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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A fast and reliable spectroscopic method for the determination of membrane--water partition coefficients of organic compounds. | 2001 Jan |
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Effect of liposomes on the rate of alkaline hydrolysis of indomethacin and acemetacin. | 2001 Mar |
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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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Treatment of congenital nephrogenic diabetes insipidus with hydrochlorothiazide and amiloride in an adult patient. | 2004 |
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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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Hydrogen peroxide scavenging activity by non-steroidal anti-inflammatory drugs. | 2005 Apr 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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Prescribing of COX-2 inhibitors in Germany after safety warnings and market withdrawals. | 2006 Oct |
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Acemetacin monohydrate. | 2007 Aug |
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Polyproline-rod approach to isolating protein targets of bioactive small molecules: isolation of a new target of indomethacin. | 2007 Jan 31 |
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Traditional nonsteroidal anti-inflammatory drugs and postmenopausal hormone therapy: a drug-drug interaction? | 2007 May |
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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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Development and validation of a highly sensitive ELISA for the determination of pharmaceutical indomethacin in water samples. | 2007 Sep 15 |
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Binding of nonsteroidal anti-inflammatory drugs to DPPC: structure and thermodynamic aspects. | 2008 Apr 15 |
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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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Lack of effects of acemetacin on signalling pathways for leukocyte adherence may explain its gastrointestinal safety. | 2008 Nov |
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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
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Record UNII |
5V141XK28X
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C026784
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CHEMBL189171
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C73068
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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
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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 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 |