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Triheptanoin

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Chemistry

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Also known as: 620-67-7, Propane-1,2,3-triyl triheptanoate, Trienanthoin, Trioenanthoin, Glyceryl triheptanoate, Glycerol triheptanoate

Molecular Formula

C₂₄H₄₄O₆

Molecular Weight

428.6 g/mol

InChI Key

PJHKBYALYHRYSK-UHFFFAOYSA-N

FDA UNII

2P6O7CFW5K

Triheptanoin is a source of heptanoate fatty acids, which can be metabolized without the enzymes of long chain fatty acid oxidation. In clinical trials, patients with long chain fatty acid oxidation disorders (lc-FAODs) treated with triheptanoin are less likely to develop hypoglycemia, cardiomyopathy, rhabdomyolysis, and hepatomegaly. Complications in lc-FAOD patients are reduced from approximately 60% to approximately 10% with the addition of triheptanoin. Triheptanoin was granted FDA approval on 30 June 2020.

1 2D Structure

Triheptanoin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2,3-di(heptanoyloxy)propyl heptanoate

2.1.2 InChI

InChI=1S/C24H44O6/c1-4-7-10-13-16-22(25)28-19-21(30-24(27)18-15-12-9-6-3)20-29-23(26)17-14-11-8-5-2/h21H,4-20H2,1-3H3

2.1.3 InChI Key

PJHKBYALYHRYSK-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCCCCCC(=O)OCC(COC(=O)CCCCCC)OC(=O)CCCCCC

2.2 Other Identifiers

2.2.1 UNII

2P6O7CFW5K

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Glyceroltriheptanoate

2. Glyceryl Triheptanoate

2.3.2 Depositor-Supplied Synonyms

1. 620-67-7

2. Propane-1,2,3-triyl Triheptanoate

3. Trienanthoin

4. Trioenanthoin

5. Glyceryl Triheptanoate

6. Glycerol Triheptanoate

7. Triheptanoic Glyceride

8. Heptanoin, Tri-

9. Ux007

10. Dermofeel Tc 7

11. Dojolvi

12. Propane-1,2,3-triyl Trisheptanoate

13. 2,3-di(heptanoyloxy)propyl Heptanoate

14. Dub Thg

15. Heptanoic Acid, 1,2,3-propanetriyl Ester

16. Dermofeel Tc-7

17. Ux-007

18. Radiamuls 2375

19. Lanol 37 T

20. Triheptanoin [usan]

21. 2p6o7cfw5k

22. 3-02-00-00769 (beilstein Handbook Reference)

23. Heptanoic Acid, 1,1',1''-(1,2,3-propanetriyl) Ester

24. Triheptanoin (usan)

25. Triheptylin

26. 1,2,3-propanetriyl Triheptanoate

27. Glyceroltriheptanoate

28. Brn 1807724

29. Lanol 37t

30. Einecs 210-647-2

31. Unii-2p6o7cfw5k

32. Trienantin

33. Dojolvi (tn)

34. Glycerol Trienanthate

35. Glyceryl Trienanthate

36. Triheptanoin [mi]

37. Triheptanoin [inn]

38. Ec 210-647-2

39. Triheptanoin [inci]

40. Schembl525618

41. Triheptanoin [who-dd]

42. Glycerol Trienanthate, >=94%

43. Chembl4297585

44. Gtpl11431

45. Dtxsid40862306

46. Propane-1,2,3-triyltriheptanoate

47. Triheptanoin [orange Book]

48. Zinc4521897

49. Ind106011

50. Mfcd00042910

51. Ux 007

52. 1r,2s-(-)-norephedrinehydrochloride

53. Cs-w013852

54. Db11677

55. Hy-w013136

56. Ind 106011

57. Ind-106011

58. Ind106011; Ux007

59. Ls-15081

60. Ft-0757070

61. D11465

62. A868568

63. Q414576

64. W-109093

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₂₄H₄₄O₆
Molecular Weight	428.6 g/mol
XLogP3	7.3
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	23
Exact Mass	428.31378912 g/mol
Monoisotopic Mass	428.31378912 g/mol
Topological Polar Surface Area	78.9 Å²
Heavy Atom Count	30
Formal Charge	0
Complexity	421
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

Triheptanoin is a medium chain triglyceride indicated to provide calories and fatty acids to treat long chain fatty acid oxidation disorders (lc-FAODs).

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Triheptanoin is a source of medium chain fatty acids for patients with lc-FAODs. It has a moderate duration of action and a wide therapeutic window. Patients should be counselled regarding the risk of feeding tube dysfunction and intestinal malabsorption due to pancreatic insufficiency.

5.2 ATC Code

A - Alimentary tract and metabolism

A16 - Other alimentary tract and metabolism products

A16A - Other alimentary tract and metabolism products

A16AX - Various alimentary tract and metabolism products

A16AX17 - Triheptanoin

5.3 Absorption, Distribution and Excretion

Absorption

A single 0.3 g/kg dose of triheptanoin reaches a C_max of 178.9 mol/L, with a T_max 0.5 h, and an AUC of 336.5 mol\*h/L. A single 0.4 g/kg dose of triheptanoin reaches a C_max of 259.1 mol/L, with a T_max 0.8 h, and an AUC of 569.1 mol\*h/L.

Route of Elimination

Triheptanoin is minimally eliminated in the urine.

Clearance

A single dose of 0.3 g/kg results in a mean apparent clearance of 6.05 L/h/kg for heptanoate. A single dose of 0.4 g/kg results in a mean apparent clearance of 4.31 L/h/kg for heptanoate.

5.4 Metabolism/Metabolites

Triheptanoin is hydrolysed to heptanoate, which can be further metabolized to -hydroxypentanoate or -hydroxybutyrate.

5.5 Biological Half-Life

Due to multiple peak concentrations of the heptanoate metabolite, the half life of triheptanoin could not be determined.

5.6 Mechanism of Action

Triheptanoin is a source of heptanoate fatty acids, which can be metabolized without the enzymes of long chain fatty acid oxidation. In clinical trials, patients with lc-FAODs treated with triheptanoin experienced improvements in hypoglycemia, cardiomyopathy, and rhabdomyolysis.

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