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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
PubMed

PubMed

TitleDatePubMed
A fast and reliable spectroscopic method for the determination of membrane--water partition coefficients of organic compounds.
2001 Jan
Effect of liposomes on the rate of alkaline hydrolysis of indomethacin and acemetacin.
2001 Mar
Cutting edge: agonistic effect of indomethacin on a prostaglandin D2 receptor, CRTH2.
2002 Feb 1
Corticosteroid injection vs. nonsteroidal antiinflammatory drug and splinting in carpal tunnel syndrome.
2002 Mar
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
Treatment of congenital nephrogenic diabetes insipidus with hydrochlorothiazide and amiloride in an adult patient.
2004
Simultaneous determination of several antalgic drugs based on their interactions with beta-cyclodextrin by capillary zone electrophoresis.
2004 Mar
Hydrogen peroxide scavenging activity by non-steroidal anti-inflammatory drugs.
2005 Apr 29
ABC transporters as multidrug resistance mechanisms and the development of chemosensitizers for their reversal.
2005 Oct 4
Prescribing of COX-2 inhibitors in Germany after safety warnings and market withdrawals.
2006 Oct
Acemetacin monohydrate.
2007 Aug
Polyproline-rod approach to isolating protein targets of bioactive small molecules: isolation of a new target of indomethacin.
2007 Jan 31
Traditional nonsteroidal anti-inflammatory drugs and postmenopausal hormone therapy: a drug-drug interaction?
2007 May
Mechanisms underlying the anti-inflammatory activity and gastric safety of acemetacin.
2007 Nov
Evaluation of the interaction between acemetacin and opioids on the hargreaves model of thermal hyperalgesia.
2007 Nov
Development and validation of a highly sensitive ELISA for the determination of pharmaceutical indomethacin in water samples.
2007 Sep 15
Binding of nonsteroidal anti-inflammatory drugs to DPPC: structure and thermodynamic aspects.
2008 Apr 15
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
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
Pharmacokinetics of acemetacin and its active metabolite indomethacin in rats during acute hepatic damage and liver regeneration.
2009 Apr-Jun
Bartter's syndrome with type 2 diabetes mellitus.
2009 Feb
Single dose oral acemetacin for acute postoperative pain in adults.
2009 Jul 8
[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
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
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
Acemetacin antinociceptive mechanism is not related to NO or K+ channel pathways.
2010 Mar
High-throughput microplate assay for the determination of drug partition coefficients.
2010 Nov
Development and evaluation of pharmacosomes of aceclofenac.
2010 Sep
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

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 Sat Dec 16 18:02:26 GMT 2023
Edited
by admin
on Sat Dec 16 18:02:26 GMT 2023
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
Acemetacin [WHO-DD]
Common Name English
RANTUDIL
Brand 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 Sat Dec 16 18:02:27 GMT 2023 , Edited by admin on Sat Dec 16 18:02:27 GMT 2023
WHO-VATC QM01AB11
Created by admin on Sat Dec 16 18:02:27 GMT 2023 , Edited by admin on Sat Dec 16 18:02:27 GMT 2023
WHO-ATC M01AB11
Created by admin on Sat Dec 16 18:02:27 GMT 2023 , Edited by admin on Sat Dec 16 18:02:27 GMT 2023
Code System Code Type Description
MESH
C026784
Created by admin on Sat Dec 16 18:02:27 GMT 2023 , Edited by admin on Sat Dec 16 18:02:27 GMT 2023
PRIMARY
ChEMBL
CHEMBL189171
Created by admin on Sat Dec 16 18:02:27 GMT 2023 , Edited by admin on Sat Dec 16 18:02:27 GMT 2023
PRIMARY
ECHA (EC/EINECS)
258-403-4
Created by admin on Sat Dec 16 18:02:27 GMT 2023 , Edited by admin on Sat Dec 16 18:02:27 GMT 2023
PRIMARY
NCI_THESAURUS
C73068
Created by admin on Sat Dec 16 18:02:27 GMT 2023 , Edited by admin on Sat Dec 16 18:02:27 GMT 2023
PRIMARY
WIKIPEDIA
ACEMETACIN
Created by admin on Sat Dec 16 18:02:27 GMT 2023 , Edited by admin on Sat Dec 16 18:02:27 GMT 2023
PRIMARY
CHEBI
31162
Created by admin on Sat Dec 16 18:02:27 GMT 2023 , Edited by admin on Sat Dec 16 18:02:27 GMT 2023
PRIMARY
DRUG CENTRAL
47
Created by admin on Sat Dec 16 18:02:27 GMT 2023 , Edited by admin on Sat Dec 16 18:02:27 GMT 2023
PRIMARY
PUBCHEM
1981
Created by admin on Sat Dec 16 18:02:27 GMT 2023 , Edited by admin on Sat Dec 16 18:02:27 GMT 2023
PRIMARY
SMS_ID
100000087912
Created by admin on Sat Dec 16 18:02:27 GMT 2023 , Edited by admin on Sat Dec 16 18:02:27 GMT 2023
PRIMARY
CAS
53164-05-9
Created by admin on Sat Dec 16 18:02:27 GMT 2023 , Edited by admin on Sat Dec 16 18:02:27 GMT 2023
PRIMARY
INN
3664
Created by admin on Sat Dec 16 18:02:27 GMT 2023 , Edited by admin on Sat Dec 16 18:02:27 GMT 2023
PRIMARY
FDA UNII
5V141XK28X
Created by admin on Sat Dec 16 18:02:27 GMT 2023 , Edited by admin on Sat Dec 16 18:02:27 GMT 2023
PRIMARY
NSC
757413
Created by admin on Sat Dec 16 18:02:27 GMT 2023 , Edited by admin on Sat Dec 16 18:02:27 GMT 2023
PRIMARY
MERCK INDEX
m1298
Created by admin on Sat Dec 16 18:02:27 GMT 2023 , Edited by admin on Sat Dec 16 18:02:27 GMT 2023
PRIMARY Merck Index
EVMPD
SUB05209MIG
Created by admin on Sat Dec 16 18:02:27 GMT 2023 , Edited by admin on Sat Dec 16 18:02:27 GMT 2023
PRIMARY
EPA CompTox
DTXSID7022540
Created by admin on Sat Dec 16 18:02:27 GMT 2023 , Edited by admin on Sat Dec 16 18:02:27 GMT 2023
PRIMARY
DRUG BANK
DB13783
Created by admin on Sat Dec 16 18:02:27 GMT 2023 , Edited by admin on Sat Dec 16 18:02:27 GMT 2023
PRIMARY
RXCUI
16695
Created by admin on Sat Dec 16 18:02:27 GMT 2023 , Edited by admin on Sat Dec 16 18:02:27 GMT 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