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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2020-02-26 21:42:02 UTC
HMDB IDHMDB0015678
Secondary Accession Numbers
  • HMDB15678
Metabolite Identification
Common NameNepafenac
DescriptionNepafenac is only found in individuals that have used or taken this drug. It is a non-steroidal anti-inflammatory prodrug (NSAID) usually sold as a prescription eye drop. It is used to treat pain and inflammation associated with cataract surgery.After penetrating the cornea as a prodrug, nepafenac undergoes rapid bioactivation to amfenac, which is a potent NSAID that uniformly inhibits the COX1 and COX2 activity.
Structure
Data?1582753322
Synonyms
ValueSource
2-Amino-3-benzoylbenzeneacetamideChEBI
AHR 9434ChEBI
AHR-9434ChEBI
AL 6515ChEBI
AL-6515ChEBI
NepafenacoChEBI
NepafenacumChEBI
NevanacChEBI
Amfenac amideHMDB
Chemical FormulaC15H14N2O2
Average Molecular Weight254.2839
Monoisotopic Molecular Weight254.105527702
IUPAC Name2-(2-amino-3-benzoylphenyl)acetamide
Traditional Namenepafenac
CAS Registry Number78281-72-8
SMILES
NC(=O)CC1=CC=CC(C(=O)C2=CC=CC=C2)=C1N
InChI Identifier
InChI=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
Ontology
Disposition

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-1490000000-472a61bcbe3904de6ac4Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03dr-1490000000-433d63cd52e5b86417daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0190000000-b6c2bf9435ad635d30bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-0890000000-1c148620fd1183334640Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-2900000000-de52c273376f27e1aec8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-1410eafe17e767b3cc39Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0w2c-3290000000-3604d63c0fc47c406eccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9200000000-0ccf405a700b155ba243Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06802 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06802 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB06802
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID133160
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNepafenac
METLIN IDNot Available
PubChem Compound151075
PDB IDNot Available
ChEBI ID75922
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:10850857 ]
  2. 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. [PubMed:10850858 ]
  3. 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. [PubMed:17189793 ]
  4. 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. [PubMed:17720067 ]
  5. 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. [PubMed:18655957 ]
  6. Summary Basis of Decision (SBD): NEVANAC. [Link]

Enzymes

General function:
Involved in peroxidase activity
Specific function:
Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:
PTGS2
Uniprot ID:
P35354
Molecular weight:
68995.625
References
  1. 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. [PubMed:10850857 ]
General function:
Involved in peroxidase activity
Specific function:
May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular weight:
68685.82
References
  1. 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. [PubMed:10850857 ]