bromfenac 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	116.99	38.22	21	825	1625	46683591
Endophthalmitis	85.10	38.22	18	828	3260	46681956
Hypopyon	82.16	38.22	14	832	797	46684419
Cataract	79.21	38.22	30	816	45385	46639831
Product packaging quantity issue	58.11	38.22	11	835	1133	46684083
Eye pain	54.26	38.22	20	826	27920	46657296
Eye irritation	52.04	38.22	17	829	16597	46668619
Toxic anterior segment syndrome	51.25	38.22	11	835	2126	46683090
Ulcerative keratitis	50.48	38.22	11	835	2282	46682934
Corneal infiltrates	47.05	38.22	7	839	165	46685051
Corneal disorder	42.16	38.22	9	837	1694	46683522
Treatment failure	41.71	38.22	24	822	93063	46592153
Visual acuity reduced	39.87	38.22	15	831	22098	46663118
Corneal perforation	39.50	38.22	7	839	499	46684717
Anterior chamber cell	38.61	38.22	7	839	568	46684648

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	89.85	43.93	26	406	21809	29930237
Ulcerative keratitis	58.55	43.93	11	421	1378	29950668
Eye pain	57.17	43.93	16	416	11773	29940273
Endophthalmitis	53.94	43.93	12	420	3468	29948578
Hypopyon	48.58	43.93	8	424	467	29951579

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
FDA EPC	N0000175722	Nonsteroidal Anti-inflammatory Drug
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
CHEBI has role	CHEBI:35475	non-steroidal anti-inflammatory drugs

Drug Use (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

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)

None

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 1	Enzyme	P23219	PGH1_HUMAN	INHIBITOR	IC50	8.29	WOMBAT-PK	CHEMBL
Prostaglandin G/H synthase 2	Enzyme	P35354	PGH2_HUMAN	INHIBITOR	IC50	8.40	WOMBAT-PK	CHEMBL
Cyclooxygenase	Enzyme		PGH1_BOVIN PGH2_BOVIN		IC50	7.10	CHEMBL

External reference:

ID	Source
864P0921DW	UNII
D07541	KEGG_DRUG
120638-55-3	SECONDARY_CAS_RN
4021048	VANDF
4024075	VANDF
C0054094	UMLSCUI
CHEBI:240107	CHEBI
27R	PDB_CHEM_ID
CHEMBL1077	ChEMBL_ID
CHEMBL751	ChEMBL_ID
DB00963	DRUGBANK_ID
5892	INN_ID
C053083	MESH_SUPPLEMENTAL_RECORD_UI
60726	PUBCHEM_CID
7131	IUPHAR_LIGAND_ID
1375918	RXNORM
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
BromSite0.075%	HUMAN PRESCRIPTION DRUG LABEL	1	49708-754	SOLUTION/ DROPS	0.76 mg	OPHTHALMIC	NDA	24 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
BROMFENULLC	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
BROMFENULLC	HUMAN PRESCRIPTION DRUG LABEL	1	72266-142	SOLUTION/ DROPS	0.90 mg	OPHTHALMIC	ANDA	22 sections