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Nepafenac

Base Information Edit
  • Chemical Name:Nepafenac
  • CAS No.:78281-72-8
  • Molecular Formula:C15H14N2O2
  • Molecular Weight:254.288
  • Hs Code.:2924299090
  • European Community (EC) Number:682-241-7
  • UNII:0J9L7J6V8C
  • DSSTox Substance ID:DTXSID0048638
  • Nikkaji Number:J332.082K
  • Wikipedia:Nepafenac
  • Wikidata:Q684379
  • NCI Thesaurus Code:C66228
  • RXCUI:298665
  • Pharos Ligand ID:5PZ2K6SHFU3D
  • Metabolomics Workbench ID:43706
  • ChEMBL ID:CHEMBL1021
  • Mol file:78281-72-8.mol
Nepafenac

Synonyms:2-amino-3-benzoylbenzeneacetamide;nepafenac;Nevanac

Suppliers and Price of Nepafenac
Supply Marketing:Edit
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
  • TRC
  • Nepafenac
  • 50mg
  • $ 130.00
  • TCI Chemical
  • Nepafenac >98.0%(HPLC)(T)
  • 1g
  • $ 486.00
  • TCI Chemical
  • Nepafenac >98.0%(HPLC)(T)
  • 200mg
  • $ 139.00
  • Sigma-Aldrich
  • Nepafenac ≥98% (HPLC)
  • 10mg
  • $ 68.20
  • Sigma-Aldrich
  • Nepafenac ≥98% (HPLC)
  • 50mg
  • $ 264.00
  • DC Chemicals
  • Nepafenac >99%
  • 100 mg
  • $ 250.00
  • DC Chemicals
  • Nepafenac >99%
  • 1 g
  • $ 1000.00
  • Crysdot
  • Nepafenac 98+%
  • 100mg
  • $ 216.00
  • ChemScene
  • Nepafenac 95.14%
  • 25mg
  • $ 50.00
  • ChemScene
  • Nepafenac 95.14%
  • 100mg
  • $ 145.00
Total 167 raw suppliers
Chemical Property of Nepafenac Edit
Chemical Property:
  • Vapor Pressure:1.11E-12mmHg at 25°C 
  • Melting Point:177-181oC 
  • Refractive Index:1.641 
  • Boiling Point:562.5 °C at 760 mmHg 
  • Flash Point:294 °C 
  • PSA:86.18000 
  • Density:1.249 g/cm3 
  • LogP:2.80910 
  • Storage Temp.:Refrigerator 
  • Solubility.:DMSO: ≥5mg/mL 
  • Water Solubility.:0.014 mg/mL in water 
  • XLogP3:1.9
  • Hydrogen Bond Donor Count:2
  • Hydrogen Bond Acceptor Count:3
  • Rotatable Bond Count:4
  • Exact Mass:254.105527694
  • Heavy Atom Count:19
  • Complexity:337
Purity/Quality:

99% *data from raw suppliers

Nepafenac *data from reagent suppliers

Safty Information:
  • Pictogram(s):
  • Hazard Codes:
  • Statements: 50/53 
  • Safety Statements: 60-61 
MSDS Files:

SDS file from LookChem

Useful:
  • Canonical SMILES:C1=CC=C(C=C1)C(=O)C2=CC=CC(=C2N)CC(=O)N
  • Recent ClinicalTrials:Macular Edema Nepafenac vs. Difluprednate Uveitis Trial
  • Recent EU Clinical Trials:Non-steroidal anti-inflammatory medication in cataract surgery
  • Recent NIPH Clinical Trials:Factors related to dry eye after ocular surgery and its treatment.
  • Description Nepafenac, launched by Alcon Laboratories, is a topical ophthalmic medication indicated for the treatment of ocular pain and inflammation associated with cataract surgery. Nepafenac is a prodrug of amfenac, which is an NSAID and a potent non-selective inhibitor of COX-1 (IC50=0.25 μM)) and COX-2 (IC50=0.15μM). Nepefenac itself exhibits only weak activity against COX-1 (IC50=64.3μM). Amfenac (Fenazox) has been marketed in Japan since 1986 for the treatment of rheumatoid arthritis, post-surgical pain, and inflammation. With most NSAIDs that are currently being used as topical ophthalmic agents, the maximum drug concentration is achieved on the ocular surface, with progressively lower concentrations in the cornea, aqueous humor, vitreous, and retina. Nepafenac has been found to have a penetration coefficient that is 4-28 times greater than that achieved with conventional NSAIDs such as diclofenac, bromofenac, and ketorolac. In addition, the bioconversion of nepefenac to amfenac is primarily mediated by ocular tissue hydrolases, specifically in the iris, ciliary body, retina, and choroid. The enhanced permeability of nepefenac combined with rapid bioactivation in the ocular tissue translates into superior anti-inflammatory efficacy at the target sites.
  • Uses Nepafenac is a non-steroidal anti-inflammatory drug (NSAID), usually sold as a prescription eye drop. It reduces pain and inflammation in the eyes. Nepafenac ophthalmic is used to reduce pain and swelling after cataract surgery.
  • Clinical Use Nepafenac is a novel ophthalmic non-steroidal anti-inflammatory drug (NSAID), for the treatment of eye pain and inflammation caused by cataract surgery, compared with traditional NSAIDs, chemical structure of Nepafenac is conducive to make it rapidly penetrate the cornea and distribute to its target site, which is helpful to reduce the accumulation of the drug in the corneal surface and to reduce the incidence of complications of the eye surface, it has many advantages such as infiltration, targeting strong, little toxic side effects and so on. August 19, 2005 ,the US Food and Drug Administration (FDA) approved nepafenac ophthalmic suspension for the treatment of cataract surgery-related pain and inflammation, it is the first ophthalmic NSAID prodrug formulation approved for marketing. Nepafenac after ocular administration, can rapidly pass through the cornea , and under the action of eye tissue hydrolytic enzymes,it can become into ammonia diclofenac (a kind of NSAID); and ammonia diclofenac by inhibiting prostaglandin H synthase ( cyclooxygenase), can block prostaglandin synthesis to play its role as an anti-inflammatory analgesic. As is known, prostaglandin is one of the media causing ocular inflammation it can lead to blood-aqueous barrier crash, vasodilatation, increased vascular permeability and leukocyte chemotaxis, etc. In addition, prostaglandins can also control contraction of the iris sphincter through non-cholinergic mechanism which can trigger the miosis reaction during eye surgery and after surgery. After ocular administration of NSAIDs, it can inhibit prostaglandins synthesis in the iris, ciliary body and conjunctiva, so people can prevent eye inflammation, and reduce the associated pain.The above information is edited by the lookchem of Tian Ye.
Technology Process of Nepafenac

There total 4 articles about Nepafenac which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:
Guidance literature:
nickel; In tetrahydrofuran; water; at 20 ℃; for 0.166667h; Product distribution / selectivity;
Guidance literature:
Multi-step reaction with 2 steps
1: 1.) tert-butyl hypochlorite, 2.) triethylamine / 1.) CH2Cl2, THF, -60 deg C, 1 h, 2.) CH2Cl2, 5 min
2: 73 percent / Raney nickel / tetrahydrofuran / 0.25 h
With tert-butylhypochlorite; nickel; triethylamine; In tetrahydrofuran;
DOI:10.1021/jm00170a039
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