基本情報
- CAS
89796-99-6- 標準SMILES
O=C(O)COC(=O)Cc1ccccc1Nc1c(Cl)cccc1Cl- InChIKey
MNIPYSSQXLZQLJ-UHFFFAOYSA-N- 分子式
- C16H13Cl2NO4
- 平均分子量
- 354.2 g/mol
- 単同位体質量
- 353.0221633
概要
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.
名称と識別子
- 優先名称
- Aceclofenac
- IUPAC
- 2-[2-[2-(2,6-dichloroanilino)phenyl]acetyl]oxyacetic acid
- 現地名
- アセクロフェナク
- 英語名
- Aceclofenac
- 分子式
- C16H13Cl2NO4
- 分子量
- 354.18
名称と別名
Aceclofenac89796-99-6AceclofenacoAirtalAceclofenacumAceclofenac betadexBiofenacClanzaDTXSID7045522RPK779R03HCHEBI:311592-[(2,6-dichlorophenyl)amino]benzeneacetic acid carboxymethyl ester
名称をさらに表示
[[2-[2-[(2,6-ジクロロフェニル)アミノ]フェニル]-1-オキソエチル]オキシ]酢酸アセクロフェナクアセクロフェナック2-[2-(2,6-ジクロロアニリノ)フェニルアセトキシ]酢酸アセクロフェナク (JAN)2-(2-(2,6-ジクロロアニリノ)フェニル)アセトキシ酢酸2-[(2-{2-[(2,6-ジクロロフェニル)アミノ]フェニル}アセチル)オキシ]酢酸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
物性
構造計算による物性
- XLogP
- 4.3
- 極性表面積
- 75.6 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 5
- 回転可能結合数
- 7
- 重原子数
- 23
- 形式電荷
- 0
- 複雑度
- 411
実験および物理化学的性質
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
物理化学的性質
- 融点
- 149 · 149-153°C
- 沸点
- 486 · 486.0±45.0 °C(Predicted)
- 比重(密度)
- 1.455 · 1.455±0.06 g/cm3(Predicted)
- 貯蔵温度
- 2 · 2-8°C
- 溶解性
- DMSOに可溶
- 外見
- 粉
- 酸解離定数(Pka)
- 2.6 · 2.60±0.10(Predicted)
- 色
- オフホワイトからライトタン
- 水溶解度
- 32 mg/L · 32mg/L(32℃)
- Merck
- 14 · 14,22
- 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)
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
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.
危険有害性情報
Hazard Classes and CategoriesAcute Tox. 3 (99%)
毒性情報
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
安全データ
- wgk
- 3
- ridadr
- UN 2811 6.1 / PGIII
- hs_code
- 29224999
- risk_code
- 25-36-50/53
- hazard_code
- T,N
- safety_code
- 26-45-60-61
- hazard_class
- 6.1
- packing_group
- III
- Hazard Classifications
- Acute Tox. 3 OralAquatic Acute 1Aquatic Chronic 1Eye Irrit. 2
化学と産業
薬理情報
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.
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