Basic information
- CAS
91714-94-2- Standard SMILES
Nc1c(CC(=O)O)cccc1C(=O)c1ccc(Br)cc1- InChIKey
ZBPLOVFIXSTCRZ-UHFFFAOYSA-N- Molecular formula
- C15H12BrNO3
- Average molar mass
- 334.16 g/mol
- Monoisotopic mass
- 333.00006
Overview
Bromfenac is amfenac in which the the hydrogen at the 4 position of the benzoyl group is substituted by bromine. It is used for the management of ocular pain and treatment of postoperative inflammation in patients who have undergone cataract extraction. It was withdrawn from the US market in 1998, following concerns over off-label abuse and hepatic failure. It has a role as a non-steroidal anti-inflammatory drug and a non-narcotic analgesic. It is a member of benzophenones, an aromatic amino acid, an organobromine compound and a substituted aniline. It is functionally related to an amfenac. It is a conjugate acid of a bromfenac(1-).
Names & identifiers
- Preferred name
- Bromfenac
- IUPAC
- 2-[2-amino-3-(4-bromobenzoyl)phenyl]acetic acid
- English name
- Bromfenac sodium
- Molecular formula
- C15H12BrNO3
- Molecular weight
- 334.16
Names & synonyms
Bromfenac91714-94-22-(2-Amino-3-(4-bromobenzoyl)phenyl)acetic acidBromfenaco2-[2-amino-3-(4-bromobenzoyl)phenyl]acetic acidBromfenacum2-Amino-3-(4-bromobenzoyl)benzeneacetic acidISV-303Benzeneacetic acid, 2-amino-3-(4-bromobenzoyl)-DTXSID7040655CHEBI:240107864P0921DW
Show more names
YelloxAHR 10282AKOS 91023BromofenacUnii-864p0921dw
[2-Amino-3-(4-bromo-benzoyl)-phenyl]-acetic acid2-{2-amino-3-[(4-bromophenyl)carbonyl]phenyl}acetic acid(2-Amino-3-(4-bromo-benzoyl)-phenyl)-acetic acid2-(2-amino-3-((4-bromophenyl)carbonyl)phenyl)acetic acidRefChem:56957DTXCID5020655S01BC11Xibrom
Database identifiers
- CAS
91714-94-2- PubChem CID
- 60726
- DTXSID
DTXSID7040655- ChEMBL
CHEMBL1077- ChEBI
CHEBI:240107
Properties
Computed structural properties
- XLogP
- 3.3
- Topological polar surface area
- 80.4 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 4
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 366
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LogP3.4
Solubility1.26e-02 g/L
Human Drugs
Breast Feeding; Lactation; Milk, Human; Analgesic Agents; Anti-inflammatory Agents, Nonsteroidal
EMA approved medicines: Human medicine
Physical DescriptionSolid
Physicochemical properties
- Boiling point
- 562.2 · 562.2±50.0 °C(Predicted)
- Density
- 1.565 · 1.565±0.06 g/cm3(Predicted)
- storage temp.
- 2 · under inert gas (nitrogen or Argon) at 2–8 °C
- pka
- 4.07 · 4.07±0.10(Predicted)
- InChI
- 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)
- InChIKey
- ZBPLOVFIXSTCRZ-UHFFFAOYSA-N
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
Drug Induced Liver Injury
Benchmark Dataset for the Liver Toxicity Knowledge Base (LTKB)
bromfenac
Duract
NSAIDs
Not Applicable is only true for the label characterization, but not for the DILI severity
most-DILI-concern
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Pharmacology
ATC Code
S - Sensory organs
QS - Sensory organs
PharmacodynamicsBromfenac ophthalmic solution is a sterile, topical, nonsteroidal anti-inflammatory drug (NSAID) for ophthalmic use.
Mechanism of Action
The mechanism of its action is thought to be due to its ability to block prostaglandin synthesis by inhibiting cyclooxygenase 1 and 2. Prostaglandins have been shown in many animal models to be mediators of certain kinds of intraocular inflammation. In studies performed in animal eyes, prostaglandins have been shown to produce disruption of the blood-aqueous humor barrier, vasodilation, increased vascular permeability, leukocytosis, and increased intraocular pressure.
FDA Pharmacological Classification
864P0921DW
BROMFENAC
Mechanisms of Action [MoA] - Cyclooxygenase Inhibitors
Chemical Structure [CS] - Anti-Inflammatory Agents, Non-Steroidal
Established Pharmacologic Class [EPC] - Nonsteroidal Anti-inflammatory Drug
Bromfenac is a Nonsteroidal Anti-inflammatory Drug. The mechanism of action of bromfenac is as a Cyclooxygenase Inhibitor.
MeSH Pharmacological Classification
Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects.
Absorption, Distribution and ExcretionThe plasma concentration of bromfenac following ocular administration in humans is unknown.
Cellular LocationsCytoplasm
Related reactions
4 records
Compound notes
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