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
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)
DescriptionSources: http://www.ncbi.nlm.nih.gov/pubmed/16272692Curator'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
Sources: http://www.ncbi.nlm.nih.gov/pubmed/16272692
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL221 Sources: http://www.ncbi.nlm.nih.gov/pubmed/16272692 |
0.64 µM [IC50] | ||
Target ID: CHEMBL230 Sources: http://www.ncbi.nlm.nih.gov/pubmed/16272692 |
1.85 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Loxonin Approved Useused 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 Date2005 |
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Primary | Loxonin Approved Useused 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 Date2005 |
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Sources: https://pharmaoffshore.com/?cPath=485 |
Primary | Loxonin Approved UseChronic articular rheumatism, osteoarthritis, lumbago, periarthritis of the shoulder & shoulder-arm-neck syndrome. Relieves pain & inflammation after operation, trauma & tooth extraction. Launch Date2005 |
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Primary | Loxonin Approved UseChronic articular rheumatism, osteoarthritis, lumbago, periarthritis of the shoulder & shoulder-arm-neck syndrome. Relieves pain & inflammation after operation, trauma & tooth extraction. Launch Date2005 |
PubMed
Title | Date | PubMed |
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Stereospecific analysis of loxoprofen in plasma by chiral column liquid chromatography with a circular dichroism-based detector. | 2002 Mar 1 |
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Cognitive decline in administration of the nonsteroidal antiinflammatory drug loxoprofen with misoprostol in a 91-year-old Japanese woman. | 2002 Oct |
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Anti-U1RNP antibody and aseptic meningitis in connective tissue diseases. | 2003 |
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Loxoprofen sodium suppresses mouse tumor growth by inhibiting vascular endothelial growth factor. | 2003 |
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Effect of celecoxib, a cyclooxygenase-2 inhibitor, on the pathophysiology of adjuvant arthritis in rat. | 2005 Apr 25 |
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Effectiveness of an anti-inflammatory drug, loxoprofen, for patients with nocturia. | 2005 Aug |
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Zaltoprofen inhibits bradykinin-induced responses by blocking the activation of second messenger signaling cascades in rat dorsal root ganglion cells. | 2005 Jun |
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Pseudogout attack induced during etidronate disodium therapy. | 2006 |
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NSAID zaltoprofen possesses novel anti-nociceptive mechanism through blockage of B2-type bradykinin receptor in nerve endings. | 2006 Apr 24 |
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Study on the mechanism of photosensitive dermatitis caused by ketoprofen in the guinea pig. | 2006 Jul |
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[Cluster like headache in a patient with the Maffucci's syndrome]. | 2006 Jun |
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Anti-inflammatory activity of 4,4'-dihydroxy-alpha-truxillic acid. | 2006 Mar |
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Case-control study on the association of upper gastrointestinal bleeding and nonsteroidal anti-inflammatory drugs in Japan. | 2006 Sep |
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Influence of loxoprofen use on recovery from naturally acquired upper respiratory tract infections: a randomized controlled trial. | 2007 |
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Micro-CT imaging analysis for the effect of celecoxib, a cyclooxygenase-2 inhibitor, on inflammatory bone destruction in adjuvant arthritis rats. | 2008 |
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Prolonged intrahepatic cholestasis after exposure to loxoprofen. | 2008 Dec |
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Analgesic effect of percutaneously absorbed non-steroidal anti-inflammatory drugs: an experimental study in a rat acute inflammation model. | 2008 Jan 31 |
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Loxoprofen sodium treatment for elderly men with refractory nocturia: effect on night-time urine production. | 2008 May |
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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 |
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Quantitative comparison of the convulsive activity of combinations of twelve fluoroquinolones with five nonsteroidal antiinflammatory agents. | 2009 |
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A questionnaire-based survey on the prescription of non-steroidal anti-inflammatory drugs by physicians in East Asian countries in 2007. | 2009 |
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A novel approach to management of nocturia in patients with benign prostatic hyperplasia. | 2009 Apr |
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Case of Chlamydia-associated arthritis. | 2009 Dec |
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Liquid chromatography-tandem mass spectrometry method of loxoprofen in human plasma. | 2009 Jul |
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Synthesis of the active form of loxoprofen by using allylic substitutions in two steps. | 2009 Mar 5 |
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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 |
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[Tendencies of prescriptions for neuralgic pain in National Suruga Sanatorium (leprosy), Japan during last 11 years]. | 2009 Sep |
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Vulnerable sites and changes in mucin in the rat small intestine after non-steroidal anti-inflammatory drugs administration. | 2010 Dec |
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Evaluation of correlation between dissolution rates of loxoprofen tablets and their surface morphology observed by scanning electron microscope and atomic force microscope. | 2010 Jan |
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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 |
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Lafutidine prevents low-dose aspirin and loxoprofen induced gastric injury: a randomized, double-blinded, placebo controlled study. | 2010 Oct |
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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 |
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
Sources: http://www.ncbi.nlm.nih.gov/pubmed/20190399
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.
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C1323
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100000082267
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C040656
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METABOLITE ACTIVE (PRODRUG)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SUBSTANCE RECORD