Aceclofenac

Aceclofenac
Clinical data
Trade names	Hifenac, Clanza CR, Preservex, others
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; EU: Rx-only;
Identifiers
	IUPAC name 2-[2-[2-[(2,6-dichlorophenyl)amino]phenyl]acetyl]oxyacetic acid;
CAS Number	89796-99-6 ;
PubChem CID	71771;
DrugBank	DB06736 ;
ChemSpider	64809 ;
UNII	RPK779R03H;
KEGG	D01545 ;
ChEBI	CHEBI:31159 ;
ChEMBL	ChEMBL93645 ;
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) ; Key:MNIPYSSQXLZQLJ-UHFFFAOYSA-N ;
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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-fold less than naproxen, 4-fold less than diclofenac, and 7-fold less 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).

References

Citations

^ "Aceclofenac international". Drugs.com. 2 November 2020. Retrieved 4 December 2020.
^ "Clanza CR- aceclofenac tablet, film coated". DailyMed. 2 November 2011. Retrieved 4 December 2020.
^ "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.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 517. ISBN 9783527607495.
^ ^a ^b 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

External links

"Aceclofenac". Drug Information Portal. U.S. National Library of Medicine.

[1] "Aceclofenac international". Drugs.com. 2 November 2020. Retrieved 4 December 2020.

[Clanza_CR_FDA_label-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.

[Fis2006-4] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 517. ISBN 9783527607495.

[J.R._Karmokeretal.2016-5] 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.

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v t e Non-steroidal anti-inflammatory drugs (NSAIDs) (primarily M01A and M02A, also N02BA)
pyrazolones / pyrazolidines	Aminophenazone Ampyrone Azapropazone Clofezone Difenamizole Famprofazone Feprazone Kebuzone Metamizole Mofebutazone Morazone Nifenazone Oxyphenbutazone Phenazone Phenylbutazone Propyphenazone Sulfinpyrazone Suxibuzone^‡
salicylates	Aspirin (acetylsalicylic acid)^# Aloxiprin Benorylate Carbasalate calcium Diflunisal Dipyrocetyl Ethenzamide Guacetisal Magnesium salicylate Methyl salicylate Salsalate Salicin Salicylamide Salicylic acid (salicylate) Sodium salicylate
acetic acid derivatives and related substances	Aceclofenac Acemetacin Alclofenac Amfenac Bendazac Bromfenac Bufexamac Bumadizone Diclofenac Difenpiramide Etodolac Felbinac Fenclozic acid Fentiazac Indometacin Indometacin farnesil Isoxepac Ketorolac Lonazolac Mofezolac Oxametacin Prodolic acid Proglumetacin Sulindac Tiopinac Tolmetin Zomepirac^†
oxicams	Ampiroxicam Droxicam Isoxicam Lornoxicam Meloxicam Piroxicam Pivoxicam Tenoxicam
propionic acid derivatives (profens)	Alminoprofen Benoxaprofen^† Carprofen^‡ Dexibuprofen Dexketoprofen Fenbufen Fenoprofen Flunoxaprofen Flurbiprofen Ibuprofen^# Ibuproxam Indoprofen^† Ketoprofen Loxoprofen Miroprofen Naproxen Oxaprozin Pelubiprofen Piketoprofen Pirprofen Suprofen Tarenflurbil Tepoxalin^‡ Tiaprofenic acid Vedaprofen^‡ Zaltoprofen COX-inhibiting nitric oxide donator: Naproxcinod
n-arylanthranilic acids (fenamates)	Azapropazone Clonixin Etofenamate Floctafenine Flufenamic acid Flunixin Flutiazin Glafenine^† Meclofenamic acid Mefenamic acid Morniflumate Niflumic acid Tolfenamic acid
COX-2 inhibitors (coxibs)	Apricoxib Celecoxib (+tramadol) Cimicoxib^‡ Deracoxib^‡ Etoricoxib Firocoxib^‡ Lumiracoxib^† Mavacoxib^‡ Parecoxib Robenacoxib^‡ Rofecoxib^† Valdecoxib^†
other	Aminopropionitrile Benzydamine Chondroitin sulfate Diacerein Fluproquazone Glucosamine Glycosaminoglycan Hyperforin Nabumetone Nimesulide Oxaceprol Proquazone Superoxide dismutase / orgotein Tenidap
NSAID combinations	Ibuprofen/famotidine Ibuprofen/hydrocodone Ibuprofen/oxycodone Ibuprofen/paracetamol Meloxicam/bupivacaine Naproxen/diphenhydramine Naproxen/esomeprazole
Key: underline indicates initially developed first-in-class compound of specific group; ^#WHO-Essential Medicines; ^†withdrawn drugs; ^‡veterinary use.
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