PRANOPROFEN

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=CC2=C(OC3=NC=CC=C3C2)C=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

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 8297

Conditions

Condition	Modality	Highest Phase	Product
Swelling in the eyes 1 Sources: https://www.unitedpharmacies.com/Niflan-Pranoprofen.html	Primary	Approved 8429	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 8429	Niflan Approved Use Unknown
Conjunctivitis 17 Sources: https://www.pharmacygeoff.md/Niflan_Pranoprofen_01_5mL_p_2478.html	Primary	Approved 8429	Niflan Approved Use Unknown
Blepharitis 37 Sources: https://www.pharmacygeoff.md/Niflan_Pranoprofen_01_5mL_p_2478.html	Primary	Approved 8429	Niflan Approved Use Unknown

PubMed

Title	Date	PubMed
Interaction between enoxacin, a new antimicrobial, and nimesulide, a new non-steroidal anti-inflammatory agent in mice.	1996 Aug	8872509
Effects of topical anti-inflammatory and antiallergic eyedrops on prostaglandin E2-induced aqueous flare elevation in pigmented rabbits.	2002 Jul	12096966
Nonsteroidal anti-inflammatory drugs induce apoptosis in association with activation of peroxisome proliferator-activated receptor gamma in rheumatoid synovial cells.	2002 Jul	12065695
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 Jul	12884398
Probenecid-induced changes in the clearance of pranoprofen enantiomers.	2003 May 5	12666238
Enantiospecific disposition of pranoprofen in beagle dogs and rats.	2003 May 5	12666237
Effects of topical corticosteroids and nonsteroidal anti-inflammatory drugs on prostaglandin e2-induced aqueous flare elevation in pigmented rabbits.	2003 Nov-Dec	14688425
Triphasic waves detected during recovery from lithium intoxication.	2003 Sep	14518689
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 Sep 5	14518776
[Tissue culture of bovine lens as an in vitro model for posterior capsule opacification and the effects of pranoprofen on the cell confluence].	2006 Jan	16638281
Enhanced transdermal delivery of pranoprofen from the bioadhesive gels.	2006 Oct	17121190
Gastrointestinal disorders in anaphylaxis.	2007	17380001
Preparation and evaluation of pranoprofen gel for percutaneous administration.	2007 Jan	17192247
Controlled release of pranoprofen from the ethylene-vinyl acetate matrix using plasticizer.	2007 Jul	17654023
Topical pranoprofen 0.1% is as effective anti-inflammatory and analgesic agent as diclofenac sodium 0.1% after strabismus surgery.	2007 Jun	17593012
A variant of thyrotoxicosis associated with chronic thyroiditis characterized by prolonged fever, absence of anti-thyroidal antibodies, and favorable response to naproxen.	2007 May	17505175
Topical ocular delivery of NSAIDs.	2008 Jun	18437583
Evaluation of the interaction between nonsteroidal anti-inflammatory drugs and methotrexate using human organic anion transporter 3-transfected cells.	2008 Oct 31	18789319
Management of ocular inflammation and pain following cataract surgery: focus on bromfenac ophthalmic solution.	2009	19668566
Collagen cross-linking with riboflavin and ultraviolet-A light in keratoconus: One-year results.	2009 Jan	21234222
Effect of pranoprofen on endoplasmic reticulum stress in the primary cultured glial cells.	2009 Jan	19114067
Cyclooxygenase (COX)-inhibiting drug reduces HSV-1 reactivation in the mouse eye model.	2009 Mar	19274523
Enhanced transdermal absorption and pharmacokinetic evaluation of pranoprofen-ethylene-vinyl acetate matrix containing penetration enhancer in rats.	2009 May	19471890
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.	2010 Dec	21818443
Enantiomeric composition analysis of pranoprofen in equine plasma and urine by chiral liquid chromatography-tandem mass spectrometry in selected reaction monitoring mode.	2010 Dec 1	21036111
Cytotoxicity of topical medications used for infection and inflammation control after cataract surgery in cultured corneal endothelial cells.	2010 Sep	20938094
Cytotoxicity of five fluoroquinolone and two nonsteroidal anti-inflammatory benzalkonium chloride-free ophthalmic solutions in four corneoconjunctival cell lines.	2010 Sep 20	20922036
Assessing the cardiovascular risk between celecoxib and nonselective nonsteroidal antiinflammatory drugs in patients with rheumatoid arthritis and osteoarthritis.	2014	24152722

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.

Name

Type

Language

PRANOPROFEN

Official 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

ELICAPRIC

Brand 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