PRANOPROFEN

Possibly Marketed Outside US

Details

Stereochemistry	RACEMIC
Molecular Formula	C15H13NO3
Molecular Weight	255.2686
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C(O)=O)C1=CC=C2OC3=NC=CC=C3CC2=C1

InChI

InChIKey=TVQZAMVBTVNYLA-UHFFFAOYSA-N

InChI=1S/C15H13NO3/c1-9(15(17)18)10-4-5-13-12(7-10)8-11-3-2-6-16-14(11)19-13/h2-7,9H,8H2,1H3,(H,17,18)

HIDE SMILES / InChI

Molecular Formula	C15H13NO3
Molecular Weight	255.2686
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.pharmacygeoff.md/Niflan_Pranoprofen_01_5mL_p_2478.html
Curator's Comment: description was created based on several sources, including https://www.unitedpharmacies.com/Niflan-Pranoprofen.html

Pranoprofen, brand name Niflan, belongs to a class of medications called non steroidal anti-inflammatory drugs (NSAID). It can be used to treat inflammation, keratitis, conjunctivitis and blepharitis after eye surgery. Its mechanism of action is the inhibition of inflammatory prostaglandin synthesis. Prostaglandins are types of lipids which are produced at the site of injury or damaged tissue as part of the body`s response to the injury. They are responsible for inflammation. However, the main ingredient in this ophthalmic medicine is a non-steroidal anti-inflammatory drug, and by blocking the formation of prostaglandins, it can alleviate eye inflammation caused by keratitis, blepharitis and other conditions. Patients who have undergone surgery on the eyes may also be given it to prevent the occurrence of eye inflammation.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
prostaglandin biosynthetic process 23 Target ID: GO:0001516 Sources: https://www.unitedpharmacies.com/Niflan-Pranoprofen.html	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Swelling in the eyes 1 Sources: https://www.unitedpharmacies.com/Niflan-Pranoprofen.html	Primary	Approved 8583	Niflan Approved Use can treat swelling in the eyes caused by conjunctivitis
Keratitis 2 Sources: https://www.pharmacygeoff.md/Niflan_Pranoprofen_01_5mL_p_2478.html	Primary	Approved 8583	Niflan Approved Use Unknown
Conjunctivitis 17 Sources: https://www.pharmacygeoff.md/Niflan_Pranoprofen_01_5mL_p_2478.html	Primary	Approved 8583	Niflan Approved Use Unknown
Blepharitis 37 Sources: https://www.pharmacygeoff.md/Niflan_Pranoprofen_01_5mL_p_2478.html	Primary	Approved 8583	Niflan Approved Use Unknown

C_max

Value	Dose	Analyte	Population
7.37 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2787808/	75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered:	PRANOPROFEN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
6.59 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2787808/	75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered:	PRANOPROFEN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
3590 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2231310/	75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered:	PRANOPROFEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

AUC

Value	Dose	Analyte	Population
19.4 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2787808/	75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered:	PRANOPROFEN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
16.3 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2787808/	75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered:	PRANOPROFEN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
9295 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2231310/	75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered:	PRANOPROFEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

T_1/2

Value	Dose	Analyte	Population
4.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2787808/	75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered:	PRANOPROFEN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2787808/	75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered:	PRANOPROFEN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
5.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2231310/	75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered:	PRANOPROFEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

F_unbound

Value	Dose	Co-administered	Analyte	Population
0.7% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1494108/			PRANOPROFEN serum	Homo sapiens
0.5% OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/400315_1149010F1136_1_110_1F.pdf#page=22	75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered:		PRANOPROFEN plasma	Homo sapiens

Doses

Dose	Population	Adverse events
225 mg 3 times / day multiple, oral Recommended Dose: 225 mg, 3 times / day Route: oral Route: multiple Dose: 225 mg, 3 times / day Sources: https://www.rad-ar.or.jp/siori/english/kekka.cgi?n=34239	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: FED Sources: https://www.rad-ar.or.jp/siori/english/kekka.cgi?n=34239	Disc. AE: Anaphylactoid shock, Asthmatic attack... AEs leading to discontinuation/dose reduction: Anaphylactoid shock Asthmatic attack Mucocutaneous disorder Toxic epidermal necrolysis Peptic ulcer Nephrotic syndrome Acute renal failure Gastrointestinal bleed Sources: https://www.rad-ar.or.jp/siori/english/kekka.cgi?n=34239
0.1 % 4 times / day multiple, ophthalmic Studied dose Dose: 0.1 %, 4 times / day Route: ophthalmic Route: multiple Dose: 0.1 %, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/23023407/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/23023407/	Sources: https://pubmed.ncbi.nlm.nih.gov/23023407/
0.1 % 4 times / day multiple, ophthalmic Studied dose Dose: 0.1 %, 4 times / day Route: ophthalmic Route: multiple Dose: 0.1 %, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8172273/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8172273/	Disc. AE: Condition worsened... AEs leading to discontinuation/dose reduction: Condition worsened (1.35%) Sources: https://pubmed.ncbi.nlm.nih.gov/8172273/

AEs

AE	Significance	Dose	Population
Acute renal failure	Disc. AE	225 mg 3 times / day multiple, oral Recommended Dose: 225 mg, 3 times / day Route: oral Route: multiple Dose: 225 mg, 3 times / day Sources: https://www.rad-ar.or.jp/siori/english/kekka.cgi?n=34239	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: FED Sources: https://www.rad-ar.or.jp/siori/english/kekka.cgi?n=34239
Anaphylactoid shock	Disc. AE	225 mg 3 times / day multiple, oral Recommended Dose: 225 mg, 3 times / day Route: oral Route: multiple Dose: 225 mg, 3 times / day Sources: https://www.rad-ar.or.jp/siori/english/kekka.cgi?n=34239	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: FED Sources: https://www.rad-ar.or.jp/siori/english/kekka.cgi?n=34239
Asthmatic attack	Disc. AE	225 mg 3 times / day multiple, oral Recommended Dose: 225 mg, 3 times / day Route: oral Route: multiple Dose: 225 mg, 3 times / day Sources: https://www.rad-ar.or.jp/siori/english/kekka.cgi?n=34239	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: FED Sources: https://www.rad-ar.or.jp/siori/english/kekka.cgi?n=34239
Gastrointestinal bleed	Disc. AE	225 mg 3 times / day multiple, oral Recommended Dose: 225 mg, 3 times / day Route: oral Route: multiple Dose: 225 mg, 3 times / day Sources: https://www.rad-ar.or.jp/siori/english/kekka.cgi?n=34239	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: FED Sources: https://www.rad-ar.or.jp/siori/english/kekka.cgi?n=34239
Mucocutaneous disorder	Disc. AE	225 mg 3 times / day multiple, oral Recommended Dose: 225 mg, 3 times / day Route: oral Route: multiple Dose: 225 mg, 3 times / day Sources: https://www.rad-ar.or.jp/siori/english/kekka.cgi?n=34239	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: FED Sources: https://www.rad-ar.or.jp/siori/english/kekka.cgi?n=34239
Nephrotic syndrome	Disc. AE	225 mg 3 times / day multiple, oral Recommended Dose: 225 mg, 3 times / day Route: oral Route: multiple Dose: 225 mg, 3 times / day Sources: https://www.rad-ar.or.jp/siori/english/kekka.cgi?n=34239	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: FED Sources: https://www.rad-ar.or.jp/siori/english/kekka.cgi?n=34239
Peptic ulcer	Disc. AE	225 mg 3 times / day multiple, oral Recommended Dose: 225 mg, 3 times / day Route: oral Route: multiple Dose: 225 mg, 3 times / day Sources: https://www.rad-ar.or.jp/siori/english/kekka.cgi?n=34239	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: FED Sources: https://www.rad-ar.or.jp/siori/english/kekka.cgi?n=34239
Toxic epidermal necrolysis	Disc. AE	225 mg 3 times / day multiple, oral Recommended Dose: 225 mg, 3 times / day Route: oral Route: multiple Dose: 225 mg, 3 times / day Sources: https://www.rad-ar.or.jp/siori/english/kekka.cgi?n=34239	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: FED Sources: https://www.rad-ar.or.jp/siori/english/kekka.cgi?n=34239
Condition worsened	1.35% Disc. AE	0.1 % 4 times / day multiple, ophthalmic Studied dose Dose: 0.1 %, 4 times / day Route: ophthalmic Route: multiple Dose: 0.1 %, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8172273/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8172273/

PubMed

Title	Date	PubMed
Assessing the cardiovascular risk between celecoxib and nonselective nonsteroidal antiinflammatory drugs in patients with rheumatoid arthritis and osteoarthritis.	2014	24152722
Enantiomeric composition analysis of pranoprofen in equine plasma and urine by chiral liquid chromatography-tandem mass spectrometry in selected reaction monitoring mode.	2010-12-01	21036111
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.	2010-12	21818443
Cytotoxicity of five fluoroquinolone and two nonsteroidal anti-inflammatory benzalkonium chloride-free ophthalmic solutions in four corneoconjunctival cell lines.	2010-09-20	20922036
Cytotoxicity of topical medications used for infection and inflammation control after cataract surgery in cultured corneal endothelial cells.	2010-09	20938094
Enhanced transdermal absorption and pharmacokinetic evaluation of pranoprofen-ethylene-vinyl acetate matrix containing penetration enhancer in rats.	2009-05	19471890
Cyclooxygenase (COX)-inhibiting drug reduces HSV-1 reactivation in the mouse eye model.	2009-03	19274523
Collagen cross-linking with riboflavin and ultraviolet-A light in keratoconus: One-year results.	2009-01	21234222
Effect of pranoprofen on endoplasmic reticulum stress in the primary cultured glial cells.	2009-01	19114067
Management of ocular inflammation and pain following cataract surgery: focus on bromfenac ophthalmic solution.	2009	19668566
Evaluation of the interaction between nonsteroidal anti-inflammatory drugs and methotrexate using human organic anion transporter 3-transfected cells.	2008-10-31	18789319
Topical ocular delivery of NSAIDs.	2008-06	18437583
Controlled release of pranoprofen from the ethylene-vinyl acetate matrix using plasticizer.	2007-07	17654023
Topical pranoprofen 0.1% is as effective anti-inflammatory and analgesic agent as diclofenac sodium 0.1% after strabismus surgery.	2007-06	17593012
A variant of thyrotoxicosis associated with chronic thyroiditis characterized by prolonged fever, absence of anti-thyroidal antibodies, and favorable response to naproxen.	2007-05	17505175
Preparation and evaluation of pranoprofen gel for percutaneous administration.	2007-01	17192247
Gastrointestinal disorders in anaphylaxis.	2007	17380001
Enhanced transdermal delivery of pranoprofen from the bioadhesive gels.	2006-10	17121190
[Tissue culture of bovine lens as an in vitro model for posterior capsule opacification and the effects of pranoprofen on the cell confluence].	2006-01	16638281
Capillary electrophoresis with laser induced-fluorescence detection of profens derivatized with the water-soluble fluorogenic reagent 4-N-(4-N'-aminoethyl)piperazino-7-nitro-2,1,3-benzoxadiazole.	2003-09-05	14518776
Triphasic waves detected during recovery from lithium intoxication.	2003-09	14518689
Thin layer chromatographic resolution of some 2-arylpropionic acid enantiomers using L-(-)-serine, L-(-)-threonine and a mixture of L-(-)-serine and L-(-)-threonine-impregnated silica gel as stationary phases.	2003-07	12884398
Probenecid-induced changes in the clearance of pranoprofen enantiomers.	2003-05-05	12666238
Enantiospecific disposition of pranoprofen in beagle dogs and rats.	2003-05-05	12666237
Effects of topical corticosteroids and nonsteroidal anti-inflammatory drugs on prostaglandin e2-induced aqueous flare elevation in pigmented rabbits.	2003-03-03	14688425
Effects of topical anti-inflammatory and antiallergic eyedrops on prostaglandin E2-induced aqueous flare elevation in pigmented rabbits.	2002-07	12096966
Nonsteroidal anti-inflammatory drugs induce apoptosis in association with activation of peroxisome proliferator-activated receptor gamma in rheumatoid synovial cells.	2002-07	12065695
In vitro and in vivo properties of recombinant human serum albumin from Pichia pastoris purified by a method of short processing time.	2001-12	11785700
Reactive oxygen species are involved in the apoptosis induced by nonsteroidal anti-inflammatory drugs in cultured gastric cells.	1999-11-03	10594327
Interaction between enoxacin, a new antimicrobial, and nimesulide, a new non-steroidal anti-inflammatory agent in mice.	1996-08	8872509

Patents

Sample Use Guides

In Vivo Use Guide

dropped into the affected eye 4 times daily

Route of Administration: Topical

In Vitro Use Guide

PPF (Pranoprofen) at concentrations ranging from 0.0625 to 1.0 g/l had poignant cytotoxicity to human corneal endothelial (HCE) cells, and the extent of its cytotoxicity was dose- and time-dependent. Further characterization indicated that PPF induced plasma membrane permeability elevation, DNA fragmentation, and apoptotic body formation, proving its apoptosis inducing effect on HCE cells. In conclusion, PPF above 0.0625 g/l has poignant cytotoxicity on HCE cells in vitro by inducing cell apoptosis, and should be carefully employed in eye clinic.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:19:34 GMT 2025` Edited by `admin` on `Mon Mar 31 19:19:34 GMT 2025`
Record UNII	2R7O1ET613
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PRANOPROFEN

Official Name

English

ELICAPRIC

Preferred Name

English

PYRANOPROFEN

Common Name

English

.ALPHA.-METHYL-5H-(1)BENZOPYRANO(2,3-B)PYRIDINE-7-ACETIC ACID

Systematic Name

English

PRANOPROFEN [MI]

Common Name

English

Pranoprofen [WHO-DD]

Common Name

English

PRANOPROFEN [JAN]

Common Name

English

pranoprofen [INN]

Common Name

English

NSC-759832

Code

English

PRANOPROFEN [MART.]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C257