nepafenac   Click here for help

GtoPdb Ligand ID: 7564

Synonyms: AHR-9434 | AL-6515 | Nevanac®
Approved drug
nepafenac is an approved drug (FDA (2005), EMA (2007))
Compound class: Synthetic organic
Comment: Nepafenac is a non-steroidal anti-inflammatory drug (NSAID).
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2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 4
Topological polar surface area 86.18
Molecular weight 254.11
XLogP 1.89
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES NC(=O)Cc1cccc(c1N)C(=O)c1ccccc1
Isomeric SMILES NC(=O)Cc1cccc(c1N)C(=O)c1ccccc1
InChI 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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Gamache DA, Graff G, Brady MT, Spellman JM, Yanni JM. (2000)
Nepafenac, a unique nonsteroidal prodrug with potential utility in the treatment of trauma-induced ocular inflammation: I. Assessment of anti-inflammatory efficacy.
Inflammation, 24 (4): 357-70. [PMID:10850857]
2. Jones BM, Neville MW. (2013)
Nepafenac: an ophthalmic nonsteroidal antiinflammatory drug for pain after cataract surgery.
Ann Pharmacother, 47 (6): 892-6. [PMID:23715071]
3. Ke TL, Graff G, Spellman JM, Yanni JM. (2000)
Nepafenac, a unique nonsteroidal prodrug with potential utility in the treatment of trauma-induced ocular inflammation: II. In vitro bioactivation and permeation of external ocular barriers.
Inflammation, 24 (4): 371-84. [PMID:10850858]
4. Lane SS. (2006)
Nepafenac: a unique nonsteroidal prodrug.
Int Ophthalmol Clin, 46 (4): 13-20. [PMID:17060788]
5. Takahashi K, Saishin Y, Saishin Y, Mori K, Ando A, Yamamoto S, Oshima Y, Nambu H, Melia MB, Bingaman DP et al.. (2003)
Topical nepafenac inhibits ocular neovascularization.
Invest Ophthalmol Vis Sci, 44 (1): 409-15. [PMID:12506103]
6. Zanetti FR, Fulco EA, Chaves FR, da Costa Pinto AP, Arieta CE, Lira RP. (2012)
Effect of preoperative use of topical prednisolone acetate, ketorolac tromethamine, nepafenac and placebo, on the maintenance of intraoperative mydriasis during cataract surgery: a randomized trial.
Indian J Ophthalmol, 60 (4): 277-81. [PMID:22824596]