bromfenac 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 ┬ÁM/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 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 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 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:

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
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)

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

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)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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

External reference:

IDSource
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:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
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