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
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
245 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1888622/ |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
ACEMETACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FED |
|
187 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1888622/ |
60 mg 2 times / day steady-state, oral dose: 60 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ACEMETACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FED |
|
705 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1888622/ |
60 mg 2 times / day steady-state, oral dose: 60 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
INDOMETHACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FED |
|
632 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1888622/ |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
INDOMETHACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FED |
|
268 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1888622/ |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
ACEMETACIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED |
|
277 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1888622/ |
60 mg 2 times / day steady-state, oral dose: 60 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ACEMETACIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED |
|
555 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1888622/ |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
INDOMETHACIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED |
|
804 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1888622/ |
60 mg 2 times / day steady-state, oral dose: 60 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
INDOMETHACIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
589 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1888622/ |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
ACEMETACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FED |
|
483 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1888622/ |
60 mg 2 times / day steady-state, oral dose: 60 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ACEMETACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FED |
|
6349 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1888622/ |
60 mg 2 times / day steady-state, oral dose: 60 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
INDOMETHACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FED |
|
4596 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1888622/ |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
INDOMETHACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FED |
|
664 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1888622/ |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
ACEMETACIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED |
|
712 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1888622/ |
60 mg 2 times / day steady-state, oral dose: 60 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ACEMETACIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED |
|
4296 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1888622/ |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
INDOMETHACIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED |
|
7586 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1888622/ |
60 mg 2 times / day steady-state, oral dose: 60 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
INDOMETHACIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.03 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1888622/ |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
ACEMETACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FED |
|
1.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1888622/ |
60 mg 2 times / day steady-state, oral dose: 60 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ACEMETACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FED |
|
7.07 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1888622/ |
60 mg 2 times / day steady-state, oral dose: 60 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
INDOMETHACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FED |
|
6.01 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1888622/ |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
INDOMETHACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FED |
|
1.03 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1888622/ |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
ACEMETACIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED |
|
2.27 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1888622/ |
60 mg 2 times / day steady-state, oral dose: 60 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ACEMETACIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED |
|
6.12 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1888622/ |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
INDOMETHACIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED |
|
7.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1888622/ |
60 mg 2 times / day steady-state, oral dose: 60 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
INDOMETHACIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED |
Doses
Dose | Population | Adverse events |
---|---|---|
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, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Disc. AE: Gastric pain, Dyspepsia... AEs leading to discontinuation/dose reduction: Gastric pain Sources: Dyspepsia Diarrhea Headache |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Diarrhea | Disc. AE | 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, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Dyspepsia | Disc. AE | 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, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Gastric pain | Disc. AE | 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, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Headache | Disc. AE | 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, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
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 [IC50 >10 uM] | ||||
Page: 72.0 |
no | |||
Page: 426.0 |
no | |||
yes [IC50 0.1 uM] | ||||
yes [Inhibition 10 uM] | ||||
yes [Inhibition 10 uM] | ||||
yes | ||||
Page: 17.0 |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 400.0 |
no |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
A double-blind, randomized, controlled parallel group study evaluating the efficacy and safety of acemetacin for the management of osteoarthritis. | 2002 |
|
[The hydroxam reaction of indometacin and acemetacin]. | 2003 Jun |
|
Treatment of congenital nephrogenic diabetes insipidus with hydrochlorothiazide and amiloride in an adult patient. | 2004 |
|
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 |
|
Simultaneous determination of several antalgic drugs based on their interactions with beta-cyclodextrin by capillary zone electrophoresis. | 2004 Mar |
|
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 |
|
Prescribing of COX-2 inhibitors in Germany after safety warnings and market withdrawals. | 2006 Oct |
|
Polyproline-rod approach to isolating protein targets of bioactive small molecules: isolation of a new target of indomethacin. | 2007 Jan 31 |
|
Accuracy of drug advertisements in medical journals under new law regulating the marketing of pharmaceutical products in Switzerland. | 2008 Dec 31 |
|
Patients with rheumatoid arthritis have an altered circulatory aggrecan profile. | 2008 May 28 |
|
Lack of effects of acemetacin on signalling pathways for leukocyte adherence may explain its gastrointestinal safety. | 2008 Nov |
|
Bartter's syndrome with type 2 diabetes mellitus. | 2009 Feb |
|
Risk of Upper Gastrointestinal Bleeding in a Cohort of New Users of Low-Dose ASA for Secondary Prevention of Cardiovascular Outcomes. | 2010 |
|
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method. | 2010 Dec |
|
High-throughput microplate assay for the determination of drug partition coefficients. | 2010 Nov |
|
Development and evaluation of pharmacosomes of aceclofenac. | 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
by
admin
on
Edited
Wed Apr 02 09:59:16 GMT 2025
by
admin
on
Wed Apr 02 09:59:16 GMT 2025
|
Record UNII |
5V141XK28X
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Preferred Name | English | ||
|
Common 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 Wed Apr 02 09:59:16 GMT 2025 , Edited by admin on Wed Apr 02 09:59:16 GMT 2025
|
||
|
WHO-VATC |
QM01AB11
Created by
admin on Wed Apr 02 09:59:16 GMT 2025 , Edited by admin on Wed Apr 02 09:59:16 GMT 2025
|
||
|
WHO-ATC |
M01AB11
Created by
admin on Wed Apr 02 09:59:16 GMT 2025 , Edited by admin on Wed Apr 02 09:59:16 GMT 2025
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
C026784
Created by
admin on Wed Apr 02 09:59:16 GMT 2025 , Edited by admin on Wed Apr 02 09:59:16 GMT 2025
|
PRIMARY | |||
|
CHEMBL189171
Created by
admin on Wed Apr 02 09:59:16 GMT 2025 , Edited by admin on Wed Apr 02 09:59:16 GMT 2025
|
PRIMARY | |||
|
258-403-4
Created by
admin on Wed Apr 02 09:59:16 GMT 2025 , Edited by admin on Wed Apr 02 09:59:16 GMT 2025
|
PRIMARY | |||
|
C73068
Created by
admin on Wed Apr 02 09:59:16 GMT 2025 , Edited by admin on Wed Apr 02 09:59:16 GMT 2025
|
PRIMARY | |||
|
ACEMETACIN
Created by
admin on Wed Apr 02 09:59:16 GMT 2025 , Edited by admin on Wed Apr 02 09:59:16 GMT 2025
|
PRIMARY | |||
|
31162
Created by
admin on Wed Apr 02 09:59:16 GMT 2025 , Edited by admin on Wed Apr 02 09:59:16 GMT 2025
|
PRIMARY | |||
|
47
Created by
admin on Wed Apr 02 09:59:16 GMT 2025 , Edited by admin on Wed Apr 02 09:59:16 GMT 2025
|
PRIMARY | |||
|
1981
Created by
admin on Wed Apr 02 09:59:16 GMT 2025 , Edited by admin on Wed Apr 02 09:59:16 GMT 2025
|
PRIMARY | |||
|
100000087912
Created by
admin on Wed Apr 02 09:59:16 GMT 2025 , Edited by admin on Wed Apr 02 09:59:16 GMT 2025
|
PRIMARY | |||
|
53164-05-9
Created by
admin on Wed Apr 02 09:59:16 GMT 2025 , Edited by admin on Wed Apr 02 09:59:16 GMT 2025
|
PRIMARY | |||
|
3664
Created by
admin on Wed Apr 02 09:59:16 GMT 2025 , Edited by admin on Wed Apr 02 09:59:16 GMT 2025
|
PRIMARY | |||
|
5V141XK28X
Created by
admin on Wed Apr 02 09:59:16 GMT 2025 , Edited by admin on Wed Apr 02 09:59:16 GMT 2025
|
PRIMARY | |||
|
757413
Created by
admin on Wed Apr 02 09:59:16 GMT 2025 , Edited by admin on Wed Apr 02 09:59:16 GMT 2025
|
PRIMARY | |||
|
m1298
Created by
admin on Wed Apr 02 09:59:16 GMT 2025 , Edited by admin on Wed Apr 02 09:59:16 GMT 2025
|
PRIMARY | Merck Index | ||
|
SUB05209MIG
Created by
admin on Wed Apr 02 09:59:16 GMT 2025 , Edited by admin on Wed Apr 02 09:59:16 GMT 2025
|
PRIMARY | |||
|
DTXSID7022540
Created by
admin on Wed Apr 02 09:59:16 GMT 2025 , Edited by admin on Wed Apr 02 09:59:16 GMT 2025
|
PRIMARY | |||
|
DB13783
Created by
admin on Wed Apr 02 09:59:16 GMT 2025 , Edited by admin on Wed Apr 02 09:59:16 GMT 2025
|
PRIMARY | |||
|
16695
Created by
admin on Wed Apr 02 09:59:16 GMT 2025 , Edited by admin on Wed Apr 02 09:59:16 GMT 2025
|
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 |