ロキソプロフェン
Loxoprofen
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基本情報
- CAS
68767-14-6- 標準SMILES
CC(C(=O)O)c1ccc(CC2CCCC2=O)cc1- InChIKey
YMBXTVYHTMGZDW-UHFFFAOYSA-N- 分子式
- C15H18O3
- 平均分子量
- 246.3 g/mol
- 単同位体質量
- 246.12559444
概要
Loxoprofen is a monocarboxylic acid that is propionic acid in which one of the hydrogens at position 2 is substituted by a 4-[(2-oxocyclopentyl)methyl]phenyl group. A prodrug that is rapidly converted into its active trans-alcohol metabolite following oral administration. It has a role as a non-steroidal anti-inflammatory drug, a non-narcotic analgesic, an antipyretic, an EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor and a prodrug. It is a monocarboxylic acid and a member of cyclopentanones. It is functionally related to a propionic acid. It is a conjugate acid of a loxoprofen(1-).
名称と識別子
- 優先名称
- Loxoprofen
- IUPAC
- 2-[4-[(2-oxocyclopentyl)methyl]phenyl]propanoic acid
- 現地名
- ロキソプロフェン
- 英語名
- Loxoprofen
- 分子式
- C15H18O3
- 分子量
- 246.31
名称と別名
Loxoprofen68767-14-62-(4-((2-Oxocyclopentyl)methyl)phenyl)propanoic acidLoxoprofeneLoxoprofenoLoxoprofen acidLoxoprofenum2-{4-[(2-oxocyclopentyl)methyl]phenyl}propanoic acid2-[4-[(2-oxocyclopentyl)methyl]phenyl]propanoic acid3583H0GZAPDTXSID1045164CS-600
名称をさらに表示
2-[p-(2-オキソシクロペンチルメチル)フェニル]プロピオン酸2-[4-(2-オキソシクロペンチルメチル)フェニル]プロピオン酸ロキソプロフェンα-メチル-4-[(2-オキソシクロペンチル)メチル]ベンゼン酢酸2-[4-[(2-オキソシクロペンチル)メチル]フェニル]プロピオン酸2-{4-[(2-オキソシクロペンチル)メチル]フェニル}プロパン酸IOXOPROFEN2-[4-(2-OXO-CYCLOPENTYLMETHYL)-PHENYL]-PROPIONIC ACIDA-METHYL-4-[(2-OXOCYCLOPENTYL)METHYL]BENZENEACETIC ACIDLoxoprofen-d6Loxoprofen RS
DTXCID9025164CHEBI:761722-(4-((2-oxocyclopentyl)methyl)phenyl)propionic acid2-OCPPP2-[4-[(2-Oxocyclopentyl)methyl]phenyl]propionic Acidalpha-Methyl-4-((2-oxocyclopentyl)methyl)benzeneacetate sodium salt dihydrateRefChem:924941Koloxo
物性
構造計算による物性補完中
- XLogP
- 2.4
- 極性表面積
- 54.4 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 3
- 回転可能結合数
- 4
- 重原子数
- 18
- 形式電荷
- 0
- 複雑度
- 316
実験および物理化学的性質
DrugsPharmaceutical
物理化学的性質
- 融点
- 108.5 · 108.5-111°
- 沸点
- 0.3 · bp0.3 190-195°
- 比重(密度)
- 1.182 · 1.182±0.06 g/cm3(Predicted)
- 貯蔵温度
- Sealed in dry,Room Temperature
- 溶解性
- クロロホルム（微量）、メタノール（微量）
- 外見
- 個体
- 酸解離定数(Pka)
- 4.39 · 4.39±0.10(Predicted)
- 色
- ホワイトからオフホワイト
- Merck
- 14 · 14,5589
- InChI
- InChI=1S/C15H18O3/c1-10(15(17)18)12-7-5-11(6-8-12)9-13-3-2-4-14(13)16/h5-8,10,13H,2-4,9H2,1H3,(H,17,18)
- InChIKey
- YMBXTVYHTMGZDW-UHFFFAOYSA-N
- SMILES
- C(C1CCCC1=O)C1C=CC(C(C)C(=O)O)=CC=1
- CAS データベース
- 68767 · 68767-14-6(CAS DataBase Reference)
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 ClassificationNot Classified
危険有害性情報
Hazard Classes and CategoriesNot Classified
毒性情報
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Loxoprofen
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
安全データ
- wgk
- 3
- hs_code
- 2918.99.3000
- safety_code
- 22-24/25
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
ATC Code
M - Musculo-skeletal system
M - Musculo-skeletal system
QM - Musculo-skeletal system
QM - Musculo-skeletal system
Protein Binding99% albumin-bound. At doses of loxoprofen greater than 500 mg/day, clearance of the drug increases as saturation of plasma protein binding occurs at higher doses.
Pharmacodynamics
Loxoprofen is a non-selective inhibitor of cyclooxygenase enzymes, which are responsible for the formation of various biologically active pain, fever, and inflammatory mediators. These include prostaglandins, prostacyclin, thromboxane, and arachidonic acid.
Mechanism of Action
Loxoprofen itself is a prodrug and carries little-to-no pharmacological activity - it is rapidly metabolized to its trans-alcohol form, which is a potent and non-selective inhibitor of cyclooxygenase. Cyclooxygenase (COX) is present in 2 forms, COX-1 and COX-2, with each serving different functions. COX-1 is present in human cells and is constitutively released, performing cellular housekeeping functions such as mucus production and platelet aggregation. COX-2 is induced in human cells post-injury or due to other stimuli, is triggered to appear in large quantities at the sites of injury/stimuli, and is ultimately responsible for the mediation of inflammation and pain. Loxoprofen's active metabolite inhibits both COX isoforms, resulting in reduced expression of several mediators of pain, inflammation, and fever (e.g. prostaglandins, prostacyclin, thromboxane, etc).
Biological Half-LifeThe elimination half-life of Loxoprofen is approximately 15 hours. Steady concentration is achieved after 2-3 doses.
Metabolism/Metabolites
Loxoprofen is a prodrug that is rapidly converted to its active trans-alcohol metabolite by carbonyl reductase in the liver. This same process also results in a cis-alcohol metabolite, though this isomer carries little pharmacological activity. The parent drug has also been observed to undergo oxidation via CYP3A4/5 to two hydroxylated metabolites (M3 and M4) and glucuronidation by UGT2B7 to two glucuronide metabolites (M5 and M6). The alcohol metabolites of loxoprofen also undergo glucuronide conjugation via UGT2B7 to two glucuronide metabolites (M7 and M8) prior to excretion. When applied in topical formulations, loxoprofen is metabolized to its active trans-alcohol form by carbonyl reductase in the skin.
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