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2D Structure
Also known as: 91714-94-2, 2-(2-amino-3-(4-bromobenzoyl)phenyl)acetic acid, Xibrom, Bromfenac [inn], Bromfenaco, Bromfenacum
Molecular Formula
C15H12BrNO3
Molecular Weight
334.16  g/mol
InChI Key
ZBPLOVFIXSTCRZ-UHFFFAOYSA-N
FDA UNII
864P0921DW

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 is a Nonsteroidal Anti-inflammatory Drug. The mechanism of action of bromfenac is as a Cyclooxygenase Inhibitor.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-[2-amino-3-(4-bromobenzoyl)phenyl]acetic acid
2.1.2 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)
2.1.3 InChI Key
ZBPLOVFIXSTCRZ-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC(=C(C(=C1)C(=O)C2=CC=C(C=C2)Br)N)CC(=O)O
2.2 Other Identifiers
2.2.1 UNII
864P0921DW
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Ahr-10282

2. Bromfenac Sodium

3. Duract

4. Isv-303

5. Sodium Bromfenac

6. Xibrom

2.3.2 Depositor-Supplied Synonyms

1. 91714-94-2

2. 2-(2-amino-3-(4-bromobenzoyl)phenyl)acetic Acid

3. Xibrom

4. Bromfenac [inn]

5. Bromfenaco

6. Bromfenacum

7. 2-[2-amino-3-(4-bromobenzoyl)phenyl]acetic Acid

8. Prolensa

9. 2-amino-3-(4-bromobenzoyl)benzeneacetic Acid

10. Bromday

11. Isv-303

12. [2-amino-3-(4-bromobenzoyl)phenyl]acetic Acid

13. Ahr-10282

14. Bromfenac (inn)

15. Yellox

16. 120638-55-3

17. Benzeneacetic Acid, 2-amino-3-(4-bromobenzoyl)-

18. Chebi:240107

19. Bromfenaco [spanish]

20. [2-amino-3-(4-bromo-benzoyl)-phenyl]-acetic Acid

21. Bromsite

22. 864p0921dw

23. 2-{2-amino-3-[(4-bromophenyl)carbonyl]phenyl}acetic Acid

24. Bromfenacum [latin]

25. Bromfenac Sodium Hydrate

26. Ahr-10282b

27. Sodium (2-amino-3-(4-bromobenzoyl)phenyl)acetate

28. Unii-864p0921dw

29. 4mjq

30. Ahr 10282

31. Bromfenac Acid

32. Bromfenac [mi]

33. Bromfenac [vandf]

34. Bromfenac [who-dd]

35. Chembl1077

36. Schembl34411

37. Mls004774052

38. Gtpl7131

39. {2-amino-3-[(4-bromophenyl)carbonyl]phenyl}acetic Acid

40. Dtxsid7040655

41. Hms3741c05

42. Hy-b1888

43. Vea63855

44. Zinc2570817

45. Bdbm50248104

46. Mfcd00864341

47. Akos015998697

48. Db00963

49. Gs-3830

50. Sb17362

51. Da-00968

52. Smr003500721

53. Cs-0013951

54. Ft-0710423

55. D07541

56. Benzeneacetic Acid,2-amino-3-(4-bromobenzoyl)-

57. 638b553

58. A844048

59. A906783

60. Sr-01000941476

61. J-519935

62. Q2487682

63. Sr-01000941476-2

64. Brd-k47679368-323-01-3

65. 2-[2-amino-3-(4-bromobenzoyl)phenyl]acetic Acid;2-(2-amino-3-(4-bromobenzoyl)phenyl)acetic Acid

66. 27r

2.4 Create Date
2005-08-08
3 Chemical and Physical Properties
Molecular Weight 334.16 g/mol
Molecular Formula C15H12BrNO3
XLogP33.3
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count4
Exact Mass333.00006 g/mol
Monoisotopic Mass333.00006 g/mol
Topological Polar Surface Area80.4 Ų
Heavy Atom Count20
Formal Charge0
Complexity366
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 4  
Drug NameBromday
PubMed HealthBromfenac (Into the eye)
Drug ClassesAnti-Inflammatory
Drug LabelBromday (bromfenac ophthalmic solution) 0.09% is a sterile, topical, nonsteroidal anti-inflammatory drug (NSAID) for ophthalmic use. Each mL of Bromday contains 1.035 mg bromfenac sodium (equivalent to 0.9 mg bromfenac free acid). Bromfenac sodi...
Active IngredientBromfenac sodium
Dosage FormSolution/drops
RouteOphthalmic
Strengtheq 0.09% acid
Market StatusPrescription
CompanyBausch And Lomb

2 of 4  
Drug NameProlensa
Drug LabelPROLENSA (bromfenac ophthalmic solution) 0.07% is a sterile, topical, nonsteroidal anti-inflammatory drug (NSAID) for ophthalmic use. Each mL of PROLENSA contains 0.805 mg bromfenac sodium sesquihydrate (equivalent to 0.7 mg bromfenac free acid). The...
Active IngredientBromfenac sodium
Dosage FormSolution/drops
RouteOphthalmic
Strengtheq 0.07% acid
Market StatusPrescription
CompanyBausch And Lomb

3 of 4  
Drug NameBromday
PubMed HealthBromfenac (Into the eye)
Drug ClassesAnti-Inflammatory
Drug LabelBromday (bromfenac ophthalmic solution) 0.09% is a sterile, topical, nonsteroidal anti-inflammatory drug (NSAID) for ophthalmic use. Each mL of Bromday contains 1.035 mg bromfenac sodium (equivalent to 0.9 mg bromfenac free acid). Bromfenac sodi...
Active IngredientBromfenac sodium
Dosage FormSolution/drops
RouteOphthalmic
Strengtheq 0.09% acid
Market StatusPrescription
CompanyBausch And Lomb

4 of 4  
Drug NameProlensa
Drug LabelPROLENSA (bromfenac ophthalmic solution) 0.07% is a sterile, topical, nonsteroidal anti-inflammatory drug (NSAID) for ophthalmic use. Each mL of PROLENSA contains 0.805 mg bromfenac sodium sesquihydrate (equivalent to 0.7 mg bromfenac free acid). The...
Active IngredientBromfenac sodium
Dosage FormSolution/drops
RouteOphthalmic
Strengtheq 0.07% acid
Market StatusPrescription
CompanyBausch And Lomb

4.2 Drug Indication

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.


5 Pharmacology and Biochemistry
5.1 Pharmacology

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


5.2 MeSH Pharmacological Classification

Anti-Inflammatory Agents, Non-Steroidal

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.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
BROMFENAC
5.3.2 FDA UNII
864P0921DW
5.3.3 Pharmacological Classes
Cyclooxygenase Inhibitors [MoA]; Nonsteroidal Anti-inflammatory Drug [EPC]; Anti-Inflammatory Agents, Non-Steroidal [CS]
5.4 ATC Code

S01BC11


S - Sensory organs

S01 - Ophthalmologicals

S01B - Antiinflammatory agents

S01BC - Antiinflammatory agents, non-steroids

S01BC11 - Bromfenac


5.5 Absorption, Distribution and Excretion

Absorption

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


5.6 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.