Aceclofenac

Clinical data
Trade names	Hifenac, Clanza CR, Preservex, others[1]
AHFS/Drugs.com	International Drug Names
License data	EU EMA: by INN US DailyMed: Aceclofenac
Routes of administration	By mouth, topical
ATC code	M01AB16 (WHO) M02AA25 (WHO)
Legal status
Legal status	UK: POM (Prescription only) US: ℞-only[2] EU: Rx-only[3]
Identifiers
IUPAC name 2-[2-[2-[(2,6-dichlorophenyl)amino]phenyl]acetyl]oxyacetic acid
CAS Number	89796-99-6 N
PubChem CID	71771
DrugBank	DB06736 Y
ChemSpider	64809 Y
UNII	RPK779R03H
KEGG	D01545 Y
ChEBI	CHEBI:31159 N
ChEMBL	ChEMBL93645 Y
CompTox Dashboard (EPA)	DTXSID7045522
ECHA InfoCard	100.169.686
Chemical and physical data
Formula	C16H13Cl2NO4
Molar mass	354.18 g·mol−1
3D model (JSmol)	Interactive image
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)

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.

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^[update]).

Brand names

Aceclofenac is available in Europe and CIS countries. Known trades names include: Acecgen (Generics UK), Aflamin, Airtal/Biofenac (Gedeon Richter Plc.), AklofEP (ExtractumPharma), Flemac (Aramis Pharma) and Hifenac-P (Intas Pharmaceuticals, India).