Details
Stereochemistry | ACHIRAL |
Molecular Formula | C21H18ClNO6 |
Molecular Weight | 415.824 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC2=C(C=C1)N(C(=O)C3=CC=C(Cl)C=C3)C(C)=C2CC(=O)OCC(O)=O
InChI
InChIKey=FSQKKOOTNAMONP-UHFFFAOYSA-N
InChI=1S/C21H18ClNO6/c1-12-16(10-20(26)29-11-19(24)25)17-9-15(28-2)7-8-18(17)23(12)21(27)13-3-5-14(22)6-4-13/h3-9H,10-11H2,1-2H3,(H,24,25)
Molecular Formula | C21H18ClNO6 |
Molecular Weight | 415.824 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: https://www.medicines.org.uk/emc/medicine/1145
Sources: https://www.medicines.org.uk/emc/medicine/1145
Acemetacin is a non-steroidal anti-inflammatory drug used for the treatment of osteoarthritis, rheumatoid arthritis, lower back pain, and relieving post-operative pain. It is manufactured by Merck KGaA under the tradename Emflex and is available in the UK as a prescription-only drug. Other brand names for acemetacin include Rheutrop (Austria), Acemetadoc, Acephlogont, Azeat, Rantudil (Germany, Hungary, Mexico, Portugal, Turkey), Gamespir (Greece), Oldan, Reudol (Spain), Tilur (Switzerland), Ost-map (Egypt). Acemetacin is a glycolic acid ester of indomethacin. The pharmacological activity resulting from acemetacin administration in man is derived from the presence of both acemetacin and indomethacin. The precise pharmacological mode of action of acemetacin is not known. However, unlike other NSAIDs, acemetacin is only a relatively weak inhibitor of prostaglandin synthetase. Prostaglandins are known to have an antisecretory and cytoprotective effect on the gastric mucosa. Acemetacin shows activity in many of the established in vitro tests of anti-inflammatory activity including inhibition of the release of a number of mediators of inflammation. Acemetacin is well absorbed after oral administration. Its major metabolite is indomethacin, which, after repeated administration is present at levels in excess of those of acemetacin. Acemetacin is bound to plasma protein to a slightly lesser extent than indomethacin and has a relatively short plasma elimination half-life. It is eliminated by both hepatic and renal mechanisms. The pharmacokinetics appear to be linear at recommended therapeutic doses, unaffected by moderate renal or hepatic impairment, and unchanged in the elderly.
Approval Year
PubMed
Title | Date | PubMed |
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Risk of upper gastrointestinal bleeding and perforation associated with low-dose aspirin as plain and enteric-coated formulations. | 2001 |
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A fast and reliable spectroscopic method for the determination of membrane--water partition coefficients of organic compounds. | 2001 Jan |
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In vitro effects of NSAIDS and paracetamol on oxidative stress-related parameters of human erythrocytes. | 2001 Jun |
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Effect of liposomes on the rate of alkaline hydrolysis of indomethacin and acemetacin. | 2001 Mar |
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Screening procedure for detection of non-steroidal anti-inflammatory drugs and their metabolites in urine as part of a systematic toxicological analysis procedure for acidic drugs and poisons by gas chromatography-mass spectrometry after extractive methylation. | 2001 May-Jun |
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Comparison of the efficacy of local corticosteroid injection and physical therapy for the treatment of adhesive capsulitis. | 2001 Sep |
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Efficacy and tolerability of acemetacin, a non-steroidal anti-inflammatory drug, in Mexican patients: result of the ETAPAM Study. | 2002 |
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A double-blind, randomized, controlled parallel group study evaluating the efficacy and safety of acemetacin for the management of osteoarthritis. | 2002 |
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Cutting edge: agonistic effect of indomethacin on a prostaglandin D2 receptor, CRTH2. | 2002 Feb 1 |
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Corticosteroid injection vs. nonsteroidal antiinflammatory drug and splinting in carpal tunnel syndrome. | 2002 Mar |
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The self-association of the drug acemetacin and its interactions and stabilization with beta-cyclodextrin in aqueous solution as inferred from NMR spectroscopy and HPLC studies. | 2002 Sep 3 |
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[The hydroxam reaction of indometacin and acemetacin]. | 2003 Jun |
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Treatment of congenital nephrogenic diabetes insipidus with hydrochlorothiazide and amiloride in an adult patient. | 2004 |
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Risk of breast cancer among users of aspirin and other anti-inflammatory drugs. | 2004 Aug 2 |
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In vitro scavenging activity for reactive oxygen and nitrogen species by nonsteroidal anti-inflammatory indole, pyrrole, and oxazole derivative drugs. | 2004 Dec 1 |
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Interaction of antiinflammatory drugs with EPC liposomes: calorimetric study in a broad concentration range. | 2004 Feb |
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Simultaneous determination of several antalgic drugs based on their interactions with beta-cyclodextrin by capillary zone electrophoresis. | 2004 Mar |
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[Flow injection chemiluminescent detection of acemetacin in KMnO4 - Na2 SO3 system]. | 2004 Nov |
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Comparison between sodium dodecylsulphate and cetyltrimethylammonium bromide as mobile phases in the micellar liquid chromatography determination of non-steroidal anti-inflammatory drugs in pharmaceuticals. | 2004 Oct 29 |
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[Treatment of osteoarthritis of the knee joint. Efficacy and tolerance to acemetacin slow release in comparison to celecoxib]. | 2004 Sep |
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Hydrogen peroxide scavenging activity by non-steroidal anti-inflammatory drugs. | 2005 Apr 29 |
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Long-term use of non-steroidal anti-inflammatory drugs and the risk of myocardial infarction in the general population. | 2005 Nov 29 |
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ABC transporters as multidrug resistance mechanisms and the development of chemosensitizers for their reversal. | 2005 Oct 4 |
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An exploratory theoretical elucidation on the peroxyl-radical-scavenging mechanism and structure-activity relationship of nonsteroidal anti-inflammatory drugs. | 2006 Jun 15 |
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Prescribing of COX-2 inhibitors in Germany after safety warnings and market withdrawals. | 2006 Oct |
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Lack of influence of body mass index on efficacy and tolerance of acemetacin in short-term treatment of musculoskeletal diseases. | 2007 Feb |
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Mechanisms underlying the anti-inflammatory activity and gastric safety of acemetacin. | 2007 Nov |
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Evaluation of the interaction between acemetacin and opioids on the hargreaves model of thermal hyperalgesia. | 2007 Nov |
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Accuracy of drug advertisements in medical journals under new law regulating the marketing of pharmaceutical products in Switzerland. | 2008 Dec 31 |
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Patients with rheumatoid arthritis have an altered circulatory aggrecan profile. | 2008 May 28 |
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A comparison of low-molecular-weight heparin and combined therapy of low-molecular-weight heparin with an anti-inflammatory agent in the treatment of superficial vein thrombosis. | 2009 Apr |
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Pharmacokinetics of acemetacin and its active metabolite indomethacin in rats during acute hepatic damage and liver regeneration. | 2009 Apr-Jun |
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Bartter's syndrome with type 2 diabetes mellitus. | 2009 Feb |
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Single dose oral acemetacin for acute postoperative pain in adults. | 2009 Jul 8 |
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[Randomized, double blind, multicentre, parallel group study to compare efficacy and safety of acemetacin and indometacin in patients with activated osteoarthrosis of the knee]. | 2009 Jun 10 |
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Risk of Upper Gastrointestinal Bleeding in a Cohort of New Users of Low-Dose ASA for Secondary Prevention of Cardiovascular Outcomes. | 2010 |
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Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method. | 2010 Dec |
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Evaluation of the short-term efficacy of NSAIDs on patients with active ankylosing spondylitis in daily practice: a 3-month, longitudinal, observational study. | 2010 Jan |
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Acemetacin antinociceptive mechanism is not related to NO or K+ channel pathways. | 2010 Mar |
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High-throughput microplate assay for the determination of drug partition coefficients. | 2010 Nov |
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Development and evaluation of pharmacosomes of aceclofenac. | 2010 Sep |
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Effect of ketorolac and diclofenac on the impairment of endothelium-dependent relaxation induced by reactive oxygen species in rabbit abdominal aorta. | 2010 Sep |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.medicines.org.uk/emc/medicine/1145
The recommended starting dose is 120 mg/day in divided doses, increasing to 180 mg/day in divided doses, depending on patient response
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15528048
acemetacin exhibited concentration-dependent effects against O(2)(-).
Substance Class |
Chemical
Created
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Record UNII |
5V141XK28X
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Record Status |
Validated (UNII)
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NCI_THESAURUS |
C257
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QM01AB11
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C026784
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CHEMBL189171
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258-403-4
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C73068
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ACEMETACIN
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
correction factors: for the calculation of content, multiply the peak areas of the following impurities by the corresponding correction factor: impurity C = 1.3
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
correction factors: for the calculation of content, multiply the peak areas of the following impurities by the corresponding correction factor: impurity F = 1.3
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
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IMPURITY -> PARENT |
correction factors: for the calculation of content, multiply the peak areas of the following impurities by the corresponding correction factor: impurity D = 1.4
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |