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This repository is under review for potential modification in compliance with Administration directives.

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
Structure of ACEMETACIN

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)

HIDE SMILES / InChI

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

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

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Emflex Capsules

Approved Use

Unknown

Launch Date

1990
Palliative
Emflex Capsules

Approved Use

Unknown

Launch Date

1990
Palliative
Emflex Capsules

Approved Use

Unknown

Launch Date

1990
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
245 ng/mL
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
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
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
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
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
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
589 ng × h/mL
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
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
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
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
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
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
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
1.03 h
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
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
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
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
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
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
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
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

Doses

DosePopulationAdverse 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
Dyspepsia
Diarrhea
Headache
Sources:
AEs

AEs

AESignificanceDosePopulation
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

Overview

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical 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]
no
no
yes [IC50 0.1 uM]
yes [Inhibition 10 uM]
yes [Inhibition 10 uM]
yes
yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
Tox targets
PubMed

PubMed

TitleDatePubMed
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

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
acemetacin exhibited concentration-dependent effects against O(2)(-).
Substance Class Chemical
Created
by admin
on Wed Apr 02 09:59:16 GMT 2025
Edited
by admin
on Wed Apr 02 09:59:16 GMT 2025
Record UNII
5V141XK28X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ACEMETACIN
EP   INN   JAN   MART.   MI   WHO-DD  
INN  
Official Name English
RANTUDIL
Preferred Name English
Acemetacin [WHO-DD]
Common Name English
acemetacin [INN]
Common Name English
NSC-757413
Code English
1-(P-CHLOROBENZOYL)-5-METHOXY-2-METHYLINDOLE-3-ACETIC ACID ESTER WITH GLYCOLIC ACID
Common Name English
ACEMETACIN [JAN]
Common Name English
ACEMETACIN [MI]
Common Name English
ACEMETACIN [EP MONOGRAPH]
Common Name English
ACEMETACIN [MART.]
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
MESH
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
ChEMBL
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
ECHA (EC/EINECS)
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
NCI_THESAURUS
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
WIKIPEDIA
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
CHEBI
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
DRUG CENTRAL
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
PUBCHEM
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
SMS_ID
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
CAS
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
INN
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
FDA UNII
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
NSC
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
MERCK INDEX
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
EVMPD
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
EPA CompTox
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
DRUG BANK
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
RXCUI
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