nepafenac ๐Ÿถ Veterinary Use | 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 ยตM/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 121.43 34.13 24 1304 2686 63485008
Toxic anterior segment syndrome 112.35 34.13 21 1307 1750 63485944
Visual acuity reduced 100.57 34.13 31 1297 21795 63465899
Corneal epithelium defect 99.38 34.13 15 1313 337 63487357
Corneal opacity 95.10 34.13 16 1312 727 63486967
Product container issue 93.29 34.13 18 1310 1775 63485919
Product quality issue 93.02 34.13 33 1295 35832 63451862
Corneal oedema 90.23 34.13 17 1311 1476 63486218
Eye pain 83.42 34.13 30 1298 33824 63453870
Cataract 81.49 34.13 34 1294 57019 63430675
Liquid product physical issue 81.23 34.13 15 1313 1167 63486527
Anterior chamber inflammation 70.26 34.13 11 1317 316 63487378
Cystoid macular oedema 64.81 34.13 13 1315 1562 63486132
Product physical consistency issue 61.92 34.13 11 1317 688 63487006
Intraocular pressure increased 56.77 34.13 15 1313 6063 63481631
Corneal infiltrates 55.22 34.13 8 1320 134 63487560
Foreign body sensation in eyes 54.68 34.13 12 1316 2222 63485472
Vision blurred 54.65 34.13 30 1298 91894 63395800
Product packaging quantity issue 54.62 34.13 11 1317 1348 63486346
Product delivery mechanism issue 54.52 34.13 9 1319 363 63487331
Uveitis 54.27 34.13 17 1311 12536 63475158
Ocular hyperaemia 53.44 34.13 20 1308 25124 63462570
Corneal scar 48.98 34.13 7 1321 106 63487588
Corneal disorder 45.82 34.13 10 1318 1804 63485890
Eye irritation 44.95 34.13 17 1311 21954 63465740
Endophthalmitis 43.97 34.13 11 1317 3581 63484113
Punctate keratitis 43.42 34.13 8 1320 613 63487081
Treatment failure 41.90 34.13 34 1294 199009 63288685
Eye discharge 38.26 34.13 11 1317 6052 63481642
Product packaging issue 38.12 34.13 8 1320 1198 63486496

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
Ulcerative keratitis 91.93 36.54 19 1113 1710 34954089
Corneal oedema 90.54 36.54 18 1114 1333 34954466
Toxic anterior segment syndrome 86.99 36.54 17 1115 1152 34954647
Intraocular pressure increased 61.16 36.54 17 1115 5366 34950433
Endophthalmitis 58.46 36.54 15 1117 3493 34952306
Visual impairment 53.19 36.54 25 1107 35777 34920022
Corneal opacity 52.74 36.54 10 1122 576 34955223
Ocular hyperaemia 52.39 36.54 18 1114 11434 34944365
Cystoid macular oedema 50.75 36.54 10 1122 705 34955094
Vision blurred 44.44 36.54 24 1108 45939 34909860
Cataract 44.22 36.54 20 1112 26166 34929633
Glaucoma 44.21 36.54 14 1118 6898 34948901
Haemolytic uraemic syndrome 44.14 36.54 11 1121 2275 34953524
Foreign body sensation in eyes 39.77 36.54 8 1124 626 34955173
Eye pain 38.61 36.54 15 1117 13447 34942352
Product quality issue 38.54 36.54 16 1116 17019 34938780
Anterior chamber cell 37.53 36.54 7 1125 368 34955431
Hypopyon 37.15 36.54 7 1125 389 34955410
Corneal disorder 36.68 36.54 8 1124 926 34954873

FDA Adverse Event Reporting System (Geriatric)

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 172.02 32.85 34 1704 3655 79738995
Corneal oedema 158.24 32.85 30 1708 2590 79740060
Toxic anterior segment syndrome 156.64 32.85 30 1708 2734 79739916
Intraocular pressure increased 115.68 32.85 29 1709 9176 79733474
Endophthalmitis 110.15 32.85 26 1712 6402 79736248
Visual acuity reduced 109.95 32.85 36 1702 29433 79713217
Cataract 90.46 32.85 38 1700 62082 79680568
Corneal epithelium defect 81.20 32.85 14 1724 705 79741945
Corneal opacity 76.31 32.85 14 1724 1006 79741644
Cystoid macular oedema 67.05 32.85 14 1724 1966 79740684
Eye pain 64.90 32.85 26 1712 37552 79705098
Corneal scar 63.10 32.85 10 1728 298 79742352
Ocular hyperaemia 61.07 32.85 23 1715 28183 79714467
Vision blurred 60.06 32.85 34 1704 105864 79636786
Visual impairment 56.09 32.85 31 1707 92100 79650550
Hypopyon 56.06 32.85 11 1727 1131 79741519
Corneal disorder 53.88 32.85 12 1726 2279 79740371
Punctate keratitis 45.38 32.85 9 1729 977 79741673
Foreign body sensation in eyes 43.68 32.85 10 1728 2147 79740503
Haemolytic uraemic syndrome 41.18 32.85 11 1727 4438 79738212
Anterior chamber cell 39.70 32.85 8 1730 941 79741709
Glaucoma 38.75 32.85 15 1723 19746 79722904
Iris atrophy 38.64 32.85 6 1732 156 79742494
Anterior chamber inflammation 37.32 32.85 7 1731 567 79742083
Corneal perforation 35.33 32.85 7 1731 756 79741894
Corneal infiltrates 34.75 32.85 6 1732 304 79742346
Photophobia 34.71 32.85 14 1724 20514 79722136
Eye irritation 34.61 32.85 14 1724 20667 79721983
Embolic pneumonia 34.23 32.85 5 1733 85 79742565

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC S01BC10 SENSORY ORGANS
OPHTHALMOLOGICALS
ANTIINFLAMMATORY AGENTS
Antiinflammatory agents, non-steroids
FDA CS M0001335 Anti-Inflammatory Agents, Non-Steroidal
FDA MoA N0000000160 Cyclooxygenase Inhibitors
MeSH PA D000700 Analgesics
MeSH PA D018712 Analgesics, Non-Narcotic
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
FDA EPC N0000175722 Nonsteroidal Anti-inflammatory Drug
CHEBI has role CHEBI:35475 non-steroidal anti-inflammatory agent
CHEBI has role CHEBI:35493 anti-pyretic
CHEBI has role CHEBI:50629 COX-2 inhibitor
CHEBI has role CHEBI:50630 COX-1 inhibitor
CHEBI has role CHEBI:50266 Prodrugs

Drug Use | Suggest Off label Use Form| |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




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

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 HARROW EYE 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
D05143 KEGG_DRUG
4024931 VANDF
C0961209 UMLSCUI
CHEBI:75922 CHEBI
CHEBI:75915 CHEBI
CHEMBL1021 ChEMBL_ID
DB06802 DRUGBANK_ID
C414203 MESH_SUPPLEMENTAL_RECORD_UI
151075 PUBCHEM_CID
7564 IUPHAR_LIGAND_ID
C014285 MESH_SUPPLEMENTAL_RECORD_UI
7685 INN_ID
0J9L7J6V8C UNII
DB15911 DRUGBANK_ID
298665 RXNORM
196661 MMSL
20485 MMSL
71034 MMSL
010980 NDDF
419460005 SNOMEDCT_US
419829002 SNOMEDCT_US
C0051572 UMLSCUI
CHEMBL25146 ChEMBL_ID
4363 INN_ID
51579-82-9 SECONDARY_CAS_RN
2136 PUBCHEM_CID
7565 IUPHAR_LIGAND_ID
28O5C1J38A UNII

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
NEVANAC HUMAN PRESCRIPTION DRUG LABEL 1 0065-0002 SUSPENSION/ DROPS 1 mg OPHTHALMIC NDA 23 sections
NEVANAC HUMAN PRESCRIPTION DRUG LABEL 1 0065-0002 SUSPENSION/ DROPS 1 mg OPHTHALMIC NDA 23 sections
ILEVRO HUMAN PRESCRIPTION DRUG LABEL 1 0078-0743 SUSPENSION/ DROPS 3 mg OPHTHALMIC NDA 22 sections
ILEVRO HUMAN PRESCRIPTION DRUG LABEL 1 0078-0743 SUSPENSION/ DROPS 3 mg OPHTHALMIC NDA 22 sections
ILEVRO HUMAN PRESCRIPTION DRUG LABEL 1 0078-0743 SUSPENSION/ DROPS 3 mg OPHTHALMIC NDA 22 sections
NEVANAC HUMAN PRESCRIPTION DRUG LABEL 1 0078-0778 SUSPENSION/ DROPS 1 mg OPHTHALMIC NDA 23 sections
NEVANAC HUMAN PRESCRIPTION DRUG LABEL 1 0078-0778 SUSPENSION/ DROPS 1 mg OPHTHALMIC NDA 23 sections
Nevanac HUMAN PRESCRIPTION DRUG LABEL 1 54868-6302 SUSPENSION 1 mg OPHTHALMIC NDA 22 sections