| Identification | More | [Name]
Aceclofenac | [CAS]
89796-99-6 | [Synonyms]
2-[2-[2-(2,6-dichlorophenyl)aminophenyl]acetyl]oxyacetic acid
ACECLOFENAC
ACECLOFENAC-D2
2-((2,6-dichlorophenyl)amino)-benzeneaceticacicarboxymethylester
2-((2,6-dichlorophenyl)amino)benzeneaceticacidcarboxymethylester
ACECLOFENAC, IMP. E (EP): ETHYL 2-[(2-{2-[(2,6-DICHLOROPHENYL)AMINO]PHENYL}ACETYL)OXY]ACETATE (ETHYL ESTER OF ACECLOFENAC) MM(CRM STANDARD)
ACECLOFENAC, IMP. B (EP): METHYL 2-{2-[(2,6-DICHLOROPHENYL)AMINO]PHENYL}ACETATE(METHYL ESTER OF DICLOFENAC) MM(CRM STANDARD)
ACECLOFENAC, IMP. C (EP): ETHYL 2-[2-[(2,6-DICHLOROPHENYL)AMINO]PHENYL]ACETATE (ETHYL ESTER OF DICLOFENAC) MM(CRM STANDARD)
ACECLOFENAC, IMP. D (EP): METHYL 2-[(2-{2-[(2,6-DICHLOROPHENYL)AMINO]PHENYL}ACETYL)OXY]ACETATE (METHYL ESTER OF ACECLOFENAC) MM(CRM STANDARD)
ACECLOFENAC, IMP. IMP. G (EP):2[[2-[[2-[2-[(2,6-DICHLORPHENYL)-AMINO]PHENYL]ACETYL]OXY]ACETYL]OXY]ACETIC ACID (ACETIC ACECLOFENAC) MM(CRM STANDARD)
ACECLOFENAC, IMP. I (EP):1-(2,6-DICHLOROPHENYL)INDOLIN-2-ONE MM(CRM STANDARD)
ACECLOFENAC REFERENCE SPECTRUM EPY(CRM STANDARD)
ACECLOFENAC, IMPURITY FBENZYL[[[2-[(2,6-DICHLOROPHENYL)AMINO] PHENYL]ACETYL]OXY]ACETATE EP STANDARD
ACECLOFENAC, MM(CRM STANDARD)
ACECLOFENAC, IMP. A (EP): 2-{2-[(2,6-DICHLOROPHENYL)AMINO]-PHENYL}ACETIC ACID (DICLOFENAC) MM(CRM STANDARD)
ACECLOFENAC, IMP. F (EP): BENZYL 2-[(2-{2-[(2,6-DICHLOROPHENYL)AMINO]PHENYL}ACETYL)OXY]ACETATE(BENZYL ESTER OF ACECLOFENAC) MM(CRM STANDARD)
ACECLOFENAC, IMPURITY H[[[[[[[2-[(2,6-DICHLOROPHENYL)AMINO]PHENYL]ACETYL]OXY]ACETYL]OXY] ACETYL]OXY] ACETIC ACID EP STANDARD
Acelofenac
Airtal
Falcol | [EINECS(EC#)]
641-844-5 | [Molecular Formula]
C16H13Cl2NO4 | [MDL Number]
MFCD00864296 | [Molecular Weight]
354.18 | [MOL File]
89796-99-6.mol |
| Questions And Answer | Back Directory | [Description]
Aceclofenac is a non-steroidal anti-inflammatory drug (NSAIDs) that is commonly prescribed for people with painful rheumatic conditions such as rheumatoid arthritis, osteoarthritis, and ankylosing spondylitis.
The drug should not be given to children, breastfeeding mothers, and people with porphyria. Pregnant women should not also be given aceclofenac as they risk developing patent ductus arteriosus in the neonate.
| [Mechanism of Action]
Aceclofenac acts by inhibiting the effect of natural substances known as cyclooxygenase (COX) enzymes. Notably, these enzymes are responsible for making other chemicals in the body, namely prostaglandins. The prostaglandins are normally produced at sites of damages or injury cause inflammation and pain. By blocking the influence of COX enzymes, production of prostaglandins is minimized, meaning that the swelling and pain is eased.
| [Precautions]
Before taking aceclofenac, it is essential to tell the doctor if one has ever had an allergic reaction to any other NSAID, for instance, diclofenac, aspirin, indomethacin, and naproxen; whether one has allergic disorders such as asthma. It is important to alert the doctor if an individual has a heart condition or problem with circulation or blood vessels. Moreover, inform the physician if one has connective tissue disorder, for instance, lupus erythematosus. One should not take the drug if he/she has high blood pressure or has blood-clotting problems.
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| Hazard Information | Back Directory | [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. | [storage]
Store at -20°C |
| Questions and Answers (Q&A) | Back Directory | [References]
Brogden, Rex N., and Lynda R. Wiseman. "Aceclofenac. A review of its pharmacodynamic properties and therapeutic potential in the treatment of rheumatic disorders and in pain management." Drugs 52.1 (1996): 113-124.
Raza, Kaisar, et al. "Topical delivery of aceclofenac: challenges and promises of novel drug delivery systems." BioMed research international 2014 (2014).
Dooley, Mukta, Caroline M. Spencer, and Christopher J. Dunn. "Aceclofenac: a reappraisal of its use in the management of pain and rheumatic disease." Drugs 61.9 (2000): 1351-1378.
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