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
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 315231
Name: Nepafenac
CAS#: 78281-72-8
Chemical Formula: C15H14N2O2
Exact Mass: 254.11
Molecular Weight: 254.289
Elemental Analysis: C, 70.85; H, 5.55; N, 11.02; O, 12.58

Price and Availability

Size Price Availability Quantity
500mg USD 150
1g USD 250
2g USD 450
5g USD 950
10g USD 1750
20g USD 2950
100g USD 5450
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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

More Info: 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.

Product Data:
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Biological target: Nepafenac(AHR 9434; AL 6515; Nevanac) is a selective COX-2 inhibitor.
In vitro activity: Nitric oxide production by macrophages was measured after exposure to melanoma-conditioned medium from both groups of cells as well as with and without Amfenac, the active metabolite of Nepafenac. The addition of Amfenac significantly decreased the proliferation rate of all cell lines. Nitric oxide production by macrophages was inhibited by the addition of melanoma conditioned medium, the addition of Amfenac partially overcame this inhibition. Reference: J Carcinog. 2007 Nov 27;6:17. https://pubmed.ncbi.nlm.nih.gov/18042295/
In vivo activity: The goal of this experiment was to investigate the efficiency of Nepafenac, a topically administered COX-2 inhibitor, in a rabbit model of UM (uveal melanoma). The control group developed more intraocular tumors and presented with metastases and higher detectable levels of CMCs before the treated group. Reference: Carcinogenesis. 2007 Sep;28(9):2053-8. https://pubmed.ncbi.nlm.nih.gov/17434930/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 30.0 117.98
DMSO 60.3 237.26
Ethanol 2.3 8.85

Preparing Stock Solutions

The following data is based on the product molecular weight 254.29 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
Formulation protocol: 1. Marshall JC, Caissie AL, Cruess SR, Cools-Lartigue J, Burnier MN Jr. The effects of a cyclooxygenase-2 (COX-2) expression and inhibition on human uveal melanoma cell proliferation and macrophage nitric oxide production. J Carcinog. 2007 Nov 27;6:17. doi: 10.1186/1477-3163-6-17. PMID: 18042295; PMCID: PMC2222223. 2. de Souza Filho JP, Correa ZM, Marshall JC, Anteka E, Coutinho AB, Martins MC, Burnier MN. The effect of a selective cyclooxygenase-2 (COX-2) inhibitor on the proliferation rate of retinoblastoma cell lines. Eye (Lond). 2006 May;20(5):598-601. doi: 10.1038/sj.eye.6701938. PMID: 16123787. 3. Marshall JC, Fernandes BF, Di Cesare S, Maloney SC, Logan PT, Antecka E, Burnier MN Jr. The use of a cyclooxygenase-2 inhibitor (Nepafenac) in an ocular and metastatic animal model of uveal melanoma. Carcinogenesis. 2007 Sep;28(9):2053-8. doi: 10.1093/carcin/bgm091. Epub 2007 Apr 13. PMID: 17434930. 4. Kapin MA, Yanni JM, Brady MT, McDonough TJ, Flanagan JG, Rawji MH, Dahlin DC, Sanders ME, Gamache DA. Inflammation-mediated retinal edema in the rabbit is inhibited by topical nepafenac. Inflammation. 2003 Oct;27(5):281-91. doi: 10.1023/a:1026024409826. PMID: 14635785.
In vitro protocol: 1. Marshall JC, Caissie AL, Cruess SR, Cools-Lartigue J, Burnier MN Jr. The effects of a cyclooxygenase-2 (COX-2) expression and inhibition on human uveal melanoma cell proliferation and macrophage nitric oxide production. J Carcinog. 2007 Nov 27;6:17. doi: 10.1186/1477-3163-6-17. PMID: 18042295; PMCID: PMC2222223. 2. de Souza Filho JP, Correa ZM, Marshall JC, Anteka E, Coutinho AB, Martins MC, Burnier MN. The effect of a selective cyclooxygenase-2 (COX-2) inhibitor on the proliferation rate of retinoblastoma cell lines. Eye (Lond). 2006 May;20(5):598-601. doi: 10.1038/sj.eye.6701938. PMID: 16123787.
In vivo protocol: 1. Marshall JC, Fernandes BF, Di Cesare S, Maloney SC, Logan PT, Antecka E, Burnier MN Jr. The use of a cyclooxygenase-2 inhibitor (Nepafenac) in an ocular and metastatic animal model of uveal melanoma. Carcinogenesis. 2007 Sep;28(9):2053-8. doi: 10.1093/carcin/bgm091. Epub 2007 Apr 13. PMID: 17434930. 2. Kapin MA, Yanni JM, Brady MT, McDonough TJ, Flanagan JG, Rawji MH, Dahlin DC, Sanders ME, Gamache DA. Inflammation-mediated retinal edema in the rabbit is inhibited by topical nepafenac. Inflammation. 2003 Oct;27(5):281-91. doi: 10.1023/a:1026024409826. PMID: 14635785.

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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.