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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
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 Weight 810.7 g/mol
Molecular Formula C42H30N6O12
XLogP33.3
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count18
Rotatable Bond Count18
Exact Mass810.19217041 g/mol
Monoisotopic Mass810.19217041 g/mol
Topological Polar Surface Area235 Ų
Heavy Atom Count60
Formal Charge0
Complexity1210
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
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.


ABOUT THIS PAGE

Inositol niacinate Manufacturers

A Inositol niacinate manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Inositol niacinate, including repackagers and relabelers. The FDA regulates Inositol niacinate manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Inositol niacinate API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

click here to find a list of Inositol niacinate manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

Inositol niacinate Suppliers

A Inositol niacinate supplier is an individual or a company that provides Inositol niacinate active pharmaceutical ingredient (API) or Inositol niacinate finished formulations upon request. The Inositol niacinate suppliers may include Inositol niacinate API manufacturers, exporters, distributors and traders.

click here to find a list of Inositol niacinate suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Inositol niacinate USDMF

A Inositol niacinate DMF (Drug Master File) is a document detailing the whole manufacturing process of Inositol niacinate active pharmaceutical ingredient (API) in detail. Different forms of Inositol niacinate DMFs exist exist since differing nations have different regulations, such as Inositol niacinate USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Inositol niacinate DMF submitted to regulatory agencies in the US is known as a USDMF. Inositol niacinate USDMF includes data on Inositol niacinate's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Inositol niacinate USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of Inositol niacinate suppliers with USDMF on PharmaCompass.

Inositol niacinate WC

A Inositol niacinate written confirmation (Inositol niacinate WC) is an official document issued by a regulatory agency to a Inositol niacinate manufacturer, verifying that the manufacturing facility of a Inositol niacinate active pharmaceutical ingredient (API) adheres to the Good Manufacturing Practices (GMP) regulations of the importing country. When exporting Inositol niacinate APIs or Inositol niacinate finished pharmaceutical products to another nation, regulatory agencies frequently require a Inositol niacinate WC (written confirmation) as part of the regulatory process.

click here to find a list of Inositol niacinate suppliers with Written Confirmation (WC) on PharmaCompass.

Inositol niacinate GMP

Inositol niacinate Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Inositol niacinate GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Inositol niacinate GMP manufacturer or Inositol niacinate GMP API supplier for your needs.

Inositol niacinate CoA

A Inositol niacinate CoA (Certificate of Analysis) is a formal document that attests to Inositol niacinate's compliance with Inositol niacinate specifications and serves as a tool for batch-level quality control.

Inositol niacinate CoA mostly includes findings from lab analyses of a specific batch. For each Inositol niacinate CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Inositol niacinate may be tested according to a variety of international standards, such as European Pharmacopoeia (Inositol niacinate EP), Inositol niacinate JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Inositol niacinate USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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