化合物信息

ID:4479

基本信息

化学结构

分子式

C₁₅H₁₄N₂O₂

分子量

254.28386

精确质量

254.1055277

电荷

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

计算属性

JChem

LogD (pH = 7.4)

2.08

LogD (pH = 5.5)

2.08

Log P

2.08

可自由旋转的化学键

质子供体

质子受体

里宾斯基五规则

true

Acid pKa

1.83

极化表面积

86.18

极化性

26.56

摩尔折射率

74.46

LOG S

-3.32

数据来源

产品目录

学术数据

数据来源

名称和标识

别名

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

商标名

Nevanac

IUPAC传统名

nepafenac

IUPAC标准名

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

国际非专利药品(INN)

nepafenacnepafenaconepafenacum

名称和标识

数据登录号

PubChem CID

151075

PubChem SID

16096791199443294164347474

CAS号

78281-72-8

HMDB数据库

HMDB0015678

PubMed文献链接

1646661216529348229277372392867510850857206742591706078810850858219320142192694223715071

维基百科标题

Nepafenac

MetaboLights数据库

MTBLS2406

ACToR数据库

78281-72-8

Drug Central Database

CHEBI ID

CompTox数据库

CHEMBL

Reaxys Registry

DrugBank ID

BindingDB数据库

KEGG DRUG Database

SureChEMBL数据库

数据登录号

化合物性质

安全信息

保存条件

-20°C

Refrigerator, Under Inert Atmosphere

MSDS下载

下载链接

产品相关信息

成盐信息

Free Base

质检报告

下载链接

理化性质

溶解度

DMSO

Methanol

外观

Light Yellow Solid

熔点

177-181°C

化合物性质

分子相关蛋白质

暂无数据

点击上传数据

分子图谱

暂无数据

点击上传数据

描述信息

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.

描述信息

参考文献

PubChem文献

数据源提供

• 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

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

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

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

参考文献

生物活性

PubChem BioAssay

生物活性

导航

基本信息

计算属性

• RDKit

• JChem

数据来源

• 产品目录

• 学术数据

名称和标识

• 别名

• 商标名

• IUPAC传统名

• IUPAC标准名

• 国际非专利药品(INN)

名称和标识

数据登录号

• PubChem CID

• PubChem SID

• CAS号

• HMDB数据库

• PubMed文献链接

• 维基百科标题

• MetaboLights数据库

• ACToR数据库

• Drug Central Database

• CHEBI ID

• CompTox数据库

• CHEMBL

• Reaxys Registry

• DrugBank ID

• BindingDB数据库

• KEGG DRUG Database

• SureChEMBL数据库

数据登录号

化合物性质

• 安全信息

• 产品相关信息

• 理化性质

分子相关蛋白质

分子图谱

描述信息

• Selleck Chemicals

• DrugBank

• TRC

• ChEBI

参考文献

• PubChem文献

• 数据源提供

生物活性

• PubChem BioAssay

别名

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

IUPAC传统名

nepafenac

IUPAC标准名

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

国际非专利药品(INN)

nepafenacnepafenaconepafenacum

HMDB数据库

维基百科标题

MetaboLights数据库

ACToR数据库

Drug Central Database

CHEBI ID

CompTox数据库

Reaxys Registry

BindingDB数据库

KEGG DRUG Database

SureChEMBL数据库

安全信息

保存条件

-20°C

Refrigerator, Under Inert Atmosphere

MSDS下载

下载链接

产品相关信息

成盐信息

Free Base

质检报告

下载链接

理化性质

溶解度

DMSO

Methanol

外观

Light Yellow Solid

熔点

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

数据源提供

• 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

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

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

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