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Chemistry

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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

Bromfenac

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 Formula	C₁₅H₁₂BrNO₃
Molecular Weight	334.16 g/mol
XLogP3	3.3
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	4
Exact Mass	333.00006 g/mol
Monoisotopic Mass	333.00006 g/mol
Topological Polar Surface Area	80.4 Å²
Heavy Atom Count	20
Formal Charge	0
Complexity	366
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 4
Drug Name	Bromday
PubMed Health	Bromfenac (Into the eye)
Drug Classes	Anti-Inflammatory
Drug Label	Bromday (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 Ingredient	Bromfenac sodium
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	eq 0.09% acid
Market Status	Prescription
Company	Bausch And Lomb

2 of 4
Drug Name	Prolensa
Drug Label	PROLENSA (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 Ingredient	Bromfenac sodium
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	eq 0.07% acid
Market Status	Prescription
Company	Bausch And Lomb

3 of 4
Drug Name	Bromday
PubMed Health	Bromfenac (Into the eye)
Drug Classes	Anti-Inflammatory
Drug Label	Bromday (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 Ingredient	Bromfenac sodium
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	eq 0.09% acid
Market Status	Prescription
Company	Bausch And Lomb

4 of 4
Drug Name	Prolensa
Drug Label	PROLENSA (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 Ingredient	Bromfenac sodium
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	eq 0.07% acid
Market Status	Prescription
Company	Bausch 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.

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