This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Linoleic acid
DrugBank Accession Number
DB14104
Background

Not Available

Type
Small Molecule
Groups
Approved, Experimental
Structure
Thumb
Weight
Average: 280.4455
Monoisotopic: 280.240230268
Chemical Formula
C18H32O2
Synonyms
  • (9Z,12Z)-Octadecadienoic acid
  • (Z,Z)-9,12-octadecadienoic acid
  • 9-cis,12-cis-Octadecadienoic acid
  • 9Z,12Z-octadecadienoic acid
  • acide cis-linoléique
  • acide linoléique
  • ácido linoleico
  • all-cis-9,12-octadecadienoic acid
  • C18:2 9c, 12c omega6 todos cis-9,12-octadienoico
  • cis,cis-9,12-octadecadienoic acid
  • cis,cis-linoleic acid
  • LA
  • Linolic acid

Pharmacology

Indication

Not Available

Pharmacology
Reduce drug development failure rates
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Associated Conditions
Associated Therapies
Contraindications & Blackbox Warnings
Contraindications
Avoid life-threatening adverse drug events
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Avoid life-threatening adverse drug events & improve clinical decision support.
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Adverseeffects
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Toxicity

Not Available

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

Products2
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dosage, form, labeller, route of administration, and marketing period.
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Product Ingredients
IngredientUNIICASInChI Key
Potassium linolate3S022W50993414-89-9BAYJYBALPIYBQQ-NBTZWHCOSA-M
Sodium linolate872C9A1W9I822-17-3WYPBVHPKMJYUEO-NBTZWHCOSA-M
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Bio-efa Borage Gla 240 CapLinoleic acid (378 mg) + Gamolenic acid (240 mg) + Vitamin E (10 unit)CapsuleOralPge Canada (86) Inc.1989-12-312006-06-19Canada flag
Bio-efa Borage Gla 90 CapLinoleic acid (216 mg / cap) + Gamolenic acid (90 mg / cap) + Vitamin E (10 unit / cap) + alpha-Linolenic acid (1 mg / cap)CapsuleOralPge Canada (86) Inc.1989-12-312006-06-19Canada flag
Black Currant Seed Oil CapLinoleic acid (78 mg) + Gamolenic acid (41 mg) + Vitamin E (10 unit)CapsuleOralPure Life International Prods Inc.1993-12-312001-08-07Canada flag
Borage Oil CapsulesLinoleic acid (220 mg) + Borage oil (500 mg) + Gamolenic acid (125 mg)CapsuleOralBioforce Canada Inc.1994-12-311999-10-14Canada flag
Borage Oil CapsulesLinoleic acid (375 mg) + Gamolenic acid (258 mg) + Oleic Acid (148 mg) + Palmitic Acid (96 mg)CapsuleOralGeneral Nutrition Canada Inc.2001-10-152009-08-05Canada flag
Evening Primrose Oil + Vit E CapLinoleic acid (375 mg) + Gamolenic acid (45 mg) + Vitamin E (15 unit)CapsuleOralBioforce Canada Inc.1993-12-312000-03-21Canada flag
Evening Primrose Oil CapLinoleic acid (350 mg) + Gamolenic acid (40 mg) + Vitamin E (14.9 unit)CapsuleOralPure Life International Prods Inc.1992-12-312001-08-07Canada flag
Evening Primrose Oil Cap 500mg W Vit ELinoleic acid (350 mg) + Gamolenic acid (40 mg) + Vitamin E (14.9 unit)CapsuleOralStanley Pharmaceuticals, A Division Of Vita Health Products Inc.1990-12-312002-07-31Canada flag
Flaxseed Oil CapsulesLinoleic acid (144 mg) + Oleic Acid (165 mg) + Palmitic Acid (54 mg) + alpha-Linolenic acid (594 mg)CapsuleOralGeneral Nutrition Canada Inc.1998-05-272007-08-01Canada flag
Gla 130 Primrose OilLinoleic acid (900 mg / cap) + Gamolenic acid (130 mg / cap) + Oleic Acid (100 mg / cap)CapsuleOralSeroyal International Inc.1996-01-312007-08-02Canada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Cavan OneLinoleic acid (30 mg/1) + Calcium (150 mg/1) + Calcium ascorbate dihydrate (25 mg/1) + Cholecalciferol (170 [iU]/1) + DL-alpha tocopheryl acetate (30 [iU]/1) + Doconexent (260 mg/1) + Ferrous asparto glycinate (7 mg/1) + Folic acid (1 mg/1) + Icosapent (40 mg/1) + Iron (20 mg/1) + Pyridoxine hydrochloride (25 mg/1) + alpha-Linolenic acid (30 mg/1)Capsule, gelatin coatedOralSeton Pharmaceuticals2009-10-302011-11-27US flag
Lancell SlimmingLinoleic acid (2.5 mL/100mL) + Stypocaulon scoparium (2 mL/100mL)GelTopicalMICELLBio Co., Ltd2010-08-19Not applicableUS flag
PrimaCareLinoleic acid (50 mg/1) + Biotin (1 mg/1) + Calcium ascorbate dihydrate (25 mg/1) + Calcium carbonate (100 mg/1) + Cholecalciferol (1000 [iU]/1) + Folic acid (1 mg/1) + Magnesium oxide (50 mg/1) + Nicotinamide (10 mg/1) + Omega-3 fatty acids (420 mg/1) + Potassium Iodide (150 ug/1) + Pyridoxine (50 mg/1) + Riboflavin (1.5 mg/1) + Zinc (15 mg/1) + alpha-Tocopherol acetate (15 [iU]/1)PillOralAvion Pharmaceuticals, Llc2017-01-23Not applicableUS flag
SIMILAC ALIMENTUM 400 G TOZLinoleic acid (0.54 g/100ml) + Arachidonic Acid (0.013 g/100ml) + Doconexent (0.007 g/100ml) + alpha-Linolenic acid (0.058 g/100ml)ABBOTT LABORATUARLARI İTHALAT İHRACAT VE TİC. LTD. ŞTİ.2020-08-14Not applicableTurkey flag

Categories

Drug Categories
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
9KJL21T0QJ
CAS number
60-33-3
InChI Key
OYHQOLUKZRVURQ-HZJYTTRNSA-N
InChI
InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6-,10-9-
IUPAC Name
(9Z,12Z)-octadeca-9,12-dienoic acid
SMILES
CCCCC\C=C/C\C=C/CCCCCCCC(O)=O

References

General References
Not Available
Human Metabolome Database
HMDB0000673
KEGG Compound
C01595
ChemSpider
4444105
BindingDB
22231
RxNav
6400
ChEBI
17351
ChEMBL
CHEMBL267476
ZINC
ZINC000004474613
PDBe Ligand
EIC
Wikipedia
Linoleic_acid
PDB Entries
1igz / 2evl / 2q9s / 4dq4 / 4ia6 / 4lkt / 4nyq / 5bvs / 5z0b / 6cng
show 7 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedSupportive CareMalnutrition1
4RecruitingTreatmentPatients Requiring Home Parenteral Nutrition1
3CompletedTreatmentCancer Gi1
2CompletedPreventionParenteral Nutrition n-3 Fatty Acids / Preterm, Infant1
2RecruitingTreatmentAmyotrophic Lateral Sclerosis (ALS)1
2RecruitingTreatmentProgressive Supranuclear Palsy (PSP)1
2, 3Active Not RecruitingTreatmentNeuroaxonal Dystrophy, Infantile1
1TerminatedTreatmentMultiple Sclerosis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Capsule, gelatin coatedOral
LiquidOral
GelTopical
Injection, emulsionIntravenous
Tablet, coatedOral
PillOral
CapsuleOral
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000154 mg/mLALOGPS
logP7.06ALOGPS
logP6.42ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)4.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity88.52 m3·mol-1ChemAxon
Polarizability35.86 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)GC-MSsplash10-000t-7900000000-b6ee03c4800464c37471
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)GC-MSsplash10-00vi-9300000000-c92dac639ced59eb5dbe
GC-MS Spectrum - GC-MS (1 TMS)GC-MSsplash10-003s-9700000000-77e67d7b1a161e6ecfa6
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-000t-7900000000-b6ee03c4800464c37471
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00vi-9300000000-c92dac639ced59eb5dbe
GC-MS Spectrum - GC-MSGC-MSsplash10-003s-9700000000-77e67d7b1a161e6ecfa6
Mass Spectrum (Electron Ionization)MSsplash10-015a-9200000000-a193c27810bedf93c498
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-0f89-0190000000-2be9501b1d4a9fcbd1c0
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-0uk9-0790000000-7f6e35a591f977bc488e
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-0udi-0090000000-c56edc2bbf9d6752aec5
MS/MS Spectrum - FAB-EBEB (JMS-HX/HX 110A, JEOL) , NegativeLC-MS/MSsplash10-004i-0090000000-baf4579e26c6b393d391
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-004i-0090000000-815c1682b2c59ba96f10
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-004i-0090000000-3406b2b2d5756807e1cd
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-004i-0090000000-2fb4975278fa4d118f43
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-0a6r-9380000000-37f833673c248405c8ef
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-0a4i-9200000000-7d34ed5900a17ffe3f9b
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 30V, NegativeLC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 30V, NegativeLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-004i-0090000000-761ea81b8bab078f93e1
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-004i-0090000000-3cc0508fd4dfd47921e5
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-004i-0090000000-48fd5edde8cf27cedd72
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-004i-2090000000-16b3fa5138f83873bd6f
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-00di-9000000000-46fdee94b5a787f1b81f
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-0090000000-815c1682b2c59ba96f10
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-0090000000-3406b2b2d5756807e1cd
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-0090000000-2fb4975278fa4d118f43
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a6r-9390000000-37f833673c248405c8ef
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-9200000000-7d34ed5900a17ffe3f9b
LC-MS/MS Spectrum - LC-ESI-IT , negativeLC-MS/MSsplash10-03di-0090000000-82b408190d4a59b1e1cb
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-004i-0090000000-adbf36f0a17c33ac33f8
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-004i-0090000000-2747c83af78732eb6e16
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-004i-0090000000-a0415b1cb63b4562b40e
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03dj-3960000000-2340777df62fe1184a7a
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-000t-6910000000-b12a8635b08a2205a4ba
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-015a-9600000000-770f56ddeb6a5596548f
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0159-9400000000-8e7d06bf03376e9d8239
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0159-9200000000-d23bb8f6f68d036e6746
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014l-9100000000-91836022b4397ea67489
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Drug created at June 21, 2018 16:16 / Updated at September 28, 2021 21:54