChI Key

MFZCIDXOLLEMOO-UHFFFAOYSA-N

FDA UNII

A99MK953KZ

Inositol Niacinate is a niacin formulation that contains no free niacin, but can be hydrolyzed to release free niacin in vivo. Use of inositol niacinate is associated with less flushing than that seen with the use of free niacin.

1 2D Structure

Inositol niacinate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[2,3,4,5,6-pentakis(pyridine-3-carbonyloxy)cyclohexyl] pyridine-3-carboxylate

2.1.2 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

2.1.3 InChI Key

MFZCIDXOLLEMOO-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CC(=CN=C1)C(=O)OC2C(C(C(C(C2OC(=O)C3=CN=CC=C3)OC(=O)C4=CN=CC=C4)OC(=O)C5=CN=CC=C5)OC(=O)C6=CN=CC=C6)OC(=O)C7=CN=CC=C7

2.2 Other Identifiers

2.2.1 UNII

A99MK953KZ

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Hmovannad

2. Hexanicit

3. Hexopal

4. Inositol Hexanicotinate

5. Inositol Nicotinate

6. Inositolniacinate

7. Meso-inositol Hexanicotinate

8. Nicolip

9. Palohex

10. Phorilingual

11. Tolanate

2.3.2 Depositor-Supplied Synonyms

1. Inositol Nicotinate

2. 6556-11-2

3. Inositol Hexanicotinate

4. Mesotal

5. Dilexpal

6. Hexanicotol

7. Myo-inositol Hexanicotinate

8. Hexanicit

9. Esantene

10. Dilcit

11. Mesonex

12. Hexanicotinoyl Inositol

13. Hexopal

14. Linodil

15. Palohex

16. Inositoli Nicotinas

17. Win 9154

18. Hamovannad

19. Hamovannid

20. Inositol Niacinate [usan]

21. Cyclohexane-1,2,3,4,5,6-hexayl Hexanicotinate

22. Myo-inositol, Hexa-3-pyridinecarboxylate

23. Nsc-49506

24. Inositol Nicotinate [inn]

25. [2,3,4,5,6-pentakis(pyridine-3-carbonyloxy)cyclohexyl] Pyridine-3-carboxylate

26. A99mk953kz

27. Chebi:31699

28. 1,2,3,5/4,6 Cyclohexanehexol Hexanicotinate

29. Nsc49506

30. Win-9154

31. Inositol Nicotinate (inn)

32. Inositol Niacinate (usan)

33. Rel-(1r,2r,3s,4r,5s,6s)-cyclohexane-1,2,3,4,5,6-hexayl Hexanicotinate

34. Inositol Hexanicotinate (jan)

35. Inositol Hexanicotinate [jan]

36. (1r,2r,3s,4s,5r,6s)-cyclohexane-1,2,3,4,5,6-hexayl Hexanicotinate

37. Nicotinato De Inositol

38. Cyclohexane-1,2,3,4,5,6-hexayl Hexapyridine-3-carboxylate

39. Inositolo Nicotinato [dcit]

40. Inositoli Nicotinas [inn-latin]

41. Nicotinic Acid, With 1,2-trans, 3-cis, 4-trans, 5-cis, 6-cis-cyclohexanehexol

42. Inositolo Nicotinato

43. Einecs 229-485-9

44. Nicotinate D'inositol [inn-french]

45. Palohex (tn)

46. Inositol, Hexanicotinate, Myo-

47. Nsc 49506

48. Nicotinate D'inositol

49. Nicotinato De Inositol [inn-spanish]

50. Inositol-hexanicotinate

51. Myo-inosithexanicotinat

52. Brn 0077649

53. Mesoinositol Hexanicotinate

54. 1,2,3,54,6 Cyclohexanehexol Hexanicotinate

55. Unii-a99mk953kz

56. Schembl122590

57. Schembl122591

58. Inositol Niacinate [mi]

59. Chembl1094982

60. Dtxsid2023147

61. Schembl13557040

62. Chebi:33064

63. Dtxsid10859980

64. Inositol Nicotinate [mart.]

65. Nsc81283

66. Zinc3830930

67. Inositol Nicotinate [who-dd]

68. Mfcd00006387

69. Nsc-81283

70. S4987

71. Akos015951374

72. Akos015960653

73. Zinc150338506

74. Ac-8131

75. Db08949

76. Ncgc00532507-01

77. 497820-05-0

78. As-13351

79. Hy-122365

80. Cs-0084450

81. Ft-0627238

82. Ft-0627239

83. D01813

84. D70660

85. 5-22-02-00067 (beilstein Handbook Reference)

86. A914042

87. Sr-01000883744

88. Q6036641

89. Sr-01000883744-1

90. Brd-k00566342-001-01-0

91. 2,3,4,5,6-pentakis((3-pyridinylcarbonyl)oxy)cyclohexyl Nicotinate

92. 3-pyridinecarboxylic Acid, 1,2,3,4,5,6-cyclohexanehexayl Ester

93. (1r,2r,3s,4r,5s,6s)-cyclohexane-1,2,3,4,5,6-hexayl Hexanicotinate

94. Rel-(1r,2r,3s,4r,5s,6s)-cyclohexane-1,2,3,4,5,6-hexaylhexanicotinate

95. Nicotinic Acid, Ester, With 1,2-trans, 3-cis, 4-trans, 5-cis, 6-cis-cyclohexanehexol

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₄₂H₃₀N₆O₁₂
Molecular Weight	810.7 g/mol
XLogP3	3.3
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	18
Rotatable Bond Count	18
Exact Mass	810.19217041 g/mol
Monoisotopic Mass	810.19217041 g/mol
Topological Polar Surface Area	235 Å²
Heavy Atom Count	60
Formal Charge	0
Complexity	1210
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug 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 Raynauds phenomenon.

5 Pharmacology and Biochemistry

5.1 Pharmacology

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.

5.2 MeSH Pharmacological Classification

Vasodilator Agents

Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)

5.3 ATC Code

C - Cardiovascular system

C04 - Peripheral vasodilators

C04A - Peripheral vasodilators

C04AC - Nicotinic acid and derivatives

C04AC03 - Inositol nicotinate

5.4 Absorption, Distribution and Excretion

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.

Route of Elimination

Unabsorbed inositol nicotinate is detected in feces.

Volume of Distribution

Mean Vd following intravenous administration of 50mg/kg of inositol nicotinate in rats is 1051250 mL/kg.

Clearance

Mean clearance rate following intravenous administration of 50mg/kg of inositol nicotinate in rats is 65.419 mL/min/kg.

5.5 Metabolism/Metabolites

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. 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.

5.6 Biological Half-Life

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

5.7 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. Niacin also inhibits hepatic expression of beta-chain adenosine triphosphate synthase which inhibits the removal or uptake of HDLapo 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.