フルルビプロフェン
フルルビプロフェン · フルルバン · アップノン · ヤクバン · 2-(2-フルオロ-1,1'-ビフェニル-4-イル)プロピオン酸 · ファルケン · セブチド · ステイバン
識別子と物理属性
| CAS No. | 5104-49-4 |
|---|---|
| 分子式 | C15H13FO2 |
| 平均分子量 | 244.26 g/mol |
| 単同位体質量 | 244.08995788 g/mol |
| SMILES | CC(C(=O)O)c1ccc(-c2ccccc2)c(F)c1 |
| InChIKey | SYTBZMRGLBWNTM-UHFFFAOYSA-N |
| PubChem CID | 3394 |
| ChEMBL | CHEMBL563 |
| ChEBI | CHEBI:5130 |
| EC No. | 225-827-6 |
| DTXSID | DTXSID0037231 |
| 現地名 | フルルビプロフェン |
化学・物理的性質
| XLogP | 4.2 |
|---|---|
| 極性表面積 | 37.3 |
| 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 | 3 |
| 重原子数 | 18 |
| 形式電荷 | 0 |
| 複雑度 | 286 |
| 医薬品 | Pharmaceuticals -> Musculo-skeletal system -> Anti-inflammatory and antirheumatic productsPharmaceuticals -> Analgesics and anti-inflammatories |
| LogP（分配係数） | 3.8 |
| 溶解度 | 2.49e-02 g/Lメタノール：可溶50mg/mL8mg/L(室温) |
| Human Drugs | Breast FeedingLactationMilk, HumanAnalgesic AgentsAnti-inflammatory Agents, NonsteroidalFDA approved drugs -> Active ingredientPharmaceuticals |
| 融点 | 110-111 °C110 - 111 °C110-112 °C(lit.) |
| Physical Description | Solid |
| Dissociation Constants | 4.034.224.3 |
| Collision Cross Section | 155.9 Ų [M+K]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards] |
| 沸点 | 376.2±30.0 °C(Predicted) |
| 密度 | 1.1795 (estimate) |
| 貯蔵条件 | Sealed in dry,Room Temperature |
| pKa（酸解離定数） | pKa 3.80(H2O) (Uncertain) |
| 外観・状態 | 白い固体 |
| 色 | ホワイトからオフホワイト |
| 由来生物 | synthetic |
| Merck | 14,4199 |
| InChI | InChI=1S/C15H13FO2/c1-10(15(17)18)12-7-8-13(14(16)9-12)11-5-3-2-4-6-11/h2-10H,1H3,(H,17,18) |
| InChIKey | SYTBZMRGLBWNTM-UHFFFAOYSA-N |
| SMILES | FC1C=C(C=CC=1C1C=CC=CC=1)C(C)C(=O)O |
| CAS データベース | 5104-49-4(CAS DataBase Reference) |
| EPAの化学物質情報 | [1,1'-Biphenyl]-4-acetic acid, 2-fluoro-?-methyl- (5104-49-4) |
化学的特性
White to Off-White Crystalline Solid
安全性と法規制
| GHS 分類 | DangerH301 (98.2%): Toxic if swallowed [Danger Acute toxicity, oral]P203, P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 114 reports by companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 規制情報 | Hazard Traits - Developmental ToxicityReproductive Toxicity |
| その他の安全情報 | IMAP assessments - [1,1'-Biphenyl]-4-acetic acid, 2-fluoro-.alpha.-methyl-: Environment tier I assessment |
| Hazard Classes and Categories | Acute Tox. 3 (98.2%) |
| Treatment | Patients should be managed by symptomatic and supportive care following overdose with a nonsteroidal anti-inflammatory drug. There are no specific antidotes. Emesis and/or activated charcoal (60 to 100 g in adults, 1 to 2 g/kg in children) and/or osmotic cathartic may be indicated in patients seen within 4 hours of ingestion with symptoms, or following a large overdose (5 to 10 times the usual dose). Forced diuresis, alkalization of urine, hemodialysis, or hemoperfusion may not be useful due to high protein binding. (L1712) |
| Hepatotoxicity | Prospective studies show that mild elevations in serum aminotransferase levels can occur in up to 15% of patients taking NSAIDs such as flurbiprofen, but the abnormalities are generally transient, mild and asymptomatic, often resolving even with drug continuation. Marked aminotransferase elevations above 3 times the upper limit of normal (ULN) occur in less than 1% of patients. Clinically apparent liver injury with jaundice from flurbiprofen is rare and only individual case descriptions have been published. The latency to onset is within 1 to 4 weeks of starting. The pattern of enzyme elevations is typically cholestatic, but hepatocellular cases have been described. Immunoallergic features are present in some cases (low grade fever, rash), but are generally not prominent, and autoantibody formation is rare. Most cases resolve promptly on stopping therapy. Flurbiprofen is not mentioned in large case series on drug induced liver injury or acute liver failure from the United States, but was listed as the second most common agent implicated in drug-induced liver injury in a case series from Turkey, one of which was fatal. |
用途
用途
イブプロフェン類縁体の非ス テロイド系抗炎症剤です。フルルビプロフェ ンはシクロオキシゲナーゼ（COX）を阻害す ることで、発熱・炎症作用を抑制します。
用途
プロピオン酸系化合物です。 シクロオキシゲナーゼ（COX）を阻害し、プ ロスタグランジン生合成抑制作用を示します。
用途
フルルビプロフェンとは、で表されるフェニルアルカン酸誘導体の1種である。プロパン酸系の非ステロイド性抗炎症薬として、関節炎による痛みの緩和などに用いられる。
説明
Flurbiprofen synthesis was originally reported in 1974. During a study of the pharmacological properties of a large number of substituted phenylalkanoic acids, including ibuprofen and ibufenac, the most potent were found to be substituted 2-(4-biphenyl)propionic acids. Further toxicological and pharmacological studies indicated that flurbiprofen possessed the most favorable therapeutic profile, so it was selected for further clinical development. It was not marketed until 1987, when it was introduced as the sodium salt as Ocufen, the first topical NSAID indicated for ophthalmic use in the United States. The indication for Ocufen is the same as that for Profenal—that is, to inhibit intraoperative miosis induced by prostaglandins in cataract surgery.
使用
An anti-inflammatory used as an analgesic.
一般的な説明
Flurbiprofen (Ansaid, Ocufen, Froben), is another drug inthis class indicated for both acute and long-term managementof RA and OA but with a more complex mechanism ofaction. Unlike the other drugs in this class, it does not undergochiral inversion (i.e., the conversion of the “inactive”[R]-enantiomer to the active, [S]-enantiomer). Similar to aspirinand other salicylates, both flurbiprofen enantiomersblock COX-2 induction as well as inhibiting the nuclearfactor-κB-mediated polymorphonuclear leukocyte apoptosissignaling; therefore, both enantiomers are believed to contributeequally to its overall anti-inflammatory action.(R)-flurbiprofen is actually a strong clinical candidate forthe treatment of Alzheimer disease, because it has beenshown to reduce Aβ42 production by human cells.