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Triheptanoin
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 Weight 428.6 g/mol
Molecular Formula C24H44O6
XLogP37.3
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count6
Rotatable Bond Count23
Exact Mass428.31378912 g/mol
Monoisotopic Mass428.31378912 g/mol
Topological Polar Surface Area78.9 Ų
Heavy Atom Count30
Formal Charge0
Complexity421
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

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 Cmax of 178.9 mol/L, with a Tmax 0.5 h, and an AUC of 336.5 mol\*h/L. A single 0.4 g/kg dose of triheptanoin reaches a Cmax of 259.1 mol/L, with a Tmax 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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