PELUBIPROFEN

Details

Stereochemistry	RACEMIC
Molecular Formula	C16H18O3
Molecular Weight	258.3123
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C(O)=O)C1=CC=C(\C=C2/CCCCC2=O)C=C1

InChI

InChIKey=AUZUGWXLBGZUPP-GXDHUFHOSA-N

InChI=1S/C16H18O3/c1-11(16(18)19)13-8-6-12(7-9-13)10-14-4-2-3-5-15(14)17/h6-11H,2-5H2,1H3,(H,18,19)/b14-10+

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21809372
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/25403311 http://adisinsight.springer.com/trials/700254420 https://www.daewonpharm.com/en/products/2_3medicine2.jsp?cd=EC11&PRD_NO=300

Pelubiprofen, 2-[4-(Oxocyclohexylidene methyl)phenyl]propionic acid, is one of the 2-arylpropionic acid class of non-steroidal anti-inflammatory drugs (NSAIDs). It has wide variety of indications proposed: osteoarthritis, rheumatoid arthritis, musculoskeletal pain, post-operative trauma, backache, neck-shoulder syndrome and dental pain. Pelubiprofen is a prodrug of 2-arylpropionic acid with relatively selective effects on cyclooxygenase-2 activity. Antiinflammatory properties of pelubiprofen are due to its ability to both decrease prostaglandin synthesis by inhibiting the activities of cyclooxygenases (COXs) and IkB kinase-b (IKK-b). Pelubiprofen was found to have an anti-edema effect in the carrageenan-induced paw edema model in rats, one of the well-established acute inflammatory models in vivo. Pelubiprofen was well tolerated in single doses up to 120mg and at a dosage of 180 mg/day. No drug accumulation was evident, suggesting that it may be useful for long term treatment.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Prostaglandin G/H synthase 2 48 Target ID: P35354 Gene ID: 5743.0 Gene Symbol: PTGS2 Target Organism: Homo sapiens (Human) Sources: http://www.ncbi.nlm.nih.gov/pubmed/25403311	Inhibitor 8297		2.88 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Rheumatoid arthritis 316 Sources: https://clinicaltrials.gov/ct2/show/NCT01781702	Primary	Phase III 656	Unknown Approved Use Unknown
Upper respiratory tract infections 12 Sources: https://clinicaltrials.gov/ct2/show/NCT01779271	Palliative	Phase III 656	Unknown Approved Use Unknown
Fever 23 Sources: https://clinicaltrials.gov/ct2/show/NCT01779271	Palliative	Phase III 656	Unknown Approved Use Unknown
Osteoarthritis of knee 23 Sources: https://clinicaltrials.gov/ct2/show/NCT02682524	Primary	Approved 8429	Pelubi Approved Use Reduce symptom of Osteoarthritis, Back pain (Lumbago)
Chronic back pain 2 Sources: https://www.daewonpharm.com/en/products/2_3medicine2.jsp?cd=EC11&PRD_NO=300	Primary	Approved 8429	Pelubi Approved Use Reduce symptom of Osteoarthritis, Back pain (Lumbago)

PubMed

Title	Date	PubMed
Anti-inflammatory effect of pelubiprofen, 2-[4-(oxocyclohexylidenemethyl)-phenyl]propionic acid, mediated by dual suppression of COX activity and LPS-induced inflammatory gene expression via NF-κB inactivation.	2011 Dec	21809372
Comparison of the efficacy and safety profiles of a pelubiprofen versus celecoxib in patients with rheumatoid arthritis: a 6-week, multicenter, randomized, double-blind, phase III, non-inferiority clinical trial.	2014 Nov 18	25403311
Development and validation of an LC-MS/MS method for the determination of pelubiprofen and its active metabolite, trans-alcohol, in human plasma and its application to pharmacokinetic study.	2015 Mar 1	25618252

Patents

Sample Use Guides

In Vivo Use Guide

1 tab. (30mg), 3 times daily after a meal

Route of Administration: Oral

In Vitro Use Guide

RAW 264.7 mouse macrophage cell line. Pelubiprofen potently diminished PGE2 productions through inhibition of COX enzyme activity (IC50 values for COX-1 and COX-2 are 10.66 +/-0.99 and 2.88 +/-1.01 uM, respectively), but also reduced the expressions of COX-2, inducible nitric oxide (iNOS), tumor necrosis factor-a (TNF-a), interleukin-1b (IL-1b), and IL-6 at transcriptional level in LPS-induced RAW 264.7 cells. Pelubiprofen attenuated the LPS-induced transcription activity and the DNA binding activity of NF-kB, which was accompanied by a parallel reduction of degradation and phosphorylation of inhibitory kappa B-a (IkB-a) and consequently by decreased nuclear translocation of NF-kB. Pelubipofen inhibited the LPS-induced phosphorylation of IKK-b and transforming growth factor-b activated kinase-1 (TAK1).

Name

Type

Language

PELUBIPROFEN

Official Name

English

BENZENEACETIC ACID, .ALPHA.-METHYL-4-((2-OXOCYCLOHEXYLIDENE)METHYL)-, (E)-

Common Name

English

Pelubiprofen [WHO-DD]

Common Name

English

CS-670

Code

English

pelubiprofen [INN]

Common Name

English

RS-2131

Code

English

PELUBIPROFEN [JAN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C257