Bromfenac (CED0007732)

Record Information

Version

1.0

Creation Date

2016-05-25 18:23:56 UTC

Update Date

2026-08-19 09:07:29 UTC

Accession Number

CHEM022209

Identification

Common Name

Bromfenac

Class

Small Molecule

Description

Bromfenac is an organic compound with the formula C15H12BrNO3 and an average molecular weight of 334.17 g/mol. Bromfenac belongs to the benzophenones, a subclass of benzene and substituted derivatives within the organic compounds. This compound acts as an inhibitor of the protein targets Prostaglandin G/H synthase 1 (PTGS1) and Prostaglandin G/H synthase 2 (PTGS2). The substance is found in or released from three recorded sources: non-electric simulated smoking devices (household cleaning & consumer products), electrically stimulated smoking devices (electrical & electronic equipment), and antiinflammatory agents (healthcare, pharmaceuticals & veterinary products). The recorded exposure route for this compound is ophthalmic.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Amino-3-(4-bromobenzoyl)benzeneacetic acid	ChEBI
[2-Amino-3-(4-bromo-benzoyl)-phenyl]-acetic acid	ChEBI
Bromfenaco	ChEBI
Bromfenacum	ChEBI
2-Amino-3-(4-bromobenzoyl)benzeneacetate	Generator
[2-Amino-3-(4-bromo-benzoyl)-phenyl]-acetate	Generator
Bromfenac sodium	HMDB
Xibrom	HMDB
Sodium bromfenac	HMDB
Wyeth brand OF sodium bromfenac	HMDB
Duract	HMDB
ISV-303	HMDB

Chemical Formula

C₁₅H₁₂BrNO₃

Average Molecular Mass

334.165 g/mol

Monoisotopic Mass

333.000 g/mol

CAS Registry Number

91714-94-2

IUPAC Name

2-[2-amino-3-(4-bromobenzoyl)phenyl]acetic acid

Traditional Name

bromfenac

SMILES

NC1=C(CC(O)=O)C=CC=C1C(=O)C1=CC=C(Br)C=C1

InChI Identifier

InChI=1S/C15H12BrNO3/c16-11-6-4-9(5-7-11)15(20)12-3-1-2-10(14(12)17)8-13(18)19/h1-7H,8,17H2,(H,18,19)

InChI Key

ZBPLOVFIXSTCRZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzophenones. These are organic compounds containing a ketone attached to two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzophenones

Direct Parent

Benzophenones

Alternative Parents

Substituents

Benzophenone
Diphenylmethane
Aryl-phenylketone
Benzoyl
Aryl ketone
Aniline or substituted anilines
Bromobenzene
Halobenzene
Aryl bromide
Aryl halide
Vinylogous amide
Amino acid
Amino acid or derivatives
Ketone
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organohalogen compound
Organopnictogen compound
Organobromide
Organonitrogen compound
Carbonyl group
Amine
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Primary amine
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

organobromine compound (CHEBI:240107 )
benzophenones (CHEBI:240107 )
substituted aniline (CHEBI:240107 )
aromatic amino acid (CHEBI:240107 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.013 g/L	ALOGPS
logP	3	ALOGPS
logP	3.66	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	3.81	ChemAxon
pKa (Strongest Basic)	1.59	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	80.39 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	80.26 m³·mol⁻¹	ChemAxon
Polarizability	29.93 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-001i-2942000000-55d5af00fe6fa398bead	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-000i-5391000000-a985cfcf083f34c1b155	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00lr-0039000000-8bc362a4cdf601ba45d1	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0292000000-5eada8c7771779cb0353	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0540-2950000000-5f5aed8a6d28056c567a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001r-0059000000-17d7c340ec08a0adaba2	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001r-1298000000-1d237d5738d709e7bf6d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0zgi-3892000000-27126ed6eaa7f4fe957e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00lr-0029000000-f6ac38419ec90ea82b48	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-0922000000-65ab9952df50df9d5a8a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-0920000000-17efdd1a42d366c24941	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0090000000-44cbc50fb0fa3719a78c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-1190000000-61dfc1dbf6f576473d58	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-003i-4091000000-4388b82a5f2e1d637fdd	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
611.0	Log mg/kg	[340:1100]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
396	Antiinflammatory agents	Healthcare, pharmaceuticals & veterinary products	Not Available
518	Electrically Stimulated Smoking Devices	Electrical & Electronic Equipment	Not Available
559	Non Electric Simulated Smoking Devices	Household cleaning & consumer products	Not Available
604	Pest Attractants	Agriculture & land management	Not Available
617	Lip Care Products	Personal care & cosmetics	Not Available

Pathways

3 pathways

Bromfenac Action Pathway

Bromfenac NSAID Action Pathway

Bromfenac Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Interleukin-8	P10145	Humans	Predicted (SEA)	6.53933
Click to view 3D structure	Prostaglandin G/H synthase 2	P35354	Humans	Predicted (SEA)	141.919
Click to view 3D structure	Prostaglandin G/H synthase 1	P23219	Humans	Predicted (SEA)	95.0539
Click to view 3D structure	Prostaglandin G/H synthase 2	Q05769	Mus musculus	Predicted (SEA)	31.2954
Click to view 3D structure	Aldo-keto reductase family 1 member B1	P15121	Humans	Predicted (SEA)	84.7778
Click to view 3D structure	Tryptase beta-2	P20231	Humans	Predicted (SEA)	14.3243
Click to view 3D structure	Prostaglandin G/H synthase 1	P05979	Ovis aries	Predicted (SEA)	110.624
Click to view 3D structure	Chloride intracellular channel protein 1	O00299	Humans	Predicted (SEA)	7.78492
Click to view 3D structure	Coagulation factor XI	P03951	Humans	Predicted (SEA)	244.369
Click to view 3D structure	Aldo-keto reductase family 1 member B1	P07943	Rattus norvegicus	Predicted (SEA)	74.1125
Click to view 3D structure	Carboxy-terminal domain RNA polymerase II polypeptide A small phosphatase 1	Q9GZU7	Humans	Predicted (SEA)	197.971
Click to view 3D structure	Prostaglandin G/H synthase 2	P79208	Ovis aries	Predicted (SEA)	67.5731
Click to view 3D structure	Dual specificity protein phosphatase 3	P51452	Humans	Predicted (SEA)	184.191
Click to view 3D structure	Tyrosine-protein phosphatase non-receptor type 11	Q06124	Humans	Predicted (SEA)	223.116
Click to view 3D structure	Complement factor D	P00746	Humans	Predicted (SEA)	37.6012
Click to view 3D structure	Calcium/calmodulin-dependent protein kinase type II subunit alpha	P11275	Rattus norvegicus	Predicted (SEA)	2.64687
Click to view 3D structure	Protective antigen	P13423	Bacillus anthracis	Predicted (SEA)	81.1189
Click to view 3D structure	Solute carrier family 22 member 6	Q4U2R8	Humans	Predicted (SEA)	18.606
Click to view 3D structure	72 kDa type IV collagenase	P08253	Humans	Predicted (SEA)	1351.54
Click to view 3D structure	Matrix metalloproteinase-9	P14780	Humans	Predicted (SEA)	1218.89
Click to view 3D structure	Urokinase-type plasminogen activator	P00749	Humans	Predicted (SEA)	633.693
Click to view 3D structure	Epidermal growth factor receptor	P00533	Humans	Predicted (SEA)	3749.3
Click to view 3D structure	Collagenase 3	P45452	Humans	Predicted (SEA)	1197.17
Click to view 3D structure	Matrix metalloproteinase-14	P50281	Humans	Predicted (SEA)	901.027
Click to view 3D structure	Macrophage metalloelastase	P39900	Humans	Predicted (SEA)	842.406