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MedKoo Cat#: 464711 | Name: Nepafenac-d5
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Nepafenac-d5 is intended for use as an internal standard for the quantification of nepafenac by GC- or LC-MS. Nepafenac is a prodrug form of amfenac, a non-steroidal anti-inflammatory drug (NSAID) and an inhibitor of COX-1 and COX-2. Nepafenac is an inhibitor of prostaglandin (PG) synthase 1 (IC50 = 64.3 µM) that inhibits the production of PGs in isolated rabbit iris/ciliary body. It also reduces protein and PGE2 (Item No. 14010) accumulation in a rabbit model of acute ocular inflammation when applied topically at a concentration of 0.1% prior to paracentesis. Formulations containing nepafenac have been used in the treatment of pain and inflammation associated with cataract surgery.

Chemical Structure

Nepafenac-d5
Nepafenac-d5
CAS#1246814-53-8

Theoretical Analysis

MedKoo Cat#: 464711

Name: Nepafenac-d5

CAS#: 1246814-53-8

Chemical Formula: C15H9D5N2O2

Exact Mass: 259.1369

Molecular Weight: 259.32

Elemental Analysis: C, 69.48; H, 7.38; N, 10.80; O, 12.34

Price and Availability

Size Price Availability Quantity
1mg USD 550.00 2 Weeks
5mg USD 1,250.00 2 Weeks
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Related CAS #
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Synonym
Nepafenac-d5; Nepafenac d5; AHR 9434-d5; AHR9434-d5; AHR-9434-d5; AL 6515-d5; AL6515-d5; AL-6515-d5;
IUPAC/Chemical Name
2-(2-amino-3-(benzoyl-d5)phenyl)acetamide
InChi Key
QEFAQIPZVLVERP-XFEWCBMOSA-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)/i1D,2D,3D,5D,6D
SMILES Code
O=C(C1=C(N)C(CC(N)=O)=CC=C1)C2=C(C([2H])=C(C([2H])=C2[2H])[2H])[2H]
Appearance
Solid powder
Purity
>99% (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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Nepafenac-d5 is the deuterium labeled Nepafenac, which 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/
Solvent mg/mL mM
Solubility
DMSO 100.0 385.62
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 259.32 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.
1: Donnenfeld ED, Solomon KD, Holland EJ. Reply to comment on: Safety and efficacy of a nepafenac punctal plug delivery system in controlling postoperative ocular pain and inflammation after cataract surgery. J Cataract Refract Surg. 2021 Jan 1;47(1):143-144. doi: 10.1097/j.jcrs.0000000000000515. PMID: 33901099. 2: Grzybowski A, Brona P. Comment on: Safety and efficacy of a nepafenac punctal plug delivery system in controlling postoperative ocular pain and inflammation after cataract surgery. J Cataract Refract Surg. 2021 Jan 1;47(1):143. doi: 10.1097/j.jcrs.0000000000000514. PMID: 33901098. 3: Mandelcorn ED, Al-Falah M, Zhao LD, Kertes P, Devenyi R, Lam WC. A prospective randomized clinical trial comparing nepafenac, intravitreal triamcinolone and no adjuvant therapy for epiretinal membrane. Acta Ophthalmol. 2021 Apr 12. doi: 10.1111/aos.14873. Epub ahead of print. PMID: 33847066. 4: Shrivastava AK, Nayak S, Anto M. Efficacy of Nepafenac versus Flurbiprofen in Maintaining Intraoperative Mydriasis During Phacoemulsification: A Comparative Study. Clin Ophthalmol. 2021 Mar 9;15:1085-1093. doi: 10.2147/OPTH.S303480. PMID: 33727791; PMCID: PMC7955764. 5: Howaidy A, Eldaly ZH, Anis M, Othman TM. Prophylaxis of macular edema after cataract surgery in diabetic patients, topical Nepafenac versus intravitreal Ranibizumab. Eur J Ophthalmol. 2021 Mar 16:11206721211001275. doi: 10.1177/11206721211001275. Epub ahead of print. PMID: 33726537. 6: Gumaste P, Vairagyam R. Blurring of vision as the only symptom in an undiagnosed case of chronic myeloid leukemia in the COVID-19 era. Indian J Ophthalmol. 2021 Mar;69(3):768-769. doi: 10.4103/ijo.IJO_3629_20. PMID: 33595523; PMCID: PMC7942071. 7: Nagai N. [Ocular Drug Delivery System-based on Solid Nanoparticles]. Yakugaku Zasshi. 2021;141(1):47-53. Japanese. doi: 10.1248/yakushi.20-00177-3. PMID: 33390447. 8: Tapia Quijada HE, Quijada Fumero E, Mesa Lugo FI, Serrano García M, Betancor Caro N. Nepafenac for cystoid macular oedema secondary to paclitaxel. Arch Soc Esp Oftalmol. 2020 Dec 25:S0365-6691(20)30435-4. English, Spanish. doi: 10.1016/j.oftal.2020.10.014. Epub ahead of print. PMID: 33372000. 9: Şahin AK, Kükner AŞ, Ulaş F, Doğan Ü. Effect of nepafenac 0.1% on retinal thickness after cataract surgery in patients without risk factors for cystoid macular edema. Int J Ophthalmol. 2020 Dec 18;13(12):1901-1907. doi: 10.18240/ijo.2020.12.09. PMID: 33344188; PMCID: PMC7708356. 10: Cevher S, Aydoğdu G. How does nepafenac affect the choroidal thickness after uneventful cataract surgery? Eur J Ophthalmol. 2020 Nov 29:1120672120976041. doi: 10.1177/1120672120976041. Epub ahead of print. PMID: 33251832. 11: Saakyan SV, Tsygankov АY, Moiseeva NI, Karamysheva АF, Garri DD. Assessment of the Chemosensitivity of Uveal Melanoma Cells Ex Vivo. Bull Exp Biol Med. 2020 Nov;170(1):142-147. doi: 10.1007/s10517-020-05020-3. Epub 2020 Nov 24. PMID: 33231795. 12: Giarmoukakis AK, Blazaki SV, Bontzos GC, Plaka AD, Seliniotakis KN, Ioannidi LD, Tsilimbaris MK. Efficacy of Topical Nepafenac 0.3% in the Management of Postoperative Cystoid Macular Edema. Ther Clin Risk Manag. 2020 Nov 6;16:1067-1074. doi: 10.2147/TCRM.S271184. PMID: 33192068; PMCID: PMC7654537. 13: Katsanos A, Gorgoli K, Asproudis I, Stefaniotou M. Recurrent Vitreomacular Traction in a Patient Treated with Ocriplasmin: A Case Report. Ophthalmol Ther. 2021 Mar;10(1):187-192. doi: 10.1007/s40123-020-00316-z. Epub 2020 Oct 27. PMID: 33108639; PMCID: PMC7886937. 14: Kendre PN, Kadam PD, Jain SP, Vibhute SK, Pote AK. Design, fabrication, and characterization of graft co-polymer assisted ocular insert: a state of art in reducing post-operative pain. Drug Dev Ind Pharm. 2020 Dec;46(12):1988-1999. doi: 10.1080/03639045.2020.1833908. Epub 2020 Oct 15. PMID: 33026260. 15: Cagini C, Pellegrino A, Iannone A, Cerquaglia A, Modugno A, Fiore T, Messina M. Comparison of anti-inflammatory effects of eye drops formulations after uncomplicated cataract surgery. Ther Adv Ophthalmol. 2020 Sep 21;12:2515841420924304. doi: 10.1177/2515841420924304. PMID: 33015542; PMCID: PMC7509714. 16: Aaronson A, Achiron A, Tuuminen R. Clinical Course of Pseudophakic Cystoid Macular Edema Treated with Nepafenac. J Clin Med. 2020 Sep 21;9(9):3034. doi: 10.3390/jcm9093034. PMID: 32967137; PMCID: PMC7563612. 17: Lo KJ, Ko YC, Hwang DK, Liu CJ. The influence of topical non-steroidal anti- inflammatory drugs on the intraocular pressure lowering effect of topical prostaglandin analogues-A systemic review and meta-analysis. PLoS One. 2020 Sep 14;15(9):e0239233. doi: 10.1371/journal.pone.0239233. PMID: 32925955; PMCID: PMC7489511. 18: Donnenfeld ED, Holland EJ, Solomon KD. Safety and efficacy of nepafenac punctal plug delivery system in controlling postoperative ocular pain and inflammation after cataract surgery. J Cataract Refract Surg. 2021 Feb 1;47(2):158-164. doi: 10.1097/j.jcrs.0000000000000414. PMID: 32925651. 19: Ching G, Covello AT, Bae SS, Holland S, McCarthy M, Ritenour R, Iovieno A, Yeung SN. Incidence and Outcomes of Cystoid Macular Edema after Descemet Membrane Endothelial Keratoplasty (DMEK) and DMEK Combined with Cataract Surgery. Curr Eye Res. 2021 May;46(5):678-682. doi: 10.1080/02713683.2020.1818260. Epub 2020 Sep 9. PMID: 32865037. 20: Gayam K, Ramulu PY, Rengaraj V, Srinivasan K. Safety and Efficacy of 0.1% Nepafenac versus 1% Prednisolone Acetate Eye Drops after Laser Peripheral Iridotomy: A Prospective, Randomized Trial. Ophthalmol Glaucoma. 2020 May- Jun;3(3):174-180. doi: 10.1016/j.ogla.2020.02.006. Epub 2020 Feb 29. PMID: 32672612.