Page last updated: 2024-12-04

amfenac

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

amfenac: RN given refers to parent cpd; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

amfenac : An oxo monocarboxylic acid that is benzophenone in which one of the phenyl groups is substituted by an amino group and a carboxymethyl group at position 2 and 3, respectively. The corresponding carboxamide, nepafenac, is a prodrug of amfenac and is used for the treatment of pain and inflammation following cataract surgery. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID2136
CHEMBL ID25146
CHEBI ID75915
SCHEMBL ID24249
MeSH IDM0062718

Synonyms (39)

Synonym
nsc-309467
51579-82-9
nsc309467
D07443
amfenac (inn)
amfenac
chebi:75915 ,
CHEMBL25146
(2-amino-3-benzoylphenyl)acetic acid
2-(2-amino-3-benzoylphenyl)acetic acid
amfenac [inn:ban]
nsc 309467
28o5c1j38a ,
amfenaco [inn-spanish]
amfenaco
amfenacum [inn-latin]
(2-amino-3-benzoylphenyl)essigsaeure
unii-28o5c1j38a
amfenacum
amfenac [inn]
amfenac [mi]
amfenac [who-dd]
2-amino-3-benzoylbenzeneacetic acid
gtpl7565
2-[2-amino-3-(benzoyl)phenyl]acetic acid
fenazox (japan)
AKOS022183018
SCHEMBL24249
SOYCMDCMZDHQFP-UHFFFAOYSA-N
2-amino-3-benzoylphenylacetic acid
DTXSID90199533
sr-01000944946
SR-01000944946-1
FT-0764816
Q4745976
bdbm50225110
SY265113
mfcd00866133
2-(2-amino-3-benzoylphenyl)aceticacid

Research Excerpts

Overview

Afenac Na is a new non-steroidal analgesic anti-inflammatory drug. It is clinically used for ailments such as rheumatoid arthritis and pain and/or inflamation after surgery.

ExcerptReferenceRelevance
"Amfenac Na is a new non-steroidal analgesic anti-inflammatory drug which is clinically used for ailments such as rheumatoid arthritis and pain and/or inflamation after surgery. "( Analgesic action of amfenac Na, a non-steroidal anti-inflammatory agent.
Hachisu, M; Hiranuma, T; Kato, S, 1988
)
2.04

Treatment

ExcerptReferenceRelevance
"Amfenac treatment failed to inhibit hypoxia-induced VEGF production. "( The effects of nepafenac and amfenac on retinal angiogenesis.
Bingaman, DP; Clark, ML; Penn, JS; Yang, R; Yanni, SE, 2010
)
2.09

Pharmacokinetics

ExcerptReferenceRelevance
" The prodrug nepafenac had the shortest time to peak concentration and the greatest peak aqueous humor concentration (C(max))."( In vivo pharmacokinetics and in vitro pharmacodynamics of nepafenac, amfenac, ketorolac, and bromfenac.
Ernest, P; Gayton, J; Lehmann, R; Raizman, M; Walters, T, 2007
)
0.57

Bioavailability

ExcerptReferenceRelevance
"Nepafenac showed significantly greater ocular bioavailability and amfenac demonstrated greater potency at COX-2 inhibition than ketorolac or bromfenac."( In vivo pharmacokinetics and in vitro pharmacodynamics of nepafenac, amfenac, ketorolac, and bromfenac.
Ernest, P; Gayton, J; Lehmann, R; Raizman, M; Walters, T, 2007
)
0.81

Dosage Studied

ExcerptRelevanceReference
" Locally-distributed compound concentrations were determined as the difference in levels between dosed and undosed eyes."( Distribution of topical ocular nepafenac and its active metabolite amfenac to the posterior segment of the eye.
Chastain, JE; Chemuturi, NV; Curtis, MA; Dahlin, DC; Gadd, ME; Kapin, MA; Markwardt, KL; Sanders, ME, 2016
)
0.67
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (5)

RoleDescription
non-steroidal anti-inflammatory drugAn anti-inflammatory drug that is not a steroid. In addition to anti-inflammatory actions, non-steroidal anti-inflammatory drugs have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins.
antipyreticA drug that prevents or reduces fever by lowering the body temperature from a raised state. An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. The body will then work to lower the temperature and the result is a reduction in fever.
cyclooxygenase 2 inhibitorA cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.
cyclooxygenase 1 inhibitorA cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1.
non-narcotic analgesicA drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (5)

ClassDescription
amino acidA carboxylic acid containing one or more amino groups.
oxo monocarboxylic acidAny monocarboxylic acid having at least one additional oxo functional group.
benzophenonesAny aromatic ketone in which the carbonyl group is bonded to 2 phenyl groups.
substituted aniline
primary amino compoundA compound formally derived from ammonia by replacing one hydrogen atom by an organyl group.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Prostaglandin-H2 D-isomeraseMus musculus (house mouse)IC50 (µMol)0.20000.07000.53401.1000AID160887
Prostaglandin G/H synthase 1 Bos taurus (cattle)IC50 (µMol)0.20000.00051.41288.2000AID160887
Prostaglandin G/H synthase 2 Bos taurus (cattle)IC50 (µMol)0.20000.00050.57393.4000AID160887
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (12)

Processvia Protein(s)Taxonomy
response to oxidative stressProstaglandin G/H synthase 1 Bos taurus (cattle)
cellular oxidant detoxificationProstaglandin G/H synthase 1 Bos taurus (cattle)
meiotic spindle organizationProstaglandin G/H synthase 2 Bos taurus (cattle)
prostaglandin biosynthetic processProstaglandin G/H synthase 2 Bos taurus (cattle)
ovarian cumulus expansionProstaglandin G/H synthase 2 Bos taurus (cattle)
positive regulation of protein phosphorylationProstaglandin G/H synthase 2 Bos taurus (cattle)
response to oxidative stressProstaglandin G/H synthase 2 Bos taurus (cattle)
cyclooxygenase pathwayProstaglandin G/H synthase 2 Bos taurus (cattle)
positive regulation of embryonic developmentProstaglandin G/H synthase 2 Bos taurus (cattle)
cellular response to interleukin-1Prostaglandin G/H synthase 2 Bos taurus (cattle)
cellular oxidant detoxificationProstaglandin G/H synthase 2 Bos taurus (cattle)
regulation of neuroinflammatory responseProstaglandin G/H synthase 2 Bos taurus (cattle)
positive regulation of oocyte maturationProstaglandin G/H synthase 2 Bos taurus (cattle)
positive regulation of meiotic cell cycle process involved in oocyte maturationProstaglandin G/H synthase 2 Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

Processvia Protein(s)Taxonomy
peroxidase activityProstaglandin G/H synthase 1 Bos taurus (cattle)
heme bindingProstaglandin G/H synthase 1 Bos taurus (cattle)
metal ion bindingProstaglandin G/H synthase 1 Bos taurus (cattle)
peroxidase activityProstaglandin G/H synthase 2 Bos taurus (cattle)
prostaglandin-endoperoxide synthase activityProstaglandin G/H synthase 2 Bos taurus (cattle)
heme bindingProstaglandin G/H synthase 2 Bos taurus (cattle)
metal ion bindingProstaglandin G/H synthase 2 Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
nucleoplasmProstaglandin-H2 D-isomeraseMus musculus (house mouse)
endoplasmic reticulum membraneProstaglandin G/H synthase 1 Bos taurus (cattle)
nuclear inner membraneProstaglandin G/H synthase 2 Bos taurus (cattle)
nuclear outer membraneProstaglandin G/H synthase 2 Bos taurus (cattle)
endoplasmic reticulum membraneProstaglandin G/H synthase 2 Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (5)

Assay IDTitleYearJournalArticle
AID187314Relative Oral Anti inflammatory activity in the 5-h Evans Blue-Carrageenan pleural assay using indomethacin as reference compound1984Journal of medicinal chemistry, Oct, Volume: 27, Issue:10
Antiinflammatory activity of N-(2-benzoylphenyl)alanine derivatives.
AID1130698Antiinflammatory activity in fasted male rat assessed as decrease in carrageenan-induced pleural fluid at 4 mg/kg, po after 5 hrs by Evans blue carrageenan pleural effusion assay relative to control1979Journal of medicinal chemistry, Sep, Volume: 22, Issue:9
Antiinflammatory agents. 1. Synthesis and antiinflammatory activity of 2-amino-3-benzoylphenylacetic acid.
AID592681Apparent permeability across human Caco2 cell membrane after 2 hrs by LC-MS/MS analysis2011Bioorganic & medicinal chemistry, Apr-15, Volume: 19, Issue:8
QSAR-based permeability model for drug-like compounds.
AID160887Inhibition of PG synthetase activity obtained from bovine seminal vesicles1984Journal of medicinal chemistry, Oct, Volume: 27, Issue:10
Antiinflammatory activity of N-(2-benzoylphenyl)alanine derivatives.
AID1130697Antiinflammatory activity in fasted male rat assessed as decrease in carrageenan-induced pleural fluid at 0.8 mg/kg, po after 5 hrs by Evans blue carrageenan pleural effusion assay relative to control1979Journal of medicinal chemistry, Sep, Volume: 22, Issue:9
Antiinflammatory agents. 1. Synthesis and antiinflammatory activity of 2-amino-3-benzoylphenylacetic acid.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (24)

TimeframeStudies, This Drug (%)All Drugs %
pre-19907 (29.17)18.7374
1990's3 (12.50)18.2507
2000's6 (25.00)29.6817
2010's8 (33.33)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 28.31

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index28.31 (24.57)
Research Supply Index3.40 (2.92)
Research Growth Index4.53 (4.65)
Search Engine Demand Index34.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (28.31)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials3 (11.54%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other23 (88.46%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]