Soybean oil

Identification

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Name
Soybean oil
Accession Number
DB09422
Type
Small Molecule
Groups
Approved
Description

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.

Synonyms
Not Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
IntralipidEmulsion20 g/100mLIntravenousHF Acquisition Co LLC, DBA HealthFirst2018-12-21Not applicableUs
IntralipidEmulsion10 g/100mLIntravenousBaxter Healthcare CORP2014-12-12Not applicableUs
IntralipidEmulsion30 g/100mLIntravenousBaxter Healthcare Corporation2004-04-01Not applicableUs
IntralipidEmulsion20 g/100mLIntravenousBaxter Healthcare Corporation2004-04-01Not applicableUs
Intralipid 10%Emulsion10 %IntravenousFresenius Kabi1995-12-31Not applicableCanada
Intralipid 20%Emulsion20 %IntravenousFresenius Kabi1995-12-31Not applicableCanada
Intralipid 30%Emulsion30 %IntravenousFresenius Kabi1996-12-30Not applicableCanada
NutriLipid I.V. Fat EmulsionInjection, solution20 g/100mLIntravenousB. Braun Medical Inc.2014-06-30Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
essenHERB Soybean 90 Deep CleansingOil91.6 g/100mLTopicalAmi Cosmetic Co.,Ltd.2015-06-11Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
10% Travamulsion Liq IVSoybean oil (10 g) + Egg phospholipids (1.2 g)LiquidIntravenousBaxter Corporation Clintec Nutrition Division1995-12-312015-08-05Canada
20% Travamulsion Liq IVSoybean oil (20 g) + Egg phospholipids (1.2 g)LiquidIntravenousBaxter Corporation Clintec Nutrition Division1995-12-312015-08-05Canada
Clinoleic 20%Soybean oil (4 %) + Olive oil (16 %)EmulsionIntravenousBaxter Laboratories2012-03-28Not applicableCanada
ClinolipidSoybean oil (4 g/100mL) + Olive oil (16 g/100mL)Injection, emulsionIntravenousBaxter Healthcare Corporation2016-01-01Not applicableUs
Colip 20%Soybean oil (5 g) + Medium-chain triglycerides (15 g)EmulsionIntravenousBaxter Corporation Clintec Nutrition Division1998-10-072007-08-02Canada
KabivenSoybean oil (3.9 g/100mL) + Aspartic acid (99 mg/100mL) + Calcium chloride dihydrate (29 mg/100mL) + D-glucose monohydrate (9.8 g/100mL) + Glutamic Acid (164 mg/100mL) + Glycine (231 mg/100mL) + Histidine (199 mg/100mL) + Isoleucine (164 mg/100mL) + L-Alanine (467 mg/100mL) + L-Arginine (330 mg/100mL) + L-Leucine (231 mg/100mL) + L-Lysine hydrochloride (263 mg/100mL) + L-Phenylalanine (231 mg/100mL) + L-Threonine (164 mg/100mL) + L-Tryptophan (55 mg/100mL) + L-Valine (213 mg/100mL) + Magnesium sulfate heptahydrate (96 mg/100mL) + Methionine (164 mg/100mL) + Potassium chloride (174 mg/100mL) + Proline (199 mg/100mL) + Serine (131 mg/100mL) + Sodium acetate trihydrate (239 mg/100mL) + Sodium glycerophosphate (147 mg/100mL) + Tyrosine (6.7 mg/100mL)Injection, emulsionIntravenousFresenius Kabi USA, LLC2014-08-25Not applicableUs
Liposyn IISoybean oil (10 g/100mL) + Egg phospholipids (1.2 g/100mL) + Safflower oil (10 g/100mL)Injection, emulsionIntravenousHospira, Inc.1984-08-272011-02-01Us
Liposyn IISoybean oil (5 g/100mL) + Egg phospholipids (1.2 g/100mL) + Safflower oil (5 g/100mL)Injection, emulsionIntravenousHospira, Inc.1984-08-272011-02-01Us
Liposyn II 10%Soybean oil (5 %) + Egg phospholipids (0.9 %) + Safflower oil (5 %)EmulsionIntravenousHospira, Inc.1987-12-312014-08-01Canada
Liposyn II 20%Soybean oil (10 %) + Egg phospholipids (1.2 %) + Safflower oil (10 %)EmulsionIntravenousHospira, Inc.1987-12-312014-08-01Canada
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
essenHERB Soybean 90 Deep CleansingSoybean oil (91.6 g/100mL)OilTopicalAmi Cosmetic Co.,Ltd.2015-06-11Not applicableUs
Categories
UNII
241ATL177A
CAS number
Not Available
Weight
Not Available
Chemical Formula
Not Available
InChI Key
Not Available
InChI
Not Available
IUPAC Name
Not Available
SMILES
Not Available

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.

Associated Therapies
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
Additional Data Available
Adverse Effects

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Additional Data Available
Contraindications

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Additional Data Available
Blackbox Warnings

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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.

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.

Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

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. [PubMed:22488002]
  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. [PubMed:21832112]
  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. [PubMed:20473991]
  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. [PubMed:20531018]
  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. [PubMed:16651709]
  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. [PubMed:26630252]
  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]
External Links
PubChem Substance
347910452
Wikipedia
Soybean_oil
AHFS Codes
  • 40:20.00 — Caloric Agents

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Not Yet RecruitingBasic ScienceInsulin Resistance / Insulin Sensitivity / Type 2 Diabetes Mellitus1
0RecruitingBasic ScienceInsulin Resistance1
1CompletedPreventionCholestasis / Parenteral Nutrition1
1Not Yet RecruitingTreatmentRecurrent Miscarriages1
1RecruitingSupportive CareHematopoietic Stem Cell Transplantation (HSCT)1
1RecruitingTreatmentAbscesses1
1, 2CompletedSupportive CareCholestasis / Jaundice, Obstructive1
1, 2CompletedTreatmentBMI >30 kg/m21
1, 2RecruitingTreatmentSevere Sepsis / Shock, Septic1
1, 2RecruitingTreatmentSubfertility1
2Active Not RecruitingPreventionAge Related Cognitive Decline / Alzheimer's Disease (AD) / Dementia, Vascular / Endothelial Dysfunction / Executive Dysfunction1
2Active Not RecruitingTreatmentSickle Cell Disorders1
2CompletedPreventionAdverse Effects / Therapeutic Agent Toxicity1
2CompletedTreatmentInfertility Due to Nonimplantation1
2Not Yet RecruitingTreatmentImperforate oesophagus1
2SuspendedTreatmentCritical Illness1
2TerminatedTreatmentAcute Respiratory Distress Syndrome (ARDS)1
2Unknown StatusTreatmentIntestinal Failure / Mucosal Enteropathy / Short Bowel Syndrome (SBS) / Upper gastrointestinal motility disorders1
2WithdrawnPreventionHuman Immunodeficiency Virus (HIV)1
2, 3CompletedBasic ScienceInsulin Sensitivity / Metabolic Diseases1
2, 3CompletedTreatmentInfertilities1
2, 3CompletedTreatmentParenteral Nutrition1
2, 3RecruitingTreatmentReperfusion Injury1
3CompletedPreventionRetinopathy of Prematurity1
3CompletedTreatmentCarcinoma Surgery / Parenteral Nutrition / Post-Operative Hospital Stay1
3CompletedTreatmentCholestasis1
3CompletedTreatmentParenteral Nutrition1
3CompletedTreatmentParents2
3CompletedTreatmentSchizophrenic Disorders2
3CompletedTreatmentSedation to be Moderate for a Diagnostic Gastrointestinal Endoscopy and Gastrointestinal Endoscopic Polypectomy1
3Not Yet RecruitingTreatmentSickle Cell Disorders1
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
3TerminatedTreatmentIschaemic Heart Diseases / Nonvalvular Atrial Fibrillation1
3TerminatedTreatmentTotal Parenteral Nutrition-Induced Cholestasis1
3Unknown StatusTreatmentInfertilities1
4CompletedNot AvailableInflammatory Reaction1
4CompletedBasic ScienceBlood Pressures / Drug Overdose / Overdose of Beta-adrenergic Blocking Drug1
4CompletedDiagnosticInsulin Resistance Syndrome X / Pancreatic Beta Cell Function1
4CompletedHealth Services ResearchSepsis Newborn1
4CompletedPreventionCholestasis / Psychomotor Disorders, Developmental1
4CompletedSupportive CareDietary and Nutritional Therapies1
4CompletedSupportive CareGastric Resection / Malnutrition1
4CompletedTreatmentCrohn's Disease (CD)1
4CompletedTreatmentHepatic Function / Inflammatory Responses1
4CompletedTreatmentHigh Blood Pressure (Hypertension) / Type 2 Diabetes Mellitus1
4CompletedTreatmentInfertility, Female / Subfertility1
4CompletedTreatmentParenteral Nutrition1
4CompletedTreatmentRecurrent Abortion / Spontaneous Abortions1
4CompletedTreatmentSedation therapy1
4Not Yet RecruitingSupportive CareMalnutrition, Child1
4Not Yet RecruitingTreatmentInfants, Premature / Prematurity, Parenteral Nutrition, Lipid Emulsion1
4RecruitingSupportive CareGeneral Surgery / Ileus / Malignancies / Malnutrition / Obstruction1
4RecruitingSupportive CareMalnutrition1
4TerminatedPreventionCholestasis1
4TerminatedTreatmentEssential Fatty Acid Deficiency (EFAD)1
4Unknown StatusPreventionPreterm, Infant1
4Unknown StatusSupportive CarePreterm, Infant1
4Unknown StatusTreatmentPregnancy Complicated by Low Implantation1
4WithdrawnTreatmentHome Parenteral Nutrition / Short Bowel Syndrome (SBS)1
Not AvailableActive Not RecruitingTreatmentParenteral Nutrition1
Not AvailableAvailableNot AvailableCholestasis / Growth Failure1
Not AvailableCompletedNot AvailableInflammatory Reaction / Insulin Resistance1
Not AvailableCompletedBasic ScienceBMI >30 kg/m2 / Diabetes Mellitus (DM)1
Not AvailableCompletedBasic ScienceBMI >30 kg/m2 / Leptin Resistance1
Not AvailableCompletedBasic ScienceHealthy Volunteers1
Not AvailableCompletedDiagnosticInsulin Resistance1
Not AvailableCompletedPreventionDiabetes Mellitus (DM) / High Blood Pressure (Hypertension)1
Not AvailableCompletedTreatmentChronic Liver Failure1
Not AvailableCompletedTreatmentFatty Acids, Nonesterified / Glomerular Filtration Rate (GFR) / Renal Circulation / Renal Plasma Flow1
Not AvailableCompletedTreatmentHyperglycemias / Type 2 Diabetes Mellitus1
Not AvailableCompletedTreatmentLiver Diseases1
Not AvailableRecruitingBasic ScienceBMI >30 kg/m2 / Hyperinsulinemia / Hypogonadotropic Hypogonadotropism / Infertilities1
Not AvailableRecruitingBasic ScienceCarnitine Palmitoyltransferase II Deficiency, Myopathic / Long-Chain 3-Hydroxyacyl-CoA Dehydrogenase Deficiency / Medium-chain Acyl-CoA Dehydrogenase Deficiency / Normal Volunteers / Trifunctional Protein Deficiency / Very Long-chain Acyl-CoA Dehydrogenase Deficiency1
Not AvailableTerminatedPreventionHypertriglyceridemias1
Not AvailableTerminatedTreatmentHyperglycemias / Hypertriglyceridemias1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
LiquidIntravenous
EmulsionIntravenous
OilTopical91.6 g/100mL
EmulsionIntravenous10 g/100mL
EmulsionIntravenous20 g/100mL
EmulsionIntravenous30 g/100mL
EmulsionIntravenous10 %
EmulsionIntravenous20 %
EmulsionIntravenous30 %
Injection, emulsionIntravenous
SprayTopical
Injection, solutionIntravenous20 g/100mL
CapsuleOral
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5840757No1998-11-242015-11-24Us
US9717852No2017-08-012033-04-08Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

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Properties

State
Not Available
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

Targets

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. [PubMed:16651709]

Drug created on November 30, 2015 12:10 / Updated on July 21, 2019 06:37