イブプロフェン
2-(4-イソブチルフェニル)プロピオン酸 · rac-(R*)-α-メチル-4-(2-メチルプロピル)ベンゼン酢酸 · (R)-イブプロフェン · rac-(R*)-2-(4-イソブチルフェニル)プロピオン酸 · モギフェン · (-)-イブプロフェン · (R)-2-(4-イソブチルフェニル)プロパン酸 · p-(2-メチルプロピル)-α-メチルフェニル酢酸
識別子と物理属性
| CAS No. | 15687-27-1 |
|---|---|
| 分子式 | C13H18O2 |
| 平均分子量 | 206.28 g/mol |
| 単同位体質量 | 206.13067982 g/mol |
| SMILES | CC(C)Cc1ccc(C(C)C(=O)O)cc1 |
| InChIKey | HEFNNWSXXWATRW-UHFFFAOYSA-N |
| PubChem CID | 3672 |
| ChEMBL | CHEMBL521 |
| ChEBI | CHEBI:5855 |
| EC No. | 239-784-6 |
| DTXSID | DTXSID5020732 |
| 現地名 | イブプロフェン |
化学・物理的性質
| XLogP | 3.5 |
|---|---|
| 極性表面積 | 37.3 |
| 水素結合供与体数 | 1 |
| 水素結合受容体数 | 2 |
| 回転可能結合数 | 4 |
| 重原子数 | 15 |
| 形式電荷 | 0 |
| 複雑度 | 203 |
| 医薬品 | PharmaceuticalsPharmaceuticals -> Used in SwitzerlandPharmaceuticals -> NSAIDs |
| LogP（分配係数） | log Kow= 3.97 |
| 臭い | Characteristic odor |
| Color/Form | Colorless, crystalline stable solid |
| 溶解度 | Readily sol in most org solventsVERY SOLUBLE IN ALCOHOLIn water, 21 mg/l @ 25 °C0.021 mg/mL at 25 °C水にほとんど溶けず、アセトン、メタノール、ジクロロメタンに溶けやすく、アルカリ溶液に溶ける。不溶性 |
| Human Drugs | FDA approved drugs -> Active ingredientEMA approved medicines: Human medicineMedicines administered to the neonate [c] |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Decomposition | When heated to decomposition it emits acrid smoke and fumes. |
| 融点 | 75-77.5 ºC75-77 °C76 °C77-78 °C |
| 蒸気圧 | 4.74X10-5 mm Hg @ 25 °C |
| Physical Description | Other Solid |
| 沸点 | 157 °C (4 mmHg) |
| 比旋光度 | [α]D20 -1~+1°(c=1,C2H5OH) |
| 密度 | 1.0364 (rough estimate) |
| 屈折率 | 1.5500 (estimate) |
| 引火点 | 9℃ |
| 貯蔵条件 | 2-8°C |
| pKa（酸解離定数） | pKa 4.45± 0.04(H2O,t = 25±0.5,I=0.15(KCl))(Approximate) |
| 外観・状態 | 結晶性粉末 |
| 色 | ホワイトからオフホワイト |
| 由来生物 | synthetic (organic) |
| Merck | 14,4881 |
| ヘンリー定数 | 6.6×101 mol/(m3Pa) at 25℃, HSDB (2015) |
| BCS Class | 2 |
| 安定性 | 安定。可燃性。強力な酸化剤とは相容れない。 |
| 化粧品成分の機能 | スキンコンディショニング |
| InChI | 1S/C13H18O2/c1-9(2)8-11-4-6-12(7-5-11)10(3)13(14)15/h4-7,9-10H,8H2,1-3H3,(H,14,15) |
| InChIKey | HEFNNWSXXWATRW-UHFFFAOYSA-N |
| SMILES | CC(C)Cc1ccc(cc1)C(C)C(O)=O |
| LogP（分配係数） | 3.970 |
| CAS データベース | 15687-27-1(CAS DataBase Reference) |
| NISTの化学物質情報 | Ibuprofen(15687-27-1) |
| EPAの化学物質情報 | Benzeneacetic acid, .alpha.-methyl-4-(2-methylpropyl)- (15687-27-1) |
化学的特性
Colourless, Crystalline Solid
安全性と法規制
| GHS 分類 | WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P203, P261, P264, P264+P265, P270, P271, P280, P301+P317, P304+P340, P305+P351+P338, P318, P319, P330, P337+P317, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 511 reports by companies from 48 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.DangerH302: Harmful if swallowed [Warning Acute toxicity, oral] |
|---|---|
| 規制情報 | Chemical: Benzeneacetic acid, .alpha.-methyl-4-(2-methylpropyl)-Benzeneacetic acid, .alpha.-methyl-4-(2-methylpropyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzeneacetic acid, .alpha.-methyl-4-(2-methylpropyl)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 29-03-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/1270Ibuprofen: Does not have an individual approval but may be used under an appropriate group standard |
| Special Reports | Aycock DGIbuprofen: A MonographAm Pharm NS31 (1): 46-9 (1991). Nonprescription ibuprofen is useful for managing minor aches and pains, reducing fever, and relieving symptoms of dysmenorrhea. For these indications, ibuprofen's effectiveness has been judged to be equal or superior to other available nonprescription analgesics. Ibuprofen is not recommended for self treatment in children less than 12 years old.Smolinske SC et alToxic Effects of Nonsteroidal Anti-inflammatory Drugs in Overdose. An Overview of Recent Evidence on Clinical Effects and Dose-response RelationshipsDrug Saf 5 (4): 252-74 (1990).Maniglia R et alNon-steroidal Anti-inflammatory NephrotoxicityAnn Clin Lab Sci 18 (3): 240-52 (1988). Non-steroidal anti-inflammatory drugs have a wide range of use in clinical practice because of their analgesic and anti-inflammatory properties. However, their potential nephrotoxicity has been noted. The case histories were studied, retrospectively, in 13 patients who were taking non-steroidal anti-inflammatory drugs as follows: four on fenoprofen (Nalfon), three on naproxen (Naprosyn), two on ibuprofen (Motrin), two on sulindac (Clinoril), one on tolmetin (Tolectin), and one on indomethacin (Indocin) and who exhibited abnormal urinalysis or a deterioration in renal function. Nine of the patients underwent renal biopsies, and eight of these biopsies were positive for interstitial nephritis. In addition to the presentation of additional cases of non-steroidal anti-inflammatory drug nephrotoxicity, a brief review of the current theories of the nephrotoxic mechanism is presented. |
用途
解説
イブプロフェン，(4-イソブチルフェニル)酢酸エチルに炭酸ジエチルを反応させて2-(4-イソブチルフェニル)マロン酸ジエチルとし，メチル化後，加水分解(脱炭酸)して合成する．無色の結晶．融点75～77 ℃．多くの有機溶媒に易溶，水にほとんど不溶．非ステロイド性の消炎，鎮痛，解熱薬で，アスピリンの16～32倍の作用を有する．LD50 1255 mg/kg(マウス，経口)．医療用医薬品や市販の風邪薬などに配合されている成分。痛みや発熱を引き起こすプロスタグランジンの合成を抑え、風邪に伴う喉の痛みや発熱の緩和に効果があるとされている。少量で効果がある一方で、胃腸障害や無菌性髄膜炎が副作用として挙げられている。2018年1月8日、同成分の摂取が男性の不妊症につながる可能性があると指摘する研究結果が米国科学アカデミー紀要(PNAS)に発表された。
用途
解熱?消炎?鎮痛剤
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
薬理研究用。
来歴
Ibuprofen was developed while searching for an alternative pain reliever to aspirin in the 1950s. It and related compounds were synthesized in 1961 by Stewart Adams, John Nicholson, and Colin Burrows who were working for the Boots Pure Drug Company in Great Britain. Adams and Nicholson filed for a British patent on ibuprofen in 1962 and obtained the patent in 1964; subsequent patents were obtained in the United States. The first clinical trials for ibuprofen were started in 1966. Ibuprofen was introduced under the trade name Brufen in 1969 in Great Britain. It was introduced in the United States in 1974. Ibuprofen was initially off ered by prescription, but it became available in over-the-counter medications in the 1980s.
使用
A common goal in the development of pain and inflammation medicines has been the creation of compounds that have the ability to treat inflammation, fever, and pain without disrupting other physiological functions. General pain relievers, such as aspirin and ibuprofen, inhibit both COX-1 and COX-2. A medication's specificaction toward COX-1 versus COX-2 determines the potential for adverse side effects. Medications with greater specificity toward COX-1 will have greater potential for producing adverse side effects. By deactivating COX-1, nonselective pain relievers increase the chance of undesirable side effects, especially digestive problems such as stomach ulcers and gastrointestinal bleeding. COX-2 inhibitors, such as Vioxx and Celebrex, selectively deactivate COX-2 and do not aff ect COX-1 at prescribed dosages. COX-2 inhibitors are widely prescribed for arthritis and pain relief. In 2004, the Food and Drug Administration (FDA) announced that an increased risk of heart attack and stroke was associated with certain COX-2 inhibitors. This led to warning labels and voluntary removal of products from the market by drug producers; for example, Merck took Vioxx off the market in 2004. Although ibuprofen inhibits both COX-1 and COX-2, it has several times the specificity toward COX-2 compared to aspirin, producing fewer gastrointestinal side effects.