Details
Stereochemistry | MIXED |
Molecular Formula | C15H17O3.Na.2H2O |
Molecular Weight | 304.314 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 0 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O.O.[Na+].CC(C([O-])=O)C1=CC=C(CC2CCCC2=O)C=C1
InChI
InChIKey=BAZQYVYVKYOAGO-UHFFFAOYSA-M
InChI=1S/C15H18O3.Na.2H2O/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);;2*1H2/q;+1;;/p-1
Molecular Formula | H2O |
Molecular Weight | 18.0153 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | Na |
Molecular Weight | 22.9898 |
Charge | 1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C15H18O3 |
Molecular Weight | 246.3016 |
Charge | 0 |
Count |
|
Stereochemistry | MIXED |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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 |
---|---|---|---|---|
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 |
|||
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 |
|||
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 |
||
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 |
---|---|---|
Pseudogout attack induced during etidronate disodium therapy. | 2006 |
|
Prostaglandin facilitates afferent nerve activity via EP1 receptors during urinary bladder inflammation in rats. | 2006 Apr |
|
[Epidural infusion of low dose bupivacaine after combined spinal-epidural anesthesia using needle through needle method provided no analgesic effect on postoperative pain after caesarian section]. | 2006 Aug |
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[A case of takotsubo cardiomyopathy provoked by taking a new quinolone antibiotic drug and a non-steroidal anti-inflammatory drug]. | 2006 Feb |
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Premedication with cyclooxygenase-2 inhibitor meloxicam reduced postoperative pain in patients after oral surgery. | 2006 Jul |
|
[Cluster like headache in a patient with the Maffucci's syndrome]. | 2006 Jun |
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Direct and simultaneous analysis of loxoprofen and its diastereometric alcohol metabolites in human serum by on-line column switching liquid chromatography and its application to a pharmacokinetic study. | 2006 May 1 |
|
Case-control study on the association of upper gastrointestinal bleeding and nonsteroidal anti-inflammatory drugs in Japan. | 2006 Sep |
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Pharmacokinetics and bioequivalence study of two brands of loxoprofen tablets in healthy volunteers. | 2007 |
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Influence of loxoprofen use on recovery from naturally acquired upper respiratory tract infections: a randomized controlled trial. | 2007 |
|
Education and Imaging. Gastrointestinal: ileal ulcers induced by non-steroidal anti-inflammatory drugs. | 2007 Aug |
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Skin irritation in transdermal drug delivery systems: a strategy for its reduction. | 2007 Feb |
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Risk of cardiovascular events in patients receiving celecoxib: a meta-analysis of randomized clinical trials. | 2007 Jan 1 |
|
Up-to-date information on gastric mucosal lesions from long-term NSAID therapy in orthopedic outpatients: a study using logistic regression analysis. | 2007 Jul |
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Safety of selective cyclooxygenase-2 inhibitors and a basic non-steroidal anti-inflammatory drug (NSAID) in Japanese patients with NSAID-induced urticaria and/or angioedema: Comparison of meloxicam, etodolac and tiaramide. | 2007 Mar |
|
[Case of loxoprofen sodium-induced eosinophilic pneumonia that occurred ipsilaterally after VATS lobectomy for lung cancer]. | 2007 Oct |
|
Massive myelinolytic leukoencephalopathy in a patient medicated with low-dose oral methotrexate for rheumatoid arthritis: an autopsy report. | 2007 Oct |
|
Short-term effect of COX-2 selective inhibitor as an adjunct for the treatment of periodontal disease: a clinical double-blind study in humans. | 2008 |
|
Micro-CT imaging analysis for the effect of celecoxib, a cyclooxygenase-2 inhibitor, on inflammatory bone destruction in adjuvant arthritis rats. | 2008 |
|
Long-lasting breaches in the bladder epithelium lead to storage dysfunction with increase in bladder PGE2 levels in the rat. | 2008 Aug |
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Prolonged intrahepatic cholestasis after exposure to loxoprofen. | 2008 Dec |
|
A clinical investigation of the mechanism of loxoprofen, a non-steroidal anti-inflammatory drug, for patients with nocturia. | 2008 Dec |
|
Analgesic effect of percutaneously absorbed non-steroidal anti-inflammatory drugs: an experimental study in a rat acute inflammation model. | 2008 Jan 31 |
|
Periodontal tissue regeneration using fibroblast growth factor-2: randomized controlled phase II clinical trial. | 2008 Jul 2 |
|
NSAID loxoprofen inhibits high threshold or wide dynamic range neuronal responses in the rat at different time-courses. | 2008 Mar-Apr |
|
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 |
|
Clinical, radiological, and biochemical characteristics in patients with diseases mimicking polymyalgia rheumatica. | 2009 |
|
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 |
|
A novel approach to management of nocturia in patients with benign prostatic hyperplasia. | 2009 Apr |
|
Overexpression of protein kinase C-delta plays a crucial role in interleukin-6-producing pheochromocytoma presenting with acute inflammatory syndrome: a case report. | 2009 Apr |
|
Case of Chlamydia-associated arthritis. | 2009 Dec |
|
Herbal medicine Shakuyaku-kanzo-to reduces paclitaxel-induced painful peripheral neuropathy in mice. | 2009 Jan |
|
Liquid chromatography-tandem mass spectrometry method of loxoprofen in human plasma. | 2009 Jul |
|
Effects of non-steroidal anti-inflammatory drugs (NSAIDs) on serum allergen levels after wheat ingestion. | 2009 Mar |
|
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 |
|
[Tendencies of prescriptions for neuralgic pain in National Suruga Sanatorium (leprosy), Japan during last 11 years]. | 2009 Sep |
|
Low direct cytotoxicity of loxoprofen on gastric mucosal cells. | 2010 |
|
[Case of food-dependent exercise-induced anaphylaxis diagnosed by the provocation test with cuttlefish after the pretreatment with 1.5 g of aspirin]. | 2010 Dec |
|
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 |
|
Protective effect of lafutidine, a histamine H2 receptor antagonist, against loxoprofen-induced small intestinal lesions in rats. | 2010 May |
|
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 |
|
[Experience of ultrasound-guided popliteal sciatic nerve block and femoral nerve perineural catheter placement in a morbidly obese patient undergoing total knee arthroplasty]. | 2010 Oct |
|
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 |
|
Loxoprofen Sodium, a Non-Selective NSAID, Reduces Atherosclerosis in Mice by Reducing Inflammation. | 2010 Sep |
|
Assessing the cardiovascular risk between celecoxib and nonselective nonsteroidal antiinflammatory drugs in patients with rheumatoid arthritis and osteoarthritis. | 2014 |
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 20:14:47 GMT 2023
by
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on
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Record UNII |
Z2DR42L11Y
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Record Status |
Validated (UNII)
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Record Version |
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31786
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SUB127513
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ACTIVE MOIETY |