Pelubiprofen

Pelubiprofen
Clinical data
Trade names	Pelubi
ATC code	None;
Legal status
Legal status	Rx in several countries;
Identifiers
	IUPAC name 2-[4-[(E)-(2-Oxocyclohexylidene)methyl]phenyl]propanoic acid;
CAS Number	69956-77-0;
PubChem CID	5282203;
DrugBank	DB12150;
UNII	1619C79FVJ;
CompTox Dashboard (EPA)	DTXSID2048795 ;
Chemical and physical data
Formula	C16H18O3
Molar mass	258.317 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(C1=CC=C(C=C1)/C=C/2\CCCCC2=O)C(=O)O;
	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+; Key:AUZUGWXLBGZUPP-GXDHUFHOSA-N;

Pelubiprofen is a nonsteroidal anti-inflammatory drug of the profen class used to treat back pain and osteoarthritis.^[1]

Pelubiprofen was developed in South Korea by Daewon Pharmaceuticals and it is marketed in Korea and Russia,^[2] among other countries.

Research

Pelubiprofen is being studied for use in combination with eperisone.^[3]

Because pelubiprofen has low water solubility, development of salt formulations with better solubility are being studied.^[4]

Synthesis

Pelubiprofen can be prepared by the reaction of 1-(1-piperidino)cyclohexene (1) with ethyl 2-(4-formylphenyl)propanoate (2).^[5]^[6]^[7]^[8]^[9]^[10]^[11]

References

^ "Pelubiprofen - Daewon Pharmaceutical". AdisInsight. Springer Nature Switzerland AG.
^ Chan-Hyuk K (26 September 2023). "Daewon Pharm wins $3 million deal to export Pelubi to Indonesia". Korea Biomedial Review.
^ "(Eperisone + pelubiprofen) by Daewon Pharmaceutical for Low Back Pain: Likelihood of Approval". pharmaceutical-technology.com. 5 June 2023.
^ Park JY, Oh DH, Park SW, Chae BR, Kim CW, Han SH, et al. (May 2021). "Development of Pelubiprofen Tromethamine with Improved Gastrointestinal Safety and Absorption". Pharmaceutics. 13 (5): 745. doi:10.3390/pharmaceutics13050745. PMC 8158122. PMID 34070062.
^ Serradell, MN; Castaer, J.; RS-2131. Drugs Fut 1984, 9, 4, 275.
^ Terada, Atsusuke; Naruto, Shunji; Wachi, Kazuyuki; Tanaka, Shigeru; Iizuka, Yoshio; Misaka, Eiichi (1984). "Synthesis and antiinflammatory activity of [(cycloalkylmethyl)phenyl]acetic acids and related compounds". Journal of Medicinal Chemistry. 27 (2): 212–216. doi:10.1021/jm00368a019.
^ Atsusuke Terada, Shigeru Tanaka, & Eiichi Misaka, US4254274 (1981 to Sankyo Co Ltd).
^ Yuan Weiguan, et al. CN111153791 (2020 to HUNAN JIUDIAN HONGYANG PHARMACEUTICAL Co., Ltd).
^ Yuan Weiguan, et al. WO2021129651 (to Hunan Jiudian Pharmaceutical Co Ltd).
^ Ning Hulin, et al. CN110041191 (2019 to HUNAN JIUDIAN HONGYANG PHARMACEUTICAL Co., Ltd.).
^ ChemDrug

[1] "Pelubiprofen - Daewon Pharmaceutical". AdisInsight. Springer Nature Switzerland AG.

[2] Chan-Hyuk K (26 September 2023). "Daewon Pharm wins $3 million deal to export Pelubi to Indonesia". Korea Biomedial Review.

[3] "(Eperisone + pelubiprofen) by Daewon Pharmaceutical for Low Back Pain: Likelihood of Approval". pharmaceutical-technology.com. 5 June 2023.

[4] Park JY, Oh DH, Park SW, Chae BR, Kim CW, Han SH, et al. (May 2021). "Development of Pelubiprofen Tromethamine with Improved Gastrointestinal Safety and Absorption". Pharmaceutics. 13 (5): 745. doi:10.3390/pharmaceutics13050745. PMC 8158122. PMID 34070062.

[5] Serradell, MN; Castaer, J.; RS-2131. Drugs Fut 1984, 9, 4, 275.

[6] Terada, Atsusuke; Naruto, Shunji; Wachi, Kazuyuki; Tanaka, Shigeru; Iizuka, Yoshio; Misaka, Eiichi (1984). "Synthesis and antiinflammatory activity of [(cycloalkylmethyl)phenyl]acetic acids and related compounds". Journal of Medicinal Chemistry. 27 (2): 212–216. doi:10.1021/jm00368a019.

[7] Atsusuke Terada, Shigeru Tanaka, & Eiichi Misaka, US4254274 (1981 to Sankyo Co Ltd).

[8] Yuan Weiguan, et al. CN111153791 (2020 to HUNAN JIUDIAN HONGYANG PHARMACEUTICAL Co., Ltd).

[9] Yuan Weiguan, et al. WO2021129651 (to Hunan Jiudian Pharmaceutical Co Ltd).

[10] Ning Hulin, et al. CN110041191 (2019 to HUNAN JIUDIAN HONGYANG PHARMACEUTICAL Co., Ltd.).

[11] ChemDrug

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v t e Non-steroidal anti-inflammatory drugs (NSAIDs) (primarily M01A and M02A, also N02BA)
pyrazolones / pyrazolidines	Aminophenazone Ampyrone Azapropazone Clofezone Difenamizole Famprofazone Feprazone Kebuzone Metamizole Mofebutazone Morazone Nifenazone Oxyphenbutazone Phenazone Phenylbutazone Propyphenazone Sulfinpyrazone Suxibuzone^‡
salicylates	Aspirin (acetylsalicylic acid)^# Aloxiprin Benorylate Carbasalate calcium Diflunisal Dipyrocetyl Ethenzamide Guacetisal Magnesium salicylate Methyl salicylate Salsalate Salicin Salicylamide Salicylic acid (salicylate) Sodium salicylate
acetic acid derivatives and related substances	Aceclofenac Acemetacin Alclofenac Amfenac Bendazac Bromfenac Bufexamac Bumadizone Diclofenac Difenpiramide Etodolac Felbinac Fenclozic acid Fentiazac Indometacin Indometacin farnesil Isoxepac Ketorolac Lonazolac Mofezolac Oxametacin Prodolic acid Proglumetacin Sulindac Tiopinac Tolmetin Zomepirac^†
oxicams	Ampiroxicam Droxicam Isoxicam Lornoxicam Meloxicam Piroxicam Pivoxicam Tenoxicam
propionic acid derivatives (profens)	Alminoprofen Benoxaprofen^† Carprofen^‡ Dexibuprofen Dexketoprofen Fenbufen Fenoprofen Flunoxaprofen Flurbiprofen Ibuprofen^# Ibuproxam Indoprofen^† Ketoprofen Loxoprofen Miroprofen Naproxen Oxaprozin Pelubiprofen Piketoprofen Pirprofen Suprofen Tarenflurbil Tepoxalin^‡ Tiaprofenic acid Vedaprofen^‡ Zaltoprofen COX-inhibiting nitric oxide donator: Naproxcinod
n-arylanthranilic acids (fenamates)	Azapropazone Clonixin Etofenamate Floctafenine Flufenamic acid Flunixin Flutiazin Glafenine^† Meclofenamic acid Mefenamic acid Morniflumate Niflumic acid Tolfenamic acid
COX-2 inhibitors (coxibs)	Apricoxib Celecoxib (+tramadol) Cimicoxib^‡ Deracoxib^‡ Etoricoxib Firocoxib^‡ Lumiracoxib^† Mavacoxib^‡ Parecoxib Robenacoxib^‡ Rofecoxib^† Valdecoxib^†
other	Aminopropionitrile Benzydamine Chondroitin sulfate Diacerein Fluproquazone Glucosamine Glycosaminoglycan Hyperforin Nabumetone Nimesulide Oxaceprol Proquazone Superoxide dismutase / orgotein Tenidap
NSAID combinations	Ibuprofen/famotidine Ibuprofen/hydrocodone Ibuprofen/oxycodone Ibuprofen/paracetamol Meloxicam/bupivacaine Naproxen/diphenhydramine Naproxen/esomeprazole
Key: underline indicates initially developed first-in-class compound of specific group; ^#WHO-Essential Medicines; ^†withdrawn drugs; ^‡veterinary use.
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