Medium-chain triglycerides

Identification

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Name
Medium-chain triglycerides
Accession Number
DB13959
Type
Small Molecule
Groups
Approved
Description

Compared to long-chain fatty acids which are dietary fats that are composed of 2 to 22 carbon atoms in length, medium-chain triglycerides (MCTs) are composed of only 6 to 12 carbon links 8,10. This shorter chain length gives MCTs properties that are unique, and perhaps pharmacologically advantageous over long-chain fatty acids 10,8. In essence, the shorter chain length chemical profile of MCTs allow them to passively and directly diffuse across the gastrointestinal tract into the portal system without undergoing the prolonged and necessary sequential molecular modifications that long-chain fatty acids must undertake 10,8. These kinds of pharmacodynamics ultimately allow for much quicker absorption and utilization of MCTs compared to long-chain triglycerides - making them important and rapid sources of calories and essential fatty acids for various medical conditions associated with malnutrition and malabsorption 8,10.

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
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Colip 20%Medium-chain triglycerides (15 g) + Soybean oil (5 g)EmulsionIntravenousBaxter Corporation Clintec Nutrition Division1998-10-072007-08-02Canada
DeNino Diaper RashMedium-chain triglycerides (18.21 mL/60mL) + Avena sativa flowering top (.6 mL/60mL) + Lanolin (2.4 mL/60mL) + Zinc oxide (7.8 mL/60mL)CreamTopicalCorpsain Sa De Cv2010-04-01Not applicableUs
SmofkabivenMedium-chain triglycerides (1.14 g) + Arginine (0.61 g) + Calcium Chloride (0.028 g) + Dextrose, unspecified form (12.7 g) + Fish oil (0.57 g) + Glycine (0.56 g) + Histidine (0.15 g) + Isoleucine (0.25 g) + L-Alanine (0.71 g) + L-Leucine (0.38 g) + L-Lysine (0.34 g) + L-Phenylalanine (0.26 g) + L-Threonine (0.22 g) + L-Tryptophan (0.10 g) + L-Valine (0.31 g) + Magnesium sulfate (0.061 g) + Methionine (0.22 g) + Nitrogen (0.8 g) + Olive oil (0.95 g) + Potassium chloride (0.23 g) + Proline (0.57 g) + Serine (0.33 g) + Sodium acetate trihydrate (0.17 g) + Sodium glycerophosphate (0.21 g) + Soybean oil (1.14 g) + Taurine (0.05 g) + Tyrosine (0.02 g) + Zinc sulfate heptahydrate (0.00066 g)EmulsionIntravenousFresenius Kabi2015-09-15Not applicableCanada
Smofkabiven Electrolyte FreeMedium-chain triglycerides (1.14 g) + Arginine (0.61 g) + Dextrose, unspecified form (12.7 g) + Fish oil (0.57 g) + Glycine (0.56 g) + Histidine (0.15 g) + Isoleucine (0.25 g) + L-Alanine (0.71 g) + L-Leucine (0.38 g) + L-Lysine (0.34 g) + L-Phenylalanine (0.26 g) + L-Threonine (0.22 g) + L-Tryptophan (0.10 g) + L-Valine (0.31 g) + Methionine (0.22 g) + Nitrogen (0.8 g) + Olive oil (0.95 g) + Proline (0.57 g) + Serine (0.33 g) + Soybean oil (1.14 g) + Taurine (0.05 g) + Tyrosine (0.02 g)EmulsionIntravenousFresenius Kabi2015-09-15Not applicableCanada
Smofkabiven PeripheralMedium-chain triglycerides (850 mg) + Arginine (380 mg) + Calcium Chloride (18 mg) + Dextrose, unspecified form (7.1 g) + Fish oil (420 mg) + Glycine (350 mg) + Histidine (93 mg) + Isoleucine (160 mg) + L-Alanine (440 mg) + L-Leucine (230 mg) + L-Lysine (210 mg) + L-Phenylalanine (160 mg) + L-Threonine (140 mg) + L-Tryptophan (63 mg) + L-Valine (200 mg) + Magnesium sulfate (38 mg) + Methionine (130 mg) + Olive oil (700 mg) + Potassium chloride (140 mg) + Proline (350 mg) + Serine (210 mg) + Sodium acetate trihydrate (110 mg) + Sodium glycerophosphate (130 mg) + Soybean oil (850 mg) + Taurine (32 mg) + Tyrosine (12 mg) + Zinc sulfate heptahydrate (0.4 mg)EmulsionIntravenousFresenius Kabi2017-02-14Not applicableCanada
SmoflipidMedium-chain triglycerides (6 g/100mL) + Fish oil (3 g/100mL) + Olive oil (5 g/100mL) + Soybean oil (6 g/100mL)Injection, emulsionIntravenousFresenius Kabi USA, LLC2016-07-13Not applicableUs
Smoflipid 20%Medium-chain triglycerides (6 g/100mL) + Olive oil (5 g/100mL) + Omega-3 fatty acids (3 g/100mL) + Soybean oil (6 g/100mL)EmulsionIntravenousFresenius Kabi2013-05-08Not applicableCanada
Categories
Not Available
UNII
C9H2L21V7U
CAS number
438544-49-1
Weight
Not Available
Chemical Formula
Not Available
InChI Key
Not Available
InChI
Not Available
IUPAC Name
Not Available
SMILES
Not Available

Pharmacology

Indication

When incorporated as an active ingredient in combination with other active components like fish oils, soya oil, and olive oil as a prescription medication (SMOFLIPID), medium chain triglycerides (MCTs) constitute a therapy indicated for supplying energy, calories, and essential fatty acids to adult patients, as part of a parenteral nutrition regimen, when oral or enteral nutrition is impossible, insufficient, or contraindicated 8,9.

However, given the predominant indication of MCTs for acting as a source of calories and essential fatty acids, the use of MCTs alone or as a component part of various unique, individual patient-tailored composite regimen therapies, MCTs are also ultimately indicated for a wide range of health conditions that involve energy deficiency, malnutrition, or disturbances in the ordinary absorption of dietary fats 2,10. Such conditions can include Crohn's disease, Waldmann disease, weight maintenance in AIDS, cachexia, and various disturbances in patient bile secretion (like cholestasis, disturbances in hepatic-intestinal circulation of bile acids, intestinal dysbacteriosis), or in pancreatic lipase secretion (like pancreatic failure in the course of cystic fibrosis) 2,10.

Associated Conditions
Pharmacodynamics

Medium chain triglycerides (MCTs) are considered a fast acting source of calories and essential fatty acids for patients with malnutrition, malabsorption, or particular fatty-acid metabolism disorders because they can passively and directly diffuse across the gastrointestinal tract into the portal system without undergoing the prolonged and necessary sequential molecular modifications that long-chain fatty acids must undertake 8. These kinds of pharmacodynamics allow for much quicker absorption and utilization of MCTs compared to long-chain triglycerides 10. In contrast, albumin-bound long-chain fatty acids do not readily enter peripheral organs and are predominantly metabolised by the liver with a preference for re-esterification to phospholipids or triglycerides and therefore potentially fat storage 8. MCFAs are subjected to a lower re-esterification rate than LCFAs with a reduced tendency to fat storage than LCTs 8. Subsequently, MCTs are predominantly catabolized, rather than stored as adipose tissue and are therefore utilized as an immediate source of energy, considering it does not require energy to absorb, use, or store MCTs 8.

Mechanism of action

Absorption of larger long-chain triglycerides (LCT) requires specific processing in the digestive tract, like emulsification with bile 2. This process is aimed at obtaining the maximum surface for digestion (lipolysis with breakage of ester bonds of triglycerides and with the release of monoglycerides, free fatty acids, and glycerol) 2. The process of digestion of fats occurs largely in the duodenum and initial segment of the jejunum 2. Lipases are found in the pancreatic juice and the brush border 2. Once the aforementioned bonds are broken and the fatty acids and monoglycerides are absorbed into an enterocyte, they undergo resynthesis to triglycerides, in the presence of ligase, co-enzyme A, and ATP. Chylomicrons are formed. They get to the lymph and only then can they be transported to blood and destination organs 2. Release of fats from chylomicrons requires the presence of plasmatic lipases, and only then can they be metabolised or stored as a reserve in the fatty tissue 2.

Conversely, hydrolysis of medium chain triglycerides (MCTs, which is faster than LCT hydrolysis anyway) does not require bile and lipase 2. Without hydrolysis, they may also be absorbed by the enterocytes and they do not require re-esterification 2. From enterocytes they are directly absorbed into the portal vein and then transported mainly to the liver. Thus, absorption of MCT is faster than that of LCTs 2. Their metabolism is facilitated as well because they are metabolised by the liver almost completely (only when the liver’s metabolic abilities are exceeded the process is taken over by peripheral tissues) with energy release, regardless of the presence of carnitine (which is necessary for the transport of long-chain fatty acids through the mitochondrial membrane) 2. Thanks to this the availability of medium-chain fatty acids for mitochondrial oxidation is better 2. This means that MCT are an easy and quick source of energy 2.

However, it should be borne in mind that quantities of MCT exceeding the abilities of the liver are metabolised peripherally in a carnitine-dependent mechanism, which can increase the demand for it 2. On the other hand, it has been observed that on the enterohormonal pathway (an important element of which is a MCT-induced increase of the YY peptide concentration and a decrease in cholecystokinin release) MCT cause a decrease of appetite and consequently a decrease in energy intake 2. They also interfere with the metabolism of the fatty tissue, by hindering the creation of a deposit from long chain acids 2. It has been proven that an MCT-enriched diet modulates metabolism of fats, which is manifested as a decrease in the concentration of triglycerides and cholesterol 2.

Moreover, unlike LCT, MCT do not affect the release of cholecystokinin or the emptying of the gallbladder and they do not increase the secretion of pancreatic enzymes 2. They can speed up the intestinal passage by affecting the release of the YY peptide, but only in the distal sections of the intestine 2. Moreover, it has been found that MCT facilitate absorption of calcium 2.

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Absorption

The absorption of medium chain triglycerides is considered rapid 2,6,8,9,10 but that both long-chain triglycerides and medium chain triglycerides share a similar absorption, which is an absorption rate of about 95% - similar to that of other ingested fats 7.

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

It has been observed that medium chain fatty acids bind weakly to albumin and as a result, they can readily cross the blood-brain barrier to cause CNS effects 8.

Metabolism

In capillaries, both medium chain triglycerides (MCTs) and long-chain triglycerides (LCTs) are hydrolysed by lipoprotein lipase to glycerol and free fatty acids, and medium chain fatty acids (MCFAs) and long chain fatty acids (LCFAs), respectively 8. MCTs are hydrolysed at a faster rate than LCTs and therefore have a faster elimination rate 8. Free MCFAs then readily enter the liver, kidney, heart and other peripheral organs where they are oxidised by β-oxidation and the citric acid cycle to carbon dioxide and water 8. Alternatively, via the ketogenesis pathway, the β-oxidation of fatty acids generates the acetyl-CoA that can lead to the formation of ketone bodies like acetoacetate and β-hydroxybutyrate 8.

Route of elimination

Readily accessible data regarding the route of elimination of medium chain fatty acids is not available.

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 4.

Toxicity

The excess use of medium chain triglycerides (MCTs) can lead to increased plasma levels of medium chain dicarboxylic acids, 3-hydroxy fatty acids and ketone bodies 8. Hyperketonaemia was observed in repeat-dose toxicity studies with SMOFLIPID 8. If excess MCTs are administered, the capacity of extrahepatic tissues to use ketone bodies is saturated and this may be of particular concern in some diabetes patients 8. The increased level of ketone bodies aggravates metabolic acidosis and accelerates the breakdown of homeostatic mechanisms 8.

Affected organisms
  • Humans and other mammals
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
Not Available

References

General References
  1. 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. [PubMed:8748191]
  2. 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. [PubMed:28053676]
  3. Vignes S, Bellanger J: Primary intestinal lymphangiectasia (Waldmann's disease). Orphanet J Rare Dis. 2008 Feb 22;3:5. doi: 10.1186/1750-1172-3-5. [PubMed:18294365]
  4. 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. [PubMed:7702024]
  5. Fat Absorption and Lipid Metabolism in Cholestasis [Link]
  6. ScienceDirect: Medium Chain Triglycerides Profile [Link]
  7. National Institutes of Health (NIH) Office of Dietary Supplements: Omega-3 Fatty Acids Fact Sheet for Health Professionals [Link]
  8. Australian Public Assessment Report for Soya oil, Medium chain triglycerides, Olive oil, Fish oil [File]
  9. SMOFLIPID FDA Label [File]
  10. Medium Chain Triglycerides Monograph [File]
External Links
Wikipedia
Medium-chain_triglycerides

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1RecruitingPreventionInfants, Premature / Prophylaxis of Candida Infections1
1, 2CompletedSupportive CareCholestasis / Jaundice, Obstructive1
1, 2RecruitingTreatmentSevere Sepsis / Shock, Septic1
2Unknown StatusTreatmentIntestinal Failure / Mucosal Enteropathy / Short Bowel Syndrome (SBS) / Upper gastrointestinal motility disorders1
2, 3CompletedTreatmentCardiac Surgical Procedures / Inflammatory Reaction1
3CompletedPreventionRetinopathy of Prematurity1
3CompletedTreatmentAdjunct to general anesthesia therapy / Elective Surgery1
3CompletedTreatmentParents2
3RecruitingPreventionCholestasis of Parenteral Nutrition1
3RecruitingSupportive CareHospitalized Neonates and Infants, Expected to Require Parenteral Nutrition for 28 Days1
3RecruitingTreatmentGeneral Surgery / Parenteral Feeding1
3RecruitingTreatmentGeneral Surgery / Parenteral Nutrition1
3TerminatedPreventionPolymorphic Light Eruption (PLE)1
4CompletedHealth Services ResearchSepsis Newborn1
4CompletedPreventionCholestasis / Psychomotor Disorders, Developmental1
4CompletedSupportive CareDietary and Nutritional Therapies1
4CompletedSupportive CareGastric Resection / Malnutrition1
4CompletedTreatmentHepatic Function / Inflammatory Responses1
4CompletedTreatmentParenteral Nutrition1
4Not Yet RecruitingSupportive CareCritical Illness1
4Not Yet RecruitingSupportive CareMalnutrition, Child1
4RecruitingPreventionNeurological Complications1
4TerminatedSupportive CareCancer-related Malnutrition1
4WithdrawnTreatmentHome Parenteral Nutrition / Short Bowel Syndrome (SBS)1
Not AvailableAvailableNot AvailableCholestasis / Growth Failure1
Not AvailableCompletedSupportive CareIntraocular Pressure1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
EmulsionIntravenous
CreamTopical
Injection, emulsionIntravenous
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

Taxonomy

Classification
Not classified

Drug created on January 17, 2018 09:57 / Updated on November 02, 2019 03:19