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 113.67 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 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 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 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 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:

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
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:

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 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