nepafenac Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
anti-inflammatory agents, ibufenac derivatives 1899 78281-72-8

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • nepafenac
  • nevanac
penetrates the cornea and is converted by ocular tissue hydrolases to amfenac, a nonsteroidal anti-inflammatory drug, amfenac is thought to inhibit the action of prostaglandin H synthase (cyclooxygenase), an enzyme required for prostaglandin production
  • Molecular weight: 254.29
  • Formula: C15H14N2O2
  • CLOGP: 1.38
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 2
  • TPSA: 86.18
  • ALOGS: -4.11
  • ROTB: 4

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

None

ADMET properties:

PropertyValueReference
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.17 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD

Approvals:

DateAgencyCompanyOrphan
Aug. 19, 2005 FDA ALCON PHARMS LTD

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Ulcerative keratitis 173.78 140.43 25 251 547 2357262

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event

Pharmacologic Action:

SourceCodeDescription
ATC S01BC10 SENSORY ORGANS
OPHTHALMOLOGICALS
ANTIINFLAMMATORY AGENTS
Antiinflammatory agents, non-steroids
FDA MoA N0000000160 Cyclooxygenase Inhibitors
FDA Chemical/Ingredient N0000175721 Nonsteroidal Anti-inflammatory Compounds
FDA EPC N0000175722 Nonsteroidal Anti-inflammatory Drug
MeSH PA D000700 Analgesics
MeSH PA D018712 Analgesics, Non-Narcotic
CHEBI has role CHEBI:50266 prodrug
CHEBI has role CHEBI:35475 non-steroidal anti-inflammatory drug
CHEBI has role CHEBI:35481 non-narcotic analgesic
MeSH PA D000893 Anti-Inflammatory Agents
MeSH PA D000894 Anti-Inflammatory Agents, Non-Steroidal
MeSH PA D018501 Antirheumatic Agents
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D018689 Sensory System Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Post-Op Ocular Inflammation indication
Postoperative Ocular Pain indication
Keratitis contraindication 5888003 DOID:4677
Tear film insufficiency contraindication 46152009
Corneal erosion contraindication 50792001
Blood coagulation disorder contraindication 64779008 DOID:1247
Rheumatoid arthritis contraindication 69896004 DOID:7148
Diabetes mellitus contraindication 73211009 DOID:9351
Perforation of cornea contraindication 74895004
Corneal ulcer contraindication 91514001 DOID:8463
Corneal epithelial degeneration contraindication 231929005
Impaired wound healing contraindication 271618001
Decreased Corneal Sensitivity contraindication
Ocular Bleeding contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 13.34 acidic
pKa2 2.94 Basic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
0.1% NEVANAC NOVARTIS N021862 Aug. 19, 2005 RX SUSPENSION/DROPS OPHTHALMIC 7834059 Jan. 31, 2027 METHOD OF TREATING OCULAR INFLAMMATION

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Prostaglandin G/H synthase 2 Enzyme INHIBITOR IC50 6.82 WOMBAT-PK KEGG DRUG
Prostaglandin G/H synthase 1 Enzyme INHIBITOR IC50 6.60 WOMBAT-PK KEGG DRUG
Cyclooxygenase Enzyme IC50 6.70 CHEMBL
Cyclooxygenase Enzyme IC50 7 CHEMBL

External reference:

IDSource
4024931 VUID
N0000171607 NUI
C0961209 UMLSCUI
D05143 KEGG_DRUG
0J9L7J6V8C UNII
7685 INN_ID
51579-82-9 SECONDARY_CAS_RN
419829002 SNOMEDCT_US
298665 RXNORM
20485 MMSL
419460005 SNOMEDCT_US
4024931 VANDF
010980 NDDF
196661 MMSL
CHEBI:75922 CHEBI
CHEMBL25146 ChEMBL_ID
CHEMBL1021 ChEMBL_ID
C414203 MESH_SUPPLEMENTAL_RECORD_UI
DB06802 DRUGBANK_ID
151075 PUBCHEM_CID
7564 IUPHAR_LIGAND_ID
C014285 MESH_SUPPLEMENTAL_RECORD_UI

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
NEVANAC HUMAN PRESCRIPTION DRUG LABEL 1 0065-0002 SUSPENSION/ DROPS 1 mg OPHTHALMIC NDA 14 sections
ILEVRO HUMAN PRESCRIPTION DRUG LABEL 1 0065-1750 SUSPENSION 3 mg OPHTHALMIC NDA 14 sections
Nevanac HUMAN PRESCRIPTION DRUG LABEL 1 54868-6302 SUSPENSION 1 mg OPHTHALMIC NDA 14 sections