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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
Structure of LOXOPROFEN SODIUM DIHYDRATE

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

HIDE SMILES / InChI

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

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
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
[A case of takotsubo cardiomyopathy provoked by taking a new quinolone antibiotic drug and a non-steroidal anti-inflammatory drug].
2006 Feb
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
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
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
Education and Imaging. Gastrointestinal: ileal ulcers induced by non-steroidal anti-inflammatory drugs.
2007 Aug
Skin irritation in transdermal drug delivery systems: a strategy for its reduction.
2007 Feb
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
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
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
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
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
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 20:14:47 GMT 2023
Edited
by admin
on Fri Dec 15 20:14:47 GMT 2023
Record UNII
Z2DR42L11Y
Record Status Validated (UNII)
Record Version
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Name Type Language
LOXOPROFEN SODIUM DIHYDRATE
WHO-DD  
Common Name English
LOXOPROFEN SODIUM HYDRATE
JP  
Common Name English
LOXOPROFEN SODIUM [MART.]
Common Name English
BENZENEACETIC ACID, .ALPHA.-METHYL-4-((2-OXOCYCLOPENTYL)METHYL)-, SODIUM SALT, HYDRATE (1:1:2)
Common Name English
LOXOPROFEN SODIUM HYDRATE [JP]
Common Name English
LOBU
Brand Name English
Loxoprofen sodium dihydrate [WHO-DD]
Common Name English
MONOSODIUM 2-(4-((2-OXOCYCLOPENTYL)METHYL)PHENYL)PROPANOATE DIHYDRATE
Systematic Name English
LOXONIN
Brand Name English
OXENO
Brand Name English
Code System Code Type Description
SMS_ID
100000153406
Created by admin on Fri Dec 15 20:14:47 GMT 2023 , Edited by admin on Fri Dec 15 20:14:47 GMT 2023
PRIMARY
CHEBI
31786
Created by admin on Fri Dec 15 20:14:47 GMT 2023 , Edited by admin on Fri Dec 15 20:14:47 GMT 2023
PRIMARY
MESH
C040656
Created by admin on Fri Dec 15 20:14:47 GMT 2023 , Edited by admin on Fri Dec 15 20:14:47 GMT 2023
PRIMARY
RXCUI
259486
Created by admin on Fri Dec 15 20:14:47 GMT 2023 , Edited by admin on Fri Dec 15 20:14:47 GMT 2023
PRIMARY RxNorm
PUBCHEM
23674745
Created by admin on Fri Dec 15 20:14:47 GMT 2023 , Edited by admin on Fri Dec 15 20:14:47 GMT 2023
PRIMARY
CAS
226721-96-6
Created by admin on Fri Dec 15 20:14:47 GMT 2023 , Edited by admin on Fri Dec 15 20:14:47 GMT 2023
PRIMARY
EVMPD
SUB127513
Created by admin on Fri Dec 15 20:14:47 GMT 2023 , Edited by admin on Fri Dec 15 20:14:47 GMT 2023
PRIMARY
FDA UNII
Z2DR42L11Y
Created by admin on Fri Dec 15 20:14:47 GMT 2023 , Edited by admin on Fri Dec 15 20:14:47 GMT 2023
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY