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Details

Stereochemistry MIXED
Molecular Formula C15H18O3
Molecular Weight 246.3016
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LOXOPROFEN

SMILES

CC(C(O)=O)C1=CC=C(CC2CCCC2=O)C=C1

InChI

InChIKey=YMBXTVYHTMGZDW-UHFFFAOYSA-N
InChI=1S/C15H18O3/c1-10(15(17)18)12-7-5-11(6-8-12)9-13-3-2-4-14(13)16/h5-8,10,13H,2-4,9H2,1H3,(H,17,18)

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including http://www.rad-ar.or.jp/siori/english/print.cgi?n=1944 http://www.meppo.com/pdf/drugs/3019-ROXONIN-1440574468.pdf

Loxoprofen (INN) is a non-steroidal anti-inflammatory drug in the propionic acid derivatives group. It is marketed in Brazil, Mexico and Japan by Sankyo as its sodium salt, loxoprofen sodium, under the trade name Loxonin, Argentina as Oxeno and in India as Loxomac. It is available in these countries for oral administration, and a transdermal preparation was approved for sale in Japan on January 2006. It is usually used to treat rheumatoid arthritis and osteoarthritis. It is also used to reduce pain and inflammation after surgery, wounds and tooth removal, as well as to bring down fever or ease pain induced by acute inflammation of upper respiratory tract Loxoprofen is a prodrug. When administered orally, loxoprofen sodium hydrate is absorbed from the gastrointestinal tract as an unchanged compound with only a modest gastric-mucosal irritation. It is then rapidly biotransformed into the active metabolite trans-OH form (SRS coordination) with a potent inhibitory effect on prostaglandin biosynthesis to exert its pharmacologic effects. Inhibition of prostaglandin biosynthesis constitutes the mechanism of action of this drug, the site of action being cyclooxygenase.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.64 µM [IC50]
1.85 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Loxonin

Approved Use

used to treat rheumatoid arthritis and osteoarthritis. It is also used to reduce pain and inflammation after surgery, wounds and tooth removal, as well as to bring down fever or ease pain induced by acute inflammation of upper respiratory tract.

Launch Date

2005
Primary
Loxonin

Approved Use

used to treat rheumatoid arthritis and osteoarthritis. It is also used to reduce pain and inflammation after surgery, wounds and tooth removal, as well as to bring down fever or ease pain induced by acute inflammation of upper respiratory tract.

Launch Date

2005
Primary
Loxonin

Approved Use

Chronic articular rheumatism, osteoarthritis, lumbago, periarthritis of the shoulder & shoulder-arm-neck syndrome. Relieves pain & inflammation after operation, trauma & tooth extraction.

Launch Date

2005
Primary
Loxonin

Approved Use

Chronic articular rheumatism, osteoarthritis, lumbago, periarthritis of the shoulder & shoulder-arm-neck syndrome. Relieves pain & inflammation after operation, trauma & tooth extraction.

Launch Date

2005
PubMed

PubMed

TitleDatePubMed
Stereospecific analysis of loxoprofen in plasma by chiral column liquid chromatography with a circular dichroism-based detector.
2002 Mar 1
Cognitive decline in administration of the nonsteroidal antiinflammatory drug loxoprofen with misoprostol in a 91-year-old Japanese woman.
2002 Oct
Anti-U1RNP antibody and aseptic meningitis in connective tissue diseases.
2003
Loxoprofen sodium suppresses mouse tumor growth by inhibiting vascular endothelial growth factor.
2003
Effect of celecoxib, a cyclooxygenase-2 inhibitor, on the pathophysiology of adjuvant arthritis in rat.
2005 Apr 25
Effectiveness of an anti-inflammatory drug, loxoprofen, for patients with nocturia.
2005 Aug
Zaltoprofen inhibits bradykinin-induced responses by blocking the activation of second messenger signaling cascades in rat dorsal root ganglion cells.
2005 Jun
Pseudogout attack induced during etidronate disodium therapy.
2006
NSAID zaltoprofen possesses novel anti-nociceptive mechanism through blockage of B2-type bradykinin receptor in nerve endings.
2006 Apr 24
Study on the mechanism of photosensitive dermatitis caused by ketoprofen in the guinea pig.
2006 Jul
[Cluster like headache in a patient with the Maffucci's syndrome].
2006 Jun
Anti-inflammatory activity of 4,4'-dihydroxy-alpha-truxillic acid.
2006 Mar
Case-control study on the association of upper gastrointestinal bleeding and nonsteroidal anti-inflammatory drugs in Japan.
2006 Sep
Influence of loxoprofen use on recovery from naturally acquired upper respiratory tract infections: a randomized controlled trial.
2007
Micro-CT imaging analysis for the effect of celecoxib, a cyclooxygenase-2 inhibitor, on inflammatory bone destruction in adjuvant arthritis rats.
2008
Prolonged intrahepatic cholestasis after exposure to loxoprofen.
2008 Dec
Analgesic effect of percutaneously absorbed non-steroidal anti-inflammatory drugs: an experimental study in a rat acute inflammation model.
2008 Jan 31
Loxoprofen sodium treatment for elderly men with refractory nocturia: effect on night-time urine production.
2008 May
Identification of degradation products in loxoprofen sodium adhesive tapes by liquid chromatography-mass spectrometry and dynamic pressurized liquid extraction-solid-phase extraction coupled to liquid chromatography-nuclear magnetic resonance spectroscopy.
2008 Oct 24
Quantitative comparison of the convulsive activity of combinations of twelve fluoroquinolones with five nonsteroidal antiinflammatory agents.
2009
A questionnaire-based survey on the prescription of non-steroidal anti-inflammatory drugs by physicians in East Asian countries in 2007.
2009
A novel approach to management of nocturia in patients with benign prostatic hyperplasia.
2009 Apr
Case of Chlamydia-associated arthritis.
2009 Dec
Liquid chromatography-tandem mass spectrometry method of loxoprofen in human plasma.
2009 Jul
Synthesis of the active form of loxoprofen by using allylic substitutions in two steps.
2009 Mar 5
The importance of brain PGE2 inhibition versus paw PGE2 inhibition as a mechanism for the separation of analgesic and antipyretic effects of lornoxicam in rats with paw inflammation.
2009 May
[Tendencies of prescriptions for neuralgic pain in National Suruga Sanatorium (leprosy), Japan during last 11 years].
2009 Sep
Vulnerable sites and changes in mucin in the rat small intestine after non-steroidal anti-inflammatory drugs administration.
2010 Dec
Evaluation of correlation between dissolution rates of loxoprofen tablets and their surface morphology observed by scanning electron microscope and atomic force microscope.
2010 Jan
Properties and synthesis of 2-{2-fluoro (or bromo)-4-[(2-oxocyclopentyl)methyl]phenyl}propanoic acid: nonsteroidal anti-inflammatory drugs with low membrane permeabilizing and gastric lesion-producing activities.
2010 Nov 11
Lafutidine prevents low-dose aspirin and loxoprofen induced gastric injury: a randomized, double-blinded, placebo controlled study.
2010 Oct
High molecular weight hyaluronic acid relieved joint pain and prevented the progression of cartilage degeneration in a rabbit osteoarthritis model after onset of arthritis.
2010 Oct
Patents

Sample Use Guides

For the use in reducing inflammation and pain induced by rheumatoid arthritis, osteoarthritis, In general, for adults, take 1 tablet (60 mg of loxoprofen sodium) at a time, 3 times a day. If taken as on-demand use, take 1 to 2 tablets (60 to 120 mg) at a time. For the use in reducing fever or pain induced by acute inflammation of upper respiratory tract: In general, for adults, take 1 tablet (60 mg of loxoprofen sodium) at a time, as needed. Usually up to twice a day. Do not exceed 3 tablets (180 mg) a day.
Route of Administration: Oral
In Vitro Use Guide
Loxoprofen induced apoptosis more effectively in cultured human gastric cancer cells than in the primary culture. Loxoprofen exhibited much lower membrane permeabilizing activities than did indomethacin and celecoxib. Low direct cytotoxicity of loxoprofen observed in vitro is involved in its relative safety on production of gastric lesions in clinical situation.
Name Type Language
LOXOPROFEN
INN   MI   WHO-DD  
INN  
Official Name English
LOXOPROFEN ACID
Common Name English
loxoprofen [INN]
Common Name English
Loxoprofen [WHO-DD]
Common Name English
(±)-P-((2-OXOCYCLOPENTYL)METHYL)HYDRATROPIC ACID
Common Name English
LOXOPROFEN [MI]
Common Name English
2-(4-((2-OXOCYCLOPENTAN-1-YL)METHYL)PHENYL)PROPIONIC ACID
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C1323
Created by admin on Fri Dec 15 17:37:30 GMT 2023 , Edited by admin on Fri Dec 15 17:37:30 GMT 2023
Code System Code Type Description
SMS_ID
100000082267
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PRIMARY
INN
5410
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PRIMARY
ChEMBL
CHEMBL19299
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PRIMARY
DRUG BANK
DB09212
Created by admin on Fri Dec 15 17:37:30 GMT 2023 , Edited by admin on Fri Dec 15 17:37:30 GMT 2023
PRIMARY
FDA UNII
3583H0GZAP
Created by admin on Fri Dec 15 17:37:30 GMT 2023 , Edited by admin on Fri Dec 15 17:37:30 GMT 2023
PRIMARY
WIKIPEDIA
LOXOPROFEN
Created by admin on Fri Dec 15 17:37:30 GMT 2023 , Edited by admin on Fri Dec 15 17:37:30 GMT 2023
PRIMARY
CHEBI
31786
Created by admin on Fri Dec 15 17:37:30 GMT 2023 , Edited by admin on Fri Dec 15 17:37:30 GMT 2023
PRIMARY
PUBCHEM
3965
Created by admin on Fri Dec 15 17:37:30 GMT 2023 , Edited by admin on Fri Dec 15 17:37:30 GMT 2023
PRIMARY
RXCUI
28908
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PRIMARY RxNorm
EVMPD
SUB08609MIG
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PRIMARY
MESH
C040656
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PRIMARY
EPA CompTox
DTXSID1045164
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PRIMARY
DRUG CENTRAL
1615
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PRIMARY
MERCK INDEX
m6917
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PRIMARY Merck Index
CHEBI
76172
Created by admin on Fri Dec 15 17:37:30 GMT 2023 , Edited by admin on Fri Dec 15 17:37:30 GMT 2023
PRIMARY
NCI_THESAURUS
C81064
Created by admin on Fri Dec 15 17:37:30 GMT 2023 , Edited by admin on Fri Dec 15 17:37:30 GMT 2023
PRIMARY
CAS
68767-14-6
Created by admin on Fri Dec 15 17:37:30 GMT 2023 , Edited by admin on Fri Dec 15 17:37:30 GMT 2023
PRIMARY