Soybean oil

Identification

Summary

Soybean oil is an oil used as a source of calories and essential fatty acids in selected patients for total parenteral nutrition (TPN) therapy and prevention of essential fatty acid deficiency.

Brand Names
Clinoleic, Clinolipid, Intralipid, Nutrilipid, Olimel, Periolimel
Generic Name
Soybean oil
DrugBank Accession Number
DB09422
Background

Derived from soybeans, soybean oil is a common vegetable oil and a source of polyunsaturated and saturated fatty acids. It is a complex mixture of triglycerides where per 100 g, soybean oil has 16 g of saturated fat, 23 g of monounsaturated fat, and 58 g of polyunsaturated fat. The major component fatty acids are linoleic (48% - 58%), oleic (17% - 30%), palmitic (9% -13%), linolenic (4% - 11%), and stearic (2.5% - 5.0%). It is used as a cooking oil and lipid emulsion for parenteral nutrition in clinical settings. Soybean oil-based lipid emulsion is the only FDA-approved lipid formulation for clinical use.

Type
Biotech
Groups
Approved
Synonyms
  • Dolichos soja seed oil
  • Glycine angustifolia seed oil
  • Glycine gracilis seed oil
  • Glycine hispida seed oil
  • Oils, soybean
  • Phalseolus max seed oil
  • Phaseolus max seed oil
  • Soja angustifolia seed oil
  • Soja hispida seed oil
  • Soja japonica seed oil
  • Soja max seed oil
  • Soja soja seed oil
  • Soja viridis seed oil
  • Soya bean seed oil
  • Soya oil
  • Soybean oil
  • Soybean seed oil

Pharmacology

Indication

Indicated for parenteral nutrition as a source of calories and essential fatty acids when oral or enteral nutrition is not possible, insufficient, or contraindicated.

Pharmacology
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Associated Conditions
Associated Therapies
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Soybean oil is a nutrition source that provides a biologically utilizable source of calories and essential fatty acids. It prevents the biochemical lesions of essential fatty acid deficiency (EFAD), and correct the clinical manifestations of the EFAD syndrome 10 by supplying energy and nutrients.

Mechanism of action

Fatty acids serve as an important substrate for energy production. The most common mechanism of action for energy production derived from fatty acid metabolism is beta oxidation. Fatty acids are also important for membrane structure and function, precursors for bioactive molecules (such as prostaglandins), and as regulators of gene expression. Soybean oil-based lipid emulsion may also cause an increase in heat production, decrease in respiratory quotient, and increase in oxygen consumption following its administration 8. Soybean oil contents prevent abnormally high triacylglycerol synthesis and its accumulation as lipid droplets in the liver by regulating hepatic lipogenesis and lipolysis. In vitro, soybean oil is shown to prevent downregulation of CYP2C2, CYP2C11 and CYP3A2 mRNA thus maintaining hepatic drug oxidation capabilities. Soybean oil is broken down into free fatty acids that activate PPAR-alpha, which regulate hepatic CYP4A1 that hydroxylate saturated and unsaturated fatty acids. Soybean oil is also shown to prevent up/downregulation of efflux transporters and maintain mRNA levels of hepatic antioxidant enzymes in vitro rat studies 5.

TargetActionsOrganism
APeroxisome proliferator-activated receptor alpha
activator
Humans
Absorption

Following infusion, there is a transient increase in plasma triglycerides.

Volume of distribution

After triglycerides are hydrolyzed, fatty acids can enter the tissues where they may be oxidized or resynthesized into triglcerides and stored.

Protein binding

Free fatty acids circulate in the plasma, bound to albumin.

Metabolism

The infused lipid particles are removed from the bloodstream in a manner generally thought to be similar to the enzymatic clearance of naturally produced chylomicrons formed after enteral fat intake. The triglycerides are hydrolyzed to free fatty acids and glycerol by the enzyme lipoprotein lipase. In the liver, circulating free fatty acids are oxidized or converted to very low density lipoproteins by hepatic lipase that re-enter the bloodstream.

Route of elimination

Converted carbon dioxide from smaller fatty acid units are excreted by the lungs.

Half-life

Not Available

Clearance

The elimination rate of lipid emulsions depends on particle size, fatty acid composition, apolipoprotein content of the lipid globules, lipoprotein lipase activity, and hepatic lipase activity 9.

Adverse Effects
Medicalerrors
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Toxicity

The most frequent adverse effects were nausea, vomiting and muscle spasm. Soybean oil-based lipid emulsions can cause hypersensitivity reactions and risks of catheter-related infections. Fat overload syndrome is a rare condition that has been reported with intravenous lipid emulsions, due to a reduced or limited ability to metabolize lipids accompanied by prolonged plasma clearance. Worsensing conditions of the patients can be seen including hematological effects, declined hepatic function and central nervous system manifestations. Hypertriglyceridema may occur. Preterm and small-for-gestational-age infants have poor clearance of intravenous lipid emulsion and increased free fatty acid plasma levels following lipid emulsion infusion, leading to accumulation in lungs. It is advised not to exceed 0.75 mL/kg/hour.

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

Products
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Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
IntralipidEmulsion20 g/100mLIntravenousBaxter Healthcare Corporation2004-04-012015-05-31US flag
IntralipidEmulsion20 g/100mLIntravenousHF Acquisition Co LLC, DBA HealthFirst2018-12-21Not applicableUS flag
IntralipidEmulsion10 g/100mLIntravenousBaxter Healthcare CORP2014-12-12Not applicableUS flag
IntralipidEmulsion30 g/100mLIntravenousBaxter Healthcare Corporation2004-04-012015-05-31US flag
Intralipid 10%Emulsion10 % w/vIntravenousFresenius Kabi1995-12-31Not applicableCanada flag
Intralipid 20%Emulsion20 % w/vIntravenousFresenius Kabi1995-12-31Not applicableCanada flag
Intralipid 30%Emulsion30 % w/vIntravenousFresenius Kabi1996-12-30Not applicableCanada flag
NutriLipid I.V. Fat EmulsionInjection, solution20 g/100mLIntravenousB. Braun Medical Inc.2014-06-30Not applicableUS flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
CELEPID 10% Intravenous Fat EmulsionInjection, emulsionIntravenousBioCare Pharmaceutical (M) Sdn. Bhd.2020-09-08Not applicableMalaysia flag
CELEPID 20% Intravenous Fat EmulsionInjection, emulsionIntravenousBioCare Pharmaceutical (M) Sdn. Bhd.2020-09-08Not applicableMalaysia flag
essenHERB Soybean 90 Deep CleansingOil91.6 g/100mLTopicalAmi Cosmetic Co.,Ltd.2015-06-112019-01-15US flag
INTRALIPID 20%Injection, emulsionIntravenousFRESENIUS KABI MALAYSIA SDN. BHD2020-09-08Not applicableMalaysia flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
10% Travamulsion Liq IVSoybean oil (10 g / 100 mL) + Egg phospholipids (1.2 g / 100 mL)LiquidIntravenousBaxter Corporation Clintec Nutrition Division1995-12-312015-08-05Canada flag
20% Travamulsion Liq IVSoybean oil (20 g / 100 mL) + Egg phospholipids (1.2 g / 100 mL)LiquidIntravenousBaxter Corporation Clintec Nutrition Division1995-12-312015-08-05Canada flag
CELEPID MCT-LCT 20% W/VSoybean oil (10 g) + Medium-chain triglycerides (10 g)EmulsionIntravenousFARMALOGICA S.A2007-03-14Not applicableColombia flag
CLINOLEIC %20 IV İNFÜZYONLUK LİPİD EMÜLSİYON, 100 MLSoybean oil (4 g/100ml) + Olive oil (16 g/100ml)InjectionIntravenousEİP ECZACIBAŞI İLAÇ PAZARLAMA A.Ş.2020-08-14Not applicableTurkey flag
CLINOLEIC %20 IV İNFÜZYONLUK LİPİD EMÜLSİYON, 1000 MLSoybean oil (4 g/100ml) + Olive oil (16 g/100ml)InjectionIntravenousEİP ECZACIBAŞI İLAÇ PAZARLAMA A.Ş.2020-08-14Not applicableTurkey flag
CLINOLEIC %20 IV İNFÜZYONLUK LİPİD EMÜLSİYON, 250 MLSoybean oil (4 g/100ml) + Olive oil (16 g/100ml)InjectionIntravenousEİP ECZACIBAŞI İLAÇ PAZARLAMA A.Ş.2020-08-14Not applicableTurkey flag
CLINOLEIC %20 IV İNFÜZYONLUK LİPİD EMÜLSİYON, 500 MLSoybean oil (4 g/100ml) + Olive oil (16 g/100ml)InjectionIntravenousEİP ECZACIBAŞI İLAÇ PAZARLAMA A.Ş.2020-08-14Not applicableTurkey flag
Clinoleic 20%Soybean oil (4 % w/w) + Olive oil (16 % w/w)EmulsionIntravenousBaxter Laboratories2012-03-28Not applicableCanada flag
ClinolipidSoybean oil (4 g/100mL) + Olive oil (16 g/100mL)Injection, emulsionIntravenousBaxter Healthcare Corporation2016-01-01Not applicableUS flag
Colip 20%Soybean oil (5 g / 100 mL) + Medium-chain triglycerides (15 g / 100 mL)EmulsionIntravenousBaxter Corporation Clintec Nutrition Division1998-10-072007-08-02Canada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
essenHERB Soybean 90 Deep CleansingSoybean oil (91.6 g/100mL)OilTopicalAmi Cosmetic Co.,Ltd.2015-06-112019-01-15US flag
KABIVEN 1026 MLSoybean oil (40 g) + Alanine (4.8 g) + Arginine (3.4 g) + Aspartic acid (1 g) + Calcium chloride dihydrate (0.29 g) + D-glucose monohydrate (110 g) + Glutamic acid (1.7 g) + Glycine (2.4 g) + Histidine (2 g) + Isoleucine (1.7 g) + Leucine (2.4 g) + Lysine (2.7 g) + Magnesium sulfate heptahydrate (0.99 g) + Methionine (1.7 g) + Phenylalanine (2.4 g) + Potassium chloride (1.8 g) + Proline (2 g) + Serine (1.4 g) + Sodium acetate trihydrate (2.5 g) + Sodium glycerophosphate (1.5 g) + Threonine (1.7 g) + Tryptophan (0.57 g) + Tyrosine (0.07 g) + Valine (2.2 g)InjectionIntravenousFRESENİUS KABİ İLAÇ SAN. VE TİC. LTD. ŞTİ.2020-08-14Not applicableTurkey flag
KABIVEN 1540 MLSoybean oil (60 g) + Alanine (7.2 g) + Arginine (5.1 g) + Aspartic acid (1.5 g) + Calcium chloride dihydrate (0.44 g) + D-glucose monohydrate (165 g) + Glutamic acid (2.5 g) + Glycine (3.6 g) + Histidine (3.1 g) + Isoleucine (2.5 g) + Leucine (3.6 g) + Lysine (4.1 g) + Magnesium sulfate heptahydrate (1.5 g) + Methionine (2.5 g) + Phenylalanine (3.6 g) + Potassium chloride (2.7 g) + Proline (3.1 g) + Serine (2 g) + Sodium acetate trihydrate (3.7 g) + Sodium glycerophosphate (2.3 g) + Threonine (2.5 g) + Tryptophan (0.86 g) + Tyrosine (0.1 g) + Valine (3.3 g)InjectionIntravenousFRESENİUS KABİ İLAÇ SAN. VE TİC. LTD. ŞTİ.2020-08-14Not applicableTurkey flag
KABIVEN 2053 MLSoybean oil (80 g) + Alanine (9.6 g) + Arginine (6.8 g) + Aspartic acid (2 g) + Calcium chloride dihydrate (0.59 g) + D-glucose monohydrate (220 g) + Glutamic acid (3.4 g) + Glycine (4.7 g) + Histidine (4.1 g) + Isoleucine (3.4 g) + Leucine (4.7 g) + Lysine (5.4 g) + Magnesium sulfate heptahydrate (2 g) + Methionine (3.4 g) + Phenylalanine (4.7 g) + Potassium chloride (3.6 g) + Proline (4.1 g) + Serine (2.7 g) + Sodium acetate trihydrate (4.9 g) + Sodium glycerophosphate (3 g) + Threonine (3.4 g) + Tryptophan (1.1 g) + Tyrosine (0.14 g) + Valine (4.4 g)InjectionIntravenousFRESENİUS KABİ İLAÇ SAN. VE TİC. LTD. ŞTİ.2020-08-14Not applicableTurkey flag
KABIVEN PERIPHERAL 1440 MLSoybean oil (51 g) + Alanine (4.8 g) + Arginine (3.4 g) + Aspartic acid (1 g) + Calcium chloride dihydrate (0.29 g) + D-glucose monohydrate (107 g) + Glutamic acid (1.7 g) + Glycine (2.4 g) + Histidine (2 g) + Isoleucine (1.7 g) + Leucine (2.4 g) + Lysine (2.7 g) + Magnesium sulfate heptahydrate (0.99 g) + Methionine (1.7 g) + Phenylalanine (2.4 g) + Potassium chloride (1.8 g) + Proline (2 g) + Serine (1.4 g) + Sodium acetate trihydrate (2.5 g) + Sodium glycerophosphate (1.5 g) + Threonine (1.7 g) + Tryptophan (0.57 g) + Tyrosine (0.069 g) + Valine (2.2 g)InjectionIntravenousFRESENİUS KABİ İLAÇ SAN. VE TİC. LTD. ŞTİ.2020-08-14Not applicableTurkey flag
KABIVEN PERIPHERAL 1920 MLSoybean oil (68 g) + Alanine (6.4 g) + Arginine (4.5 g) + Aspartic acid (1.4 g) + Calcium chloride dihydrate (0.39 g) + D-glucose monohydrate (143 g) + Glutamic acid (2.2 g) + Glycine (3.2 g) + Histidine (2.7 g) + Isoleucine (2.2 g) + Leucine (3.2 g) + Lysine (3.6 g) + Magnesium sulfate heptahydrate (1.3 g) + Methionine (2.2 g) + Phenylalanine (3.2 g) + Potassium chloride (2.4 g) + Proline (2.7 g) + Serine (1.8 g) + Sodium acetate trihydrate (3.3 g) + Sodium glycerophosphate (2 g) + Threonine (2.2 g) + Tryptophan (0.76 g) + Tyrosine (0.092 g) + Valine (2.9 g)InjectionIntravenousFRESENİUS KABİ İLAÇ SAN. VE TİC. LTD. ŞTİ.2020-08-14Not applicableTurkey flag

Categories

Drug Categories
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
241ATL177A
CAS number
8001-22-7

References

General References
  1. Umpierrez GE, Spiegelman R, Zhao V, Smiley DD, Pinzon I, Griffith DP, Peng L, Morris T, Luo M, Garcia H, Thomas C, Newton CA, Ziegler TR: A double-blind, randomized clinical trial comparing soybean oil-based versus olive oil-based lipid emulsions in adult medical-surgical intensive care unit patients requiring parenteral nutrition. Crit Care Med. 2012 Jun;40(6):1792-8. doi: 10.1097/CCM.0b013e3182474bf9. [Article]
  2. Siqueira J, Smiley D, Newton C, Le NA, Gosmanov AR, Spiegelman R, Peng L, Osteen SJ, Jones DP, Quyyumi AA, Ziegler TR, Umpierrez GE: Substitution of standard soybean oil with olive oil-based lipid emulsion in parenteral nutrition: comparison of vascular, metabolic, and inflammatory effects. J Clin Endocrinol Metab. 2011 Oct;96(10):3207-16. doi: 10.1210/jc.2011-0480. Epub 2011 Aug 10. [Article]
  3. Jiang ZM, Wilmore DW, Wang XR, Wei JM, Zhang ZT, Gu ZY, Wang S, Han SM, Jiang H, Yu K: Randomized clinical trial of intravenous soybean oil alone versus soybean oil plus fish oil emulsion after gastrointestinal cancer surgery. Br J Surg. 2010 Jun;97(6):804-9. doi: 10.1002/bjs.6999. [Article]
  4. Tomsits E, Pataki M, Tolgyesi A, Fekete G, Rischak K, Szollar L: Safety and efficacy of a lipid emulsion containing a mixture of soybean oil, medium-chain triglycerides, olive oil, and fish oil: a randomised, double-blind clinical trial in premature infants requiring parenteral nutrition. J Pediatr Gastroenterol Nutr. 2010 Oct;51(4):514-21. doi: 10.1097/MPG.0b013e3181de210c. [Article]
  5. Nishimura M, Yamaguchi M, Naito S, Yamauchi A: Soybean oil fat emulsion to prevent TPN-induced liver damage: possible molecular mechanisms and clinical implications. Biol Pharm Bull. 2006 May;29(5):855-62. [Article]
  6. Kapoor V, Glover R, Malviya MN: Alternative lipid emulsions versus pure soy oil based lipid emulsions for parenterally fed preterm infants. Cochrane Database Syst Rev. 2015 Dec 2;(12):CD009172. doi: 10.1002/14651858.CD009172.pub2. [Article]
  7. SMOFLIPID (lipid injectable emulsion) FDA Label [Link]
  8. NUTRILIPID® (lipid injectable emulsion) FDA Label [Link]
  9. CLINOLEIC 20% (Lipid Emulsion for Intravenous Nutrition) FDA Label [Link]
  10. INTRALIPID (soybean oil emulsion) Dailymed drug label information [Link]
PubChem Substance
347910452
RxNav
9949
Wikipedia
Soybean_oil

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedNot AvailableInflammation1
4CompletedBasic ScienceBlood Pressures / Overdose of Beta-adrenergic Blocking Drug / Overdose, Drug1
4CompletedDiagnosticInsulin Resistance Syndrome X / Pancreatic Beta Cell Function1
4CompletedHealth Services ResearchSepsis Newborn1
4CompletedPreventionAnaesthesia therapy1
4CompletedPreventionCholestasis / Psychomotor Disorders, Developmental1
4CompletedPreventionCirrhosis of the Liver / Liver Cancer1
4CompletedSupportive CareDietary and Nutritional Therapies1
4CompletedSupportive CareGastric Resection / Malnutrition1
4CompletedSupportive CareIleus / Malignancies / Malnutrition / Obstruction / Surgery1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
LiquidIntravenous
Injection, emulsionIntravenous
EmulsionIntravenous10 g
EmulsionParenteral
EmulsionIntravenous20 g
OilTopical91.6 g/100mL
Capsule
EmulsionIntravenous
EmulsionIntravenous10 g/100mL
EmulsionIntravenous20 g/100mL
EmulsionIntravenous30 g/100mL
SolutionIntravenous
EmulsionIntravenous10 % w/v
EmulsionIntravenous20 % w/v
InjectionIntravenous
EmulsionParenteral
EmulsionIntravenous30 % w/v
InjectionParenteral10 g
SuspensionParenteral20 g
SuspensionParenteral100 g
EmulsionParenteral200 g
Injection, emulsionIntravenous drip
Injection, emulsionIntravenous
InjectionIntravenous12 g/L
EmulsionIntravenous0.2 g
SprayTopical
Injection, emulsionParenteral
Injection, emulsion; injection, solutionIntravenous
EmulsionIntravenous
Injection, solutionIntravenous20 g/100mL
EmulsionIntravenous4 g
SolutionIntravenous
InjectionIntravenous
EmulsionIntravenous3 g
CapsuleOral
Injection, solutionIntravenous
SolutionParenteral
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5840757No1998-11-242015-11-24US flag
US9717852No2017-08-012033-04-08US flag

Properties

State
Not Available
Experimental Properties
Not Available

Targets

Drugtargets
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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Activator
General Function
Zinc ion binding
Specific Function
Ligand-activated transcription factor. Key regulator of lipid metabolism. Activated by the endogenous ligand 1-palmitoyl-2-oleoyl-sn-glycerol-3-phosphocholine (16:0/18:1-GPC). Activated by oleyleth...
Gene Name
PPARA
Uniprot ID
Q07869
Uniprot Name
Peroxisome proliferator-activated receptor alpha
Molecular Weight
52224.595 Da
References
  1. Nishimura M, Yamaguchi M, Naito S, Yamauchi A: Soybean oil fat emulsion to prevent TPN-induced liver damage: possible molecular mechanisms and clinical implications. Biol Pharm Bull. 2006 May;29(5):855-62. [Article]

Drug created on November 30, 2015 19:10 / Updated on August 04, 2021 18:23