U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

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.

Originator

Approval Year

2005
131
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 64.3 µM [IC50]
Inhibitor
8297
 0.15 µM [IC50]
Inhibitor
8297
 0.25 µM [IC50]
Inhibitor
8297
 0.15 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Approved
8429
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
Approved
8429
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
DRUG LABEL
https://iovs.arvojournals.org/article.aspx?articleid=2383342
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
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/203491s001lbl.pdf
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
DRUG LABEL
https://iovs.arvojournals.org/article.aspx?articleid=2383342
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:
https://pubmed.ncbi.nlm.nih.gov/24345529
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:
https://pubmed.ncbi.nlm.nih.gov/24345529
Page: p.209
Disc. AE: Hypersensitivity...
AEs leading to
discontinuation/dose reduction:
Hypersensitivity (0.12%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/24345529
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/203491s001lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Pain and inflammation associated with cataract surgery
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/203491s001lbl.pdf
Page: p.1
Disc. AE: Bleeding, Healing delayed...
AEs leading to
discontinuation/dose reduction:
Bleeding
Healing delayed
Corneal disorder (NOS)
Keratitis
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/203491s001lbl.pdf
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:
https://pubmed.ncbi.nlm.nih.gov/24345529
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:
https://pubmed.ncbi.nlm.nih.gov/24345529
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/203491s001lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Pain and inflammation associated with cataract surgery
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/203491s001lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/203491s001lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Pain and inflammation associated with cataract surgery
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/203491s001lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/203491s001lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Pain and inflammation associated with cataract surgery
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/203491s001lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/203491s001lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Pain and inflammation associated with cataract surgery
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/203491s001lbl.pdf
Page: p.1
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
1587
inhibitor
1767
inhibitor
1852

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
1524

CYP2C19
1478

CYP2E1
882

P-gp
1461
CYP
270

P-gp
1537

UGT enzymes
27
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
P-gp
1650
 inconclusive
P-gp
1650
 inconclusive
amfenac
4
CYP1A2
1692
 no
CYP1A2
1692
 no
amfenac
4
CYP2C19
1553
 no
CYP2C19
1553
 no
amfenac
4
CYP2C9
1819
 no
CYP2C9
1819
 no
amfenac
4
CYP2D6
1891
 no
CYP2D6
1891
 no
amfenac
4
CYP2E1
970
 no
CYP2E1
970
 no
amfenac
4
CYP3A4
1925
 no
CYP3A4
1925
 no
amfenac
4
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP
270
 inconclusive
amfenac
4
P-gp
1537
 inconclusive
P-gp
1537
 inconclusive
amfenac
4
UGT enzymes
27
 likely
UGT enzymes
27
 likely
amfenac
4
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:75922
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:75922
ChemicalBook
CB01116872
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB01116872
MolPort
MolPort-003-987-236
https://www.molport.com/shop/molecule-link/MolPort-003-987-236
Selleck Chemicals
Nepafenac
http://www.selleckchem.com/products/Nepafenac.html
ZINC
ZINC000005162311
http://zinc15.docking.org/substances/ZINC000005162311
eMolecules
10510502
https://www.emolecules.com/cgi-bin/more?vid=10510502
PubMed

PubMed

TitleDatePubMed
Topical nepafenac inhibits ocular neovascularization.
2003 Jan
Cystoid and diabetic macular edema treated with nepafenac 0.1%.
2007 Dec
Topical administration of nepafenac inhibits diabetes-induced retinal microvascular disease and underlying abnormalities of retinal metabolism and physiology.
2007 Feb
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
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
Increased neuronal nitric oxide synthase activity in retinal neurons in early diabetic retinopathy.
2009 Nov 9
Vitreous nonsteroidal antiinflammatory drug concentrations and prostaglandin E2 levels in vitrectomy patients treated with ketorolac 0.4%, bromfenac 0.09%, and nepafenac 0.1%.
2009 Oct
Comparison of three strains of diabetic rats with respect to the rate at which retinopathy and tactile allodynia develop.
2010 Aug 15
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
Patents

Patents

20020035264
14
JP2007537168A
10
JP2010037262A
4
JP2010059058A
4

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).
Name Type Language
NEPAFENAC
EMA EPAR   INN   JAN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
nepafenac [INN]
Common Name English
Nepafenac [WHO-DD]
Common Name English
NEPAFENAC [USAN]
Common Name English
NEPAFENAC [EMA EPAR]
Common Name English
2-(2-Amino-3-benzoylphenyl)acetamide
Systematic Name English
NEVANAC
Brand Name English
NEPAFENAC [MART.]
Common Name English
AL-6515
Code English
NEPAFENAC [ORANGE BOOK]
Common Name English
2-AMINO-3-BENZOYLBENZENEACETAMIDE
Systematic Name English
NEPAFENAC [USP-RS]
Common Name English
NEPAFENAC [MI]
Common Name English
NEPAFENAC [VANDF]
Common Name English
NEPAFENAC [JAN]
Common Name English
AHR-9434
Code English
Classification Tree Code System Code
NDF-RT N0000000160
Created by admin on Fri Dec 15 15:45:15 GMT 2023 , Edited by admin on Fri Dec 15 15:45:15 GMT 2023
NDF-RT N0000175721
Created by admin on Fri Dec 15 15:45:15 GMT 2023 , Edited by admin on Fri Dec 15 15:45:15 GMT 2023
NDF-RT N0000175722
Created by admin on Fri Dec 15 15:45:15 GMT 2023 , Edited by admin on Fri Dec 15 15:45:15 GMT 2023
NCI_THESAURUS C257
Created by admin on Fri Dec 15 15:45:15 GMT 2023 , Edited by admin on Fri Dec 15 15:45:15 GMT 2023
WHO-VATC QS01BC10
Created by admin on Fri Dec 15 15:45:15 GMT 2023 , Edited by admin on Fri Dec 15 15:45:15 GMT 2023
EMA ASSESSMENT REPORTS NEVANAC (AUTHORIZED: PAIN, POSTOPERATIVE)
Created by admin on Fri Dec 15 15:45:15 GMT 2023 , Edited by admin on Fri Dec 15 15:45:15 GMT 2023
WHO-ATC S01BC10
Created by admin on Fri Dec 15 15:45:15 GMT 2023 , Edited by admin on Fri Dec 15 15:45:15 GMT 2023
EMA ASSESSMENT REPORTS NEVANAC (AUTHORIZED: OPTHALMOLOGIC SURGICAL PROCEDURES)
Created by admin on Fri Dec 15 15:45:15 GMT 2023 , Edited by admin on Fri Dec 15 15:45:15 GMT 2023
Code System Code Type Description
MESH
C414203
Created by admin on Fri Dec 15 15:45:15 GMT 2023 , Edited by admin on Fri Dec 15 15:45:15 GMT 2023
PRIMARY
PUBCHEM
151075
Created by admin on Fri Dec 15 15:45:15 GMT 2023 , Edited by admin on Fri Dec 15 15:45:15 GMT 2023
PRIMARY
LACTMED
Nepafenac
Created by admin on Fri Dec 15 15:45:15 GMT 2023 , Edited by admin on Fri Dec 15 15:45:15 GMT 2023
PRIMARY
CHEBI
75922
Created by admin on Fri Dec 15 15:45:15 GMT 2023 , Edited by admin on Fri Dec 15 15:45:15 GMT 2023
PRIMARY
INN
7685
Created by admin on Fri Dec 15 15:45:15 GMT 2023 , Edited by admin on Fri Dec 15 15:45:15 GMT 2023
PRIMARY
SMS_ID
100000085451
Created by admin on Fri Dec 15 15:45:15 GMT 2023 , Edited by admin on Fri Dec 15 15:45:15 GMT 2023
PRIMARY
WIKIPEDIA
Nepafenac
Created by admin on Fri Dec 15 15:45:15 GMT 2023 , Edited by admin on Fri Dec 15 15:45:15 GMT 2023
PRIMARY
DRUG BANK
DB06802
Created by admin on Fri Dec 15 15:45:15 GMT 2023 , Edited by admin on Fri Dec 15 15:45:15 GMT 2023
PRIMARY
NCI_THESAURUS
C66228
Created by admin on Fri Dec 15 15:45:15 GMT 2023 , Edited by admin on Fri Dec 15 15:45:15 GMT 2023
PRIMARY
RXCUI
298665
Created by admin on Fri Dec 15 15:45:15 GMT 2023 , Edited by admin on Fri Dec 15 15:45:15 GMT 2023
PRIMARY RxNorm
EPA CompTox
DTXSID0048638
Created by admin on Fri Dec 15 15:45:15 GMT 2023 , Edited by admin on Fri Dec 15 15:45:15 GMT 2023
PRIMARY
RS_ITEM_NUM
1460317
Created by admin on Fri Dec 15 15:45:15 GMT 2023 , Edited by admin on Fri Dec 15 15:45:15 GMT 2023
PRIMARY
EVMPD
SUB09197MIG
Created by admin on Fri Dec 15 15:45:15 GMT 2023 , Edited by admin on Fri Dec 15 15:45:15 GMT 2023
PRIMARY
DAILYMED
0J9L7J6V8C
Created by admin on Fri Dec 15 15:45:15 GMT 2023 , Edited by admin on Fri Dec 15 15:45:15 GMT 2023
PRIMARY
DRUG CENTRAL
1899
Created by admin on Fri Dec 15 15:45:15 GMT 2023 , Edited by admin on Fri Dec 15 15:45:15 GMT 2023
PRIMARY
ChEMBL
CHEMBL1021
Created by admin on Fri Dec 15 15:45:15 GMT 2023 , Edited by admin on Fri Dec 15 15:45:15 GMT 2023
PRIMARY
FDA UNII
0J9L7J6V8C
Created by admin on Fri Dec 15 15:45:15 GMT 2023 , Edited by admin on Fri Dec 15 15:45:15 GMT 2023
PRIMARY
MERCK INDEX
m7823
Created by admin on Fri Dec 15 15:45:15 GMT 2023 , Edited by admin on Fri Dec 15 15:45:15 GMT 2023
PRIMARY Merck Index
IUPHAR
7564
Created by admin on Fri Dec 15 15:45:15 GMT 2023 , Edited by admin on Fri Dec 15 15:45:15 GMT 2023
PRIMARY
CAS
78281-72-8
Created by admin on Fri Dec 15 15:45:15 GMT 2023 , Edited by admin on Fri Dec 15 15:45:15 GMT 2023
PRIMARY
USAN
II-86
Created by admin on Fri Dec 15 15:45:15 GMT 2023 , Edited by admin on Fri Dec 15 15:45:15 GMT 2023
PRIMARY
ACTIVE MOIETY
Structure of AMFENAC
SUBSTANCE RECORD
Structure of NEPAFENAC
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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