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Details

Stereochemistry ACHIRAL
Molecular Formula C15H12NO3.Na.H2O
Molecular Weight 295.2657
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMFENAC SODIUM

SMILES

O.[Na+].NC1=C(C=CC=C1CC([O-])=O)C(=O)C2=CC=CC=C2

InChI

InChIKey=QZNJPJDUBTYMRS-UHFFFAOYSA-M
InChI=1S/C15H13NO3.Na.H2O/c16-14-11(9-13(17)18)7-4-8-12(14)15(19)10-5-2-1-3-6-10;;/h1-8H,9,16H2,(H,17,18);;1H2/q;+1;/p-1

HIDE SMILES / InChI

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
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 unknown
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
331.1 ng × h/mL
1 drop single, ocular
NEPAFENAC aqueous humor
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).