Benoxaprofen

Identification

Name
Benoxaprofen
Accession Number
DB04812
Type
Small Molecule
Groups
Withdrawn
Description

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.

Structure
Thumb
Synonyms
  • (1)-2-(4-Chlorophenyl)benzoxazole-5-propionic acid
  • 2-(2-(4-Chlorophenyl)-1,3-benzoxazol-5-yl)propanoic acid
  • 2-(4-Chlorophenyl)-alpha-methyl-5-benzoxazoleacetic acid
  • 2-[2-(4-Chlorophenyl)-1,3-benzoxazol-5-yl]propanoic acid
  • Benoxaprofene
  • Benoxaprofeno
  • Benoxaprofenum
  • DL-benoxaprofen
International/Other Brands
Coxigon (Lilly) / Inflamid (Lilly) / Opren (Lilly) / Oraflex (Lilly)
Categories
UNII
17SZX404IM
CAS number
51234-28-7
Weight
Average: 301.724
Monoisotopic: 301.050570962
Chemical Formula
C16H12ClNO3
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

Pharmacology

Indication
Not Available
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
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of bleeding and hemorrhage can be increased when Benoxaprofen is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding and hemorrhage can be increased when Benoxaprofen is combined with (S)-Warfarin.
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic AcidThe risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Benoxaprofen is combined with 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid.
4-hydroxycoumarinThe risk or severity of bleeding and hemorrhage can be increased when Benoxaprofen is combined with 4-hydroxycoumarin.
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.
AcarboseBenoxaprofen may decrease the excretion rate of Acarbose which could result in a higher serum level.
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.
Food Interactions
Not Available

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
External Links
PubChem Compound
39941
PubChem Substance
46508496
ChemSpider
36518
ChEBI
76114
ChEMBL
CHEMBL340978
Therapeutic Targets Database
DCL000338
PharmGKB
PA166049178
Wikipedia
Benoxaprofen
ATC Codes
M01AE06 — Benoxaprofen

Clinical Trials

Clinical Trials
Not Available

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

Taxonomy

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
Phenyl-1,3-oxazole / Benzoxazole / Chlorobenzene / Halobenzene / Aryl chloride / Aryl halide / Monocyclic benzene moiety / Benzenoid / Heteroaromatic compound / Carboxylic acid derivative
show 15 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
1,3-benzoxazoles, monocarboxylic acid, monochlorobenzenes (CHEBI:76114)

Drug created on September 11, 2007 14:01 / Updated on November 02, 2018 06:05