Basic information
- CAS
620-67-7- Standard SMILES
CCCCCCC(=O)OCC(COC(=O)CCCCCC)OC(=O)CCCCCC- InChIKey
PJHKBYALYHRYSK-UHFFFAOYSA-N- Molecular formula
- C24H44O6
- Average molar mass
- 428.6 g/mol
- Monoisotopic mass
- 428.31378912
Overview
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.
Names & identifiers
- Preferred name
- Triheptanoin
- IUPAC
- 2,3-di(heptanoyloxy)propyl heptanoate
- English name
- TRIHEPTANOIN
- Molecular formula
- C24H44O6
- Molecular weight
- 428.6
Names & synonyms
Triheptanoin620-67-7TrienanthoinTrioenanthoinTriheptylinGlycerol triheptanoateHeptanoin, tri-Triheptanoic glycerideDermofeel TC 7DojolviGLYCERYL TRIHEPTANOATEglyceroltriheptanoate
Show more names
C7 oilTRIOENANTHINTRIHEPTANIONtri-heptanoiC7 fatty acid
2,3-di(heptanoyloxy)propyl heptanoateUX007Dub thgDermofeel tc-7Radiamuls 2375Lanol 37 ttriheptanoinatriheptanoine
Database identifiers
- CAS
620-67-7- PubChem CID
- 69286
- DTXSID
DTXSID40862306- ChEMBL
CHEMBL4297585- UNII
- 2P6O7CFW5K
- EC Number
- 210-647-2
- Nikkaji
- J53.997J
Properties
Computed structural properties
- XLogP
- 7.3
- Topological polar surface area
- 78.9 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 23
- Heavy atoms
- 30
- Formal charge
- 0
- Complexity
- 421
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Cosmetics
Cosmetic ingredients (Triheptanoin) -> CIR (Cosmetic Ingredient Review)
Skin conditioning; Surfactant
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Physicochemical properties
- Boiling point
- 200 °C · 200 °C(Press: 1 Torr)
- Density
- 0.966 g/mL · 0.966 g/mL at 20 °C(lit.)
- refractive index
- 20 · n20/D 1.444
- storage temp.
- -20 °C, · Store at -20°C, protect from light
- solubility
- 30 mg/ml; · DMF: 30 mg/ml; DMSO: 30 mg/ml; Ethanol: 30 mg/ml
- form
- A liquid
- color
- Colorless to light yellow
- Viscosity
- 20 mm2/s · 20mm2/s
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 62.1% (64 of 103) of all reports.
Warning
H315 (37.9%): Causes skin irritation [Warning Skin corrosion/irritation]
P264, P273, P280, P302+P352, P321, P332+P317, P362+P364, P391, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 103 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance.
REACH registered substance: Propane-1,2,3-triyl trisheptanoate (EC: 210-647-2)
Triheptanoin: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesSkin Irrit. 2 (37.9%)
Toxicology
Hepatotoxicity
Serum enzyme elevations during triheptanoin therapy are frequent, mostly reflecting the underlying condition of muscle and hepatic accumulation of toxic fatty acid products and lack of adequate energy production. Elevations in CPK were present in 81%, ALT in 72% and AST in 68% of subjects treated in preregistration studies. The elevations were greater than 5 times the upper limit of normal (ULN) of CPK in 47%, ALT in 24% and AST in 15%. Nevertheless, the changes were not considered due to the triheptanoin or MCT therapy but rather to the underlying metabolic disorder and mitochondrial dysfunction. In small trials of triheptanoin in other genetic metabolic diseases, laboratory values were reported to be unchanged during supplementation. Since its approval and more widescale use, there have been no published cases of clinically apparent liver injury attributed to triheptanoin therapy, although its total clinical experience with its use has been limited.
Chemistry & industry
Pharmacology
ATC Code
A - Alimentary tract and metabolism
QA - Alimentary tract and metabolism
Protein BindingTriheptanoin is approximately 80% protein bound in plasma, likely serum albumin.
Pharmacodynamics
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.
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.
Biological Half-LifeDue to multiple peak concentrations of the heptanoate metabolite, the half life of triheptanoin could not be determined.
Metabolism/MetabolitesTriheptanoin is hydrolysed to heptanoate, which can be further metabolized to β-hydroxypentanoate or β-hydroxybutyrate.
FDA Pharmacological Classification
2P6O7CFW5K
TRIHEPTANOIN
Established Pharmacologic Class [EPC] - Medium-chain Triglyceride
Chemical Structure [CS] - Triglycerides
Triheptanoin is a Medium-chain Triglyceride.
TRIHEPTANOIN
Absorption, Distribution and Excretion
A single 0.3 g/kg dose of triheptanoin reaches a Cmax of 178.9 µmol/L, with a Tmax 0.5 h, and an AUC of 336.5 µmol\*h/L. A single 0.4 g/kg dose of triheptanoin reaches a Cmax of 259.1 µmol/L, with a Tmax 0.8 h, and an AUC of 569.1 µmol\*h/L.
Triheptanoin is minimally eliminated in the urine.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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