Basic information
- CAS
89796-99-6- Standard SMILES
O=C(O)COC(=O)Cc1ccccc1Nc1c(Cl)cccc1Cl- InChIKey
MNIPYSSQXLZQLJ-UHFFFAOYSA-N- Molecular formula
- C16H13Cl2NO4
- Average molar mass
- 354.2 g/mol
- Monoisotopic mass
- 353.0221633
Overview
Aceclofenac is 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. It has a role as a non-steroidal anti-inflammatory drug, a non-narcotic analgesic and an EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor. It is a dichlorobenzene, a monocarboxylic acid, a carboxylic ester, an amino acid and a secondary amino compound. It is functionally related to a diclofenac.
Names & identifiers
- Preferred name
- Aceclofenac
- IUPAC
- 2-[2-[2-(2,6-dichloroanilino)phenyl]acetyl]oxyacetic acid
- English name
- Aceclofenac
- Molecular formula
- C16H13Cl2NO4
- Molecular weight
- 354.18
Names & synonyms
Aceclofenac89796-99-6AceclofenacoAirtalAceclofenacumAceclofenac betadexBiofenacClanzaDTXSID7045522RPK779R03HCHEBI:311592-[(2,6-dichlorophenyl)amino]benzeneacetic acid carboxymethyl ester
Show more names
ZerodolPreservexAcelofenacAceclofenac-D4GerbinFalcolPR-82/3Tresquim
2-((2,6-dichlorophenyl)amino)phenylacetoxyacetic acidGlycolic Acid [o-(2,6-Dichloroanilino)phenyl]acetate EsterDTXCID50255222-((2,6-Dichlorophenyl)amino)benzeneacetic acid carboxymethyl ester2-[(2-{2-[(2,6-dichlorophenyl)amino]phenyl}acetyl)oxy]acetic acid2-[(2,6-dichlorophenyl)amino]phenylacetoxyacetic acid2-[(2',6'-dichlorophenyl)amino]phenylacetoxyacetic acidBeofenac
Database identifiers
- CAS
89796-99-6- PubChem CID
- 71771
- DTXSID
DTXSID7045522- ChEMBL
CHEMBL93645- ChEBI
CHEBI:31159
Properties
Computed structural properties
- XLogP
- 4.3
- Topological polar surface area
- 75.6 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 7
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 411
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals
LogP2.7
Solubility
Insoluble
>53.1 [ug/mL] (The mean of the results at pH 7.4)
Human DrugsBreast Feeding; Lactation; Milk, Human; Anti-Inflammatory Agents, Non-Steroidal
Melting Point149-153
Physicochemical properties
- Melting point
- 149 · 149-153°C
- Boiling point
- 486 · 486.0±45.0 °C(Predicted)
- Density
- 1.455 · 1.455±0.06 g/cm3(Predicted)
- RTECS
- 1577900 · CY1577900
- storage temp.
- 2 · 2-8°C
- solubility
- Soluble in DMSO
- form
- powder
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 1% (1 of 96) of reports.
Danger
H301 (99%): Toxic if swallowed [Danger Acute toxicity, oral]
P264, P264+P265, P270, P273, P280, P301+P316, P305+P351+P338, P321, P330, P337+P317, P391, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 96 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 3 (99%)
Toxicology
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Aceclofenac
vLess-DILI-concern
0
No match
DOI:10.1016/j.drudis.2016.02.015
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Safety data
- wgk
- 3
- ridadr
- UN 2811 6.1 / PGIII
- hs_code
- 29224999
- risk_code
- 25-36-50/53
- Signal word
- Danger
- Symbol(GHS)
- GHS06,GHS09
- hazard_code
- T,N
Chemistry & industry
Pharmacology
ATC Code
M01AB16
M - Musculo-skeletal system
M - Musculo-skeletal system
QM - Musculo-skeletal system
QM - Musculo-skeletal system
Protein BindingIt is reported to be highly protein-bound (>99%).
Pharmacodynamics
Aceclofenac is a NSAID that inhibits both isoforms of COX enzyme, a key enzyme involved in the inflammatory cascade. COX-1 enzyme is a constitutive enzyme involved in prostacyclin production and protective functions of gastric mucosa whereas COX-2 is an inducible enzyme involved in the production of inflammatory mediators in response to inflammatory stimuli. Aceclofenac displays more selectivity towards COX-2 (IC50 of 0.77uM) than COX-1 (IC50 of >100uM), which promotes its gastric tolerance compared to other NSAIDs. The primary metabolite, 4'-hydroxyaceclofenac, also minimally inhibits COX-2 with IC50 value of 36uM. Although the mode of action of aceclofenac is thought to mainly arise from the inhibition of synthesis of prostaglandins (PGE2), aceclofenac also inhibits the production of inflammatory cytokines, interleukins (IL-1β, IL-6), and tumor necrosis factors (TNF). It is also reported that aceclofenac also affects the cell adhesion molecules from neutrophils. Aceclofenac also targets the synthesis of glycosaminoglycan and mediates chrondroprotective effects.
Mechanism of Action
Through COX-2 inhibition, aceclofenac downregulates the production of various inflammatory mediators including prostaglandin E2 (PGE2), IL-1β, and TNF from the arachidonic acid (AA) pathway. Inhibition of IL-6 is thought to be mediated by diclofenac converted from aceclofenac. Suppressed action of inflammatory cytokines decreases the production of reactive oxygen species. Aceclofenac is shown to decreased production of nitrous oxide in human articular chondrocytes. In addition, aceclofenac interferes with neutrophil adhesion to endothelium by decreasing the expression of L-selectin (CD62L), which is a cell adhesion molecule expressed on lymphocytes. Aceclofenac is proposed to stimulate the synthesis of glycosaminoglycan in human osteoarthritic cartilage which may be mediated through its inhibitory action on IL-1 production and activity. The chrondroprotective effects are generated by 4'-hydroxyaceclofenac which suppresses IL-1 mediated production of promatrix metalloproteinase-1 and metalloproteinase-3 and interferes with the release of proteoglycan from chrondrocytes.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…