Medium-chain triglycerides
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Identification
- Summary
Medium-chain triglycerides is a source of essential fatty acids used as a source of calories in parenteral nutrition.
- Generic Name
- Medium-chain triglycerides
- DrugBank Accession Number
- DB13959
- Background
Medium-chain triglycerides (MCTs) are triglycerides made up of a glycerol backbone and three fatty acids with an aliphatic tail of six to 12 carbon atoms. MCTs are found in natural foods, such as coconut oil, palm kernel oil, and raw coconut meat. In the body, MCTs are broken down into glycerol and free fatty acids, which are directly absorbed into the blood stream and transported to the target organs to exert a range of biological and metabolic effects.4 MCTs are used in parenteral nutrition therapy: they serve as a source of calories and essential fatty acids in conditions associated with malnutrition and malabsorption.10
- Type
- Small Molecule
- Groups
- Approved
- Synonyms
- Caprylic/capric triglyceride
- Caprylic/capric triglycerides
- Coconut oil, fractioned
- Fractionated coconut oil
- Fractionated triglyceride of coconut oil
- MCT
- Medium chain triglyceride
- Medium-chain glycerides
- Triglycerides, medium-chain
- External IDs
- MIGLYOL 810 N
- MIGLYOL 812 N
Pharmacology
- Indication
Medium-chain triglycerides (MCTs), in combination with other compounds like fish oils, soya oil, and olive oil, is indicated in adult and pediatric patients, including term and preterm neonates, as a source of calories and essential fatty acids for parenteral nutrition when oral or enteral nutrition is not possible, insufficient, or contraindicated.10 MCTs are also available as over-the-counter natural products and health supplements.
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- Contraindications & Blackbox Warnings
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- Pharmacodynamics
Medium-chain triglycerides (MCTs) contained in injectable lipid emulsions serve as a source of calories and essential fatty acids, which are important substrate for energy production.10 MCTs exert several metabolic effects: they were shown to reduce weight, metabolic syndrome, abdominal obesity, and inflammation in animal studies. It is proposed that MCTs induces weight loss through increasing energy expenditure and fat oxidation, and altering body composition.4 However, it is unknown whether the effects of MCTs on energy expenditure and body weight are long-lasting and sustainable.9 MCTs can also play a role in food intake and satiety, as some studies showed that MCT consumption led to reduced food intake.4,6,7 While MCTs was shown to reduce energy intake, it was not shown to affect appetite.8 MCT may facilitate the absorption of calcium.2
- Mechanism of action
Medium-chain triglycerides (MCTs) are broken down into glycerol and medium-chain fatty acids, which are directly absorbed into the blood stream and transported to the target organs,4 where they undergo β-oxidation to form acetyl-CoA. The β-oxidation is the most common mechanism of action for energy production derived from fatty acid metabolism.10 Because medium-chain fatty acids are rapidly oxidized, it leads to greater energy expenditure.9 Fatty acids are important substrates for energy production and also play a critical role in membrane structure and function. Additionally, fatty acids act as precursors for bioactive molecules (such as prostaglandins) and as regulators of gene expression.10
Fatty acids may mediate their effects on energy expenditure, food consumption, and fat deposition by upregulating the expression and protein levels of genes involved in mitochondrial biogenesis and metabolism via activating Akt and AMPK signaling pathways and inhibiting the TGF-β signaling pathway. It is proposed that the promotion of weight loss by MCTs may be due to sympathetic activation of brown fat thermogenesis.4
- Absorption
Medium chain triglycerides are rapidly absorbed.2,11 They passively and directly diffuse across the gastrointestinal tract into the portal system then to liver, where they are oxidized.9,11
- Volume of distribution
The apparent volumes of distribution have been researched as approximately 4.5 L for medium chain triglycerides and 19 L for medium chain fatty acids in a typical 70-kg subject.1
- Protein binding
Medium chain triglycerides bind weakly to serum albumin. They can readily cross the blood-brain barrier.11
- Metabolism
Medium chain triglycerides are hydrolyzed by lipoprotein lipase to glycerol and medium-chain free fatty acids such as alpha-linolenic acid and linoleic acid.4,10,11 Free fatty acids then undergo β-oxidation in the organs such as the liver, kidneys, and heart. Alpha-linolenic acid and linoleic acid are metabolized within a common biochemical pathway through a series of desaturation and elongation steps. Downstream products of alpha-linolenic acid are eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), and linoleic acid is converted to arachidonic acid.10
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- Route of elimination
There is limited information available regarding the main route of elimination.
- Half-life
The plasma half-life of medium chain triglycerides is recorded to be 11 minutes and that of medium chain fatty acids is about 17 minutes.1
- Clearance
The clearance of medium chain triglycerides in healthy control subjects was measured to be about 1.93 +/- 0.34 mL.kg-1.min-1.3
- Adverse Effects
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- Toxicity
There is limited information regarding the LD50 of medium-chain triglycerides; however, MCTs at doses up to levels of 1g/kg have been safely consumed by humans in several clinical trials.5
Fat overload syndrome is a condition rarely reported with the use of intravenous lipid emulsions that is most frequently observed when the recommended lipid dose or infusion rate was exceeded. However, some cases still occurred when the lipid formulation was administered according to instructions. Fat overload syndrome results from a reduced or limited ability to metabolize lipids, accompanied by prolonged plasma clearance, leading to a sudden deterioration in the patient's condition.10
If signs or symptoms of fat overload syndrome occur, stop the infusion of medium chain triglyceride-containing emulsions until triglyceride levels have normalized and symptoms have abated. The effects are usually reversible by stopping the lipid infusion. If medically appropriate, further intervention may be indicated. Lipids are not dialyzable from plasma.10
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- No interactions found.
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image CELEPID MCT-LCT 20% W/V Medium-chain triglycerides (10 g) + Soybean oil (10 g) Emulsion Intravenous FARMALOGICA S.A. 2007-03-14 Not applicable Colombia Colip 20% Medium-chain triglycerides (15 g / 100 mL) + Soybean oil (5 g / 100 mL) Emulsion Intravenous Baxter Corporation Clintec Nutrition Division 1998-10-07 2007-08-02 Canada DeNino Diaper Rash Medium-chain triglycerides (18.21 mL/60mL) + Avena sativa flowering top (.6 mL/60mL) + Lanolin (2.4 mL/60mL) + Zinc oxide (7.8 mL/60mL) Cream Topical Corpsain Sa De Cv 2010-04-01 Not applicable US FINOMEL Medium-chain triglycerides (10.3 g/1435ml) + Alanine (11.41 g/1435ml) + Arginine (6.34 g/1435ml) + Calcium chloride dihydrate (0.41 g/1435ml) + D-glucose monohydrate (151.5 g/1435ml) + Fish oil (8.24 g/1435ml) + Glycine (5.68 g/1435ml) + Histidine (2.64 g/1435ml) + Isoleucine (3.31 g/1435ml) + Leucine (4.02 g/1435ml) + Lysine hydrochloride (3.99 g/1435ml) + Magnesium sulfate heptahydrate (1.36 g/1435ml) + Methionine (2.2 g/1435ml) + Olive oil (10.3 g/1435ml) + Phenylalanine (3.09 g/1435ml) + Potassium chloride (2.47 g/1435ml) + Proline (3.75 g/1435ml) + Serine (2.76 g/1435ml) + Sodium acetate trihydrate (3.1 g/1435ml) + Sodium glycerophosphate hydrate (3.26 g/1435ml) + Soybean oil (12.36 g/1085ml) + Threonine (2.31 g/1085ml) + Tryptophan (0.99 g/1085ml) + Tyrosine (0.22 g/1085ml) + Valine (3.2 g/1085ml) + Zinc sulfate heptahydrate (0.013 g/1085ml) Injection, emulsion Intravenous Baxter S.P.A. 2019-09-03 Not applicable Italy FINOMEL Medium-chain triglycerides (10.3 g/1085ml) + Alanine (11.41 g/1085ml) + Arginine (6.34 g/1085ml) + Calcium chloride dihydrate (0.41 g/1085ml) + D-glucose monohydrate (151.5 g/1085ml) + Fish oil (8.24 g/1085ml) + Glycine (5.68 g/1085ml) + Histidine (2.64 g/1085ml) + Isoleucine (3.31 g/1085ml) + Leucine (4.02 g/1085ml) + Lysine hydrochloride (3.99 g/1085ml) + Magnesium sulfate heptahydrate (1.36 g/1085ml) + Methionine (2.2 g/1085ml) + Olive oil (10.3 g/1085ml) + Phenylalanine (3.09 g/1085ml) + Potassium chloride (2.47 g/1085ml) + Proline (3.75 g/1085ml) + Serine (2.76 g/1085ml) + Sodium acetate trihydrate (3.1 g/1085ml) + Sodium glycerophosphate hydrate (3.26 g/1085ml) + Soybean oil (12.36 g/1085ml) + Threonine (2.31 g/1085ml) + Tryptophan (0.99 g/1085ml) + Tyrosine (0.22 g/1085ml) + Valine (3.2 g/1085ml) + Zinc sulfate heptahydrate (0.013 g/1085ml) Injection, emulsion Intravenous Baxter S.P.A. 2019-09-03 Not applicable Italy
Categories
- Drug Categories
- Classification
- Not classified
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- C9H2L21V7U
- CAS number
- 438544-49-1
- InChI Key
- Not Available
- InChI
- Not Available
- IUPAC Name
- Not Available
- SMILES
- Not Available
References
- General References
- Mingrone G, De Gaetano A, Greco AV, Capristo E, Castagneto M, Gasbarrini G: Medium-chain triglycerides for parenteral nutrition: kinetic profile in humans. Nutrition. 1995 Sep-Oct;11(5):418-22. [Article]
- Los-Rycharska E, Kieraszewicz Z, Czerwionka-Szaflarska M: Medium chain triglycerides (MCT) formulas in paediatric and allergological practice. Prz Gastroenterol. 2016;11(4):226-231. doi: 10.5114/pg.2016.61374. Epub 2016 Jul 20. [Article]
- Druml W, Fischer M, Pidlich J, Lenz K: Fat elimination in chronic hepatic failure: long-chain vs medium-chain triglycerides. Am J Clin Nutr. 1995 Apr;61(4):812-7. doi: 10.1093/ajcn/61.4.812. [Article]
- Wang Y, Liu Z, Han Y, Xu J, Huang W, Li Z: Medium Chain Triglycerides enhances exercise endurance through the increased mitochondrial biogenesis and metabolism. PLoS One. 2018 Feb 8;13(2):e0191182. doi: 10.1371/journal.pone.0191182. eCollection 2018. [Article]
- Traul KA, Driedger A, Ingle DL, Nakhasi D: Review of the toxicologic properties of medium-chain triglycerides. Food Chem Toxicol. 2000 Jan;38(1):79-98. doi: 10.1016/s0278-6915(99)00106-4. [Article]
- Clegg ME: Medium-chain triglycerides are advantageous in promoting weight loss although not beneficial to exercise performance. Int J Food Sci Nutr. 2010 Nov;61(7):653-79. doi: 10.3109/09637481003702114. [Article]
- St-Onge MP, Ross R, Parsons WD, Jones PJ: Medium-chain triglycerides increase energy expenditure and decrease adiposity in overweight men. Obes Res. 2003 Mar;11(3):395-402. doi: 10.1038/oby.2003.53. [Article]
- Maher T, Clegg ME: A systematic review and meta-analysis of medium-chain triglycerides effects on acute satiety and food intake. Crit Rev Food Sci Nutr. 2021;61(4):636-648. doi: 10.1080/10408398.2020.1742654. Epub 2020 Mar 26. [Article]
- St-Onge MP, Jones PJ: Physiological effects of medium-chain triglycerides: potential agents in the prevention of obesity. J Nutr. 2002 Mar;132(3):329-32. doi: 10.1093/jn/132.3.329. [Article]
- FDA Approved Drug Products: SMOFLIPID (lipid injectable emulsion), for intravenous use [Link]
- Australian Government Therapeutic Goods Administration: Australian Public Assessment Report for SMOFlipid [Link]
- External Links
- 1310578
- Wikipedia
- Medium-chain_triglyceride
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Available Not Available Cholestasis / Growth Failure 1 somestatus stop reason just information to hide Not Available Completed Supportive Care Intraocular Pressure (IOP) 1 somestatus stop reason just information to hide Not Available Completed Treatment Hematological Malignancy 1 somestatus stop reason just information to hide Not Available Unknown Status Prevention Ischemic Reperfusion Injury 1 somestatus stop reason just information to hide 4 Completed Health Services Research Sepsis Newborn 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Cream Topical Injection, emulsion Intravenous drip Injection Intravenous Emulsion Parenteral Emulsion Intravenous Injection, emulsion Intravenous 4.656 g/1000ml Injection, emulsion Intravenous 6.792 g/1000ml Emulsion Intravenous 13.000 g Emulsion Parenteral 42.00 g Injection, emulsion Intravenous 14 g/1000ml Injection, emulsion Intravenous Injection, solution Intravenous Solution Parenteral - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
- Not Available
- Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Not Available
- Chromatographic Properties
Collision Cross Sections (CCS)
Not Available
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Binds water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs (Probable). Its main function is the regulation of the colloidal osmotic pressure of blood (Probable). Major zinc transporter in plasma, typically binds about 80% of all plasma zinc (PubMed:19021548). Major calcium and magnesium transporter in plasma, binds approximately 45% of circulating calcium and magnesium in plasma (By similarity). Potentially has more than two calcium-binding sites and might additionally bind calcium in a non-specific manner (By similarity). The shared binding site between zinc and calcium at residue Asp-273 suggests a crosstalk between zinc and calcium transport in the blood (By similarity). The rank order of affinity is zinc > calcium > magnesium (By similarity). Binds to the bacterial siderophore enterobactin and inhibits enterobactin-mediated iron uptake of E.coli from ferric transferrin, and may thereby limit the utilization of iron and growth of enteric bacteria such as E.coli (PubMed:6234017). Does not prevent iron uptake by the bacterial siderophore aerobactin (PubMed:6234017)
- Specific Function
- antioxidant activity
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Albumin
- Molecular Weight
- 69365.94 Da
References
- Australian Government Therapeutic Goods Administration: Australian Public Assessment Report for SMOFlipid [Link]
Drug created at January 17, 2018 16:57 / Updated at June 01, 2022 17:06