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Details

Stereochemistry RACEMIC
Molecular Formula C16H22O3
Molecular Weight 262.3441
Optical Activity ( + / - )
Defined Stereocenters 2 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Pelubiprofen trans-alcohol

SMILES

CC(C(O)=O)C1=CC=C(C[C@@H]2CCCC[C@H]2O)C=C1

InChI

InChIKey=MCDKWYZDOMTURB-YUIIUQSRSA-N
InChI=1S/C16H22O3/c1-11(16(18)19)13-8-6-12(7-9-13)10-14-4-2-3-5-15(14)17/h6-9,11,14-15,17H,2-5,10H2,1H3,(H,18,19)/t11?,14-,15+/m0/s1

HIDE SMILES / InChI
Molecular Formula C16H22O3
Molecular Weight 262.3441
Charge 0
Count
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 2 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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

Sankyo
35
Curator's Comment: Sankyo (http://www.daiichisankyo.com/) discontinued its own development of pelubiprofen and licensed the product to Daewon Pharmaceutical Co., Ltd..

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Prostaglandin G/H synthase 2
51
Target ID: P35354
Gene ID: 5743.0
Gene Symbol: PTGS2
Target Organism: Homo sapiens (Human)
Inhibitor
8504
 2.88 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase III
665
Unknown

Approved Use

Unknown
Palliative
Phase III
665
Unknown

Approved Use

Unknown
Palliative
Phase III
665
Unknown

Approved Use

Unknown
Primary
Approved
8583
Pelubi

Approved Use

Reduce symptom of Osteoarthritis, Back pain (Lumbago)
Primary
Approved
8583
Pelubi

Approved Use

Reduce symptom of Osteoarthritis, Back pain (Lumbago)
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
453.04 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/27989618/
45 mg single, oral
dose: 45 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PELUBIPROFEN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
484.31 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/27989618/
45 mg single, oral
dose: 45 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PELUBIPROFEN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
0.37 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/27989618/
45 mg single, oral
dose: 45 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PELUBIPROFEN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
30 mg 3 times / day multiple, oral
Studied dose
Dose: 30 mg, 3 times / day
Route: oral
Route: multiple
Dose: 30 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/32991606/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/32991606/
Sources:
https://pubmed.ncbi.nlm.nih.gov/32991606/
PubMed

PubMed

TitleDatePubMed
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.
2015-03-01
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.
2014-11-18
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.
2011-12
Patents

Patents

US 9006294
2
US20110206762
2

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).
Substance Class Chemical
Created
by admin
on Wed Apr 02 18:48:28 GMT 2025
Edited
by admin
on Wed Apr 02 18:48:28 GMT 2025
Record UNII
48LBY5RAT5
Record Status Validated (UNII)
Record Version
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Name Type Language
Pelubiprofen trans-alcohol
Common Name English
trans-alcohol pelubiprofen
Preferred Name English
rel-4-[[(1R,2S)-2-Hydroxycyclohexyl]methyl]-?-methylbenzeneacetic acid
Systematic Name English
Benzeneacetic acid, 4-[[(1R,2S)-2-hydroxycyclohexyl]methyl]-?-methyl-, rel-
Systematic Name English
Code System Code Type Description
FDA UNII
48LBY5RAT5
Created by admin on Wed Apr 02 18:48:28 GMT 2025 , Edited by admin on Wed Apr 02 18:48:28 GMT 2025
PRIMARY
PUBCHEM
18603098
Created by admin on Wed Apr 02 18:48:28 GMT 2025 , Edited by admin on Wed Apr 02 18:48:28 GMT 2025
PRIMARY
CAS
1652582-08-5
Created by admin on Wed Apr 02 18:48:28 GMT 2025 , Edited by admin on Wed Apr 02 18:48:28 GMT 2025
PRIMARY
Related Record Type Details
Structure of PELUBIPROFEN
PRODRUG -> METABOLITE ACTIVE
Related Record Type Details
Structure of Pelubiprofen trans-alcohol
ACTIVE MOIETY
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