Nepafenac
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MedKoo CAT#: 315231

CAS#: 78281-72-8

Description: Nepafenac is a non-steroidal anti-inflammatory drug (NSAID), usually sold as a prescription eye drop (0.1% solution. Nepafenac is manufactured by Alcon as Nevanac. It is used to treat pain and inflammation associated with cataract surgery. 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. Its side effects 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. (Source: http://en.wikipedia.org/wiki/Nepafenac).


Chemical Structure

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Nepafenac
CAS# 78281-72-8

Theoretical Analysis

MedKoo Cat#: 315231
Name: Nepafenac
CAS#: 78281-72-8
Chemical Formula: C15H14N2O2
Exact Mass: 254.10553
Molecular Weight: 254.28
Elemental Analysis: C, 70.85; H, 5.55; N, 11.02; O, 12.58

Price and Availability

Size Price Availability Quantity
500.0mg USD 150.0 2 Weeks
1.0g USD 250.0 2 Weeks
2.0g USD 450.0 2 Weeks
5.0g USD 950.0 2 Weeks
10.0g USD 1750.0 2 Weeks
20.0g USD 2950.0 2 Weeks
100.0g USD 5450.0 2 Weeks
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Synonym: AL 6515; AL6515; AL-6515; AHR 9434; AHR9434; AHR-9434; Nevanac; Nepafenac; Nevanac.

IUPAC/Chemical Name: 2-(2-amino-3-benzoylphenyl)acetamide

InChi Key: QEFAQIPZVLVERP-UHFFFAOYSA-N

InChi Code: 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)

SMILES Code: O=C(N)CC1=CC=CC(C(C2=CC=CC=C2)=O)=C1N

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO.

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 254.28 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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 1: Chen E, Benz MS, Fish RH, Brown DM, Wong TP, Kim RY, Major JC. Use of nepafenac (Nevanac) in combination with intravitreal anti-VEGF agents in the treatment of recalcitrant exudative macular degeneration requiring monthly injections. Clin Ophthalmol. 2010 Oct 28;4:1249-52. PubMed PMID: 21151329; PubMed Central PMCID: PMC2993124.

2: Yoon MK, Naseri A, Porco T, McLeod SD. Nepafenac-assisted mydriasis in a rabbit model. J Cataract Refract Surg. 2010 Oct;36(10):1779-82. Epub 2010 Jul 31. PubMed PMID: 20674259.

3: Warren KA, Bahrani H, Fox JE. NSAIDs in combination therapy for the treatment of chronic pseudophakic cystoid macular edema. Retina. 2010 Feb;30(2):260-6. PubMed PMID: 20175270.

4: Heier JS, Awh CC, Busbee BG, Waterbury LD, Daniel P, Stoller GL, Cleary TS. Vitreous nonsteroidal antiinflammatory drug concentrations and prostaglandin E2 levels in vitrectomy patients treated with ketorolac 0.4%, bromfenac 0.09%, and nepafenac 0.1%. Retina. 2009 Oct;29(9):1310-3. PubMed PMID: 19934822.

5: Yanni SE, Clark ML, Yang R, Bingaman DP, Penn JS. The effects of nepafenac and amfenac on retinal angiogenesis. Brain Res Bull. 2010 Feb 15;81(2-3):310-9. Epub 2009 Nov 6. PubMed PMID: 19897019; PubMed Central PMCID: PMC2815002.

6: Lal N, Kumar J, Erdahl WE, Pfeiffer DR, Gadd ME, Graff G, Yanni JM. Differential effects of non-steroidal anti-inflammatory drugs on mitochondrial dysfunction during oxidative stress. Arch Biochem Biophys. 2009 Oct 1;490(1):1-8. PubMed PMID: 19810214.

7: Nepafenac: new drug. After cataract surgery: just another NSAID eye drop. No better than other NSAID eye drops, and less convenient to use. Prescrire Int. 2009 Aug;18(102):156. PubMed PMID: 19743570.

8: Cervantes-Coste G, Sánchez-Castro YG, Orozco-Carroll M, Mendoza-Schuster E, Velasco-Barona C. Inhibition of surgically induced miosis and prevention of postoperative macular edema with nepafenac. Clin Ophthalmol. 2009;3:219-26. Epub 2009 Jun 2. PubMed PMID: 19668569; PubMed Central PMCID: PMC2708994.

9: Hariprasad SM, Akduman L, Clever JA, Ober M, Recchia FM, Mieler WF. Treatment of cystoid macular edema with the new-generation NSAID nepafenac 0.1%. Clin Ophthalmol. 2009;3:147-54. Epub 2009 Jun 2. PubMed PMID: 19668559; PubMed Central PMCID: PMC2709014.

10: Callanan D, Williams P. Topical nepafenac in the treatment of diabetic macular edema. Clin Ophthalmol. 2008 Dec;2(4):689-92. PubMed PMID: 19668417; PubMed Central PMCID: PMC2699803.

Nepafenac

500.0mg / USD 150.0


Additional Information

NEVANAC® (nepafenac ophthalmic suspension) 0.1% is a sterile, topical, nonsteroidal antiinflammatory (NSAID) prodrug for ophthalmic use. Each mL of NEVANAC ® suspension contains 1 mg of nepafenac. Nepafenac is designated chemically as 2-amino-3-benzoylbenzeneacetamide with an empirical formula of C15H14N2O2. Nepafenac is a yellow crystalline powder. The molecular weight of nepafenac is 254.28. NEVANAC®ophthalmic suspension is supplied as a sterile, aqueous 0.1% suspension with a pH approximately of 7.4. The osmolality of NEVANAC®ophthalmic suspension is approximately 305 mOsmol/kg. Each mL of NEVANAC® contains: Active: nepafenac 0.1% Inactives: mannitol, carbomer 974P, sodium chloride, tyloxapol, edetate disodium, benzalkonium chloride 0.005% (preservative), sodium hydroxide and/or hydrochloric acid to adjust pH and purified water, USP.

Mechanism of Action: After topical ocular dosing, nepafenac penetrates the cornea and is converted by ocular tissue hydrolases to amfenac, a nonsteroidal anti-inflammatory drug. Amfenac is thought to inhibit the action of prostaglandin H synthase (cyclooxygenase), an enzyme required for prostaglandin production.

Pharmacokinetics: Low but quantifiable plasma concentrations of nepafenac and amfenac were observed in the majority of subjects 2 and 3 hours postdose, respectively, following bilateral topical ocular three-times-daily dosing of nepafenac ophthalmic suspension, 0.1%. The mean steady-state Cmax for nepafenac and for amfenac were 0.310 ± 0.104 ng/ml and 0.422 ± 0.121 ng/ml, respectively, following ocular administration. Nepafenac at concentrations up to 300 ng/mL did not inhibit the in vitro metabolism of 6 specific marker substrates of cytochrome P450 (CYP) isozymes (CYP1A2, CYP2C9, CYP2C19, CYP2D6, CYP2E1, and CYP3A4). Therefore, drug-drug interactions involving CYP mediated metabolism of concomitantly administered drugs are unlikely. Drug-drug interactions mediated by protein binding are also unlikely.