Aceclofenac

Structural formula
General
Non-proprietary name	Aceclofenac
other names	2 - [(2,6-dichlorophenyl) amino] phenyl-acetoxyacetic acid
Molecular formula	C 16 H 13 Cl 2 NO 4
Brief description	almost white, crystalline and odorless powder
External identifiers / databases
EC number	641-844-5
ECHA InfoCard	100.169.686
PubChem	71771
ChemSpider	64809
DrugBank	DB06736
Wikidata	Q481757
Drug information
ATC code	M01 AB16 ; M02 AA25 ;
Drug class	non-opioid analgesic
properties
Molar mass	354.18 g · mol -1
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
H and P phrases	H: 301-319-410
	P: 273-301 + 310-305 + 351 + 338-501
Toxicological data	130 mg kg −1 ( LD 50 , rat , oral ) ; 1.4 mg kg −1 ( TD Lo , human , oral ) ; 20 mg kg −1 ( TD Lo , human , oral , female) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Aceclofenac (trade name Beofenac ^® ) is a drug from the group of non-opioid analgesics that is used in the treatment of mild to moderate pain. It is the glycolic acid ester of diclofenac . Aceclofenac was patented by Prodesfarma in 1984 as a cyclooxygenase inhibitor and is currently produced by Almirall .

Extraction and presentation

Aceclofenac can be prepared from diclofenac by reaction with sodium hydroxide and benzyl bromoacetate as well as hydrogenation on a Pd / C catalyst.

Clinical information

Application areas (indications)

Aceclofenac is for the symptomatic treatment of pain and inflammation associated with osteoarthritis , rheumatoid arthritis (chronic polyarthritis ) and ankylosing spondylitis admitted.

Contraindications (contraindications)

Patients with acute, suspected, or recurrent gastric and duodenal ulcers, gastrointestinal or other acute bleeding are excluded from treatment with aceclofenac.

In October 2014, the manufacturer announced in a Rote-Hand-Brief that therapy with the antirheumatic drug Beofenac (Aceclofenac) was associated with an increased risk of arterial thrombotic events, which is comparable to that of selective COX-2 inhibitors . Aceclofenac is therefore contraindicated in patients with ischemic heart disease, peripheral artery disease, cerebrovascular disease, and existing heart failure (New York Heart Association, NYHA, stages II-IV). These contraindications will be listed in the Beofenac product information sheet along with other warnings.

Drug interactions

Since aceclofenac is metabolized by the cytochrome P450 2C9 , interactions with other drugs such as tolbutamide or amiodarone are to be expected. Simultaneous administration of ASA can lead to a pseudoallergic reaction.

Adverse effects (side effects)

After taking aceclofenac, gastrointestinal complaints and abdominal pain may occur. Aceclofenac is said to be more tolerable than conventional representatives of the active ingredient group.

Pharmacological properties

Aceclofenac has anti-inflammatory, analgesic and antipyretic effects. The absorption in the body takes place quickly, the bioavailability is almost 100%.

literature

Brogden, RN, Wiseman, LR: Aceclofenac: Pharmacodynamic Properties and Therapeutic Potential in the Treatment of Rheumatic Diseases and Pain . In: Drugs 1996 52, 1; 113-124.

Individual evidence

↑ ^a ^b entry on aceclofenac. In: Römpp Online . Georg Thieme Verlag, accessed on May 19, 2014.
↑ ^a ^b ^c ^d ^e data sheet Aceclofenac at Sigma-Aldrich , accessed on May 18, 2014 ( PDF ).
↑ Michael Freissmuth, Stefan Offermanns: Pharmacology and Toxicology: From the molecular basis for pharmacotherapy . Springer 2012. ISBN 978-3642123535 , p. 180.
^ Laboratory Synthesis Of Aceclofenac
↑ Almirall: Beofenac (Aceclofenac): New Contraindications and Warnings. (PDF) Medicines Commission of the German Medical Association, October 8, 2014, archived from the original on October 30, 2014 ; Retrieved October 29, 2014 .
↑ Ernst Mutschler, Monika Schäfer-Korting: Textbook of Pharmacology and Toxicology . 8th, completely revised and expanded edition. Wissenschaftliche Verlagsgesellschaft Stuttgart 2001. ISBN 3-8047-1763-2 . P. 237.

[roempp-1] try on aceclofenac. In: Römpp Online . Georg Thieme Verlag, accessed on May 19, 2014.

[Sigma-Aldrich-2] ↑ ^a ^b ^c ^d ^e data sheet Aceclofenac at Sigma-Aldrich , accessed on May 18, 2014 ( PDF ).

[3] Michael Freissmuth, Stefan Offermanns: Pharmacology and Toxicology: From the molecular basis for pharmacotherapy . Springer 2012. ISBN 978-3642123535 , p. 180.

[4] Laboratory Synthesis Of Aceclofenac

[5] Almirall: Beofenac (Aceclofenac): New Contraindications and Warnings. (PDF) Medicines Commission of the German Medical Association, October 8, 2014, archived from the original on October 30, 2014 ; Retrieved October 29, 2014 .

[Mutschler-6] Ernst Mutschler, Monika Schäfer-Korting: Textbook of Pharmacology and Toxicology . 8th, completely revised and expanded edition. Wissenschaftliche Verlagsgesellschaft Stuttgart 2001. ISBN 3-8047-1763-2 . P. 237.