CAS 78281-72-8|2-(2-amino-3-benzoylphenyl)acetamide|Nepafenac|Nevanac|nepafenac|Amfenac amide|Nevanac|AHR 9434|AL 6515|2-Amino-3-benzoylbenzeneacetamide|2-amino-3-benzoylbenzeneacetamide|nepafenac|n...

General Information

Structure

Molecular Formula

C₁₅H₁₄N₂O₂

Molecular Mass

254.28386

Exact Mass

254.1055277

Charge

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)

InChIKey

QEFAQIPZVLVERP-UHFFFAOYSA-N

Canonic Smiles

NC(=O)Cc1cccc(c1N)C(=O)c1ccccc1

Isomeric Smiles

c1ccc(cc1)C(=O)c1c(c(ccc1)CC(=O)N)N

Calculated Properties

JChem

LogD (pH = 7.4)

2.08

LogD (pH = 5.5)

2.08

Log P

2.08

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

1.83

Polar Surface Area

86.18

Polarizability

26.56

Molar Refractivity

74.46

LOG S

-3.32

Data Source

Commercial Catalog

Academic Data

Data Source

Names and Identifiers

Synonyms

NepafenacAmfenac amideNevanacAHR 9434AL 65152-Amino-3-benzoylbenzeneacetamideAHR 94342-amino-3-benzoylbenzeneacetamidenepafenacAL 6515AL-6515AHR-9434

Brand Name

Nevanac

IUPAC Traditional name

nepafenac

IUPAC name

2-(2-amino-3-benzoylphenyl)acetamide

International Nonproprietary Name (INN)

nepafenacnepafenaconepafenacum

Names and Identifiers

Registration numbers

PubChem CID

151075

PubChem SID

16096791199443294164347474

CAS Number

78281-72-8

HMDB Database

HMDB0015678

PubMed Citation Links

1646661216529348229277372392867510850857206742591706078810850858219320142192694223715071

Wikipedia Title

Nepafenac

MetaboLights Database

MTBLS2406

ACToR Database

78281-72-8

Drug Central Database

CHEBI ID

CompTox Database

CHEMBL

Reaxys Registry

DrugBank ID

BindingDB Database

KEGG DRUG Database

SureChEMBL Database

Registration numbers

Properties

Safety Information

Storage Condition

-20°C

Refrigerator, Under Inert Atmosphere

MSDS Link

Download link

Product Information

Salt Data

Free Base

Certificate of Analysis

Download link

Physical Property

Solubility

DMSO

Methanol

Apperance

Light Yellow Solid

Melting Point

177-181°C

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

Selleck Chemicals

S1255

Research Area: Retinal oedema
Biological Activity:
Nepafenac is a non-steroidal anti-inflammatory drug (NSAID), usually sold as a prescription eye drop. It reduces pain and inflammation in the eyes. Nepafenac ophthalmic is used to reduce pain and swelling after cataract surgery. 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.

DrugBank

DB06802

Drug Groups

approved

Description

Nepafenac is a non-steroidal anti-inflammatory prodrug (NSAID) usually sold as a prescription eye drop. It is used to treat pain and inflammation associated with cataract surgery.

Indication

For the treatment of pain and inflammation associated with cataract surgery.

Pharmacology

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 TID 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.

Toxicity

Ocularly applied non-steroidal anti-inflammatory drugs may cause increased bleeding of ocular tissues (including hyphemas) in conjunction with ocular surgery.

Biotransformation

Nepafenac (prodrug) is deaminated to amfenac (active compound) in the ciliary body epithelium, retina, and choroid by intraocular hydrolases. Subsequently, amfenac undergoes extensive metabolism to more polar metabolites involving hydroxylation of the aromatic ring leading to glucuronide conjugate formation.

Absorption

Nepafenac rapidly cross the cornea (6 times faster than diclofenac in vitro).

Protein Binding

Amfenac has high affinity toward serum albumin proteins. In vitro, the percent bound to human albumin and human serum was 95.4% and 99.1% respectively.

Elimination

After oral administration of 14C-nepafenac to healthy volunteers, urinary excretion was found to be the major route of radioactivity elimination, accounting for approximately 85% of the dose, while fecal excretion represented approximately 6% of the dose. Nepafenac (prodrug) and amfenac (active compound) were not quantifiable in the urine.

References

• Gamache DA, Graff G, Brady MT, Spellman JM, Yanni JM: Nepafenac, a unique nonsteroidal prodrug with potential utility in the treatment of trauma-induced ocular inflammation: I. Assessment of anti-inflammatory efficacy. Inflammation. 2000 Aug;24(4):357-70. [Pubmed]

• Ke TL, Graff G, Spellman JM, Yanni JM: 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. 2000 Aug;24(4):371-84. [Pubmed]

• Lane SS, Modi SS, Lehmann RP, Holland EJ: Nepafenac ophthalmic suspension 0.1% for the prevention and treatment of ocular inflammation associated with cataract surgery. J Cataract Refract Surg. 2007 Jan;33(1):53-8. [Pubmed]

• Walters T, Raizman M, Ernest P, Gayton J, Lehmann R: In vivo pharmacokinetics and in vitro pharmacodynamics of nepafenac, amfenac, ketorolac, and bromfenac. J Cataract Refract Surg. 2007 Sep;33(9):1539-45. [Pubmed]

• Bucci FA Jr, Waterbury LD: Re: Pharmacokinetics and pharmacodynamics of nepafenac, amfenac, ketorolac, and bromfenac. J Cataract Refract Surg. 2008 Aug;34(8):1226; author reply 1226-7. [Pubmed]

• Summary Basis of Decision (SBD): NEVANAC. [Health Canada]

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

TRC

N390080

A non-steroidal anti-inflammatory with analgesic activity; selective COX-2 inhibitor. Prodrug of Amfenac.

ChEBI

CHEBI:75922

A monocarboxylic acid amide that is amfenac in which the carboxylic acid group has been converted into the corresponding carboxamide. It is a prodrug for amfenac, used in eye drops to treat pain and inflammation following cataract surgery.

Molecule Details

References

PubChem Literature

From Data Sources

• Bucci FA Jr, Waterbury LD: Re: Pharmacokinetics and pharmacodynamics of nepafenac, amfenac, ketorolac, and bromfenac. J Cataract Refract Surg. 2008 Aug;34(8):1226; author reply 1226-7. Pubmed

• Summary Basis of Decision (SBD): NEVANAC. Health Canada

• http://en.wikipedia.org/wiki/Nepafenac

• Lindstrom, R., et al.: Curr. Med. Res. Opin., 22, 397 (1990)

• Gamache, D.A., et al.: Inflammation, 24, 357 (1990)

• Walsh, D.A., et al.: J. Med. Chem., 33, 2296 (1990)

References

Bioactivity

PubChem BioAssay

Bioactivity

Navigation

General Information

Calculated Properties

• RDKit

• JChem

Data Source

• Commercial Catalog

• Academic Data

Names and Identifiers

• Synonyms

• Brand Name

• IUPAC Traditional name

• IUPAC name

• International Nonproprietary Name (INN)

Names and Identifiers

Registration numbers

• PubChem CID

• PubChem SID

• CAS Number

• HMDB Database

• PubMed Citation Links

• Wikipedia Title

• MetaboLights Database

• ACToR Database

• Drug Central Database

• CHEBI ID

• CompTox Database

• CHEMBL

• Reaxys Registry

• DrugBank ID

• BindingDB Database

• KEGG DRUG Database

• SureChEMBL Database

Registration numbers

Properties

• Safety Information

• Product Information

• Physical Property

Related Proteins

Molecular Spectra

Molecule Details

• Selleck Chemicals

• DrugBank

• TRC

• ChEBI

References

• PubChem Literature

• From Data Sources

Bioactivity

• PubChem BioAssay

Commercial Catalog

Synonyms

NepafenacAmfenac amideNevanacAHR 9434AL 65152-Amino-3-benzoylbenzeneacetamideAHR 94342-amino-3-benzoylbenzeneacetamidenepafenacAL 6515AL-6515AHR-9434

IUPAC Traditional name

nepafenac

IUPAC name

2-(2-amino-3-benzoylphenyl)acetamide

International Nonproprietary Name (INN)

nepafenacnepafenaconepafenacum

CAS Number

78281-72-8

HMDB Database

HMDB0015678

Wikipedia Title

Nepafenac

MetaboLights Database

MTBLS2406

ACToR Database

78281-72-8

Drug Central Database

CHEBI ID

CompTox Database

Reaxys Registry

BindingDB Database

KEGG DRUG Database

SureChEMBL Database

Safety Information

Storage Condition

-20°C

Refrigerator, Under Inert Atmosphere

MSDS Link

Download link

Product Information

Salt Data

Free Base

Certificate of Analysis

Download link

Physical Property

Solubility

DMSO

Methanol

Apperance

Light Yellow Solid

Melting Point

177-181°C

Selleck Chemicals

S1255

DrugBank

DB06802

Drug Groups

approved

Description

Nepafenac is a non-steroidal anti-inflammatory prodrug (NSAID) usually sold as a prescription eye drop. It is used to treat pain and inflammation associated with cataract surgery.

Indication

For the treatment of pain and inflammation associated with cataract surgery.

Pharmacology

Toxicity

Ocularly applied non-steroidal anti-inflammatory drugs may cause increased bleeding of ocular tissues (including hyphemas) in conjunction with ocular surgery.

Biotransformation

Absorption

Nepafenac rapidly cross the cornea (6 times faster than diclofenac in vitro).

Protein Binding

Amfenac has high affinity toward serum albumin proteins. In vitro, the percent bound to human albumin and human serum was 95.4% and 99.1% respectively.

Elimination

References

• Bucci FA Jr, Waterbury LD: Re: Pharmacokinetics and pharmacodynamics of nepafenac, amfenac, ketorolac, and bromfenac. J Cataract Refract Surg. 2008 Aug;34(8):1226; author reply 1226-7. [Pubmed]

• Summary Basis of Decision (SBD): NEVANAC. [Health Canada]

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

TRC

N390080

A non-steroidal anti-inflammatory with analgesic activity; selective COX-2 inhibitor. Prodrug of Amfenac.

ChEBI

CHEBI:75922

From Data Sources

• Bucci FA Jr, Waterbury LD: Re: Pharmacokinetics and pharmacodynamics of nepafenac, amfenac, ketorolac, and bromfenac. J Cataract Refract Surg. 2008 Aug;34(8):1226; author reply 1226-7. Pubmed

• Summary Basis of Decision (SBD): NEVANAC. Health Canada

• http://en.wikipedia.org/wiki/Nepafenac

• Lindstrom, R., et al.: Curr. Med. Res. Opin., 22, 397 (1990)

• Gamache, D.A., et al.: Inflammation, 24, 357 (1990)

• Walsh, D.A., et al.: J. Med. Chem., 33, 2296 (1990)

Molecule

ID:4479