CAPRIC ACID

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C10H20O2
Molecular Weight	172.2646
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCCCCCCC(O)=O

InChI

InChIKey=GHVNFZFCNZKVNT-UHFFFAOYSA-N

InChI=1S/C10H20O2/c1-2-3-4-5-6-7-8-9-10(11)12/h2-9H2,1H3,(H,11,12)

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23177536 | https://www.ncbi.nlm.nih.gov/pubmed/26912516 | https://www.ncbi.nlm.nih.gov/pubmed/27080638

Capric acid (decanoic acid) is a medium-chain fatty acid found in saturated fats (cow butter, and plant oils like coconut oil). Capric acid is a major constituent of the MCT ketogenic diet, providing about 40% of the medium chain fat within the diet. The acid is discussed to have positive effect on seizure control through direct AMPA receptor inhibition and on mitochondrial diseases through the binding to PPARgamma. It readily crosses the blood-brain barrier, probably by a combination of diffusion and saturable carrier-mediated transport via a medium-chain fatty acid transporter.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Glutamate receptor ionotropic AMPA 41 Target ID: CHEMBL2096670 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26608744	Antagonist 2778		0.43 mM [IC50]
Peroxisome proliferator-activated receptor gamma 111 Target ID: P37231\|\|\|Q15179 Gene ID: 5468.0 Gene Symbol: PPARG Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/27080638	Modulator 828		41.7 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Inherited metabolic diseases 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27080638	Primary		Basic research	Unknown Approved Use Unknown
Seizure 4 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26608744	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Subjective response to antipsychotic treatment and compliance in schizophrenia. A naturalistic study comparing olanzapine, risperidone and haloperidol (EFESO Study).	2001	11835695
Evaluation of insulin permeability and effects of absorption enhancers on its permeability by an in vitro pulmonary epithelial system using Xenopus pulmonary membrane.	2001 Apr	11305600
[New data on composition of esssential oil from inflorescence of everlasting (Helichrysum arenarium(L.) Moench.)].	2001 Aug	11862667
Biosynthesis and structural characterization of medium-chain-length poly(3-hydroxyalkanoates) produced by Pseudomonas aeruginosa from fatty acids.	2001 Aug 20	11518582
Biosynthesis of acaterin: coupling of C(5) unit with octanoate.	2001 Aug 24	11511235
Increased incidence of dyskinesias and other behavioral effects of re-exposure to neuroleptic treatment in social colonies of Cebus apella monkeys.	2001 Jan	11271400
Decreased choline acetyltransferase immunoreactivity in discrete striatal subregions following chronic haloperidol in rats.	2001 Jan	11071709
Significance of substrate hydrophobicity for recognition by an oligopeptide transporter (PEPT1).	2001 Jul-Aug	11459451
Estimation of absorption enhancement by medium-chain fatty acids in rat large intestine.	2001 Mar-Apr	11758652
Computer-aided control of water activity for lipase-catalyzed esterification in solvent-free systems.	2001 Mar-Apr	11312702
D2 but not D3 receptors are elevated after 9 or 11 months chronic haloperidol treatment: influence of withdrawal period.	2001 May	11252025
A fluorogenic reagent, 4-mercapto-7-methylthio-2,1,3-benzoxadiazole for carboxylic acids, designed by prediction of the fluorescence intensity.	2001 May 15	11393836
Clinical outcome following neuroleptic discontinuation in patients with remitted recent-onset schizophrenia.	2001 Nov	11691689
Chemical characterization of lipid A from some marine proteobacteria.	2001 Sep	11703190
Effect of chronic treatment with haloperidol on vasopressin release and behavioral changes by osmotic stimulation of the supraoptic nucleus.	2001 Sep 21	11669458
Kinetic analysis of hydroxylation of saturated fatty acids by recombinant P450foxy produced by an Escherichia coli expression system.	2002 Apr	11985584
Penetration of engineered antibody fragments into the eye.	2002 Apr	11982592
Saturated triglycerides and fatty acids activate neutrophils depending on carbon chain-length.	2002 Apr	11952815
A multidose study of haloperidol decanoate in the maintenance treatment of schizophrenia.	2002 Apr	11925292
Antioxidant and cyclooxygenase activities of fatty acids found in food.	2002 Apr 10	11929276
Detection of fast light-activated H+ release and M intermediate formation from proteorhodopsin.	2002 Apr 9	11943070
Identification of bacteria in drinking and purified water during the monitoring of a typical water purification system.	2002 Aug 15	12182763
Ranking the toxicity of fatty acids on Jurkat and Raji cells by flow cytometric analysis.	2002 Dec	12423658
Enhancement of paracellular transport of heparin disaccharide across Caco-2 cell monolayers.	2002 Feb	11885699
Palmitate-induced cardiac apoptosis is mediated through CPT-1 but not influenced by glucose and insulin.	2002 Feb	11788422
Self-assembled vesicles of monocarboxylic acids and alcohols: conditions for stability and for the encapsulation of biopolymers.	2002 Feb 10	11825583
Hydroxylation of fatty acids by microsomal and reconstituted cytochrome P450 2B1.	2002 Feb 13	11852103
The enhancing effect of nasal absorption of FITC-dextran 4,400 by beta-sitosterol beta-D-glucoside in rabbits.	2002 Feb 19	11853926
Nasal glucagon delivery using microcrystalline cellulose in healthy volunteers.	2002 Feb 21	11897411
Preparation and catalytic performance of lipases encapsulated in sol-gel materials.	2002 Jan	11866115
Fluphenazine plasma level monitoring for patients receiving fluphenazine decanoate.	2002 Jan 1	11728835
Comparison of effects of khat extract and amphetamine on motor behaviors in mice.	2002 Jun	12020929
Evidence in favor of a facilitated transport system for FA uptake in cultured L6 cells.	2002 Mar	11942478
Tardive dyskinesia model in the common marmoset.	2002 Mar	11921124
Augmented increase in tight junction permeability by luminal stimuli in the non-inflamed ileum of Crohn's disease.	2002 Mar	11839706
Purification and characterization of a novel cholesterol esterase from Pseudomonas aeruginosa, with its application to cleaning lipid-stained contact lenses.	2002 Nov	12506971
In vitro evaluation of the release of albuterol sulfate from polymer gels: effect of fatty acids on drug transport across biological membranes.	2002 Nov	12476868
Acyl CoA profiles of transgenic plants that accumulate medium-chain fatty acids indicate inefficient storage lipid synthesis in developing oilseeds.	2002 Nov	12445123
The effect of age on the pharmacological management of ambulatory patients treated with depot neuroleptic medications for schizophrenia and related psychotic disorders.	2002 Nov	12404650
Effect of sodium caprate on the intestinal absorption of two modified antisense oligonucleotides in pigs.	2002 Nov	12393140
[Deterioration of schizoaffective disorder due to an interaction between haloperidol and carbamazepine].	2002 Oct 12	12404911
Solid-phase microextraction in combination with GC/MS for quantification of the major volatile free fatty acids in ewe cheese.	2002 Oct 15	12403571
Metabolic engineering of Escherichia coli for the production of medium-chain-length polyhydroxyalkanoates rich in specific monomers.	2002 Sep 10	12351234
Gastric emptying in rats following administration of a range of different fats measured as acetaminophen concentration in plasma.	2003	12743464
Research on psychological testing supervision using the Holloway (1995) method: a critique of DeCato (2002).	2003 Feb	12674272
The relationship between dopamine D2 receptor occupancy and the vacuous chewing movement syndrome in rats.	2003 Jan	12417967
The effect of conjugated linoleic acid and medium-chain fatty acids on transepithelial calcium transport in human intestinal-like Caco-2 cells.	2003 May	12720584
Fatty acids as an energy source for the operation of axoplasmic transport.	2003 May 16	12711076
Triacylglycerols determine the unusual storage physiology of Cuphea seed.	2003 Sep	12743824
Synthesis of monocaprin catalyzed by lipase.	2003 Spring	12721413

Patents

Sample Use Guides

In Vivo Use Guide

The oral minimal dose is 1723 mg/kg (animal model).

Route of Administration: Oral

In Vitro Use Guide

In a seizure model, rat cortex-hippocampus slices were incubated with 100 uM and 1 mM of capric acid. The fatty acid was found to reduce the frequency of epileptiform discharges at these conentrations.

Name

Type

Language

CAPRIC ACID

Official Name

English

N-CAPRIC ACID [MI]

Common Name

English

PRIFAC-2906

Code

English

DECANOIC ACID [FCC]

Common Name

English

CAPRIC ACID [INCI]

Common Name

English

DECANOIC ACID

Systematic Name

English

DECANOIC ACID [FHFI]

Common Name

English

N-DECANOIC ACID

Common Name

English

1-NONANECARBOXYLIC ACID

Systematic Name

English

N-CAPRIC ACID

Common Name

English

PALMAC-99-10

Code

English

NSC-5025

Code

English

N-Capric acid [WHO-DD]

Common Name

English

CAPRIC ACID (CONSTITUENT OF SAW PALMETTO) [DSC]

Common Name

English

DECANOIC ACID [HSDB]

Common Name

English

FEMA NO. 2364

Code

English

Classification Tree Code System Code

CFR

21 CFR 172.860