Nepafenac (CED0008053)

Record Information
Version1.0
Creation Date2016-05-22 06:36:05 UTC
Update Date2026-08-19 09:47:43 UTC
Accession NumberCHEM019876
Identification
Common NameNepafenac
ClassSmall Molecule
Description
Nepafenac is an organic compound with the formula C15H14N2O2 and an average molecular weight of 254.28 g/mol. Nepafenac belongs to the benzophenones, a subclass of benzene and substituted derivatives within the organic compounds. It is recorded as being found in or released from two sources: healthcare, pharmaceuticals & veterinary products (specifically antiinflammatory agents) and household cleaning & consumer products (specifically non electric simulated smoking devices). The recorded exposure route for this compound is ophthalmic. At the molecular level, nepafenac interacts with two recorded protein targets. It acts as an inhibitor of Prostaglandin G/H synthase 1 (PTGS1) and Prostaglandin G/H synthase 2 (PTGS2).
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Amino-3-benzoylbenzeneacetamideChEBI
AHR 9434ChEBI
AHR-9434ChEBI
AL 6515ChEBI
AL-6515ChEBI
NepafenacoChEBI
NepafenacumChEBI
NevanacChEBI
Amfenac amideHMDB
Chemical FormulaC15H14N2O2
Average Molecular Mass254.284 g/mol
Monoisotopic Mass254.106 g/mol
CAS Registry Number78281-72-8
IUPAC Name2-(2-amino-3-benzoylphenyl)acetamide
Traditional Namenepafenac
SMILESNC(=O)CC1=CC=CC(C(=O)C2=CC=CC=C2)=C1N
InChI IdentifierInChI=1S/C15H14N2O2/c16-13(18)9-11-7-4-8-12(14(11)17)15(19)10-5-2-1-3-6-10/h1-8H,9,17H2,(H2,16,18)
InChI KeyQEFAQIPZVLVERP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzophenones. These are organic compounds containing a ketone attached to two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzophenones
Direct ParentBenzophenones
Alternative Parents
Substituents
  • Benzophenone
  • Aryl-phenylketone
  • Diphenylmethane
  • Phenylacetamide
  • Benzoyl
  • Aniline or substituted anilines
  • Aryl ketone
  • Vinylogous amide
  • Amino acid or derivatives
  • Carboxamide group
  • Primary carboxylic acid amide
  • Ketone
  • Carboxylic acid derivative
  • Amine
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.02 g/LALOGPS
logP1.53ALOGPS
logP2.08ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)15.82ChemAxon
pKa (Strongest Basic)1.83ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area86.18 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity74.46 m³·mol⁻¹ChemAxon
Polarizability26.63 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-03di-1490000000-472a61bcbe3904de6ac4Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03dr-1490000000-433d63cd52e5b86417daNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4r-0190000000-b6c2bf9435ad635d30bfNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4r-0890000000-1c148620fd1183334640Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-2900000000-de52c273376f27e1aec8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0090000000-1410eafe17e767b3cc39Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0w2c-3290000000-3604d63c0fc47c406eccNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9200000000-0ccf405a700b155ba243Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0090000000-3060c6f1d3f25782b5f6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-06si-0970000000-521792df462056dc0554Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-9400000000-b292dc56c56def4c3cc1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ik9-0090000000-db943419dc26289ab4feNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0090000000-409cecc16290d2050d37Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9540000000-5ae94d44ecaaabdcabf9Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
853.0Log mg/kg[480:1500]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
396Antiinflammatory agentsHealthcare, pharmaceuticals & veterinary productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
604Pest AttractantsAgriculture & land managementNot Available
Pathways
4 pathways
Nepafenac Action Pathway
Nepafenac Action Pathway
Nepafenac NSAID Action Pathway
Nepafenac NSAID Action Pathway
Nepafenac Drug Metabolism
Nepafenac Drug Metabolism
Nepafenac Drug Metabolism Action Pathway
Nepafenac Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Protective antigen structureClick to view 3D structureProtective antigenP13423Bacillus anthracisPredicted (SEA)24.5225
Prostaglandin G/H synthase 2 structureClick to view 3D structureProstaglandin G/H synthase 2P35354HumansPredicted (SEA)177.652
Prostaglandin G/H synthase 1 structureClick to view 3D structureProstaglandin G/H synthase 1P23219HumansPredicted (SEA)108.6
Nicotinate phosphoribosyltransferase structureClick to view 3D structureNicotinate phosphoribosyltransferaseQ6XQN6HumansPredicted (SEA)7.47353
Click to view 3D structureAminodeoxyfutalosine synthaseQ5SK48Thermus thermophilus (strain HB8 / ATCC 27634 / DSM 579)Predicted (SEA)9.03051
Click to view 3D structureProstaglandin G/H synthase 1P05979Ovis ariesPredicted (SEA)99.2578
Click to view 3D structureProstaglandin G/H synthase 2P79208Ovis ariesPredicted (SEA)40.5594
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)447.633
Click to view 3D structureCocaine esteraseO00748HumansPredicted (SEA)14.3243
Tryptase beta-2 structureClick to view 3D structureTryptase beta-2P20231HumansPredicted (SEA)18.2167
Coagulation factor XI structureClick to view 3D structureCoagulation factor XIP03951HumansPredicted (SEA)220.625
Prothrombin structureClick to view 3D structureProthrombinP00734HumansPredicted (SEA)641.867
Coagulation factor X structureClick to view 3D structureCoagulation factor XP00742HumansPredicted (SEA)554.909
D(2) dopamine receptor structureClick to view 3D structureD(2) dopamine receptorP14416HumansPredicted (SEA)1450.1
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)802.003
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)662.497
Interleukin-8 structureClick to view 3D structureInterleukin-8P10145HumansPredicted (SEA)17.1268
Epidermal growth factor receptor structureClick to view 3D structureEpidermal growth factor receptorP00533HumansPredicted (SEA)2250.47
Histone deacetylase 1 structureClick to view 3D structureHistone deacetylase 1Q13547HumansPredicted (SEA)1340.33
Urokinase-type plasminogen activator structureClick to view 3D structureUrokinase-type plasminogen activatorP00749HumansPredicted (SEA)350.01
Click to view 3D structureLuciferin 4-monooxygenaseP08659Photinus pyralisPredicted (SEA)285.395
Liver carboxylesterase 1 structureClick to view 3D structureLiver carboxylesterase 1P23141HumansPredicted (SEA)61.1895
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)659.539
Click to view 3D structureSortase AQ8CM62Streptococcus mutansPredicted (SEA)26.313
Protein mono-ADP-ribosyltransferase PARP10 structureClick to view 3D structureProtein mono-ADP-ribosyltransferase PARP10Q53GL7HumansPredicted (SEA)92.407
Concentrations
Not Available
External Links
DrugBank IDDB06802
HMDB IDHMDB0015678
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNepafenac
Chemspider ID133160
ChEBI ID75922
PubChem Compound ID151075
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10850857
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=10850858
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=16466612
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=16529348
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=17060788
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=20674259
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21926942
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=21932014
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=22927737
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=23715071
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=23928675
12. Gamache DA, Graff G, Brady MT, Spellman JM, Yanni JM: Nepafenac, a unique nonsteroidal prodrug with potential utility in the treatment of trauma-induced ocular inflammation: I. Assessment of anti-inflammatory efficacy. Inflammation. 2000 Aug;24(4):357-70.
13. Ke TL, Graff G, Spellman JM, Yanni JM: Nepafenac, a unique nonsteroidal prodrug with potential utility in the treatment of trauma-induced ocular inflammation: II. In vitro bioactivation and permeation of external ocular barriers. Inflammation. 2000 Aug;24(4):371-84.
14. Lane SS, Modi SS, Lehmann RP, Holland EJ: Nepafenac ophthalmic suspension 0.1% for the prevention and treatment of ocular inflammation associated with cataract surgery. J Cataract Refract Surg. 2007 Jan;33(1):53-8.
15. Walters T, Raizman M, Ernest P, Gayton J, Lehmann R: In vivo pharmacokinetics and in vitro pharmacodynamics of nepafenac, amfenac, ketorolac, and bromfenac. J Cataract Refract Surg. 2007 Sep;33(9):1539-45.
16. Bucci FA Jr, Waterbury LD: Re: Pharmacokinetics and pharmacodynamics of nepafenac, amfenac, ketorolac, and bromfenac. J Cataract Refract Surg. 2008 Aug;34(8):1226; author reply 1226-7. doi: 10.1016/j.jcrs.2008.05.019.
17. Summary Basis of Decision (SBD): NEVANAC.: http://www.hc-sc.gc.ca/dhp-mps/prodpharma/sbd-smd/drug-med/sbd_smd_2008_nevanac_114004-eng.php