Acemetacin

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Acemetacin
Clinical data
Trade namesEmflex, many others
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral
ATC code
Legal status
Legal status
  • UK: POM (Prescription only)
biliary
Identifiers
  • 2-[2-[1-(4-Chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetyl]oxyacetic acid
JSmol)
Melting point150 to 153 °C (302 to 307 °F)
  • Clc1ccc(cc1)C(=O)n3c2ccc(OC)cc2c(c3C)CC(=O)OCC(=O)O
  • 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) checkY
  • Key:FSQKKOOTNAMONP-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Acemetacin is a

Merck KGaA under the tradename Emflex. It is no longer available in the UK (since 2018),[1] however is available in other countries as a prescription-only drug.[2]

Medical uses

Acemetacin has proven effective in the treatment of osteoarthritis, rheumatoid arthritis, ankylosing spondylitis, and other kinds of rheumatoid inflammation, as well as in post-operative and post-traumatic pain and attack of gout.[3][4] Application of a single dose of acemetacin for post-operative pain is not well supported by studies.[5]

Contraindications

Contraindications are basically the same as with other NSAIDs:

anaemia, leukopenia), and during the third trimester of pregnancy.[3][6]

Adverse effects

Common side effects (in about 1–10% of patients) include gastrointestinal problems typical of NSAIDs, such as nausea, diarrhoea, stomach pain, and peptic ulcer; central nervous effects like headache and dizziness; and skin reactions. Gastrointestinal tolerability is better than that of the related drug indometacin. Severe allergic reactions and haematopoietic disorders occur in fewer than 0.01% of patients.[3][4]

Interactions

The following interactions, typical of NSAIDs, have been described:[3][4]

  • other NSAIDs, corticosteroids: increased frequency of side effects, especially peptic ulcers and gastrointestinal bleeding
  • ACE inhibitors
    and other antihypertensive drugs: reduced effectiveness of these drugs
  • with ACE inhibitors or ciclosporin, increased risk of kidney function disorders
  • anticoagulants such as warfarin: increased risk of bleeding
  • increased blood plasma concentrations of digoxin and methotrexate
  • decreased plasma concentrations of lithium

Pharmacology

Main article:
Non-steroidal anti-inflammatory drug § Mechanism of action

Acemetacin acts as an inhibitor of

analgetic (pain relieving) effects. In the body, it is partly metabolized to indomethacin, which also acts as a COX inhibitor. The same mechanism is responsible for the antipyretic and antiplatelet effects, which are however not clinically used, as well as for the typical NSAID adverse effects.[3][4]

An advantage of acemetacin is that it reduces gastric damage as compared to indometacin, possibly because acemetacin has less effect on the increase of

leukocyte-endothelial adherence.[7][8]

Pharmacokinetics

Metabolism of acemetacin. Cleaving of the glycolic acid ester (green) activates the substance to indometacin, cleaving of the methoxy ether or the 4-chlorobenzoate (orange) inactivate it.

The substance is quickly and almost completely absorbed from the gut. Highest blood plasma concentrations are reached after two hours. It is bound to

plasma proteins to 80–90%. Concentrations in the synovial fluid and membranes, muscle and bone are higher than in the blood.[3]

Apart from the active

Elimination half-life is 4.5±2.8 hours (in some individuals up to 16 hours) under steady state conditions. 40% are eliminated via the kidney, and 50% via the faeces.[3][4]

Chemistry

Acemetacin is the

monohydrate crystalline forms.[4]

Society and culture

Brand names

Other brand names include Zadex (Hungary), Rheutrop (Austria), Acemetadoc, Acephlogont, Azeat, Rantudil (Germany, Hungary, Mexico, Poland, Portugal, Turkey), Gamespir (Greece), Oldan, Reudol (Spain), Tilur (Switzerland), ACEO (Taiwan), Ost-map (Egypt).

References

  1. ^ "Acemetacin capsules for pain and inflammation - Emflex". 29 March 2023.
  2. ^ International Drug Names: Acemetacin.
  3. ^ a b c d e f g Haberfeld H, ed. (2015). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag.
  4. ^
    ISBN 978-3-7741-9846-3
    .
  5. PMID 19588437
    .
  6. ^ UK Drug Information on Emflex.
  7. PMID 17876306
    .
  8. PMID 18695646
    .
  9. ^ "Acemetacin". MediQ.ch. Retrieved 16 September 2016.
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