Chemical Properties
White Crystalline Solid
Originator
Prodes (Prodesfarma) (Spain)
Uses
Labeled Aceclofenac, intended for use as an internal standard for the quantification of Aceclofenac by GC- or LC-mass spectrometry.
Definition
ChEBI: A monocarboxylic acid that is the carboxymethyl ester of diclofenac. A non-steroidal anti-inflammatory drug related to diclofenac, it is used in the management of osteoarthritis, rheumatoid arthritis, and ankylosing spondylitis.
Manufacturing Process
50 g of sodium 2-[(2,6-dichlorphenyl)amino]phenylacetate were dissolved in
300 ml of N,N-dimethylformamide under heating to 50°C, and 44.22 g of
benzyl bromoacetate were added thereto. Under these condition stirring was continued for 9 hours. Upon completion of the reaction, the solvent was
removed at reduced pressure, and the sodium salt were precipitated with
addition of 400 ml of ether. The solution was then filtered and the ether phase
was washed twice time with 100 ml of hexane. The resulting product was
crystallized from the hexane/ether and then from acetone/chloroform (1:9)
thus obtaining 44.1 g (61%) of benzyl 2-[(2,6-
dichlorphenyl)amino]phenylacetoxyacetate in the form of white crystals having
a melting point of 67-69°C.
45.28 g of benzyl 2-[(2,6-dichlorphenyl)amino]phenylacetoxyacetate were
dissolved in 1500 ml of ethyl acetate, and the resulting solution was mixed
with 7 g of Pd/C 10% and then hydrogen ted at atmospheric pressure for 14
hours. The solution was filtered, concentrated and crystallized; thereby
obtaining 23.51 g (65%) of 2-[(2,6-dichlorphenyl)amino]phenylacetoxyacetic
acid; melting point 149-150°C.
Brand name
Airtal; Gerbin
Therapeutic Function
Analgesic, Antiinflammatory
Biochem/physiol Actions
Non-steroidal, anti-inflammatory drug (NSAID), with selectivity for COX-2 over COX-1.
Clinical Use
NSAID and analgesic
Drug interactions
Potentially hazardous interactions with other drugs
ACE inhibitors and angiotensin-II antagonists:
antagonism of hypotensive effect; increased risk of
nephrotoxicity and hyperkalaemia.
Analgesics: avoid concomitant use of 2 or more
NSAIDs, including aspirin (increased side effects);
avoid with ketorolac (increased risk of side effects
and haemorrhage).
Antibacterials: possible increased risk of convulsions
with quinolones.
Anticoagulants: effects of coumarins and
phenindione enhanced; possibly increased risk of
bleeding with heparins, dabigatran and edoxaban -
avoid long term use with edoxaban.
Antidepressants: increased risk of bleeding with
SSRIs and venlaflaxine.
Antidiabetic agents: effects of sulphonylureas enhanced.
Antiepileptics: possibly increased phenytoin
concentration.
Antivirals: increased risk of haematological toxicity
with zidovudine; concentration possibly increased by
ritonavir.
Ciclosporin: may potentiate nephrotoxicity
Cytotoxics: reduced excretion of methotrexate;
increased risk of bleeding with erlotinib.
Diuretics: increased risk of nephrotoxicity;
antagonism of diuretic effect, hyperkalaemia with
potassium-sparing diuretics.
Lithium: excretion decreased.
Pentoxifylline: increased risk of bleeding.
Tacrolimus: increased risk of nephrotoxicity.
Metabolism
About two-thirds of a dose is excreted in the urine,
mainly as hydroxymetabolites, the principal one being
4-hydroxyaceclofenac. A small amount is converted to
diclofenac.
