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Bromfenac

Bromfenac structure

Bromfenac 

structure
  • CAS No:

    91714-94-2

  • Formula:

    C15H12BrNO3

  • Chemical Name:

    Bromfenac

  • Synonyms:

    Benzeneacetic acid,2-amino-3-(4-bromobenzoyl)-;2-Amino-3-(4-bromobenzoyl)benzeneacetic acid;Bromfenac;AHR 10282;[2-Amino-3-(p-bromobenzoyl)phenyl]acetic acid;Xibrom;Bromday;2-(2-Amino-3-(4-bromobenzoyl)phenyl)acetic acid;Broxinac

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Description

ChEBI: 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 withdraw from the US market in 1998, following concerns over off-label abuse and hepatic failure.


Solid


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 It was withdrawn from the US market in 1998, following concerns over off-label abuse and hepatic failure.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, a substituted aniline, an aromatic amino acid and an organobromine compound. It derives from an amfenac. It is a conjugate acid of a bromfenac(1-).|Bromfenac is a nonsteroidal anti-inflammatory drug (NSAID) for ophthalmic use. Ophthalmic NSAIDs are becoming a cornerstone for the management of ocular pain and inflammation. Their well-characterized anti-inflammatory activity, analgesic property, and established safety record have also made NSAIDs an important tool to optimize surgical outcomes.|Bromfenac is a Nonsteroidal Anti-inflammatory Drug. The mechanism of action of bromfenac is as a Cyclooxygenase Inhibitor.|Bromfenac is a nonsteroidal anti-inflammatory drug (NSAID) with analgesic and anti-inflammatory activities. Upon ophthalmic administration, bromfenac binds to and inhibits the activity of cyclooxygenase II (COX II), an enzyme which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins (PG). By inhibiting PG formation, bromfenac is able to inhibit PG-induced inflammation, thereby preventing vasodilation, leukocytosis, disruption of the blood-aqueous humor barrier, an increase in vascular permeability and an increase in intraocular pressure (IOP).

Bromfenac Basic Attributes

334.16

334.16

864P0921DW

DTXSID7040655

C65271

S01BC11|S - Sensory organs

2922509090

Characteristics

80.4

3.3

Solid

1.6±0.1 g/cm3

-129ºC

562.2°C at 760 mmHg

293.8±30.1 °C

1.663

1.26e-02 g/L

Safety Information

|Danger|H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]|P201, P202, P260, P264, P270, P273, P281, P301+P310, P308+P313, P309+P311, P314, P321, P330, P391, P405, and P501|Aggregated GHS information provided by 2 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

For the treatment of postoperative inflammation in patients who have undergone cataract extraction.|FDA Label|Treatment of postoperative ocular inflammation following cataract extraction in adults.

Bromfenac ophthalmic solution is a sterile, topical, nonsteroidal anti-inflammatory drug (NSAID) for ophthalmic use.

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. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)

The plasma concentration of bromfenac following ocular administration in humans is unknown.

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.

AHR-10282

Bromfenac Use and Manufacturing

Uses

Analgesic. Bromfenac (Xibrom, ISTA Pharmaceuticals, Irvine, USA; Bronuck, Senju Pharmaceutical, Osaka, Japan) is indicated for the treatment of postoperative inflammation and the reduction of ocular pain in patients after undergoing cataract extraction. For this task, one drop of Xibrom may be applied to the affected eye twice daily beginning 24 hours after cataract surgery and continuing for the first 2 weeks of the postoperative period. The clinical safety and efficacy of bromfenac have been extensively studied in diverse comparative investigations, including the treatment of external or anterior ocular inflammatory diseases, allergic conjunctivitis, scleritis, and postoperative inflammation.The results of two phase III multicenter, randomized double-masked placebo-controlled clinical trials showed that bromfenac ophthalmic solution 0.09% was effective in the rapid resolution of ocular pain after cataract surgery, and there was a statistically significant difference between the bromfenac and placebo groups demonstrated in these phase III clinical trials.

Human drugs -> Yellox -> EMA Drug Category|Ophthalmologicals -> Human pharmacotherapeutic group|Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:334.16
XLogP3:3.3
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:4
Exact Mass:333.00006
Monoisotopic Mass:333.00006
Topological Polar Surface Area:80.4
Heavy Atom Count:20
Complexity:366
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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