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Details

Stereochemistry ACHIRAL
Molecular Formula C15H12NO3.Na
Molecular Weight 277.2504
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMFENAC SODIUM ANHYDROUS

SMILES

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

InChI

InChIKey=MJAQSCHBMPGJES-UHFFFAOYSA-M
InChI=1S/C15H13NO3.Na/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);/q;+1/p-1

HIDE SMILES / InChI

Description
Curator's Comment: Description was created based on several sources, including https://link.springer.com/article/10.1007/BF03299088 | http://www.rad-ar.or.jp/siori/english/kekka.cgi?n=35377 | https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/203491Orig1s000MedR.pdf | https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/021862lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/10850857

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.

Approval Year

Targets

Targets

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
NEVANAC

Approved Use

NEVANAC ophthalmic suspension is a nonsteroidal, antiinflammatory prodrug indicated for the treatment of pain and inflammation associated with cataract surgery

Launch Date

2005
Primary
FENAZOX

Approved Use

FENAZOX CAPSULES (Amfenac sodium hydrate) is usually used to relieve inflammation and pain in chronic rheumatoid arthritis, osteoarthritis, low back pain, shoulder periarthritis, cervico-omo-brachial syndrome, temporomandibular joint disease, post-operative state, post-traumatic state or post-odontectomy state.

Launch Date

1985
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
205.3 ng/mL
1 drop single, ocular
dose: 1 drop
route of administration: Ocular
experiment type: SINGLE
co-administered:
NEPAFENAC aqueous humor
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
0.847 ng/mL
1 drop 1 times / day steady-state, ocular
dose: 1 drop
route of administration: Ocular
experiment type: STEADY-STATE
co-administered:
NEPAFENAC unknown
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
331.1 ng × h/mL
1 drop single, ocular
dose: 1 drop
route of administration: Ocular
experiment type: SINGLE
co-administered:
NEPAFENAC aqueous humor
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
1 drop 1 times / day multiple, topical
Recommended
Dose: 1 drop, 1 times / day
Route: topical
Route: multiple
Dose: 1 drop, 1 times / day
Sources: Page: p.209
unhealthy, 68.7+/- 9.08
n = 817
Health Status: unhealthy
Condition: Pain and inflammation associated with cataract surgery
Age Group: 68.7+/- 9.08
Sex: M+F
Population Size: 817
Sources: Page: p.209
Disc. AE: Hypersensitivity...
AEs leading to
discontinuation/dose reduction:
Hypersensitivity (0.12%)
Sources: Page: p.209
1 drop 1 times / day multiple, topical
Recommended
Dose: 1 drop, 1 times / day
Route: topical
Route: multiple
Dose: 1 drop, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Pain and inflammation associated with cataract surgery
Sources: Page: p.1
Disc. AE: Bleeding, Healing delayed...
AEs leading to
discontinuation/dose reduction:
Bleeding
Healing delayed
Corneal disorder (NOS)
Keratitis
Sources: Page: p.1
AEs

AEs

AESignificanceDosePopulation
Hypersensitivity 0.12%
Disc. AE
1 drop 1 times / day multiple, topical
Recommended
Dose: 1 drop, 1 times / day
Route: topical
Route: multiple
Dose: 1 drop, 1 times / day
Sources: Page: p.209
unhealthy, 68.7+/- 9.08
n = 817
Health Status: unhealthy
Condition: Pain and inflammation associated with cataract surgery
Age Group: 68.7+/- 9.08
Sex: M+F
Population Size: 817
Sources: Page: p.209
Bleeding Disc. AE
1 drop 1 times / day multiple, topical
Recommended
Dose: 1 drop, 1 times / day
Route: topical
Route: multiple
Dose: 1 drop, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Pain and inflammation associated with cataract surgery
Sources: Page: p.1
Corneal disorder (NOS) Disc. AE
1 drop 1 times / day multiple, topical
Recommended
Dose: 1 drop, 1 times / day
Route: topical
Route: multiple
Dose: 1 drop, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Pain and inflammation associated with cataract surgery
Sources: Page: p.1
Healing delayed Disc. AE
1 drop 1 times / day multiple, topical
Recommended
Dose: 1 drop, 1 times / day
Route: topical
Route: multiple
Dose: 1 drop, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Pain and inflammation associated with cataract surgery
Sources: Page: p.1
Keratitis Disc. AE
1 drop 1 times / day multiple, topical
Recommended
Dose: 1 drop, 1 times / day
Route: topical
Route: multiple
Dose: 1 drop, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Pain and inflammation associated with cataract surgery
Sources: Page: p.1
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer







Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
inconclusive
inconclusive
no
no
no
no
no
no
no
no
no
no
no
no
Drug as victim
PubMed

PubMed

TitleDatePubMed
Topical nepafenac inhibits ocular neovascularization.
2003 Jan
Pharmacokinetics of topical ocular drug delivery: potential uses for the treatment of diseases of the posterior segment and beyond.
2003 Jun
Inflammation-mediated retinal edema in the rabbit is inhibited by topical nepafenac.
2003 Oct
Comparison of the analgesic efficacy and safety of nepafenac ophthalmic suspension compared with diclofenac ophthalmic solution for ocular pain and photophobia after excimer laser surgery: a phase II, randomized, double-masked trial.
2006 Apr
New drugs 06, part II.
2006 Aug
Nepafenac: a unique nonsteroidal prodrug.
2006 Fall
Ocular permeation and inhibition of retinal inflammation: an examination of data and expert opinion on the clinical utility of nepafenac.
2006 Feb
New drugs: ramelteon, tipranavir, nepafenac, and deferasirox.
2006 Jan-Feb
The effect of a selective cyclooxygenase-2 (COX-2) inhibitor on the proliferation rate of retinoblastoma cell lines.
2006 May
Contributions of inflammatory processes to the development of the early stages of diabetic retinopathy.
2007
Analgesic and anti-inflammatory effectiveness of nepafenac 0.1% for cataract surgery.
2007 Dec
Re: Prostaglandin E(2) inhibition and aqueous concentration of ketorolac 0.4% and nepafenac 0.1% in patients undergoing phacoemulsification.
2007 Dec
Cystoid and diabetic macular edema treated with nepafenac 0.1%.
2007 Dec
Effects of topical anti-inflammatory agents in a botulinum toxin B-induced mouse model of keratoconjunctivitis sicca.
2007 Feb
Topical administration of nepafenac inhibits diabetes-induced retinal microvascular disease and underlying abnormalities of retinal metabolism and physiology.
2007 Feb
Comparative effects of the nonsteroidal anti-inflammatory drug nepafenac on corneal sensory nerve fibers responding to chemical irritation.
2007 Jan
Nepafenac ophthalmic suspension 0.1% for the prevention and treatment of ocular inflammation associated with cataract surgery.
2007 Jan
Prostaglandin E2 inhibition and aqueous concentration of ketorolac 0.4% (acular LS) and nepafenac 0.1% (nevanac) in patients undergoing phacoemulsification.
2007 Jul
Double-masked comparison of ketorolac tromethamine 0.4% versus nepafenac sodium 0.1% for postoperative healing rates and pain control in eyes undergoing surface ablation.
2007 Jul
Double-masked study of the effects of nepafenac 0.1% and ketorolac 0.4% on corneal epithelial wound healing and pain after photorefractive keratectomy.
2007 Jul-Aug
Nepafenac-associated corneal melt.
2007 Nov
Ketorolac tromethamine LS 0.4% versus nepafenac 0.1% in patients having cataract surgery. Prospective randomized double-masked clinical trial.
2007 Nov
The effects of a cyclooxygenase-2 (COX-2) expression and inhibition on human uveal melanoma cell proliferation and macrophage nitric oxide production.
2007 Nov 27
Effects of nonsteroidal ophthalmic drops on epithelial healing and pain in patients undergoing bilateral photorefractive keratectomy (PRK).
2007 Nov-Dec
Case of corneal melting associated with the use of topical nepafenac.
2007 Sep
Incidence of visually significant pseudophakic macular edema after uneventful phacoemulsification in patients treated with nepafenac.
2007 Sep
In vivo pharmacokinetics and in vitro pharmacodynamics of nepafenac, amfenac, ketorolac, and bromfenac.
2007 Sep
The use of a cyclooxygenase-2 inhibitor (Nepafenac) in an ocular and metastatic animal model of uveal melanoma.
2007 Sep
Topical nepafenac in the treatment of diabetic macular edema.
2008 Dec
Nepafenac dosing frequency for ocular pain and inflammation associated with cataract surgery.
2008 Dec
Topical ophthalmic NSAIDs: a discussion with focus on nepafenac ophthalmic suspension.
2008 Jun
Topical ocular delivery of NSAIDs.
2008 Jun
Amfenac increases the radiosensitivity of uveal melanoma cell lines.
2008 May
Topical nepafenac as an alternate treatment for cystoid macular edema in steroid responsive patients.
2008 Nov-Dec
Effect of nepafenac sodium 0.1% on delayed corneal epithelial healing and haze after photorefractive keratectomy: retrospective comparative study.
2008 Sep
Etiology and treatment of the inflammatory causes of cystoid macular edema.
2009
Intracameral dexamethasone reduces inflammation on the first postoperative day after cataract surgery in eyes with and without glaucoma.
2009
Inhibition of surgically induced miosis and prevention of postoperative macular edema with nepafenac.
2009
Management of ocular inflammation and pain following cataract surgery: focus on bromfenac ophthalmic solution.
2009
Treatment of cystoid macular edema with the new-generation NSAID nepafenac 0.1%.
2009
Gateways to clinical trials.
2009 Apr
Nepafenac: new drug. After cataract surgery: just another NSAID eye drop. No better than other NSAID eye drops, and less convenient to use.
2009 Aug
Nepafenac dosing frequency for ocular pain and inflammation associated with cataract surgery.
2009 Aug
Nepafenac-associated bilateral corneal melt after photorefractive keratectomy.
2009 Sep
Diabetic cataract-pathogenesis, epidemiology and treatment.
2010
Ocular pharmacokinetics of 0.45% ketorolac tromethamine.
2010 Dec 1
Impact of nepafenac 0.1% on macular thickness and postoperative visual acuity after cataract surgery in patients at low risk for cystoid macular oedema.
2010 Jan
Topical nepafenac for treatment of exudative age-related macular degeneration.
2010 Mar
Effect of preoperative use of topical prednisolone acetate, ketorolac tromethamine, nepafenac and placebo, on the maintenance of intraoperative mydriasis during cataract surgery: a randomized trial.
2012 Jul
Nepafenac: an ophthalmic nonsteroidal antiinflammatory drug for pain after cataract surgery.
2013 Jun
Patents

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
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).
Name Type Language
AMFENAC SODIUM ANHYDROUS
Common Name English
BENZENEACETIC ACID, 2-AMINO-3-BENZOYL-, SODIUM SALT
Common Name English
BENZENEACETIC ACID, 2-AMINO-3-BENZOYL-, SODIUM SALT (1:1)
Systematic Name English
SODIUM 2-AMINO-3-BENZOYLBENZENEACETATE
Systematic Name English
Amfenac sodium [WHO-DD]
Common Name English
AHR-5850
Code English
Code System Code Type Description
EPA CompTox
DTXSID8048658
Created by admin on Fri Dec 15 15:23:47 GMT 2023 , Edited by admin on Fri Dec 15 15:23:47 GMT 2023
PRIMARY
CAS
61941-56-8
Created by admin on Fri Dec 15 15:23:47 GMT 2023 , Edited by admin on Fri Dec 15 15:23:47 GMT 2023
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FDA UNII
C20288EWAG
Created by admin on Fri Dec 15 15:23:47 GMT 2023 , Edited by admin on Fri Dec 15 15:23:47 GMT 2023
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PUBCHEM
23665728
Created by admin on Fri Dec 15 15:23:47 GMT 2023 , Edited by admin on Fri Dec 15 15:23:47 GMT 2023
PRIMARY