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
Structure for AR-9281 (DB06345)
- 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.
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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.
Target Actions Organism UBifunctional epoxide hydrolase 2 Not Available Humans - 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
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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
- 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]
- External Links
- ChemSpider
- 10173264
- BindingDB
- 100423
- ChEMBL
- CHEMBL436774
- ZINC
- ZINC000036330562
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 2 Completed Treatment Hypertension / Impaired Glucose Tolerance 1
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
Property Value Source Water Solubility 0.148 mg/mL ALOGPS logP 1.84 ALOGPS logP 0.43 Chemaxon logS -3.3 ALOGPS pKa (Strongest Acidic) 15.08 Chemaxon pKa (Strongest Basic) 0.33 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 61.44 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 88.28 m3·mol-1 Chemaxon Polarizability 36.24 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-00di-0209000000-d89515a4c54f651bf4fd Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-1922000000-8af1f4f445512228c8f7 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-000i-0902000000-2ef550faa1e56a8ce824 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-009b-6901000000-be4732213e39bed1a77f Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-000i-0900000000-cc4ead3e65dcc0ee8353 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0udl-8940000000-5ac726db74e7ff92da10 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Not Available
Targets
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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
- 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 at March 19, 2008 16:25 / Updated at June 12, 2020 16:52