Benoxaprofen

Identification

Generic Name
Benoxaprofen
DrugBank Accession Number
DB04812
Background

The use of benoxaprofen, formerly marketed as Oraflex tablets, was associated with fatal cholestatic jaundice among other serious adverse reactions. The holder of the approved application voluntarily withdrew Oraflex tablets from the market on August 5, 1982.

Type
Small Molecule
Groups
Approved, Withdrawn
Structure
Thumb
Weight
Average: 301.724
Monoisotopic: 301.050570962
Chemical Formula
C16H12ClNO3
Synonyms
  • (±)-benoxaprofen
  • (1)-2-(4-Chlorophenyl)benzoxazole-5-propionic acid
  • 2-(4-Chlorophenyl)-alpha-methyl-5-benzoxazoleacetic acid
  • 2-(4-chlorophenyl)-α-methyl-5-benzoxazoleacetic acid
  • 2-(p-chlorophenyl)-α-methyl-5-benzoxazoleacetic acid
  • Benoxaprofen
  • Benoxaprofene
  • Benoxaprofeno
  • Benoxaprofenum
  • DL-benoxaprofen
External IDs
  • Lilly 90459

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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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.
DrugInteraction
AbacavirBenoxaprofen may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbciximabThe risk or severity of bleeding and hemorrhage can be increased when Benoxaprofen is combined with Abciximab.
AcebutololBenoxaprofen may decrease the antihypertensive activities of Acebutolol.
AceclofenacThe risk or severity of adverse effects can be increased when Benoxaprofen is combined with Aceclofenac.
AcemetacinThe risk or severity of adverse effects can be increased when Benoxaprofen is combined with Acemetacin.
AcenocoumarolThe risk or severity of bleeding and hemorrhage can be increased when Benoxaprofen is combined with Acenocoumarol.
AcetaminophenThe risk or severity of adverse effects can be increased when Acetaminophen is combined with Benoxaprofen.
AcetohexamideThe protein binding of Acetohexamide can be decreased when combined with Benoxaprofen.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Acetylsalicylic acid is combined with Benoxaprofen.
AclidiniumBenoxaprofen may decrease the excretion rate of Aclidinium which could result in a higher serum level.
Interactions
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Food Interactions
Not Available

Products

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International/Other Brands
Coxigon (Lilly) / Inflamid (Lilly) / Opren (Lilly) / Oraflex (Lilly)

Categories

ATC Codes
M01AE06 — Benoxaprofen
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenyl-1,3-oxazoles. These are aromatic heterocyclic compounds containing a 1,3-oxazole substituted at one or more positions by a phenyl group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Azoles
Sub Class
Oxazoles
Direct Parent
Phenyl-1,3-oxazoles
Alternative Parents
Benzoxazoles / Chlorobenzenes / Aryl chlorides / Heteroaromatic compounds / Oxacyclic compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds
show 4 more
Substituents
Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Benzenoid / Benzoxazole / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Chlorobenzene
show 15 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
1,3-benzoxazoles, monocarboxylic acid, monochlorobenzenes (CHEBI:76114)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
17SZX404IM
CAS number
51234-28-7
InChI Key
MITFXPHMIHQXPI-UHFFFAOYSA-N
InChI
InChI=1S/C16H12ClNO3/c1-9(16(19)20)11-4-7-14-13(8-11)18-15(21-14)10-2-5-12(17)6-3-10/h2-9H,1H3,(H,19,20)
IUPAC Name
2-[2-(4-chlorophenyl)-1,3-benzoxazol-5-yl]propanoic acid
SMILES
CC(C(O)=O)C1=CC2=C(OC(=N2)C2=CC=C(Cl)C=C2)C=C1

References

Synthesis Reference

Evans, D., Dunwell, D.W. and Hicks, A.; US. Patent 3,912, 18; October 14, 1975; assigned to Lilly Industries Ltd. Evans, D., Dunwell, D.W. and Hicks, T.A.; U.S. Patent 3,962,441; June 8, 1976; assigned to Lilly Industries, Ltd. Evans, D., Dunwell, D.W. and Hicks, T.A.; US. Patent 3,962,452; June 8, 1976; assigned to Lilly Industries, Ltd.

General References
Not Available
KEGG Drug
D03080
PubChem Compound
39941
PubChem Substance
46508496
ChemSpider
36518
BindingDB
50088388
ChEBI
76114
ChEMBL
CHEMBL340978
Therapeutic Targets Database
DCL000338
PharmGKB
PA166049178
Wikipedia
Benoxaprofen

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
PropertyValueSource
melting point (°C)196Evans, D., Dunwell, D.W. and Hicks, A.; US. Patent 3,912, 18; October 14, 1975; assigned to Lilly Industries Ltd. Evans, D., Dunwell, D.W. and Hicks, T.A.; U.S. Patent 3,962,441; June 8, 1976; assigned to Lilly Industries, Ltd. Evans, D., Dunwell, D.W. and Hicks, T.A.; US. Patent 3,962,452; June 8, 1976; assigned to Lilly Industries, Ltd.
logP3.23JACK,DB ET AL. (1988)
Predicted Properties
PropertyValueSource
Water Solubility0.0317 mg/mLALOGPS
logP4.22ALOGPS
logP4.13ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)4.66ChemAxon
pKa (Strongest Basic)0.091ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.33 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity88.51 m3·mol-1ChemAxon
Polarizability31.34 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9799
Caco-2 permeable-0.5319
P-glycoprotein substrateNon-substrate0.8015
P-glycoprotein inhibitor INon-inhibitor0.9594
P-glycoprotein inhibitor IINon-inhibitor0.8703
Renal organic cation transporterNon-inhibitor0.92
CYP450 2C9 substrateNon-substrate0.7222
CYP450 2D6 substrateNon-substrate0.7458
CYP450 3A4 substrateNon-substrate0.5062
CYP450 1A2 substrateInhibitor0.6452
CYP450 2C9 inhibitorNon-inhibitor0.8178
CYP450 2D6 inhibitorNon-inhibitor0.9669
CYP450 2C19 inhibitorNon-inhibitor0.6701
CYP450 3A4 inhibitorNon-inhibitor0.9678
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7368
Ames testNon AMES toxic0.9206
CarcinogenicityNon-carcinogens0.8368
BiodegradationNot ready biodegradable0.9684
Rat acute toxicity3.3303 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9951
hERG inhibition (predictor II)Non-inhibitor0.9003
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (8.83 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0a4i-7294000000-6fce0cace9618294c879
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

Drug created on September 11, 2007 20:01 / Updated on February 21, 2021 18:51