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Details

Stereochemistry ACHIRAL
Molecular Formula C27H50O6
Molecular Weight 470.6823
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRICAPRILIN

SMILES

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

InChI

InChIKey=VLPFTAMPNXLGLX-UHFFFAOYSA-N
InChI=1S/C27H50O6/c1-4-7-10-13-16-19-25(28)31-22-24(33-27(30)21-18-15-12-9-6-3)23-32-26(29)20-17-14-11-8-5-2/h24H,4-23H2,1-3H3

HIDE SMILES / InChI

Description
Curator's Comment: Description was created based on several sources, including https://www.drugs.com/cdi/axona.html and https://www.ncbi.nlm.nih.gov/pubmed/19664276

Tricaprylin is a triester of glycerin and caprylic acid. It is used as a fragrance ingredient, solvent, and primarily as an emollient in a variety of personal care products, including makeup, creams and lotions, deodorants, sunscreens, hair conditioners, and skin cleansers. Tricaprylin is an ingredient of Axona, a prescription medical food intended for the clinical dietary management of the metabolic processes associated with mild to moderate Alzheimer’s disease. Axona provides a simple and safe method to induce hyperketonemia, thus providing an alternative energy substrate to glucose in the brain of patients with AD. After oral administration of Axona, Tricaprylin in Axona is processed by enzymes in the gut, and the resulting medium-chain fatty acids (MCFAs) are absorbed into the blood supply leading to the liver. The MCFAs rapidly pass directly to the liver, where they undergo oxidation to form ketones. Since the liver does not use ketones, they are released into the circulation to be used by nonliver tissues. Some ketones can cross the blood-brain barrier and are then taken up by brain cells. While glucose is the brain’s chief energy source, ketones normally serve as the "backup" energy source. Ketones the body produces after Axona is consumed, act as an alternative energy source for brain cells that have lost their ability to use glucose (sugar) as a result of Alzheimer’s disease.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Axona

Approved Use

For the clinical dietary management of the metabolic processes associated with mild to moderate Alzheimer’s disease (AD)

Launch Date

2009
PubMed

PubMed

TitleDatePubMed
Interstrain differences in susceptibility to liver carcinogenesis initiated by N-nitrosodiethylamine and its promotion by phenobarbital in C57BL/6NCr, C3H/HeNCrMTV- and DBA/2NCr mice.
1986 Feb
Final report on the safety assessment of trilaurin, triarachidin, tribehenin, tricaprin, tricaprylin, trierucin, triheptanoin, triheptylundecanoin, triisononanoin, triisopalmitin, triisostearin, trilinolein, trimyristin, trioctanoin, triolein, tripalmitin, tripalmitolein, triricinolein, tristearin, triundecanoin, glyceryl triacetyl hydroxystearate, glyceryl triacetyl ricinoleate, and glyceryl stearate diacetate.
2001
Effects of gum arabic on lipase interfacial binding and activity.
2001 Jul 1
Flavor production from edible oils and their constituents by Penicillium corylophilum.
2002 Jun
The beta 5' loop of the pancreatic lipase C2-like domain plays a critical role in the lipase-lipid interactions.
2002 Nov 19
Quantitative evaluation of reconstruction methods after gastrectomy using a new type of examination: digestion and absorption test with stable isotope 13C-labeled lipid compound.
2003
The sustained granulopoietic effect of progenipoietin encapsulated in multivesicular liposomes.
2003 Aug 11
Preparation of a water-in-oil-in-water (W/O/W) type microcapsules by a single-droplet-drying method and change in encapsulation efficiency of a hydrophilic substance during storage.
2003 Jun
On the calculation of disjoining pressure isotherms for nonaqueous films.
2004 Feb 15
[Effect of triester glycerol type of plasticizers on release of albumin from biodegradable polymer matrices].
2004 Jan
Might the kinetic behavior of hormone-sensitive lipase reflect the absence of the lid domain?
2004 Jul 27
Structural characterisation of water-Tween 40/Imwitor 308-isopropyl myristate microemulsions using different experimental methods.
2004 May 19
Dialkylphosphatidylcholine and egg yolk lecithin for emulsification of various triglycerides.
2005 Apr 10
Mutations in the "lid" region affect chain length specificity and thermostability of a Pseudomonas fragi lipase.
2005 Apr 25
Substrate specificity and kinetic properties of enzymes belonging to the hormone-sensitive lipase family: comparison with non-lipolytic and lipolytic carboxylesterases.
2005 Dec 30
Topical absorption of piroxicam from organogels--in vitro and in vivo correlations.
2005 Jul 14
Tricaprylin microemulsion for oral delivery of low molecular weight heparin conjugates.
2005 Jun 20
Transitions induced by solubilized fat into reverse hexagonal mesophases.
2005 Jun 25
Effects of protein composition and enzymatic activity on formation and properties of potato protein stabilized emulsions.
2006 Aug 23
Lymphatic transport of a physical mixture of medium- and long-chain TAG in rats.
2006 Jan
Secretion of pro- and mature Rhizopus arrhizus lipases by Pichia pastoris and properties of the proteins.
2006 Jan
Stability of triglyceride liquid films on hydrophilic and hydrophobic glasses.
2006 Jul 1
Technological properties of Enterococcus faecium isolated from ewe's milk and cheese with importance for flavour development.
2006 Mar
Val-407 and Ile-408 in the beta5'-loop of pancreatic lipase mediate lipase-colipase interactions in the presence of bile salt micelles.
2006 Mar 24
An HII liquid crystal-based delivery system for cyclosporin A: physical characterization.
2007 Apr 15
A comparative study on two fungal lipases from Thermomyces lanuginosus and Yarrowia lipolytica shows the combined effects of detergents and pH on lipase adsorption and activity.
2007 Dec
Kinetic model of 1,3-specific triacylglycerols alcoholysis catalyzed by lipases.
2007 Jan 20
Isolation of lipase producing Bacillus sp. from olive mill wastewater and improving its enzyme activity.
2007 Nov 19
Competition between lipases and monoglycerides at interfaces.
2008 Jul 15
Quantitative solubility relationships and the effect of water uptake in triglyceride/monoglyceride microemulsions.
2008 May
Action of Humicola lanuginosa lipase on mixed monomolecular films of tricaprylin and polyethylene glycol stearate.
2008 May 1
Molecular dynamics simulations of functional group effects on solvation thermodynamics of model solutes in decane and tricaprylin.
2008 Nov-Dec
Achievements and new knowledge unraveled by metagenomic approaches.
2009 Nov
Fatty acid selectivity of lipases during acidolysis reaction between oleic acid and monoacid triacylglycerols.
2009 Nov 11
Structural rearrangements and interaction within H(II) mesophase induced by cosolubilization of vitamin E and ascorbic acid.
2009 Nov 17
Blood D-(-)-3-hydroxybutyrate concentrations after oral administration of trioctanoin, trinonanoin, or tridecanoin to newborn rhesus monkeys (Macaca mulatta).
2010 Dec
Lysozyme entrapped within reverse hexagonal mesophases: physical properties and structural behavior.
2010 Jan 1
Patents

Patents

Sample Use Guides

Axona is taken orally once a day shortly after a full meal. Patients should start with a graduated dosing regimen for 7 days, or as directed by the supervising healthcare provider, before taking one full packet (40 grams) per day. Axona should be added to 4 to 8 ounces (118 to 236 milliliters) of water or other liquids, and shaken or blended until fully mixed. Axona consists primarily of a proprietary formulation of >95% pure semisynthetic caprylic triglyceride (Tricaprylin). Each 40g packet contains 20 g of Tricaprylin
Route of Administration: Oral
In Vitro Use Guide
Unknown
Name Type Language
TRICAPRYLIN
II   INCI   MART.  
INCI  
Preferred Name English
TRICAPRILIN
HSDB   JAN  
INN   USAN  
Official Name English
AXONA
VANDF  
Brand Name English
CER-0001
Code English
CAPRYLIC TRIGLYCERIDE [VANDF]
Common Name English
TRICAPRYLIC GLYCERIDE
Common Name English
tricaprilin [INN]
Common Name English
AXONA [VANDF]
Common Name English
CAPRYLIC ACID TRIGLYCERIDE
Common Name English
TRICAPRILIN [JAN]
Common Name English
TRICAPRILIN [HSDB]
Common Name English
Octanoic acid, 1,2,3-propanetriyl ester
Common Name English
NSC-4059
Code English
CAPRYLIC TRIGLYCERIDE
VANDF  
Common Name English
TRICAPRYLYL GLYCEROL
Systematic Name English
GLYCERYL TRICAPRYLATE [NF]
Common Name English
TRICAPRYLIN [MART.]
Common Name English
MIGLYOL 808
Brand Name English
AC-1204
Code English
Tricaprilin [WHO-DD]
Common Name English
TRICAPRYLIN [INCI]
Common Name English
GLYCEROL TRIOCTANOATE
Systematic Name English
TRICAPRYLYL GLYCERIN
Systematic Name English
AC-1202
Code English
Octanoic acid, 1,2,3-propanetriyl ester
Systematic Name English
GLYCERYL TRICAPRYLATE [USP-RS]
Common Name English
TRICAPRILIN [USAN]
Common Name English
TRICAPRYLIN [II]
Common Name English
GLYCEROL TRICAPRYLATE
Systematic Name English
GLYCERYL TRICAPRYLATE
Common Name English
OCTANOIC ACID, 1,1',1''-(1,2,3-PROPANETRIYL) ESTER
Systematic Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 777020
Created by admin on Fri Dec 15 15:48:26 GMT 2023 , Edited by admin on Fri Dec 15 15:48:26 GMT 2023
Code System Code Type Description
WIKIPEDIA
AXONA
Created by admin on Fri Dec 15 15:48:26 GMT 2023 , Edited by admin on Fri Dec 15 15:48:26 GMT 2023
PRIMARY
HSDB
7829
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PRIMARY
ECHA (EC/EINECS)
208-686-5
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PRIMARY
NSC
4059
Created by admin on Fri Dec 15 15:48:26 GMT 2023 , Edited by admin on Fri Dec 15 15:48:26 GMT 2023
PRIMARY
EPA CompTox
DTXSID6021375
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PRIMARY
INN
10584
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PRIMARY
EVMPD
SUB126762
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PRIMARY
RXCUI
1314420
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PRIMARY RxNorm
FDA UNII
6P92858988
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PRIMARY
PUBCHEM
10850
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PRIMARY
DRUG BANK
DB12176
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PRIMARY
DAILYMED
6P92858988
Created by admin on Fri Dec 15 15:48:26 GMT 2023 , Edited by admin on Fri Dec 15 15:48:26 GMT 2023
PRIMARY
CAS
538-23-8
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PRIMARY
ChEMBL
CHEMBL1406148
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USAN
FG-180
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PRIMARY
RS_ITEM_NUM
1295797
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PRIMARY
CHEBI
76978
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PRIMARY
NCI_THESAURUS
C45678
Created by admin on Fri Dec 15 15:48:26 GMT 2023 , Edited by admin on Fri Dec 15 15:48:26 GMT 2023
CONCEPT Industrial Aid
NCI_THESAURUS
C29861
Created by admin on Fri Dec 15 15:48:26 GMT 2023 , Edited by admin on Fri Dec 15 15:48:26 GMT 2023
PRIMARY
SMS_ID
100000152983
Created by admin on Fri Dec 15 15:48:26 GMT 2023 , Edited by admin on Fri Dec 15 15:48:26 GMT 2023
PRIMARY