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Chemistry

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Also known as: 78281-72-8, Nevanac, 2-(2-amino-3-benzoylphenyl)acetamide, 2-amino-3-benzoylbenzeneacetamide, Ahr-9434, Ilevro
Molecular Formula
C15H14N2O2
Molecular Weight
254.28  g/mol
InChI Key
QEFAQIPZVLVERP-UHFFFAOYSA-N
FDA UNII
0J9L7J6V8C

Nepafenac
Nepafenac is a topical nonsteroidal anti-inflammatory drug that is used in eye drops for the treatment of eye pain and swelling.
Nepafenac is a Nonsteroidal Anti-inflammatory Drug. The mechanism of action of nepafenac is as a Cyclooxygenase Inhibitor.
1 2D Structure

Nepafenac

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-(2-amino-3-benzoylphenyl)acetamide
2.1.2 InChI
InChI=1S/C15H14N2O2/c16-13(18)9-11-7-4-8-12(14(11)17)15(19)10-5-2-1-3-6-10/h1-8H,9,17H2,(H2,16,18)
2.1.3 InChI Key
QEFAQIPZVLVERP-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC=C(C=C1)C(=O)C2=CC=CC(=C2N)CC(=O)N
2.2 Other Identifiers
2.2.1 UNII
0J9L7J6V8C
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2-amino-3-benzoylbenzeneacetamide

2. Nevanac

2.3.2 Depositor-Supplied Synonyms

1. 78281-72-8

2. Nevanac

3. 2-(2-amino-3-benzoylphenyl)acetamide

4. 2-amino-3-benzoylbenzeneacetamide

5. Ahr-9434

6. Ilevro

7. Al 6515

8. Al-6515

9. Ahr 9434

10. Benzeneacetamide, 2-amino-3-benzoyl-

11. Chebi:75922

12. 0j9l7j6v8c

13. Ahr 9434;al 6515

14. Ncgc00185741-01

15. Dsstox_cid_28564

16. Dsstox_rid_82836

17. Dsstox_gsid_48638

18. Nepafenac [usan]

19. Amfenac Amide

20. Smr002529588

21. Cas-78281-72-8

22. Nepafenaco

23. Nepafenacum

24. Unii-0j9l7j6v8c

25. Nepafena

26. Nepafenac [usan:inn:ban:jan]

27. Nevanac (tn)

28. Mfcd08067732

29. 2-(2-amino-3-benzoyl-phenyl)acetamide

30. 2-[2-amino-3-(benzoyl)phenyl]acetamide

31. Nepafenac [inn]

32. Nepafenac [jan]

33. Nepafenac [mi]

34. Nepafenac [vandf]

35. Nepafenac [mart.]

36. Nepafenac [usp-rs]

37. Nepafenac [who-dd]

38. Chembl1021

39. Schembl93835

40. Nepafenac [ema Epar]

41. Mls003915618

42. Mls004774140

43. Mls006010644

44. Nepafenac (jan/usan/inn)

45. Gtpl7564

46. Nepafenac [orange Book]

47. Dtxsid0048638

48. Nepafenac, >=98% (hplc)

49. 2-amino-3-benzoyl-phenylacetamide

50. Hms3654p07

51. Hms3884e07

52. Act02914

53. Amy10899

54. Bcp21333

55. Ex-a1350

56. Wzb81453

57. Zinc5162311

58. Tox21_112985

59. Bdbm50228731

60. S1255

61. Stl451069

62. Akos005146108

63. Tox21_112985_1

64. Ac-6949

65. Ccg-267004

66. Cs-0899

67. Db06802

68. Ncgc00185741-02

69. 2-(2-amino-3-benzoyl-phenyl)-acetamide

70. As-19176

71. Hy-17357

72. 2-amino-3-benzoylbenzeneacetamide;nepafenac

73. Ft-0603701

74. N0932

75. Sw219197-1

76. 2-[2-amino-3-(phenylcarbonyl)phenyl]acetamide

77. A26218

78. D05143

79. Ab01274763-01

80. Ab01274763_02

81. 281n728

82. A890381

83. Q684379

84. Sr-01000931908

85. J-507774

86. Sr-01000931908-2

87. Brd-k04112579-001-02-1

2.4 Create Date
2005-08-08
3 Chemical and Physical Properties
Molecular Weight 254.28 g/mol
Molecular Formula C15H14N2O2
XLogP31.9
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count3
Rotatable Bond Count4
Exact Mass254.105527694 g/mol
Monoisotopic Mass254.105527694 g/mol
Topological Polar Surface Area86.2 Ų
Heavy Atom Count19
Formal Charge0
Complexity337
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 2  
Drug NameNevanac
Drug LabelNEVANAC (nepafenac ophthalmic suspension) 0.1% is a sterile, topical, nonsteroidal anti-inflammatory (NSAID) prodrug for ophthalmic use. Each mL of NEVANAC suspension contains 1 mg of nepafenac. Nepafenac is designated chemically as 2-amino-3-ben...
Active IngredientNepafenac
Dosage FormSuspension/drops
RouteOphthalmic
Strength0.1%
Market StatusPrescription
CompanyAlcon Pharms

2 of 2  
Drug NameNevanac
Drug LabelNEVANAC (nepafenac ophthalmic suspension) 0.1% is a sterile, topical, nonsteroidal anti-inflammatory (NSAID) prodrug for ophthalmic use. Each mL of NEVANAC suspension contains 1 mg of nepafenac. Nepafenac is designated chemically as 2-amino-3-ben...
Active IngredientNepafenac
Dosage FormSuspension/drops
RouteOphthalmic
Strength0.1%
Market StatusPrescription
CompanyAlcon Pharms

4.2 Drug Indication

For the treatment of pain and inflammation associated with cataract surgery.


FDA Label


Nevanac is indicated for:

- prevention and treatment of postoperative pain and inflammation associated with cataract surgery;

- reduction in the risk of postoperative macular oedema associated with cataract surgery in diabetic patients.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Low but quantifiable plasma concentrations of nepafenac and amfenac were observed in the majority of subjects 2 and 3 hours postdose, respectively, following bilateral topical ocular TID dosing of nepafenac ophthalmic suspension, 0.1%. The mean steady-state Cmax for nepafenac and for amfenac were 0.310 0.104 ng/ml and 0.422 0.121 ng/ml, respectively, following ocular administration.


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
NEPAFENAC
5.3.2 FDA UNII
0J9L7J6V8C
5.3.3 Pharmacological Classes
Cyclooxygenase Inhibitors [MoA]; Nonsteroidal Anti-inflammatory Drug [EPC]; Anti-Inflammatory Agents, Non-Steroidal [CS]
5.4 ATC Code

S01BC10


S01BC10

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


S - Sensory organs

S01 - Ophthalmologicals

S01B - Antiinflammatory agents

S01BC - Antiinflammatory agents, non-steroids

S01BC10 - Nepafenac


5.5 Absorption, Distribution and Excretion

Absorption

Nepafenac rapidly cross the cornea (6 times faster than diclofenac in vitro).


Route of Elimination

After oral administration of 14C-nepafenac to healthy volunteers, urinary excretion was found to be the major route of radioactivity elimination, accounting for approximately 85% of the dose, while fecal excretion represented approximately 6% of the dose. Nepafenac (prodrug) and amfenac (active compound) were not quantifiable in the urine.


5.6 Metabolism/Metabolites

Nepafenac (prodrug) is deaminated to amfenac (active compound) in the ciliary body epithelium, retina, and choroid by intraocular hydrolases. Subsequently, amfenac undergoes extensive metabolism to more polar metabolites involving hydroxylation of the aromatic ring leading to glucuronide conjugate formation.


5.7 Mechanism of Action

Nepafenac is a prodrug. After penetrating the cornea, nepafenac undergoes rapid bioactivation to amfenac, which is a potent NSAID that uniformly inhibits the COX1 and COX2 activity.


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02-Jan-2021
24-Oct-2024
KGS
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DOSAGE - SUSPENSION/DROPS;OPHTHALMIC - 0.3%

USFDA APPLICATION NUMBER - 203491

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DOSAGE - SUSPENSION/DROPS;OPHTHALMIC - 0.1%

USFDA APPLICATION NUMBER - 21862

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