ACECLOFENAC

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H13Cl2NO4
Molecular Weight	354.185
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)COC(=O)CC1=C(NC2=C(Cl)C=CC=C2Cl)C=CC=C1

InChI

InChIKey=MNIPYSSQXLZQLJ-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Molecular Formula	C16H13Cl2NO4
Molecular Weight	354.185
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.drugs.com/pro/clanza-cr.html

Aceclofenac is a non-steroidal anti-inflammatory drug (NSAID) analog of Diclofenac. It is used for the relief of pain and inflammation in rheumatoid arthritis, osteoarthritis and ankylosing spondylitis. The dose is 100 mg twice daily, and should not be given to people with porphyria or breastfeeding mothers and is not recommended for children. Aceclofenac is a cytokine inhibitor. Aceclofenac works by blocking the action of a substance in the body called cyclo-oxygenase. Cyclo-oxygenase is involved in the production of prostaglandins (chemicals in the body which cause pain, swelling and inflammation). Aceclofenac is the glycolic acid ester of diclofenac. The incidence of gastric ulcerogenicity of aceclofenac has been reported to be significantly lower than that of other frequently prescribed NSAIDs: for instance, 2-fold less than naproxen, 4-fold less than diclofenac, and 7-fold less than indomethacin. Aceclofenac 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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cyclooxygenase-2 196 Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18547825	Inhibitor 8297		3.0 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Rheumatoid arthritis 316 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=8a023942-01e8-4849-aa3c-1a640ffc7fd3	Palliative	Approved 8429	Clanza CR Approved Use CLANZA CR is indicated for Rheumatoid arthritis, ankylosing spondylitis, osteoarthritis and periarthritis of scapulohumerous, lumbago, ischiadynia, pain caused by nonaticular rheutism. Launch Date 1.30515835E12
Ankylosing spondylitis 33 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=8a023942-01e8-4849-aa3c-1a640ffc7fd3	Palliative	Approved 8429	Clanza CR Approved Use CLANZA CR is indicated for Rheumatoid arthritis, ankylosing spondylitis, osteoarthritis and periarthritis of scapulohumerous, lumbago, ischiadynia, pain caused by nonaticular rheutism. Launch Date 1.30515835E12
Osteoarthritis of scapulohumerous 1 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=8a023942-01e8-4849-aa3c-1a640ffc7fd3	Palliative	Approved 8429	Clanza CR Approved Use CLANZA CR is indicated for Rheumatoid arthritis, ankylosing spondylitis, osteoarthritis and periarthritis of scapulohumerous, lumbago, ischiadynia, pain caused by nonaticular rheutism. Launch Date 1.30515835E12
Periarthritis of scapulohumerous 1 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=8a023942-01e8-4849-aa3c-1a640ffc7fd3	Palliative	Approved 8429	Clanza CR Approved Use CLANZA CR is indicated for Rheumatoid arthritis, ankylosing spondylitis, osteoarthritis and periarthritis of scapulohumerous, lumbago, ischiadynia, pain caused by nonaticular rheutism. Launch Date 1.30515835E12

PubMed

Title	Date	PubMed
Aceclofenac: a reappraisal of its use in the management of pain and rheumatic disease.	2001	11511027
In-vitro test system for the evaluation of cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2) inhibitors based on a single HPLC run with UV detection using bovine aortic coronary endothelial cells (BAECs).	2001 May	11409489
Patient and physician satisfaction with aceclofenac: results of the European Observational Cohort Study (experience with aceclofenac for inflammatory pain in daily practice). Aceclofenac is the treatment of choice for patients and physicians in the management of inflammatory pain.	2002	12094824
Regulation by reactive oxygen species of interleukin-1beta, nitric oxide and prostaglandin E(2) production by human chondrocytes.	2002 Jul	12127835
Structure-function relationship and role of tumor necrosis factor-alpha-converting enzyme in the down-regulation of L-selectin by non-steroidal anti-inflammatory drugs.	2002 Oct 11	12147693
Management pattern for patients with osteoarthritis treated with traditional non-steroidal anti-inflammatory drugs in Spain prior to introduction of Coxibs.	2003	12841920
Upper gastrointestinal bleeding associated with the use of NSAIDs: newer versus older agents.	2004	15144234
[Function of non-steroids in dentistry and oral surgery. A favourable experiences with aceclofenac].	2004 Dec	15690916
Pain and osteoarthritis: new drugs and mechanisms.	2004 Sep	15314506
[Aceclofenac (aertal) in rheumatological practice].	2005	15989015
Anaphylactic reaction after aceclofenac intake.	2006 Apr	16512820
Allergic contact dermatitis due to aceclofenac.	2006 Dec	17101014
Risk of upper gastrointestinal ulcer bleeding associated with selective cyclo-oxygenase-2 inhibitors, traditional non-aspirin non-steroidal anti-inflammatory drugs, aspirin and combinations.	2006 Dec	16687434
Consumption costs of inappropriate medicines estimated from bulk purchase data: The example of NSAids in Guatemala.	2006 Nov	17176623
Evaluation of bioequivalence of two formulations containing 100 milligrams of aceclofenac.	2006 Nov-Dec	17090444
Influence of amorphous cyclodextrin derivatives on aceclofenac release from directly compressible tablets.	2007 Apr	17484283
Aceclofenac vs paracetamol in the management of symptomatic osteoarthritis of the knee: a double-blind 6-week randomized controlled trial.	2007 Aug	17387026
Immunomodulatory effect of nonsteroidal anti-inflammatory drugs (NSAIDs) at the clinically available doses.	2007 Jan	17328244
Improved bioavailability of aceclofenac from spherical agglomerates: development, in vitro and preclinical studies.	2007 Jul	17545107
Mathematical evaluation of similarity factor using various weighing approaches on aceclofenac marketed formulations by model-independent method.	2008 Jan	18271300
Preventing peridural fibrosis with nonsteroidal anti-inflammatory drugs.	2008 Mar	18172695

Patents

Sample Use Guides

In Vivo Use Guide

is 200 mg daily, taken as one dose (every 24 hours).

Route of Administration: Oral

In Vitro Use Guide

In vitro adhesion assays were developed to examine the effects of aceclofenac on both neutrophil adhesion to tumor necrosis factor alpha stimulated human umbilical vein endothelial cells under nonstatic conditions, and homotypic neutrophil aggregation induced by anti-ICAM-3 and anti-CD18 monoclonal antibodies (Mab)

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:47:37 UTC 2023` Edited by `admin` on `Fri Dec 15 15:47:37 UTC 2023`
Record UNII	RPK779R03H
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ACECLOFENAC

Official Name

English

ACECLOFENAC [EP MONOGRAPH]

Common Name

English

Aceclofenac betadex [WHO-DD]

Common Name

English

ACECLOFENAC [MART.]

Common Name

English

GLYCOLIC ACID, (O-(2,6-DICHLOROANILINO)PHENYL)ACETATE (ESTER)

Common Name

English

Aceclofenac [WHO-DD]

Common Name

English

ACECLOFENAC [MI]

Common Name

English

aceclofenac [INN]

Common Name

English

ACECLOFENAC [JAN]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QM02AA25