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Revision as of 06:41, 1 September 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{drugbox}} (no changed fields - added verified revid - updated 'ChEBI_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report errors or bugs)← Previous edit Latest revision as of 08:12, 1 November 2024 edit undoBioMed-03 (talk | contribs)30 edits Category:Ophthalmology drugs 
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{{Short description|NSAID analgesic and anti-inflammatory drug}}
{{Drugbox {{Drugbox
| Verifiedfields = changed
| verifiedrevid = 444024277
| Watchedfields = changed
| IUPAC_name = 2-amino-3-benzoylbenzeneacetamide
| verifiedrevid = 447808600
| image = Nepafenac-2D-skeletal.png
| image = Nepafenac-2D-skeletal.svg
| alt =


<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename = Nevanac, Ilevro, Amnac, others
| Drugs.com = {{drugs.com|monograph|nepafenac}} | Drugs.com = {{drugs.com|monograph|nepafenac}}
| MedlinePlus = a606007 | MedlinePlus = a606007
| DailyMedID = Nepafenac
| pregnancy_category = C
| pregnancy_AU = C
| pregnancy_AU_comment = <ref name="Drugs.com pregnancy">{{cite web | title=Nepafenac ophthalmic Use During Pregnancy | website=Drugs.com | date=6 June 2019 | url=https://www.drugs.com/pregnancy/nepafenac-ophthalmic.html | access-date=13 September 2020}}</ref>
| licence_EU = yes
| legal_AU = S4
| legal_AU_comment = <ref>{{cite web | title=Prescription medicines: registration of new chemical entities in Australia, 2015 | website=Therapeutic Goods Administration (TGA) | date=21 June 2022 | url=https://www.tga.gov.au/prescription-medicines-registration-new-chemical-entities-australia-2015 | access-date=10 April 2023}}</ref>
| legal_US = Rx-only | legal_US = Rx-only
| legal_status = | legal_status = Rx-only
| routes_of_administration = ] | routes_of_administration = ]
| ATC_prefix = S01
| ATC_suffix = BC10
| ATC_supplemental =


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| bioavailability = | bioavailability =
| protein_bound = | protein_bound =
| metabolism = | metabolism =
| elimination_half-life = | elimination_half-life =


<!--Identifiers--> <!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number =
| CAS_number = 78281-72-8
| ATC_prefix = S01
| ATC_suffix = BC10
| ATC_supplemental =
| PubChem = 151075 | PubChem = 151075
| IUPHAR_ligand = 7564
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB06802 | DrugBank = DB06802
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| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D05143 | KEGG = D05143
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 75922
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1021 | ChEMBL = 1021


<!--Chemical data--> <!--Chemical data-->
| IUPAC_name = 2-amino-3-benzoylbenzeneacetamide
| C=15 | H=14 | N=2 | O=2
| C=15 | H=14 | N=2 | O=2
| molecular_weight = 254.28 ]/]
| smiles = O=C(c1cccc(c1N)CC(=O)N)c2ccccc2 | SMILES = O=C(c1cccc(c1N)CC(=O)N)c2ccccc2
| InChI = 1/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)
| InChIKey = QEFAQIPZVLVERP-UHFFFAOYAP
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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) | StdInChI = 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)
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}} }}


'''Nepafenac''' is a ] (NSAID), usually sold as a ] ] (0.1% solution. Nepafenac is manufactured by ] as '''Nevanac'''. It is used to treat pain and inflammation associated with cataract surgery. '''Nepafenac''', sold under the brand name '''Nevanac''' among others, is a ] (NSAID), usually sold as a ] ] 0.1% solution (Nevanac) or 0.3% solution (Ilevro). It is used to treat pain and inflammation associated with ] surgery.<ref name="Drugs.com">Nepafenac {{drugs.com|monograph|nepafenac}}</ref> Nepafenac is a ] of ], an inhibitor of ] and ] activity.<ref>Drugbank: </ref><ref>{{cite journal | vauthors = Zanetti FR, Fulco EA, Chaves FR, da Costa Pinto AP, Arieta CE, Lira RP | title = 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 | journal = Indian Journal of Ophthalmology | volume = 60 | issue = 4 | pages = 277–81 | date = July 2012 | pmid = 22824596 | pmc = 3442462 | doi = 10.4103/0301-4738.98705 | doi-access = free }}</ref>

==Medical uses==

Nepafenac is indicated for use in the treatment of pain and inflammation following cataract surgery.<ref name = "Drugs.com" /><ref name="Nevanac Package Insert">{{cite web | title=Nevanac- nepafenac suspension/ drops | website=DailyMed | date=9 September 2019 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=3ad48650-75e3-4c74-9302-01b0088f164e | access-date=6 July 2020}}</ref><ref name="Ilevro Package Insert">{{cite web | title=Ilevro- nepafenac suspension | website=DailyMed | date=9 September 2019 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=6c212466-ff8d-ecfc-ede2-ef8bdcaaf114 | access-date=6 July 2020}}</ref><ref name="Nevanac EPAR" />

In the European Union nepafenac is also indicated for the reduction in the risk of postoperative ] associated with cataract surgery in people with diabetes.<ref name="Nevanac EPAR">{{cite web | title=Nevanac EPAR | website=] (EMA) | date=17 September 2018 | url=https://www.ema.europa.eu/en/medicines/human/EPAR/nevanac | access-date=6 July 2020}}</ref>

==Pharmacology==

===Mechanism of action===

Nepafenac is an NSAID, thought to be a prodrug of amfenac after conversion by ocular tissue hydrolases after penetration via the ].<ref name ="Nevanac Package Insert" /><ref name = "Ilevro Package Insert" /> Amfenac, like other NSAIDs, is thought to inhibit ] action.<ref name ="Nevanac Package Insert" /><ref name = "Ilevro Package Insert" />

==Adverse events==

] include headache; runny nose; pain or pressure in the face; nausea; vomiting; and dry, itchy, sticky eyes.<ref name="Medline Nepafenac">{{cite web|title=Nepafenac Ophthalmic|url=https://medlineplus.gov/druginfo/meds/a606007.html|website=MedlinePlus|publisher=U.S. National Library of Medicine|access-date=October 31, 2017}}</ref> Serious side effects include red or bloody eyes; foreign body sensation in the eye; sensitivity to light; decreased ]; seeing specks or spots; teary eyes; or eye discharge or crusting.<ref name = "Medline Nepafenac" />

==Regulatory==

===Nevanac===

On February 25, 2005, Alcon filed a ] (NDA) with the U.S. ] (FDA) for Nevanac 0.1%.<ref name="Nevanac Approval">{{cite web|title=Nevanac Approval Package|url=https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/021862s000_Nevanac_approv.pdf|website=U.S. ] (FDA)|access-date=October 31, 2017}}</ref> Results from the two trials referenced in the NDA (Phase 2/3 study C-02-53; Phase 3 study C-03-32) have not been published.<ref name="Topical Opthalmic NSAIDS">{{cite journal | vauthors = Gaynes BI, Onyekwuluje A | title = Topical ophthalmic NSAIDs: a discussion with focus on nepafenac ophthalmic suspension | journal = Clinical Ophthalmology | volume = 2 | issue = 2 | pages = 355–68 | date = June 2008 | pmid = 19668727 | pmc = 2693998 | doi = 10.2147/opth.s1067 | doi-access = free }}</ref> Study C-02-53 consisted of 228 patients across 10 centers in the United States.<ref name="Nevanac Stat Review">{{cite web|title=Nevanac Statistical Review|url=https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/021862s000_Nevanac_statr.pdf|website=U.S. ] (FDA)|access-date=October 31, 2017}}</ref> Study C-03-32 consisted of 522 patients across 22 centers in the United States.<ref name = "Nevanac Stat Review" /> The efficacy results presented were confirmed in a study published in 2007.<ref>{{cite journal | vauthors = Lane SS, Modi SS, Lehmann RP, Holland EJ | title = Nepafenac ophthalmic suspension 0.1% for the prevention and treatment of ocular inflammation associated with cataract surgery | journal = Journal of Cataract and Refractive Surgery | volume = 33 | issue = 1 | pages = 53–8 | date = January 2007 | pmid = 17189793 | doi = 10.1016/j.jcrs.2006.08.043 | s2cid = 38881826 }}</ref>

Nevanac was approved by the FDA on August 19, 2005, with application number 021–862.<ref name="Nevanac DAP">{{cite web|title=Drug Approval Package: Nevanac (Nepafenac) Ophthalmic Suspension NDA #021862|url=https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/021862s000_NevanacTOC.cfm|website=U.S. ] (FDA)|access-date=October 27, 2017|date=January 6, 2005 }}</ref>

===Ilevro===

An NDA for Ilevro was filed on December 15, 2011.<ref name="Ilevro Approval">{{cite web|title=Ilevro Approval Package|url=https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/203491Orig1s000Approv.pdf|website=U.S. ] (FDA)|access-date=October 31, 2017}}</ref> In a one-month study, no new toxicities arose in the new formulation of nepafenac.<ref name="Ilevro PC Review">{{cite web|title=203491 Pharmacology Review|url=https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/203491Orig1s000PharmR.pdf|website=U.S. ] (FDA)|access-date=October 31, 2017}}</ref> Safety and efficacy information was derived from the previous Nevanac application.<ref name = "Ilevro PC Review" /> In June 2010, a confirmatory study began (Study C09055) consisting of over 2000 patients from 49 US sites and 37 European sites.<ref name="Ilevro Stat Review">{{cite web|title=Ilevro Statistical Review|url=https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/203491Orig1s000StatR.pdf|website=U.S. ] (FDA)|access-date=October 31, 2017}}</ref><ref name="Ilevro CT 1">{{cite journal|title=Confirmatory Study Nepafenac 0.3%|url=https://clinicaltrials.gov/ct2/show/NCT01109173|website=ClinicalTrials.gov|date=29 November 2012 |publisher=U.S. National Library of Medicine|access-date=October 31, 2017}}</ref> A second phase 3 trial (Study C11003) was conducted in a population of 1,342 patients at 37 sites across the United States which failed to demonstrate superiority over Nevanac in an altered dosing regimen.<ref name = "Ilevro Stat Review" />

Ilevro was approved by the FDA on October 16, 2012, with application number 203–491.<ref name="Ilevro DAP">{{cite web|title=Drug Approval Package: Nepafenac Ophthalmic Suspension, 0.3% NDA #203491|url=https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/203491_nepafenac_toc.cfm|website=U.S. ] (FDA)|access-date=October 27, 2017|date=April 8, 2013}}</ref>

==Commercialization==

Both Nevanac and Ilevro are manufactured and sold by ], Inc.<ref name = "Nevanac Package Insert" /><ref name = "Ilevro Package Insert" /> Alcon is currently a division of ] International AG, which is primarily based out of Switzerland.<ref name="Novartis About Us">{{cite web|title=About Us|url=https://www.novartis.com/about-us|website=Novartis|access-date=October 27, 2017}}</ref> Alcon, Inc. also holds locations in both Switzerland and the United States.<ref name="Nevanac Correspondence">{{cite web|title=Nevanac Administrative Documents and Correspondence|url=https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/021862s000_Nevanac_admincorres.pdf|website=U.S. ] (FDA)|access-date=October 27, 2017}}</ref> The company has gone through several name changes, from Alcon Laboratories, Inc. to Alcon Universal, Ltd., to Alcon, Inc.<ref name = "Nevanac Correspondence" />

Nevanac entered the market in 2005 as a product of Alcon, at the time a subsidiary of Nestlé.<ref name="Alcon 2010 20F">{{cite web|title=Alcon Annual Report 2010|url=https://www.sec.gov/Archives/edgar/data/1167379/000116737911000037/acl20f2010.pdf|website=SEC EDGAR|publisher=United States Securities and Exchange Commission|access-date=October 30, 2017}}</ref> On April 6, 2008, Novartis agreed to purchase approximately 74 million shares of Alcon from Nestlé at $143.18 per share.<ref name = "Alcon 2010 20F" /> On January 4, 2010, Novartis agreed to purchase all remaining shares of Alcon from Nestlé, totalling 156 million shares or 77% of the shares in the company.<ref name = "Alcon 2010 20F" /> At the time of the purchase, a proposal for a merger under Swiss merger law was given to the Alcon board of directors.<ref name = "Alcon 2010 20F" /> The merger was agreed upon on December 15, 2010, making Alcon "the second largest division within Novartis."<ref name = "Alcon 2010 20F" /> The merger was completed on April 8, 2011.<ref name="Alcon Form 15">{{cite web|title=Alcon Form 15|url=https://www.sec.gov/Archives/edgar/data/1167379/000110465911021611/a11-7954_41512b.htm|website=SEC EDGAR|publisher=United States Securities and Exchange Commission|access-date=October 30, 2017}}</ref>

Ilevro was launched by Alcon on January 21, 2013.<ref name="Ilevro Launch">{{cite web|title=Alcon Launches ILEVRO™ (nepafenac ophthalmic suspension) 0.3%, a New Non-Steroidal Anti-Inflammatory Drug, for the Treatment of Pain and Inflammation Associated with Cataract Surgery|url=https://www.alcon.com/news/media-releases/alcon-launches-ilevro-nepafenac-ophthalmic-suspension-03-new-non-steroidal-anti|website=Alcon|access-date=October 30, 2017|archive-date=December 15, 2018|archive-url=https://web.archive.org/web/20181215122150/https://www.alcon.com/news/media-releases/alcon-launches-ilevro-nepafenac-ophthalmic-suspension-03-new-non-steroidal-anti|url-status=dead}}</ref> In 2014 and 2015, net sales by Alcon grew, contributed to in part by the increased volume in sales of Ilevro.<ref name="2013 20F">{{cite web|title=Form 20-F|url=https://www.sec.gov/Archives/edgar/data/1114448/000104746914000415/a2217883z20-f.htm|website=SEC EDGAR|publisher=United States Securities and Exchange Commission|access-date=October 30, 2017}}</ref><ref name="2014 20F">{{cite web|title=Form 20-F|url=https://www.sec.gov/Archives/edgar/data/1114448/000104746915000433/a2222787z20-f.htm|website=SEC EDGAR|publisher=United States Securities and Exchange Commission|access-date=October 30, 2017}}</ref><ref name="2015 20F">{{cite web|title=Form 20F|url=https://www.sec.gov/Archives/edgar/data/1114448/000104746916009872/a2227040z20-f.htm|website=SEC EDGAR|publisher=United States Securities and Exchange Commission|access-date=October 30, 2017}}</ref> That financial year, Novartis reported $18 billion in total financial debt.<ref name = "2013 20F" /> That figure has grown steadily since. In 2016, Novartis reported a total debt of $23.8 billion,<ref name="2016 20F">{{cite web|title=Form 20-F|url=https://www.sec.gov/Archives/edgar/data/1114448/000104746917000338/a2230622z20-f.htm|website=SEC EDGAR|publisher=United States Securities and Exchange Commission|access-date=October 31, 2017}}</ref> up from the $21.9 billion reported in 2015 <ref name = "2015 20F" /> and the $20.4 billion reported in 2014.<ref name = "2014 20F" /> As of May 2017, Novartis is estimated to be worth $193.2 billion.<ref name="Novartis Forbes">{{cite web|title=Novartis on the Forbes Top Multinational Performers List|url=https://www.forbes.com/companies/novartis/|website=Forbes|access-date=October 31, 2017}}</ref>

On January 27, 2016, Alcon was moved to become a branch of the Innovative Medicines Division at Novartis.<ref name = "2016 20F" /> Early in 2016, Alcon formed agreements with both TrueVision and PowerVision, and acquired Transcend Medical.<ref name = "2016 20F" /> As of January 2017, Novartis is weighing options for Alcon in the business structure.<ref name = "2016 20F" />

===Commercial risks===

Alcon faced declining growth in 2016, having faced challenges in development and marketing of new products.<ref name = "2016 20F" />

===Marketing===

Novartis maintains a detailing unit geared toward health professionals consisting of over 3,000 employees within the United States and an additional 21,000 worldwide.<ref name = "2016 20F" /> Novartis is also seeking to expand direct-to-consumer advertising and entrance into specialty product markets.<ref name = "2016 20F" /> Novartis also notes the influence of position and preference on US Centers for Medicare & Medicaid formularies in expanding their market value.<ref name = "2016 20F" />

Nepafenac, Nevanac, and Ilevro are all absent from the 2016 Annual Report issued from Novartis.<ref name = "2016 20F" />

===Intellectual property===

There are currently{{when|date=July 2020}} seven U.S. patents filed that are directly associated with the modernized formulations of nepafenac, all stemming from Novartis.<ref name="PharmaCompass">{{cite web|title=Nepafenac|url=https://www.pharmacompass.com/patent-expiry-expiration/nepafenac|website=U.S. Patents|publisher=PharmaCompass|access-date=October 30, 2017}}</ref> There are three patents associated with Nevanac that are still{{when|date=July 2020}} active<ref name="Nevanac Patent Count">{{cite web|title=Generic Nevanac Availability|url=https://www.drugs.com/availability/generic-nevanac.html|website=Drugs.com|access-date=October 31, 2017}}</ref> and four associated with Ilevro.<ref name="Ilevro Patent Count">{{cite web|title=Generic Ilevro Availability|url=https://www.drugs.com/availability/generic-ilevro.html|website=Drugs.com|access-date=October 31, 2017}}</ref> The earliest patent related to the modern formulations of nepafenac was approved on June 11, 2002, after being filed in 1999, by Bahram Asgharian.<ref name="Asgharian Patent">{{cite web|title=United States Patent Application: 6403609|url=http://patft.uspto.gov/netacgi/nph-Parser?Sect2=PTO1&Sect2=HITOFF&p=1&u=/netahtml/PTO/search-bool.html&r=1&f=G&l=50&d=PALL&RefSrch=yes&Query=PN/6403609|website=United States Patent and Trademark Office|access-date=October 31, 2017}}</ref> A patent was filed by Warren Wong, associated with Alcon, Inc. based out of ], on December 2, 2005, for aqueous suspensions of nepafenac.<ref name="Wong Nepafenac PTO">{{cite web|title=United States Patent Application: 0060122277|url=http://appft1.uspto.gov/netacgi/nph-Parser?Sect1=PTO1&Sect2=HITOFF&d=PG01&p=1&u=/netahtml/PTO/srchnum.html&r=1&f=G&l=50&s1=20060122277.PGNR.|website=United States Patent and Trademark Office|access-date=October 30, 2017}}</ref> Another patent for a nepafenac-based drug was filed on May 8, 2006, by Geoffrey Owen, Amy Brooks, and Gustav Graff.<ref name="Nepafenac PTO">{{cite web|title=United States Patent Application: 0060257487|url=http://appft1.uspto.gov/netacgi/nph-Parser?Sect1=PTO1&Sect2=HITOFF&d=PG01&p=1&u=/netahtml/PTO/srchnum.html&r=1&f=G&l=50&s1=20060257487.PGNR.|website=United States Patent and Trademark Office|access-date=October 27, 2017}}</ref> A patent was filed by Masood A. Chowhan and Huagang Chen on February 9, 2007, and approved on May 24, 2011,<ref name="Chowhan Chen Patent">{{cite web|title=United States Patent: 7947295|url=http://patft.uspto.gov/netacgi/nph-Parser?Sect2=PTO1&Sect2=HITOFF&p=1&u=/netahtml/PTO/search-bool.html&r=1&f=G&l=50&d=PALL&RefSrch=yes&Query=PN/7947295|website=United States Patent and Trademark Office|access-date=October 31, 2017}}</ref> followed closely by a patent filed by Warren Wong on September 23, 2010, and approved on December 6, 2011.<ref name="Wong Patent 2">{{cite web|title=United States Patent: 8071648|url=http://patft.uspto.gov/netacgi/nph-Parser?Sect2=PTO1&Sect2=HITOFF&p=1&u=/netahtml/PTO/search-bool.html&r=1&f=G&l=50&d=PALL&RefSrch=yes&Query=PN/8071648|website=United States Patent and Trademark Office|access-date=October 31, 2017}}</ref> Masood A. Chowhan, Malay Ghosh, Bahram Asgharian, and Wesley Wehsin Han filed another patent on December 1, 2010, and approved on December 30, 2014.<ref name="Chowhan et al Patent">{{cite web|title=United States Patent: 8921337|url=http://patft.uspto.gov/netacgi/nph-Parser?Sect2=PTO1&Sect2=HITOFF&p=1&u=/netahtml/PTO/search-bool.html&r=1&f=G&l=50&d=PALL&RefSrch=yes&Query=PN/8921337|website=United States Patent and Trademark Office|access-date=October 31, 2017}}</ref> The most recent{{when|date=July 2020}} patent was filed by Masood A. Chowhan, Malay Ghosh, Bahram Asgharian, and Wesley Weshin Han on November 12, 2014, and approved on May 30, 2017.<ref name="Chowhan et. al. 2">{{cite web|title=United States Patent: 9662398|url=http://patft.uspto.gov/netacgi/nph-Parser?Sect2=PTO1&Sect2=HITOFF&p=1&u=/netahtml/PTO/search-bool.html&r=1&f=G&l=50&d=PALL&RefSrch=yes&Query=PN/9662398|website=United States Patent and Trademark Office|access-date=October 31, 2017}}</ref> These patents are in effect until dates ranging between July 17, 2018, and March 31, 2032.<ref name = "Ilevro Patent Count" />


Novartis also maintains patents on nepafenac in 26 countries outside the United States.<ref name="Worldwide Patent Count">{{cite web|title=Nepafenac - Generic Drug Details|url=https://www.drugpatentwatch.com/p/generic-api/nepafenac|website=DrugPatentWatch|publisher=thinkBiotech LLC|access-date=October 31, 2017}}</ref>
The usual dose is 1 drop in each affected eye beginning 1 day prior to cataract surgery, continued on the day of surgery and through the first 2 weeks of the postoperative period.


== References ==
Its ] may include decreased visual acuity, a feeling that something is in the eye, increased eye pressure or a sticky sensation, as well as other effects.
{{reflist}}


== External links == == External links ==
* {{cite web | url = https://druginfo.nlm.nih.gov/drugportal/name/nepafenac | publisher = U.S. National Library of Medicine | work = Drug Information Portal | title = Nepafenac }}
*


{{NSAIDs}} {{NSAIDs}}
{{Portal bar | Medicine}}


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