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Details

Stereochemistry ACHIRAL
Molecular Formula C15H14N2O2
Molecular Weight 254.2839
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NEPAFENAC

SMILES

NC(=O)CC1=C(N)C(=CC=C1)C(=O)C2=CC=CC=C2

InChI

InChIKey=QEFAQIPZVLVERP-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C15H14N2O2
Molecular Weight 254.2839
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Amfenac (AHR 5850) is a non-steroidal anti-inflammatory compound possessing antipyretic and analgesic properties. It is an inhibitor of cyclooxygenases. Amfenac sodium has been on the Japanese market since 1986 (as FENAZOX®, Meiji) in an oral dosage form (50 mg, four-times-daily) indicated for the treatment of pain and inflammation associated with rheumatoid and osteoarthritis and low back pain, as well as the treatment of pain and inflammation following surgery, injury or tooth extraction. Amfenac is an active moiety of nepafenac (amfenac amide), the prodrug has very weak cyclooxygenase inhibitory activity whereas amfenac exhibits more potent cyclooxygenase activity. Nepafenac at a concentration of 0.1% (NEVANAC) was approved for marketing in the US in 2005. Nepafenac is also approved for marketing in the European Union(EU) and Japan as well as over 60 other countries for the treatment of postoperative pain and inflammation associated with cataract surgery.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
64.3 µM [IC50]
0.15 µM [IC50]
0.25 µM [IC50]
0.15 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
NEVANAC
Primary
FENAZOX

Cmax

ValueDoseCo-administeredAnalytePopulation
5.62 μg/mL
50 mg single, oral
AMFENAC plasma
Homo sapiens
70.1 ng/mL
1 drop single, ocular
AMFENAC aqueous humor
Homo sapiens
205.3 ng/mL
1 drop single, ocular
NEPAFENAC aqueous humor
Homo sapiens
0.847 ng/mL
1 drop 1 times / day steady-state, ocular
NEPAFENAC plasma
Homo sapiens
0.921 ng/mL
1 drop single, ocular
NEPAFENAC plasma
Homo sapiens
0.847 ng/mL
1 drop 1 times / day steady-state, ocular
NEPAFENAC plasma
Homo sapiens
1.15 ng/mL
1 drop single, ocular
AMFENAC plasma
Homo sapiens
1.13 ng/mL
1 drop 1 times / day steady-state, ocular
AMFENAC plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
6.11 μg × h/mL
50 mg single, oral
AMFENAC plasma
Homo sapiens
178.1 ng × h/mL
1 drop single, ocular
AMFENAC aqueous humor
Homo sapiens
331.1 ng × h/mL
1 drop single, ocular
NEPAFENAC aqueous humor
Homo sapiens
1.57 ng × h/mL
1 drop single, ocular
NEPAFENAC plasma
Homo sapiens
1.43 ng × h/mL
1 drop 1 times / day steady-state, ocular
NEPAFENAC plasma
Homo sapiens
3.6 ng × h/mL
1 drop single, ocular
AMFENAC plasma
Homo sapiens
3.7 ng × h/mL
1 drop 1 times / day steady-state, ocular
AMFENAC plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
1.3 h
50 mg single, oral
AMFENAC plasma
Homo sapiens
0.85 h
1 drop single, ocular
NEPAFENAC plasma
Homo sapiens
0.74 h
1 drop 1 times / day steady-state, ocular
NEPAFENAC plasma
Homo sapiens
5.49 h
1 drop single, ocular
AMFENAC plasma
Homo sapiens
6.26 h
1 drop 1 times / day steady-state, ocular
AMFENAC plasma
Homo sapiens

Doses

AEs

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer







Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
One drop of Nepafenac ophthalmic suspension, 0.3% should be applied to the affected eye one-time-daily beginning 1 day prior to cataract surgery, continued on the day of surgery and through the first 2 weeks of the postoperative period. An additional drop should be administered 30 to 120 minutes prior to surgery.
Route of Administration: Topical
In Vitro Use Guide
Nepafenac exhibited only weak COX-1 inhibitory activity (IC50 = 64.3 uM). However, amfenac, an active metabolite of nepafenac, was a potent inhibitor of COX-1 (IC50 = 0.25 uM) and COX-2 activity (IC50 = 0.15 uM).
Substance Class Chemical
Record UNII
0J9L7J6V8C
Record Status Validated (UNII)
Record Version