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)
| 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 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
6.6 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27121671/ |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
LOXOPROFEN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
3.58 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17915642/ |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
LOXOPROFEN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
11.5 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27121671/ |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
LOXOPROFEN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
3.54 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17915642/ |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
LOXOPROFEN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27121671/ |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
LOXOPROFEN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1.92 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17915642/ |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
LOXOPROFEN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
| Dose | Population | Adverse events |
|---|---|---|
6000 mg single, oral Overdose Dose: 6000 mg Route: oral Route: single Dose: 6000 mg Sources: |
unknown |
Other AEs: Consciousness loss... |
60 mg 3 times / day multiple, oral Recommended Dose: 60 mg, 3 times / day Route: oral Route: multiple Dose: 60 mg, 3 times / day Sources: |
unhealthy |
Other AEs: Nausea, Upper abdominal pain... Other AEs: Nausea (5.1%) Sources: Upper abdominal pain (2.6%) Diarrhea (1.7%) Dyspepsia (1.7%) Abdominal pain (0.9%) Soft faeces (0.9%) Gastritis (0.9%) Vomiting (0.9%) Toothache (0.9%) Headache (6.8%) Somnolence (3.4%) Dizziness (1.7%) Dysuria (0.9%) Renal colic (0.9%) |
100 mg 1 times / day multiple, topical Studied dose Dose: 100 mg, 1 times / day Route: topical Route: multiple Dose: 100 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: |
Other AEs: Upper abdominal pain, Headache... Other AEs: Upper abdominal pain (0.8%) Sources: Headache (4.2%) Somnolence (0.8%) Dizziness (0.8%) Dysgeusia (0.8%) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Consciousness loss | 1 pt | 6000 mg single, oral Overdose Dose: 6000 mg Route: oral Route: single Dose: 6000 mg Sources: |
unknown |
| Abdominal pain | 0.9% | 60 mg 3 times / day multiple, oral Recommended Dose: 60 mg, 3 times / day Route: oral Route: multiple Dose: 60 mg, 3 times / day Sources: |
unhealthy |
| Dysuria | 0.9% | 60 mg 3 times / day multiple, oral Recommended Dose: 60 mg, 3 times / day Route: oral Route: multiple Dose: 60 mg, 3 times / day Sources: |
unhealthy |
| Gastritis | 0.9% | 60 mg 3 times / day multiple, oral Recommended Dose: 60 mg, 3 times / day Route: oral Route: multiple Dose: 60 mg, 3 times / day Sources: |
unhealthy |
| Renal colic | 0.9% | 60 mg 3 times / day multiple, oral Recommended Dose: 60 mg, 3 times / day Route: oral Route: multiple Dose: 60 mg, 3 times / day Sources: |
unhealthy |
| Soft faeces | 0.9% | 60 mg 3 times / day multiple, oral Recommended Dose: 60 mg, 3 times / day Route: oral Route: multiple Dose: 60 mg, 3 times / day Sources: |
unhealthy |
| Toothache | 0.9% | 60 mg 3 times / day multiple, oral Recommended Dose: 60 mg, 3 times / day Route: oral Route: multiple Dose: 60 mg, 3 times / day Sources: |
unhealthy |
| Vomiting | 0.9% | 60 mg 3 times / day multiple, oral Recommended Dose: 60 mg, 3 times / day Route: oral Route: multiple Dose: 60 mg, 3 times / day Sources: |
unhealthy |
| Diarrhea | 1.7% | 60 mg 3 times / day multiple, oral Recommended Dose: 60 mg, 3 times / day Route: oral Route: multiple Dose: 60 mg, 3 times / day Sources: |
unhealthy |
| Dizziness | 1.7% | 60 mg 3 times / day multiple, oral Recommended Dose: 60 mg, 3 times / day Route: oral Route: multiple Dose: 60 mg, 3 times / day Sources: |
unhealthy |
| Dyspepsia | 1.7% | 60 mg 3 times / day multiple, oral Recommended Dose: 60 mg, 3 times / day Route: oral Route: multiple Dose: 60 mg, 3 times / day Sources: |
unhealthy |
| Upper abdominal pain | 2.6% | 60 mg 3 times / day multiple, oral Recommended Dose: 60 mg, 3 times / day Route: oral Route: multiple Dose: 60 mg, 3 times / day Sources: |
unhealthy |
| Somnolence | 3.4% | 60 mg 3 times / day multiple, oral Recommended Dose: 60 mg, 3 times / day Route: oral Route: multiple Dose: 60 mg, 3 times / day Sources: |
unhealthy |
| Nausea | 5.1% | 60 mg 3 times / day multiple, oral Recommended Dose: 60 mg, 3 times / day Route: oral Route: multiple Dose: 60 mg, 3 times / day Sources: |
unhealthy |
| Headache | 6.8% | 60 mg 3 times / day multiple, oral Recommended Dose: 60 mg, 3 times / day Route: oral Route: multiple Dose: 60 mg, 3 times / day Sources: |
unhealthy |
| Dizziness | 0.8% | 100 mg 1 times / day multiple, topical Studied dose Dose: 100 mg, 1 times / day Route: topical Route: multiple Dose: 100 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: |
| Dysgeusia | 0.8% | 100 mg 1 times / day multiple, topical Studied dose Dose: 100 mg, 1 times / day Route: topical Route: multiple Dose: 100 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: |
| Somnolence | 0.8% | 100 mg 1 times / day multiple, topical Studied dose Dose: 100 mg, 1 times / day Route: topical Route: multiple Dose: 100 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: |
| Upper abdominal pain | 0.8% | 100 mg 1 times / day multiple, topical Studied dose Dose: 100 mg, 1 times / day Route: topical Route: multiple Dose: 100 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: |
| Headache | 4.2% | 100 mg 1 times / day multiple, topical Studied dose Dose: 100 mg, 1 times / day Route: topical Route: multiple Dose: 100 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no [EC50 13.8029 uM] | ||||
| no [EC50 4.3649 uM] | ||||
| no [IC50 >10 uM] | ||||
| no [IC50 >10 uM] | ||||
| no [IC50 >10 uM] | ||||
| no [IC50 >10 uM] | ||||
| no [IC50 >10 uM] | ||||
| no [IC50 >10 uM] | ||||
| no | ||||
| no | ||||
| yes [IC50 12.2 uM] | ||||
| yes [IC50 27.1 uM] | ||||
| yes [IC50 320 uM] | ||||
| yes [IC50 4.5 uM] | ||||
| yes [IC50 8.7 uM] |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| major | ||||
| major | ||||
| major | ||||
| major | ||||
| major | ||||
| minor | ||||
| minor | ||||
| minor | ||||
| minor | ||||
| minor | ||||
| minor | ||||
| minor | ||||
| minor | ||||
| minor | ||||
| minor | ||||
| minor | ||||
| minor | ||||
| minor | ||||
| minor | ||||
| minor | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no |
Tox targets
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| Assessing the cardiovascular risk between celecoxib and nonselective nonsteroidal antiinflammatory drugs in patients with rheumatoid arthritis and osteoarthritis. | 2014 |
|
| [Case of food-dependent exercise-induced anaphylaxis diagnosed by the provocation test with cuttlefish after the pretreatment with 1.5 g of aspirin]. | 2010-12 |
|
| Vulnerable sites and changes in mucin in the rat small intestine after non-steroidal anti-inflammatory drugs administration. | 2010-12 |
|
| 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. | 2010-11-11 |
|
| [Experience of ultrasound-guided popliteal sciatic nerve block and femoral nerve perineural catheter placement in a morbidly obese patient undergoing total knee arthroplasty]. | 2010-10 |
|
| Lafutidine prevents low-dose aspirin and loxoprofen induced gastric injury: a randomized, double-blinded, placebo controlled study. | 2010-10 |
|
| High molecular weight hyaluronic acid relieved joint pain and prevented the progression of cartilage degeneration in a rabbit osteoarthritis model after onset of arthritis. | 2010-10 |
|
| Loxoprofen Sodium, a Non-Selective NSAID, Reduces Atherosclerosis in Mice by Reducing Inflammation. | 2010-09 |
|
| Protective effect of lafutidine, a histamine H2 receptor antagonist, against loxoprofen-induced small intestinal lesions in rats. | 2010-05 |
|
| Evaluation of correlation between dissolution rates of loxoprofen tablets and their surface morphology observed by scanning electron microscope and atomic force microscope. | 2010-01 |
|
| Low direct cytotoxicity of loxoprofen on gastric mucosal cells. | 2010 |
|
| Case of Chlamydia-associated arthritis. | 2009-12 |
|
| [Tendencies of prescriptions for neuralgic pain in National Suruga Sanatorium (leprosy), Japan during last 11 years]. | 2009-09 |
|
| Liquid chromatography-tandem mass spectrometry method of loxoprofen in human plasma. | 2009-07 |
|
| 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. | 2009-05 |
|
| A novel approach to management of nocturia in patients with benign prostatic hyperplasia. | 2009-04 |
|
| Overexpression of protein kinase C-delta plays a crucial role in interleukin-6-producing pheochromocytoma presenting with acute inflammatory syndrome: a case report. | 2009-04 |
|
| Synthesis of the active form of loxoprofen by using allylic substitutions in two steps. | 2009-03-05 |
|
| Effects of non-steroidal anti-inflammatory drugs (NSAIDs) on serum allergen levels after wheat ingestion. | 2009-03 |
|
| Herbal medicine Shakuyaku-kanzo-to reduces paclitaxel-induced painful peripheral neuropathy in mice. | 2009-01 |
|
| 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 |
|
| A questionnaire-based survey on the prescription of non-steroidal anti-inflammatory drugs by physicians in East Asian countries in 2007. | 2009 |
|
| Prolonged intrahepatic cholestasis after exposure to loxoprofen. | 2008-12 |
|
| A clinical investigation of the mechanism of loxoprofen, a non-steroidal anti-inflammatory drug, for patients with nocturia. | 2008-12 |
|
| 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. | 2008-10-24 |
|
| Long-lasting breaches in the bladder epithelium lead to storage dysfunction with increase in bladder PGE2 levels in the rat. | 2008-08 |
|
| Periodontal tissue regeneration using fibroblast growth factor-2: randomized controlled phase II clinical trial. | 2008-07-02 |
|
| Loxoprofen sodium treatment for elderly men with refractory nocturia: effect on night-time urine production. | 2008-05 |
|
| Analgesic effect of percutaneously absorbed non-steroidal anti-inflammatory drugs: an experimental study in a rat acute inflammation model. | 2008-01-31 |
|
| 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 |
|
| [Case of loxoprofen sodium-induced eosinophilic pneumonia that occurred ipsilaterally after VATS lobectomy for lung cancer]. | 2007-10 |
|
| Massive myelinolytic leukoencephalopathy in a patient medicated with low-dose oral methotrexate for rheumatoid arthritis: an autopsy report. | 2007-10 |
|
| NSAID loxoprofen inhibits high threshold or wide dynamic range neuronal responses in the rat at different time-courses. | 2007-09-28 |
|
| Education and Imaging. Gastrointestinal: ileal ulcers induced by non-steroidal anti-inflammatory drugs. | 2007-08 |
|
| Up-to-date information on gastric mucosal lesions from long-term NSAID therapy in orthopedic outpatients: a study using logistic regression analysis. | 2007-07 |
|
| 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. | 2007-03 |
|
| Skin irritation in transdermal drug delivery systems: a strategy for its reduction. | 2007-02 |
|
| Risk of cardiovascular events in patients receiving celecoxib: a meta-analysis of randomized clinical trials. | 2007-01-01 |
|
| Pharmacokinetics and bioequivalence study of two brands of loxoprofen tablets in healthy volunteers. | 2007 |
|
| Influence of loxoprofen use on recovery from naturally acquired upper respiratory tract infections: a randomized controlled trial. | 2007 |
|
| Case-control study on the association of upper gastrointestinal bleeding and nonsteroidal anti-inflammatory drugs in Japan. | 2006-09 |
|
| [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]. | 2006-08 |
|
| Premedication with cyclooxygenase-2 inhibitor meloxicam reduced postoperative pain in patients after oral surgery. | 2006-07 |
|
| [Cluster like headache in a patient with the Maffucci's syndrome]. | 2006-06 |
|
| 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. | 2006-05-01 |
|
| Prostaglandin facilitates afferent nerve activity via EP1 receptors during urinary bladder inflammation in rats. | 2006-04 |
|
| [A case of takotsubo cardiomyopathy provoked by taking a new quinolone antibiotic drug and a non-steroidal anti-inflammatory drug]. | 2006-02 |
|
| Pseudogout attack induced during etidronate disodium therapy. | 2006 |
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
Mon Mar 31 18:49:40 GMT 2025
by
admin
on
Mon Mar 31 18:49:40 GMT 2025
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| Record UNII |
3583H0GZAP
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| Record Status |
Validated (UNII)
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C1323
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100000082267
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5410
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CHEMBL19299
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3583H0GZAP
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LOXOPROFEN
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76172
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C81064
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68767-14-6
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SALT/SOLVATE -> PARENT | |||
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METABOLITE ACTIVE -> PRODRUG |
MAJOR
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