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SML0288

Sigma-Aldrich

Nepafenac

≥98% (HPLC)

Synonym(s):

2-Amino-3-benzoyl-benzeneacetamide, AHR 9434, AL 6515

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About This Item

Empirical Formula (Hill Notation):
C15H14N2O2
CAS Number:
78281-72-8
Molecular Weight:
254.28
MDL number:
MFCD08067732
UNSPSC Code:
12352200
PubChem Substance ID:
329825296
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

faintly yellow to dark yellow

solubility

DMSO: ≥5 mg/mL

storage temp.

room temp

SMILES string

NC(=O)Cc1cccc(c1N)C(=O)c2ccccc2

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)

InChI key

QEFAQIPZVLVERP-UHFFFAOYSA-N

Gene Information

human ... PTGS1(5742) , PTGS2(5743)

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Biochem/physiol Actions

Nepafenac is a NSAID (nonsteroidal anti inflammatory drug) that is routinely used in opthamology to control pain following cataract surgery.
Nepafenac, a prodrug of amfenac, is used in the treatment of diabetic retinopathy. It is metabolized to its active form through intraocular enzymatic hydrolysis. Nepafenac has a molecular weight of 254.28 kDa and effectively penetrates through the cornea. Its molecule structure enables nepafenac to possess better permeability. Nepafenac has a low inhibitory effect on cyclooxygenase.

Pictograms

Environment
GHS09

Signal Word

Warning

Hazard Statements

H410

Precautionary Statements

P273 - P391 - P501

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Retinal Pharmacotherapeutics: Retinal Pharmacotherapeutics (2015)
Topical administration of nepafenac inhibits diabetes-induced retinal microvascular disease and underlying abnormalities of retinal metabolism and physiology
Kern TS, et al.
Diabetes, 56(2), 373-379 (2007)
In vivo pharmacokinetics and in vitro pharmacodynamics of nepafenac, amfenac, ketorolac, and bromfenac
Walters T, et al.
Journal of Cataract and Refractive Surgery, 33(9), 1539-1545 (2007)
Eric Chen et al.
Clinical ophthalmology (Auckland, N.Z.), 4, 1249-1252 (2010-12-15)
The purpose of this study is to determine the efficacy of combining topical nepafenac with monthly intravitreal injections of ranibizumab or bevacizumab in the treatment of recalcitrant exudative macular degeneration. This was a retrospective, consecutive case series of patients with
Haley Shelley et al.
AAPS PharmSciTech, 19(6), 2554-2563 (2018-06-28)
Nepafenac is a nonsteroidal anti-inflammatory drug (NSAID), currently only available as 0.1% ophthalmic suspension (Nevanac®). This study utilized hydroxypropyl-β-cyclodextrin (HPBCD) to increase the water solubility and trans-corneal permeation of nepafenac. The nepafenac-HPBCD complexation in the liquid and solid states were

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