AR-9281

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

Identification

Generic Name
AR-9281
DrugBank Accession Number
DB06345
Background

AR-9281 inhibits soluble epoxide hydrolase.

Type
Small Molecule
Groups
Investigational
Structure
Thumb
Weight
Average: 319.449
Monoisotopic: 319.225977186
Chemical Formula
C18H29N3O2
Synonyms
  • APAU
External IDs
  • AR 9281
  • AR-9281
  • AR9281

Pharmacology

Indication

Investigated for use/treatment in hypertension.

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action

AR9281 inhibits soluble epoxide hydrolase (s-EH), an enzyme that plays a key role in the cytochrome P450 pathway of arachidonic acid metabolism. Nuclear factor alpha B (NF-alphaB) is a transcription factor implicated in cardiac hypertrophy, and can be anti or pro apoptotic under different conditions. Epoxyeicosatrienoic acids (EETs), a product of cytochrome P450 epoxygenase enzyme action, have a variety of anti-hypertensive and anti-inflammatory effects. EETs have a vasodilatory action similar to endothelium derived hyperpolarizing factor and may inhibit NF-alphaB through a currently unknown mechanism. The enzyme s-EH catalyzes the breakdown of EETs to dihydroxyeicosatrienoic acids. AR9281's inhibition of s-EH enhances EETs anti-hypertensive and anti-inflammatory activities by preventing their breakdown by s-EH, as well as inhibiting NF-alphaB.

TargetActionsOrganism
UBifunctional epoxide hydrolase 2Not AvailableHumans
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
Medicalerrors
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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
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as n-acylpiperidines. These are compounds containing an N-acyethanolamine moiety, which is characterized by an acyl group is linked to the nitrogen atom of a piperidine.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Piperidines
Sub Class
N-acylpiperidines
Direct Parent
N-acylpiperidines
Alternative Parents
Tertiary carboxylic acid amides / Acetamides / Ureas / Azacyclic compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Acetamide / Aliphatic heteropolycyclic compound / Azacycle / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Hydrocarbon derivative / N-acyl-piperidine / Organic nitrogen compound / Organic oxide
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
4HA03Q8EZ9
CAS number
913548-29-5
InChI Key
HUDQLWBKJOMXSZ-UHFFFAOYSA-N
InChI
InChI=1S/C18H29N3O2/c1-12(22)21-4-2-16(3-5-21)19-17(23)20-18-9-13-6-14(10-18)8-15(7-13)11-18/h13-16H,2-11H2,1H3,(H2,19,20,23)
IUPAC Name
1-(1-acetylpiperidin-4-yl)-3-(adamantan-1-yl)urea
SMILES
CC(=O)N1CCC(CC1)NC(=O)NC12CC3CC(CC(C3)C1)C2

References

General References
  1. Xu D, Li N, He Y, Timofeyev V, Lu L, Tsai HJ, Kim IH, Tuteja D, Mateo RK, Singapuri A, Davis BB, Low R, Hammock BD, Chiamvimonvat N: Prevention and reversal of cardiac hypertrophy by soluble epoxide hydrolase inhibitors. Proc Natl Acad Sci U S A. 2006 Dec 5;103(49):18733-8. Epub 2006 Nov 27. [Article]
ChemSpider
10173264
BindingDB
100423
ChEMBL
CHEMBL436774
ZINC
ZINC000036330562

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentHigh Blood Pressure (Hypertension) / Impaired Glucose Tolerance1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.148 mg/mLALOGPS
logP1.84ALOGPS
logP0.43ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)15.08ChemAxon
pKa (Strongest Basic)0.33ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area61.44 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity88.28 m3·mol-1ChemAxon
Polarizability36.24 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Targets

Drugtargets
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Toxic substance binding
Specific Function
Bifunctional enzyme. The C-terminal domain has epoxide hydrolase activity and acts on epoxides (alkene oxides, oxiranes) and arene oxides. Plays a role in xenobiotic metabolism by degrading potenti...
Gene Name
EPHX2
Uniprot ID
P34913
Uniprot Name
Bifunctional epoxide hydrolase 2
Molecular Weight
62615.22 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created on March 19, 2008 16:25 / Updated on June 12, 2020 16:52