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 |
---|---|---|
Risk of upper gastrointestinal bleeding and perforation associated with low-dose aspirin as plain and enteric-coated formulations. | 2001 |
|
A fast and reliable spectroscopic method for the determination of membrane--water partition coefficients of organic compounds. | 2001 Jan |
|
In vitro effects of NSAIDS and paracetamol on oxidative stress-related parameters of human erythrocytes. | 2001 Jun |
|
Effect of liposomes on the rate of alkaline hydrolysis of indomethacin and acemetacin. | 2001 Mar |
|
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 |
|
Comparison of the efficacy of local corticosteroid injection and physical therapy for the treatment of adhesive capsulitis. | 2001 Sep |
|
Efficacy and tolerability of acemetacin, a non-steroidal anti-inflammatory drug, in Mexican patients: result of the ETAPAM Study. | 2002 |
|
Cutting edge: agonistic effect of indomethacin on a prostaglandin D2 receptor, CRTH2. | 2002 Feb 1 |
|
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 |
|
Risk of breast cancer among users of aspirin and other anti-inflammatory drugs. | 2004 Aug 2 |
|
Interaction of antiinflammatory drugs with EPC liposomes: calorimetric study in a broad concentration range. | 2004 Feb |
|
[Flow injection chemiluminescent detection of acemetacin in KMnO4 - Na2 SO3 system]. | 2004 Nov |
|
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 |
|
Hydrogen peroxide scavenging activity by non-steroidal anti-inflammatory drugs. | 2005 Apr 29 |
|
Long-term use of non-steroidal anti-inflammatory drugs and the risk of myocardial infarction in the general population. | 2005 Nov 29 |
|
ABC transporters as multidrug resistance mechanisms and the development of chemosensitizers for their reversal. | 2005 Oct 4 |
|
An exploratory theoretical elucidation on the peroxyl-radical-scavenging mechanism and structure-activity relationship of nonsteroidal anti-inflammatory drugs. | 2006 Jun 15 |
|
Traditional nonsteroidal anti-inflammatory drugs and postmenopausal hormone therapy: a drug-drug interaction? | 2007 May |
|
Binding of nonsteroidal anti-inflammatory drugs to DPPC: structure and thermodynamic aspects. | 2008 Apr 15 |
|
Single dose oral acemetacin for acute postoperative pain in adults. | 2009 Jul 8 |
|
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method. | 2010 Dec |
|
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 |
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
by
admin
on
Edited
Sat Dec 16 18:02:26 UTC 2023
by
admin
on
Sat Dec 16 18:02:26 UTC 2023
|
Record UNII |
5V141XK28X
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
NCI_THESAURUS |
C257
Created by
admin on Sat Dec 16 18:02:27 UTC 2023 , Edited by admin on Sat Dec 16 18:02:27 UTC 2023
|
||
|
WHO-VATC |
QM01AB11
Created by
admin on Sat Dec 16 18:02:27 UTC 2023 , Edited by admin on Sat Dec 16 18:02:27 UTC 2023
|
||
|
WHO-ATC |
M01AB11
Created by
admin on Sat Dec 16 18:02:27 UTC 2023 , Edited by admin on Sat Dec 16 18:02:27 UTC 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
C026784
Created by
admin on Sat Dec 16 18:02:27 UTC 2023 , Edited by admin on Sat Dec 16 18:02:27 UTC 2023
|
PRIMARY | |||
|
CHEMBL189171
Created by
admin on Sat Dec 16 18:02:27 UTC 2023 , Edited by admin on Sat Dec 16 18:02:27 UTC 2023
|
PRIMARY | |||
|
258-403-4
Created by
admin on Sat Dec 16 18:02:27 UTC 2023 , Edited by admin on Sat Dec 16 18:02:27 UTC 2023
|
PRIMARY | |||
|
C73068
Created by
admin on Sat Dec 16 18:02:27 UTC 2023 , Edited by admin on Sat Dec 16 18:02:27 UTC 2023
|
PRIMARY | |||
|
ACEMETACIN
Created by
admin on Sat Dec 16 18:02:27 UTC 2023 , Edited by admin on Sat Dec 16 18:02:27 UTC 2023
|
PRIMARY | |||
|
31162
Created by
admin on Sat Dec 16 18:02:27 UTC 2023 , Edited by admin on Sat Dec 16 18:02:27 UTC 2023
|
PRIMARY | |||
|
47
Created by
admin on Sat Dec 16 18:02:27 UTC 2023 , Edited by admin on Sat Dec 16 18:02:27 UTC 2023
|
PRIMARY | |||
|
1981
Created by
admin on Sat Dec 16 18:02:27 UTC 2023 , Edited by admin on Sat Dec 16 18:02:27 UTC 2023
|
PRIMARY | |||
|
100000087912
Created by
admin on Sat Dec 16 18:02:27 UTC 2023 , Edited by admin on Sat Dec 16 18:02:27 UTC 2023
|
PRIMARY | |||
|
53164-05-9
Created by
admin on Sat Dec 16 18:02:27 UTC 2023 , Edited by admin on Sat Dec 16 18:02:27 UTC 2023
|
PRIMARY | |||
|
3664
Created by
admin on Sat Dec 16 18:02:27 UTC 2023 , Edited by admin on Sat Dec 16 18:02:27 UTC 2023
|
PRIMARY | |||
|
5V141XK28X
Created by
admin on Sat Dec 16 18:02:27 UTC 2023 , Edited by admin on Sat Dec 16 18:02:27 UTC 2023
|
PRIMARY | |||
|
757413
Created by
admin on Sat Dec 16 18:02:27 UTC 2023 , Edited by admin on Sat Dec 16 18:02:27 UTC 2023
|
PRIMARY | |||
|
m1298
Created by
admin on Sat Dec 16 18:02:27 UTC 2023 , Edited by admin on Sat Dec 16 18:02:27 UTC 2023
|
PRIMARY | Merck Index | ||
|
SUB05209MIG
Created by
admin on Sat Dec 16 18:02:27 UTC 2023 , Edited by admin on Sat Dec 16 18:02:27 UTC 2023
|
PRIMARY | |||
|
DTXSID7022540
Created by
admin on Sat Dec 16 18:02:27 UTC 2023 , Edited by admin on Sat Dec 16 18:02:27 UTC 2023
|
PRIMARY | |||
|
DB13783
Created by
admin on Sat Dec 16 18:02:27 UTC 2023 , Edited by admin on Sat Dec 16 18:02:27 UTC 2023
|
PRIMARY | |||
|
16695
Created by
admin on Sat Dec 16 18:02:27 UTC 2023 , Edited by admin on Sat Dec 16 18:02:27 UTC 2023
|
PRIMARY | RxNorm |
Related Record | Type | Details | ||
---|---|---|---|---|
|
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
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
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
|
||
|
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
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |