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	121.34	36.69	24	1211	2309	50601580
Toxic anterior segment syndrome	111.72	36.69	21	1214	1544	50602345
Visual acuity reduced	98.35	36.69	31	1204	20108	50583781
Corneal epithelium defect	97.82	36.69	15	1220	320	50603569
Product container issue	94.56	36.69	18	1217	1414	50602475
Product quality issue	89.13	36.69	32	1203	30826	50573063
Corneal opacity	87.79	36.69	15	1220	639	50603250
Eye pain	84.03	36.69	30	1205	28419	50575470
Corneal oedema	82.67	36.69	16	1219	1371	50602518
Liquid product physical issue	78.45	36.69	14	1221	769	50603120
Cataract	75.85	36.69	32	1203	47268	50556621
Anterior chamber inflammation	69.78	36.69	11	1224	282	50603607
Product physical consistency issue	64.54	36.69	11	1224	461	50603428
Cystoid macular oedema	64.35	36.69	13	1222	1386	50602503
Product packaging quantity issue	55.45	36.69	11	1224	1069	50602820
Foreign body sensation in eyes	55.35	36.69	12	1223	1799	50602090
Corneal infiltrates	55.07	36.69	8	1227	116	50603773
Vision blurred	54.72	36.69	30	1205	78617	50525272
Ocular hyperaemia	54.62	36.69	20	1215	20272	50583617
Product delivery mechanism issue	54.54	36.69	9	1226	309	50603580
Intraocular pressure increased	51.23	36.69	14	1221	5502	50598387
Corneal scar	48.82	36.69	7	1228	92	50603797
Eye irritation	46.51	36.69	17	1218	17123	50586766
Corneal disorder	45.37	36.69	10	1225	1616	50602273
Endophthalmitis	44.57	36.69	11	1224	2905	50600984
Punctate keratitis	43.06	36.69	8	1227	549	50603340
Product packaging issue	38.66	36.69	8	1227	959	50602930
Eye discharge	38.42	36.69	11	1224	5112	50598777

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	95.29	41.40	19	957	1404	29572147
Toxic anterior segment syndrome	88.74	41.40	17	959	1019	29572532
Corneal oedema	87.08	41.40	17	959	1125	29572426
Endophthalmitis	61.30	41.40	15	961	2833	29570718
Intraocular pressure increased	58.17	41.40	16	960	4773	29568778
Corneal opacity	53.88	41.40	10	966	503	29573048
Cystoid macular oedema	51.74	41.40	10	966	626	29572925
Visual impairment	50.80	41.40	23	953	29685	29543866
Ocular hyperaemia	44.03	41.40	15	961	9112	29564439
Cataract	43.61	41.40	19	957	22359	29551192

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	174.46	34.76	34	1526	3063	64494109
Corneal oedema	158.50	34.76	30	1530	2313	64494859
Toxic anterior segment syndrome	157.30	34.76	30	1530	2409	64494763
Endophthalmitis	112.15	34.76	26	1534	5339	64491833
Intraocular pressure increased	110.71	34.76	28	1532	8274	64488898
Visual acuity reduced	109.22	34.76	36	1524	27105	64470067
Cataract	90.30	34.76	37	1523	51225	64445947
Corneal epithelium defect	80.43	34.76	14	1546	671	64496501
Corneal opacity	76.54	34.76	14	1546	891	64496281
Cystoid macular oedema	67.13	34.76	14	1546	1760	64495412
Eye pain	66.65	34.76	26	1534	31599	64465573
Corneal scar	63.27	34.76	10	1550	263	64496909
Vision blurred	56.37	34.76	32	1528	90284	64406888
Ocular hyperaemia	56.33	34.76	21	1539	22543	64474629
Hypopyon	56.07	34.76	11	1549	1018	64496154
Corneal disorder	54.10	34.76	12	1548	2015	64495157
Visual impairment	53.77	34.76	29	1531	74048	64423124
Punctate keratitis	45.63	34.76	9	1551	856	64496316
Foreign body sensation in eyes	44.73	34.76	10	1550	1739	64495433
Iris atrophy	40.02	34.76	6	1554	110	64497062
Anterior chamber cell	40	34.76	8	1552	816	64496356
Eye irritation	36.81	34.76	14	1546	15842	64481330
Photophobia	35.63	34.76	14	1546	17279	64479893
Corneal perforation	35.37	34.76	7	1553	677	64496495

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	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:

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
7565	IUPHAR_LIGAND_ID
7685	INN_ID
51579-82-9	SECONDARY_CAS_RN
0J9L7J6V8C	UNII
2136	PUBCHEM_CID
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
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
ILEVRO	HUMAN PRESCRIPTION DRUG LABEL	1	0078-0743	SUSPENSION/ DROPS	3 mg	OPHTHALMIC	NDA	22 sections
Nevanac	HUMAN PRESCRIPTION DRUG LABEL	1	54868-6302	SUSPENSION	1 mg	OPHTHALMIC	NDA	22 sections