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
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
DescriptionSources: http://www.about-axona.com/assets/files/us-en/global/pdf/Axona-PrescribingInformation.pdfCurator'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
Sources: http://www.about-axona.com/assets/files/us-en/global/pdf/Axona-PrescribingInformation.pdf
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.
CNS Activity
Approval Year
PubMed
Title | Date | PubMed |
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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 |
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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 |
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Effects of gum arabic on lipase interfacial binding and activity. | 2001 Jul 1 |
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Flavor production from edible oils and their constituents by Penicillium corylophilum. | 2002 Jun |
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The beta 5' loop of the pancreatic lipase C2-like domain plays a critical role in the lipase-lipid interactions. | 2002 Nov 19 |
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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 |
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The sustained granulopoietic effect of progenipoietin encapsulated in multivesicular liposomes. | 2003 Aug 11 |
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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 |
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On the calculation of disjoining pressure isotherms for nonaqueous films. | 2004 Feb 15 |
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[Effect of triester glycerol type of plasticizers on release of albumin from biodegradable polymer matrices]. | 2004 Jan |
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Might the kinetic behavior of hormone-sensitive lipase reflect the absence of the lid domain? | 2004 Jul 27 |
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Structural characterisation of water-Tween 40/Imwitor 308-isopropyl myristate microemulsions using different experimental methods. | 2004 May 19 |
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Dialkylphosphatidylcholine and egg yolk lecithin for emulsification of various triglycerides. | 2005 Apr 10 |
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Mutations in the "lid" region affect chain length specificity and thermostability of a Pseudomonas fragi lipase. | 2005 Apr 25 |
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Substrate specificity and kinetic properties of enzymes belonging to the hormone-sensitive lipase family: comparison with non-lipolytic and lipolytic carboxylesterases. | 2005 Dec 30 |
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Topical absorption of piroxicam from organogels--in vitro and in vivo correlations. | 2005 Jul 14 |
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Tricaprylin microemulsion for oral delivery of low molecular weight heparin conjugates. | 2005 Jun 20 |
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Transitions induced by solubilized fat into reverse hexagonal mesophases. | 2005 Jun 25 |
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Effects of protein composition and enzymatic activity on formation and properties of potato protein stabilized emulsions. | 2006 Aug 23 |
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Lymphatic transport of a physical mixture of medium- and long-chain TAG in rats. | 2006 Jan |
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Secretion of pro- and mature Rhizopus arrhizus lipases by Pichia pastoris and properties of the proteins. | 2006 Jan |
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Stability of triglyceride liquid films on hydrophilic and hydrophobic glasses. | 2006 Jul 1 |
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Technological properties of Enterococcus faecium isolated from ewe's milk and cheese with importance for flavour development. | 2006 Mar |
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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 |
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An HII liquid crystal-based delivery system for cyclosporin A: physical characterization. | 2007 Apr 15 |
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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 |
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Kinetic model of 1,3-specific triacylglycerols alcoholysis catalyzed by lipases. | 2007 Jan 20 |
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Isolation of lipase producing Bacillus sp. from olive mill wastewater and improving its enzyme activity. | 2007 Nov 19 |
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Competition between lipases and monoglycerides at interfaces. | 2008 Jul 15 |
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Quantitative solubility relationships and the effect of water uptake in triglyceride/monoglyceride microemulsions. | 2008 May |
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Action of Humicola lanuginosa lipase on mixed monomolecular films of tricaprylin and polyethylene glycol stearate. | 2008 May 1 |
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Molecular dynamics simulations of functional group effects on solvation thermodynamics of model solutes in decane and tricaprylin. | 2008 Nov-Dec |
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Achievements and new knowledge unraveled by metagenomic approaches. | 2009 Nov |
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Fatty acid selectivity of lipases during acidolysis reaction between oleic acid and monoacid triacylglycerols. | 2009 Nov 11 |
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Structural rearrangements and interaction within H(II) mesophase induced by cosolubilization of vitamin E and ascorbic acid. | 2009 Nov 17 |
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Blood D-(-)-3-hydroxybutyrate concentrations after oral administration of trioctanoin, trinonanoin, or tridecanoin to newborn rhesus monkeys (Macaca mulatta). | 2010 Dec |
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Lysozyme entrapped within reverse hexagonal mesophases: physical properties and structural behavior. | 2010 Jan 1 |
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
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777020
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AXONA
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C45678
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C29861
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ACTIVE MOIETY