NAV

Fenoxaprop-ethyl

Identification

Generic Name
Fenoxaprop-ethyl
DrugBank Accession Number
DB05252
Background

Fenoxaprop-ethyl (organic nitrate combined with L-arginine), is an oral proprietary nitrate therapeutic shown to induce coronary vasodilation while overcoming the significant problem of drug tolerance. Fenoxaprop-ethyl has been investigated to treat chronic angina, the chest pain that occurs from inadequate blood flow to the coronary arteries around the heart.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 361.776
Monoisotopic: 361.071700334
Chemical Formula
C18H16ClNO5
Synonyms
  • Fenoxaprop ethyl
External IDs
  • HOE 33171
  • HOE-A 25-01

Pharmacology

Indication

Chronic angina and Coronary Artery Disease

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action

Fenoxaprop-ethyl is a proprietary combination of nitrate and L-arginine that provides the beneficial cardiovascular effects of nitrates. Combining L-arginine with organic nitrates prevents the endothelial cell's depletion of L-arginine and the associated problem of nitrate tolerance. By eliminating nitrate tolerance, Fenoxaprop-ethyl allows patients to receive the continuous, 24-hour benefit of a potent nitrate product, thus sustaining the desired vasodilation effect.

TargetActionsOrganism
UNitric oxide synthase, inducibleNot 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
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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 2-phenoxypropionic acid esters. These are aromatic compounds hat contain a phenol ether attached to the C2-atom of a phenylpropionic acid ester.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
2-phenoxypropionic acid esters
Direct Parent
2-phenoxypropionic acid esters
Alternative Parents
Phenoxyacetic acid derivatives / Diarylethers / Benzoxazoles / Phenoxy compounds / Phenol ethers / Alkyl aryl ethers / Aryl chlorides / Oxazoles / Heteroaromatic compounds / Carboxylic acid esters
show 9 more
Substituents
2-phenoxypropionic acid ester / Alkyl aryl ether / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Azole / Benzoxazole / Carbonyl group / Carboxylic acid derivative
show 20 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
aromatic ether (CHEBI:5008)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
7U20WEM458
CAS number
66441-23-4
InChI Key
PQKBPHSEKWERTG-UHFFFAOYSA-N
InChI
InChI=1S/C18H16ClNO5/c1-3-22-17(21)11(2)23-13-5-7-14(8-6-13)24-18-20-15-9-4-12(19)10-16(15)25-18/h4-11H,3H2,1-2H3
IUPAC Name
ethyl 2-{4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy}propanoate
SMILES
CCOC(=O)C(C)OC1=CC=C(OC2=NC3=C(O2)C=C(Cl)C=C3)C=C1

References

General References
Not Available
KEGG Compound
C11024
PubChem Compound
47938
PubChem Substance
175426962
ChemSpider
43609
ChEBI
5008
ChEMBL
CHEMBL37932

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility0.0273 mg/mLALOGPS
logP4.69ALOGPS
logP4.5Chemaxon
logS-4.1ALOGPS
pKa (Strongest Basic)-2.7Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area70.79 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity89.8 m3·mol-1Chemaxon
Polarizability36.68 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9769
Caco-2 permeable-0.5126
P-glycoprotein substrateNon-substrate0.7053
P-glycoprotein inhibitor INon-inhibitor0.8633
P-glycoprotein inhibitor IINon-inhibitor0.5277
Renal organic cation transporterNon-inhibitor0.8806
CYP450 2C9 substrateNon-substrate0.8137
CYP450 2D6 substrateNon-substrate0.6952
CYP450 3A4 substrateSubstrate0.6476
CYP450 1A2 substrateInhibitor0.8903
CYP450 2C9 inhibitorNon-inhibitor0.5234
CYP450 2D6 inhibitorNon-inhibitor0.8759
CYP450 2C19 inhibitorInhibitor0.5851
CYP450 3A4 inhibitorNon-inhibitor0.633
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9045
Ames testNon AMES toxic0.5402
CarcinogenicityNon-carcinogens0.8986
BiodegradationNot ready biodegradable0.9962
Rat acute toxicity2.2173 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9753
hERG inhibition (predictor II)Non-inhibitor0.8118
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
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
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

Targets

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Details1. Nitric oxide synthase, inducible
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Tetrahydrobiopterin binding
Specific Function
Produces nitric oxide (NO) which is a messenger molecule with diverse functions throughout the body. In macrophages, NO mediates tumoricidal and bactericidal actions. Also has nitrosylase activity ...
Gene Name
NOS2
Uniprot ID
P35228
Uniprot Name
Nitric oxide synthase, inducible
Molecular Weight
131116.3 Da

Drug created at November 18, 2007 18:09 / Updated at June 12, 2020 16:52