Aceclofenac

Aceclofenac is a nonsteroidal anti-inflammatory drug (NSAID) analog of diclofenac. It is used for the relief of pain and inflammation in rheumatoid arthritis, osteoarthritis and ankylosing spondylitis.

Acelofenac
Clinical data
Trade namesHifenac, Clanza CR, Preservex, others[1]
AHFS/Drugs.comInternational Drug Names
License data
Routes of
administration		By mouth, topical
ATC code
Legal status
Legal status
Identifiers
IUPAC name
  • 2-[2-[2-[(2,6-dichlorophenyl)amino]phenyl]acetyl]oxyacetic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.169.686
Chemical and physical data
FormulaC16H13Cl2NO4
Molar mass354.18 g·mol−1
3D model (JSmol)
SMILES
  • Clc2cccc(Cl)c2Nc1ccccc1CC(=O)OCC(=O)O
InChI
  • InChI=1S/C16H13Cl2NO4/c17-11-5-3-6-12(18)16(11)19-13-7-2-1-4-10(13)8-15(22)23-9-14(20)21/h1-7,19H,8-9H2,(H,20,21) Y
  • Key:MNIPYSSQXLZQLJ-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

It was patented in 1983 and approved for medical use in 1992.[4]

Side effects

Aceclofenac should not be given to people with porphyria or breast-feeding mothers, and is not recommended for children. It should be avoided near term in a pregnant woman because of the risk of having a premature closure of ductus arteriosus leading to fetal hydrops in the neonate.

Chemistry

Aceclofenac (C16H13Cl2NO4), chemically [(2-{2, 6-dichlorophenyl) amino} phenylacetooxyacetic acid], is a crystalline powder with a molecular weight of 354.19. It is practically insoluble in water with good permeability. It is metabolized in human hepatocytes and human microsomes to form [2-(2',6'-dichloro-4'-hydroxy- phenylamino) phenyl] acetoxyacetic acid as the major metabolite, which is then further conjugated. According to the Biopharmaceutical Classification System (BCS) drug substances are classified to four classes upon their solubility and permeability. Aceclofenac falls under the BCS Class II, poorly soluble and highly permeable drug.[5]

Aceclofenac works by inhibiting the action of cyclooxygenase (COX) that is involved in the production of prostaglandins (PG) which is accountable for pain, swelling, inflammation and fever. The incidence of gastric ulcerogenicity of aceclofenac has been reported to be significantly lower than that of the other frequently prescribed NSAIDs, for instance, 2-folds lesser than naproxen, 4-folds lesser than diclofenac, and 7-folds lesser than indomethacin.[5]

Society and culture

Economics

Aceclofenac is available in Hungary as a prescription only medicine. The cost of the drug is low, around US$0.14 per 100 mg tablet (as of 2019).

Brand names

Aceclofenac is available in Europe and CIS countries. Known trades names include: Acecgen (Generics UK), Aflamin (Gedeon Richter Plc.), AklofEP (ExtractumPharma) and Flemac (Aramis Pharma).

References

Citations
  1. "Aceclofenac international". Drugs.com. 2 November 2020. Retrieved 4 December 2020.
  2. "Clanza CR- aceclofenac tablet, film coated". DailyMed. 2 November 2011. Retrieved 4 December 2020.
  3. "List of nationally authorised medicinal products. Active substance: aceclofenac" (pdf). European Medicines Agency. 26 November 2020. Archived (PDF) from the original on 4 November 2021. Retrieved 31 October 2022.
  4. Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 517. ISBN 9783527607495.
  5. Karmoker JR, Sarkar S, Joydhar P, Chowdhury SF (March 2016). "Comparative in vitro equivalence evaluation of some Aceclofenac generic tablets marketed in Bangladesh" (PDF). The Pharma Innovation Journal. 5: 3–7. Retrieved 2016-09-01.

General and cited sources
  • British National Formulary 55, March 2008; ISBN 978-0-85369-776-3, p. 537
  • "Aceclofenac". Drug Information Portal. U.S. National Library of Medicine.


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