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

Stem definition	Drug id	CAS RN
anti-inflammatory agents, ibufenac derivatives	1899	78281-72-8

Description:

Molecule	Description
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

Molecule

Description

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:

Property	Value	Reference
MRTD (Maximum Recommended Therapeutic Daily Dose)	0.17 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD

Approvals:

Date	Agency	Company	Orphan
Aug. 19, 2005	FDA	ALCON PHARMS LTD

FDA Adverse Event Reporting System (Female)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients 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 term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients 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 term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients 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:

Source	Code	Description
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|

Disease	Relation	SNOMED_ID	DOID
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

🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	13.34	acidic
pKa2	2.94	Basic

Orange Book patent data (new drug applications)

Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent 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:

Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Prostaglandin G/H synthase 2	Enzyme	P35354	PGH2_HUMAN	INHIBITOR	IC50	6.82	WOMBAT-PK	KEGG DRUG
Prostaglandin G/H synthase 1	Enzyme	P23219	PGH1_HUMAN	INHIBITOR	IC50	6.60	WOMBAT-PK	KEGG DRUG
Cyclooxygenase	Enzyme		PGH1_BOVIN PGH2_BOVIN		IC50	6.70	CHEMBL
Cyclooxygenase	Enzyme		PGH2_RAT PGH1_RAT		IC50	7	CHEMBL

External reference:

ID	Source
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:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
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