pelubiprofen   Click here for help

GtoPdb Ligand ID: 9876

Synonyms: compound 13b [PMID: 6607354] | CS-670 [2] | DW-330SR | DW330SR | RS-2131 [4]
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Pelubiprofen is a nonsteroidal anti-inflammatory type compound [6]. Structurally it is an aryl propionic acid derivative, like ibuprofen. The INN-defined agent is a racemic mixture of enantiomers. We show the structure without specified stereochemistry to represent the mixture. Pelubiprofen is described as a prodrug of 2-arylpropionic acid with modest selectivity for COX2 [3].
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 54.37
Molecular weight 258.13
XLogP 2.37
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES OC(=O)C(c1ccc(cc1)C=C1CCCCC1=O)C
Isomeric SMILES OC(=O)C(c1ccc(cc1)/C=C/1\CCCCC1=O)C
InChI 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+
InChI Key AUZUGWXLBGZUPP-GXDHUFHOSA-N
References
1. Asami M, Shigeta A, Tanaka Y. (1996)
Disposition of CS-670, a novel nonsteroidal anit-inflammatory drug, and its metabolites in healthy human volunteers.
Chirality, 8 (2): 207-13. [PMID:8857182]
2. Asami M, Takasaki W, Iwabuchi H, Haruyama H, Wachi K, Terada A, Tanaka Y. (1995)
Stereospecific taurine conjugation of the trans-OH metabolite (active metabolite) of CS-670, a new 2-arylpropionic acid nonsteroidal anti-inflammatory drug, in dogs.
Biol Pharm Bull, 18 (11): 1584-9. [PMID:8593485]
3. Choi IA, Baek HJ, Cho CS, Lee YA, Chung WT, Park YE, Lee YJ, Park YB, Lee J, Lee SS et al.. (2014)
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.
BMC Musculoskelet Disord, 15: 375. [PMID:25403311]
4. Kobayashi K, Abe C, Iizuka Y, Shiokawa Y. (1986)
Immunomodulation by RS-2131, a new non-steroidal antiinflammatory drug.
Immunopharmacology, 12 (3): 213-20. [PMID:3546192]
5. Shin JS, Baek SR, Sohn SI, Cho YW, Lee KT. (2011)
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.
J Cell Biochem, 112 (12): 3594-603. [PMID:21809372]
6. Terada A, Naruto S, Wachi K, Tanaka S, Iizuka Y, Misaka E. (1984)
Synthesis and antiinflammatory activity of [(cycloalkylmethyl)phenyl]acetic acids and related compounds.
J Med Chem, 27 (2): 212-6. [PMID:6607354]