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Details

Stereochemistry ACHIRAL
Molecular Formula C15H12NO3.Na.H2O
Molecular Weight 295.2657
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMFENAC SODIUM

SMILES

O.[Na+].NC1=C(C=CC=C1CC([O-])=O)C(=O)C2=CC=CC=C2

InChI

InChIKey=QZNJPJDUBTYMRS-UHFFFAOYSA-M
InChI=1S/C15H13NO3.Na.H2O/c16-14-11(9-13(17)18)7-4-8-12(14)15(19)10-5-2-1-3-6-10;;/h1-8H,9,16H2,(H,17,18);;1H2/q;+1;/p-1

HIDE SMILES / InChI
Molecular Formula HO
Molecular Weight 17.0073
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C15H13NO3
Molecular Weight 255.2686
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including https://link.springer.com/article/10.1007/BF03299088 | http://www.rad-ar.or.jp/siori/english/kekka.cgi?n=35377 | https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/203491Orig1s000MedR.pdf | https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/021862lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/10850857

Amfenac (AHR 5850) is a non-steroidal anti-inflammatory compound possessing antipyretic and analgesic properties. It is an inhibitor of cyclooxygenases. Amfenac sodium has been on the Japanese market since 1986 (as FENAZOX®, Meiji) in an oral dosage form (50 mg, four-times-daily) indicated for the treatment of pain and inflammation associated with rheumatoid and osteoarthritis and low back pain, as well as the treatment of pain and inflammation following surgery, injury or tooth extraction. Amfenac is an active moiety of nepafenac (amfenac amide), the prodrug has very weak cyclooxygenase inhibitory activity whereas amfenac exhibits more potent cyclooxygenase activity. Nepafenac at a concentration of 0.1% (NEVANAC) was approved for marketing in the US in 2005. Nepafenac is also approved for marketing in the European Union(EU) and Japan as well as over 60 other countries for the treatment of postoperative pain and inflammation associated with cataract surgery.

Originator

Approval Year

2005
131
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 64.3 µM [IC50]
Inhibitor
8297
 0.15 µM [IC50]
Inhibitor
8297
 0.25 µM [IC50]
Inhibitor
8297
 0.15 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Approved
8429
NEVANAC

Approved Use

NEVANAC ophthalmic suspension is a nonsteroidal, antiinflammatory prodrug indicated for the treatment of pain and inflammation associated with cataract surgery

Launch Date

2005
Primary
Approved
8429
FENAZOX

Approved Use

FENAZOX CAPSULES (Amfenac sodium hydrate) is usually used to relieve inflammation and pain in chronic rheumatoid arthritis, osteoarthritis, low back pain, shoulder periarthritis, cervico-omo-brachial syndrome, temporomandibular joint disease, post-operative state, post-traumatic state or post-odontectomy state.

Launch Date

1985
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
205.3 ng/mL
DRUG LABEL
https://iovs.arvojournals.org/article.aspx?articleid=2383342
1 drop single, ocular
dose: 1 drop
route of administration: Ocular
experiment type: SINGLE
co-administered:
NEPAFENAC aqueous humor
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
0.847 ng/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/203491s001lbl.pdf
1 drop 1 times / day steady-state, ocular
dose: 1 drop
route of administration: Ocular
experiment type: STEADY-STATE
co-administered:
NEPAFENAC unknown
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
331.1 ng × h/mL
DRUG LABEL
https://iovs.arvojournals.org/article.aspx?articleid=2383342
1 drop single, ocular
dose: 1 drop
route of administration: Ocular
experiment type: SINGLE
co-administered:
NEPAFENAC aqueous humor
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
1 drop 1 times / day multiple, topical
Recommended
Dose: 1 drop, 1 times / day
Route: topical
Route: multiple
Dose: 1 drop, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/24345529
Page: p.209
unhealthy, 68.7+/- 9.08
n = 817
Health Status: unhealthy
Condition: Pain and inflammation associated with cataract surgery
Age Group: 68.7+/- 9.08
Sex: M+F
Population Size: 817
Sources:
https://pubmed.ncbi.nlm.nih.gov/24345529
Page: p.209
Disc. AE: Hypersensitivity...
AEs leading to
discontinuation/dose reduction:
Hypersensitivity (0.12%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/24345529
Page: p.209
1 drop 1 times / day multiple, topical
Recommended
Dose: 1 drop, 1 times / day
Route: topical
Route: multiple
Dose: 1 drop, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/203491s001lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Pain and inflammation associated with cataract surgery
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/203491s001lbl.pdf
Page: p.1
Disc. AE: Bleeding, Healing delayed...
AEs leading to
discontinuation/dose reduction:
Bleeding
Healing delayed
Corneal disorder (NOS)
Keratitis
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/203491s001lbl.pdf
Page: p.1
AEs

AEs

AESignificanceDosePopulation
Hypersensitivity 0.12%
Disc. AE
1 drop 1 times / day multiple, topical
Recommended
Dose: 1 drop, 1 times / day
Route: topical
Route: multiple
Dose: 1 drop, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/24345529
Page: p.209
unhealthy, 68.7+/- 9.08
n = 817
Health Status: unhealthy
Condition: Pain and inflammation associated with cataract surgery
Age Group: 68.7+/- 9.08
Sex: M+F
Population Size: 817
Sources:
https://pubmed.ncbi.nlm.nih.gov/24345529
Page: p.209
Bleeding Disc. AE
1 drop 1 times / day multiple, topical
Recommended
Dose: 1 drop, 1 times / day
Route: topical
Route: multiple
Dose: 1 drop, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/203491s001lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Pain and inflammation associated with cataract surgery
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/203491s001lbl.pdf
Page: p.1
Corneal disorder (NOS) Disc. AE
1 drop 1 times / day multiple, topical
Recommended
Dose: 1 drop, 1 times / day
Route: topical
Route: multiple
Dose: 1 drop, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/203491s001lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Pain and inflammation associated with cataract surgery
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/203491s001lbl.pdf
Page: p.1
Healing delayed Disc. AE
1 drop 1 times / day multiple, topical
Recommended
Dose: 1 drop, 1 times / day
Route: topical
Route: multiple
Dose: 1 drop, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/203491s001lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Pain and inflammation associated with cataract surgery
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/203491s001lbl.pdf
Page: p.1
Keratitis Disc. AE
1 drop 1 times / day multiple, topical
Recommended
Dose: 1 drop, 1 times / day
Route: topical
Route: multiple
Dose: 1 drop, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/203491s001lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Pain and inflammation associated with cataract surgery
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/203491s001lbl.pdf
Page: p.1
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
1587
inhibitor
1767
inhibitor
1852

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
1524

CYP2C19
1478

CYP2E1
882

P-gp
1461
CYP
270

P-gp
1537

UGT enzymes
27
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
P-gp
1650
 inconclusive
P-gp
1650
 inconclusive
amfenac
4
CYP1A2
1692
 no
CYP1A2
1692
 no
amfenac
4
CYP2C19
1553
 no
CYP2C19
1553
 no
amfenac
4
CYP2C9
1819
 no
CYP2C9
1819
 no
amfenac
4
CYP2D6
1891
 no
CYP2D6
1891
 no
amfenac
4
CYP2E1
970
 no
CYP2E1
970
 no
amfenac
4
CYP3A4
1925
 no
CYP3A4
1925
 no
amfenac
4
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP
270
 inconclusive
amfenac
4
P-gp
1537
 inconclusive
P-gp
1537
 inconclusive
amfenac
4
UGT enzymes
27
 likely
UGT enzymes
27
 likely
amfenac
4
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:75922
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:75922
ChemicalBook
CB01116872
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB01116872
MolPort
MolPort-003-987-236
https://www.molport.com/shop/molecule-link/MolPort-003-987-236
Selleck Chemicals
Nepafenac
http://www.selleckchem.com/products/Nepafenac.html
ZINC
ZINC000005162311
http://zinc15.docking.org/substances/ZINC000005162311
eMolecules
10510502
https://www.emolecules.com/cgi-bin/more?vid=10510502
PubMed

PubMed

TitleDatePubMed
Pharmacokinetics of topical ocular drug delivery: potential uses for the treatment of diseases of the posterior segment and beyond.
2003 Jun
Ketorolac tromethamine LS 0.4% versus nepafenac 0.1% in patients having cataract surgery. Prospective randomized double-masked clinical trial.
2007 Nov
The use of a cyclooxygenase-2 inhibitor (Nepafenac) in an ocular and metastatic animal model of uveal melanoma.
2007 Sep
Re: Pharmacokinetics and pharmacodynamics of nepafenac, amfenac, ketorolac, and bromfenac.
2008 Aug
Topical ocular delivery of NSAIDs.
2008 Jun
Nepafenac dosing frequency for ocular pain and inflammation associated with cataract surgery.
2009 Aug
Differential effects of non-steroidal anti-inflammatory drugs on mitochondrial dysfunction during oxidative stress.
2009 Oct 1
Comparison of three strains of diabetic rats with respect to the rate at which retinopathy and tactile allodynia develop.
2010 Aug 15
Ocular pharmacokinetics of 0.45% ketorolac tromethamine.
2010 Dec 1
The effects of nepafenac and amfenac on retinal angiogenesis.
2010 Feb 15
Randomized clinical trial of treatment for TMJ disc displacement.
2010 Nov
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.
2012 Jul
Nepafenac: an ophthalmic nonsteroidal antiinflammatory drug for pain after cataract surgery.
2013 Jun
Patents

Patents

20020035264
14
JP2007537168A
10
JP2010037262A
4
JP2010059058A
4

Sample Use Guides

In Vivo Use Guide
One drop of Nepafenac ophthalmic suspension, 0.3% should be applied to the affected eye one-time-daily beginning 1 day prior to cataract surgery, continued on the day of surgery and through the first 2 weeks of the postoperative period. An additional drop should be administered 30 to 120 minutes prior to surgery.
Route of Administration: Topical
In Vitro Use Guide
Nepafenac exhibited only weak COX-1 inhibitory activity (IC50 = 64.3 uM). However, amfenac, an active metabolite of nepafenac, was a potent inhibitor of COX-1 (IC50 = 0.25 uM) and COX-2 activity (IC50 = 0.15 uM).
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:00:53 GMT 2023
Edited
by admin
on Fri Dec 15 17:00:53 GMT 2023
Record UNII
PPF9V8J28Y
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AMFENAC SODIUM
MART.   USAN  
USAN  
Official Name English
AMFENAC SODIUM [USAN]
Common Name English
AHR-5850D
Code English
FENAZOX
Brand Name English
AMFENAC SODIUM SALT MONOHYDRATE
MI  
Common Name English
AMFENAC SODIUM SALT MONOHYDRATE [MI]
Common Name English
AMFENAC SODIUM HYDRATE [JAN]
Common Name English
Sodium (2-amino-3-benzoylphenyl)acetate monohydrate
Systematic Name English
AMFENAC SODIUM [MART.]
Common Name English
BENZENEACETIC ACID, 2-AMINO-3-BENZOYL-, SODIUM SALT, MONOHYDRATE
Common Name English
AMFENAC SODIUM HYDRATE
JAN  
Common Name English
SODIUM AMFENAC
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C257
Created by admin on Fri Dec 15 17:00:54 GMT 2023 , Edited by admin on Fri Dec 15 17:00:54 GMT 2023
Code System Code Type Description
PUBCHEM
23663941
Created by admin on Fri Dec 15 17:00:54 GMT 2023 , Edited by admin on Fri Dec 15 17:00:54 GMT 2023
PRIMARY
CHEBI
31202
Created by admin on Fri Dec 15 17:00:54 GMT 2023 , Edited by admin on Fri Dec 15 17:00:54 GMT 2023
PRIMARY
NCI_THESAURUS
C142919
Created by admin on Fri Dec 15 17:00:54 GMT 2023 , Edited by admin on Fri Dec 15 17:00:54 GMT 2023
PRIMARY
FDA UNII
PPF9V8J28Y
Created by admin on Fri Dec 15 17:00:54 GMT 2023 , Edited by admin on Fri Dec 15 17:00:54 GMT 2023
PRIMARY
ChEMBL
CHEMBL25146
Created by admin on Fri Dec 15 17:00:54 GMT 2023 , Edited by admin on Fri Dec 15 17:00:54 GMT 2023
PRIMARY
EVMPD
SUB00433MIG
Created by admin on Fri Dec 15 17:00:54 GMT 2023 , Edited by admin on Fri Dec 15 17:00:54 GMT 2023
PRIMARY
SMS_ID
100000085129
Created by admin on Fri Dec 15 17:00:54 GMT 2023 , Edited by admin on Fri Dec 15 17:00:54 GMT 2023
PRIMARY
MERCK INDEX
m1659
Created by admin on Fri Dec 15 17:00:54 GMT 2023 , Edited by admin on Fri Dec 15 17:00:54 GMT 2023
PRIMARY Merck Index
CAS
61618-27-7
Created by admin on Fri Dec 15 17:00:54 GMT 2023 , Edited by admin on Fri Dec 15 17:00:54 GMT 2023
PRIMARY
EPA CompTox
DTXSID30977216
Created by admin on Fri Dec 15 17:00:54 GMT 2023 , Edited by admin on Fri Dec 15 17:00:54 GMT 2023
PRIMARY
Related Record Type Details
Structure of AMFENAC
PARENT -> SALT/SOLVATE
Structure of AMFENAC SODIUM ANHYDROUS
ANHYDROUS->SOLVATE
Related Record Type Details
Structure of AMFENAC
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