bromfenac ๐Ÿถ Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
anti-inflammatory agents, ibufenac derivatives 401 91714-94-2

Description:

MoleculeDescription

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:

PropertyValueReference
MRTD (Maximum Recommended Therapeutic Daily Dose) 4.28 ยตM/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:

DateAgencyCompanyOrphan
March 24, 2005 FDA BAUSCH AND LOMB INC

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
Corneal oedema 113.14 37.29 20 929 1367 50602808
Endophthalmitis 92.41 37.29 19 930 2897 50601278
Hypopyon 84.36 37.29 14 935 655 50603520
Cataract 73.44 37.29 29 920 47271 50556904
Toxic anterior segment syndrome 72.48 37.29 14 935 1551 50602624
Eye irritation 71.54 37.29 22 927 17118 50587057
Eye pain 64.37 37.29 23 926 28426 50575749
Product packaging quantity issue 58.36 37.29 11 938 1069 50603106
Corneal infiltrates 49.10 37.29 7 942 117 50604058
Corneal disorder 48.01 37.29 10 939 1616 50602559
Visual impairment 44.96 37.29 23 926 68252 50535923
Ocular hyperaemia 40.61 37.29 15 934 20277 50583898
Corneal perforation 39.60 37.29 7 942 475 50603700
Anterior chamber cell 39.43 37.29 7 942 487 50603688
Corneal opacity 37.47 37.29 7 942 647 50603528

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
Cataract 82.44 48.59 25 443 22353 29551706
Ulcerative keratitis 51.09 48.59 10 458 1413 29572646
Hypopyon 50.46 48.59 8 460 334 29573725
Endophthalmitis 49.65 48.59 11 457 2837 29571222

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
Corneal oedema 149.95 38.04 27 1047 2316 64495342
Endophthalmitis 145.01 38.04 30 1044 5335 64492323
Hypopyon 128.56 38.04 21 1053 1008 64496650
Toxic anterior segment syndrome 116.75 38.04 22 1052 2417 64495241
Eye pain 88.16 38.04 29 1045 31596 64466062
Cataract 78.04 38.04 30 1044 51232 64446426
Corneal disorder 70.51 38.04 14 1060 2013 64495645
Corneal opacity 68.24 38.04 12 1062 893 64496765
Ocular hyperaemia 68.13 38.04 22 1052 22542 64475116
Corneal infiltrates 66.58 38.04 10 1064 275 64497383
Ulcerative keratitis 64.60 38.04 14 1060 3083 64494575
Anterior chamber cell 62.62 38.04 11 1063 813 64496845
Visual acuity reduced 52.65 38.04 19 1055 27122 64470536
Corneal perforation 51.10 38.04 9 1065 675 64496983
Eye irritation 50.05 38.04 16 1058 15840 64481818
Lacrimation increased 43.82 38.04 15 1059 18331 64479327
Visual impairment 42.82 38.04 22 1052 74055 64423603
Punctate keratitis 42.60 38.04 8 1066 857 64496801
Intraocular pressure increased 41.77 38.04 12 1062 8290 64489368
Vision blurred 41.45 38.04 23 1051 90293 64407365
Metamorphopsia 40.45 38.04 8 1066 1124 64496534
Eye inflammation 38.30 38.04 10 1064 4847 64492811

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
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|

DiseaseRelationSNOMED_IDDOID
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




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 4.32 acidic
pKa2 3.17 Basic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent 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:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Prostaglandin G/H synthase 2 Enzyme INHIBITOR IC50 8.40 WOMBAT-PK CHEMBL
Prostaglandin G/H synthase 1 Enzyme INHIBITOR IC50 8.29 WOMBAT-PK CHEMBL
Cyclooxygenase Enzyme IC50 7.10 CHEMBL

External reference:

IDSource
D07541 KEGG_DRUG
120638-55-3 SECONDARY_CAS_RN
1375918 RXNORM
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
4021048 VANDF
4024075 VANDF

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
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 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