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

Stem definition	Drug id	CAS RN
anti-inflammatory agents, ibufenac derivatives	401	91714-94-2

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: yellox bromfenac sodium sesquihydrate prolensa bromfenac xibrom bromfenac sodium	Bromfenac is a nonsteroidal anti-inflammatory drug (NSAID). The mechanism of its action is thought to be due to its ability to block prostaglandin synthesis by inhibiting cyclooxygenase 1 and 2, prostaglandins are mediators of certain kinds of intraocular inflammation. Molecular weight: 334.17 Formula: C15H12BrNO3 CLOGP: 3.28 LIPINSKI: 0 HAC: 4 HDO: 2 TPSA: 80.39 ALOGS: -4.42 ROTB: 4 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

yellox
bromfenac sodium sesquihydrate
prolensa
bromfenac
xibrom
bromfenac sodium

Bromfenac is a nonsteroidal anti-inflammatory drug (NSAID). The mechanism of its action is thought to be due to its ability to block prostaglandin synthesis by inhibiting cyclooxygenase 1 and 2, prostaglandins are mediators of certain kinds of intraocular inflammation.

Molecular weight: 334.17
Formula: C15H12BrNO3
CLOGP: 3.28
LIPINSKI: 0
HAC: 4
HDO: 2
TPSA: 80.39
ALOGS: -4.42
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)	4.28 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BDDCS (Biopharmaceutical Drug Disposition Classification System)	2	Hosey CM, Chan R, Benet LZ
BA (Bioavailability)	67 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution)	0.11 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	1.30 mL/min/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.00 %	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	2.60 hours	Lombardo F, Berellini G, Obach RS

Approvals:

Date	Agency	Company	Orphan
March 24, 2005	FDA	BAUSCH AND LOMB INC

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
Corneal oedema	113.67	39.28	20	982	1402	56289663
Endophthalmitis	91.97	39.28	19	983	3124	56287941
Hypopyon	84.27	39.28	14	988	695	56290370
Eye pain	79.08	39.28	27	975	30820	56260245
Toxic anterior segment syndrome	78.39	39.28	15	987	1667	56289398
Cataract	76.13	39.28	30	972	51217	56239848
Eye irritation	74.61	39.28	23	979	19005	56272060
Product packaging quantity issue	57.64	39.28	11	991	1203	56289862
Corneal opacity	50.35	39.28	9	993	687	56290378
Corneal infiltrates	48.18	39.28	7	995	142	56290923
Corneal disorder	47.73	39.28	10	992	1752	56289313
Visual impairment	44.27	39.28	23	979	74179	56216886
Ocular hyperaemia	43.89	39.28	16	986	21963	56269102
Anterior chamber cell	39.42	39.28	7	995	514	56290551
Corneal perforation	39.30	39.28	7	995	523	56290542

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
Cataract	91.80	45.84	28	510	23779	31673027
Hypopyon	63.88	45.84	10	528	358	31696448
Toxic anterior segment syndrome	59.05	45.84	11	527	1114	31695692
Eye pain	58.26	45.84	17	521	12287	31684519
Corneal oedema	51.74	45.84	10	528	1231	31695575
Endophthalmitis	51.50	45.84	12	526	3604	31693202
Ulcerative keratitis	49.23	45.84	10	528	1586	31695220

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
Corneal oedema	155.62	37.72	28	1133	2432	70924851
Endophthalmitis	146.62	37.72	31	1130	6224	70921059
Hypopyon	141.86	37.72	23	1138	1072	70926211
Toxic anterior segment syndrome	134.42	37.72	25	1136	2605	70924678
Eye pain	115.10	37.72	36	1125	34066	70893217
Cataract	86.83	37.72	33	1128	55612	70871671
Corneal opacity	80.82	37.72	14	1147	972	70926311
Corneal disorder	69.74	37.72	14	1147	2165	70925118
Ulcerative keratitis	69.43	37.72	15	1146	3312	70923971
Ocular hyperaemia	66.59	37.72	22	1139	24617	70902666
Corneal infiltrates	65.75	37.72	10	1151	305	70926978
Anterior chamber cell	61.78	37.72	11	1150	894	70926389
Eye irritation	52.55	37.72	17	1144	17771	70909512
Visual acuity reduced	52.42	37.72	19	1142	27911	70899372
Lacrimation increased	50.68	37.72	17	1144	19882	70907401
Corneal perforation	50.67	37.72	9	1152	721	70926562
Visual impairment	47.26	37.72	24	1137	80226	70847057
Vision blurred	43.46	37.72	24	1137	94960	70832323
Punctate keratitis	42.24	37.72	8	1153	912	70926371
Cystoid macular oedema	41.83	37.72	9	1152	1943	70925340
Intraocular pressure increased	41.14	37.72	12	1149	8889	70918394
Metamorphopsia	40.37	37.72	8	1153	1155	70926128

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

Source	Code	Description
ATC	S01BC11	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

Drug Use | Suggest Off label Use Form| |View source of the data|

Disease	Relation	SNOMED_ID	DOID
Pain	indication	22253000
Postoperative Ocular Pain	indication
Post-Op Ocular Inflammation	indication
Rheumatoid arthritis	contraindication	69896004	DOID:7148
Diabetes mellitus	contraindication	73211009	DOID:9351
Red eye	contraindication	75705005
Epithelial Keratopathy	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	4.32	acidic
pKa2	3.17	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
EQ 0.07% ACID	PROLENSA	BAUSCH AND LOMB	N203168	April 5, 2013	RX	SOLUTION/DROPS	OPHTHALMIC	8927606	Jan. 16, 2024	METHOD OF TREATING OCULAR INFLAMMATION
EQ 0.07% ACID	PROLENSA	BAUSCH AND LOMB	N203168	April 5, 2013	RX	SOLUTION/DROPS	OPHTHALMIC	8927606	Jan. 16, 2024	METHOD OF TREATMENT TO ALLEVIATE INFLAMMATION OF THE EYE
EQ 0.07% ACID	PROLENSA	BAUSCH AND LOMB	N203168	April 5, 2013	RX	SOLUTION/DROPS	OPHTHALMIC	9561277	Jan. 16, 2024	TREATMENT OF POSTOPERATIVE INFLAMMATION AND REDUCTION OF OCULAR PAIN IN PATIENTS WHO HAVE UNDERGONE CATARACT SURGERY
EQ 0.075% ACID	BROMSITE	SUN PHARM	N206911	April 8, 2016	RX	SOLUTION/DROPS	OPHTHALMIC	8778999	Aug. 7, 2029	TREATMENT OF POSTOPERATIVE INFLAMMATION AND PREVENTION OF OCULAR PAIN IN PATIENTS UNDERGOING CATARACT SURGERY
EQ 0.07% ACID	PROLENSA	BAUSCH AND LOMB	N203168	April 5, 2013	RX	SOLUTION/DROPS	OPHTHALMIC	9517220	Nov. 11, 2033	TREATMENT OF POSTOPERATIVE INFLAMMATION AND REDUCTION OF OCULAR PAIN IN PATIENTS WHO HAVE UNDERGONE CATARACT SURGERY

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	8.40	WOMBAT-PK	CHEMBL
Prostaglandin G/H synthase 1	Enzyme	P23219	PGH1_HUMAN	INHIBITOR	IC50	8.29	WOMBAT-PK	CHEMBL
Cyclooxygenase	Enzyme		PGH1_BOVIN PGH2_BOVIN		IC50	7.10	CHEMBL

External reference:

ID	Source
D07541	KEGG_DRUG
120638-55-3	SECONDARY_CAS_RN
1375918	RXNORM
4021048	VANDF
4024075	VANDF
C0054094	UMLSCUI
CHEBI:240107	CHEBI
27R	PDB_CHEM_ID
CHEMBL1077	ChEMBL_ID
CHEMBL751	ChEMBL_ID
DB00963	DRUGBANK_ID
C053083	MESH_SUPPLEMENTAL_RECORD_UI
60726	PUBCHEM_CID
7131	IUPHAR_LIGAND_ID
5892	INN_ID
864P0921DW	UNII
181436	MMSL
200626	MMSL
31652	MMSL
34500	MMSL
35934	MMSL
4299	MMSL
67379	MMSL
d04150	MMSL
006757	NDDF
006758	NDDF
108520008	SNOMEDCT_US
108521007	SNOMEDCT_US
417155005	SNOMEDCT_US
725788000	SNOMEDCT_US

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Prolensa	HUMAN PRESCRIPTION DRUG LABEL	1	24208-602	SOLUTION/ DROPS	0.70 mg	OPHTHALMIC	NDA	22 sections
Prolensa	HUMAN PRESCRIPTION DRUG LABEL	1	24208-602	SOLUTION/ DROPS	0.70 mg	OPHTHALMIC	NDA	22 sections
BROMSITE0.075%	Human Prescription Drug Label	1	49708-754	SOLUTION/ DROPS	0.76 mg	OPHTHALMIC	NDA	23 sections
bromfenac	HUMAN PRESCRIPTION DRUG LABEL	1	50383-249	SOLUTION/ DROPS	1.04 mg	OPHTHALMIC	ANDA	25 sections
bromfenac	HUMAN PRESCRIPTION DRUG LABEL	1	50383-249	SOLUTION/ DROPS	1.04 mg	OPHTHALMIC	ANDA	25 sections
Bromday	HUMAN PRESCRIPTION DRUG LABEL	1	50436-6301	SOLUTION/ DROPS	0.90 mg	OPHTHALMIC	NDA	22 sections
Bromday	HUMAN PRESCRIPTION DRUG LABEL	1	54868-6301	SOLUTION/ DROPS	0.90 mg	OPHTHALMIC	NDA	22 sections
Bromfenac	HUMAN PRESCRIPTION DRUG LABEL	1	54868-6343	SOLUTION/ DROPS	1.04 mg	OPHTHALMIC	ANDA	23 sections
Bromfenac Ophthalmic Solution 0.09%	Human Prescription Drug Label	1	62332-508	SOLUTION/ DROPS	1.04 mg	OPHTHALMIC	ANDA	22 sections
Bromfenac Ophthalmic Solution 0.09%	Human Prescription Drug Label	1	62332-508	SOLUTION/ DROPS	1.04 mg	OPHTHALMIC	ANDA	22 sections
Bromfenac	Human Prescription Drug Label	1	65862-789	SOLUTION/ DROPS	0.90 mg	OPHTHALMIC	ANDA	22 sections
BROMFENAC	Human Prescription Drug Label	1	68083-313	SOLUTION/ DROPS	0.90 mg	OPHTHALMIC	ANDA	22 sections
Pred-Gati-Brom	HUMAN PRESCRIPTION DRUG LABEL	3	70261-504	SUSPENSION/ DROPS	0.75 mg	OPHTHALMIC	unapproved drug other	2 sections
Pred-Brom	HUMAN PRESCRIPTION DRUG LABEL	2	70261-505	SUSPENSION/ DROPS	0.75 mg	OPHTHALMIC	unapproved drug other	2 sections
Pred-Brom	HUMAN PRESCRIPTION DRUG LABEL	2	71384-505	SUSPENSION/ DROPS	0.75 mg	OPHTHALMIC	unapproved drug other	2 sections
Pred Phos - Brom	HUMAN PRESCRIPTION DRUG LABEL	2	71384-552	SOLUTION/ DROPS	0.75 mg	OPHTHALMIC	unapproved drug other	2 sections
BROMFENAC	HUMAN PRESCRIPTION DRUG LABEL	1	72266-142	SOLUTION/ DROPS	0.90 mg	OPHTHALMIC	ANDA	22 sections