プレドニゾン
プレドニゾン · 17,21-ジヒドロキシプレグナ-1,4-ジエン-3,11,20-トリオン · アンコトン · ビコルトン · メタコルタンドラシン · デルタソン · パラコルト · セルビソン

識別子と物理属性
| CAS No. | 53-03-2 |
|---|---|
| 分子式 | C21H26O5 |
| 平均分子量 | 358.4 g/mol |
| 単同位体質量 | 358.17802393 g/mol |
| SMILES | C[C@]12C=CC(=O)C=C1CC[C@@H]1[C@@H]2C(=O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO |
| InChIKey | XOFYZVNMUHMLCC-ZPOLXVRWSA-N |
| PubChem CID | 5865 |
| ChEMBL | CHEMBL635 |
| ChEBI | CHEBI:8382 |
| EC No. | 200-160-3 |
| DTXSID | DTXSID4021185 |
| 現地名 | プレドニゾン |
化学・物理的性質
| XLogP | 1.5 |
|---|---|
| 極性表面積 | 91.7 |
| 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 | 2 |
| 重原子数 | 26 |
| 形式電荷 | 0 |
| 複雑度 | 764 |
| pH | Prednisone-syrup has a pH of 3-4.5 and contains 2-5% alcohol. Prednisone oral solution has a pH of 2.6-3.6 and contains 4-6% alcohol, and the oral concentrate solution has a pH of 3-4 and contains about 30% alcohol. |
| LogP(分配係数) | 1.46log Kow = 1.460.6 |
| 臭い | Odorless |
| 味 | Persistent bitter after-taste |
| Color/Form | CrystalsWhite to practically white, crystalline powder |
| 溶解度 | Very slightly soluble (NTP, 1992)Very slightly solubleVery slightly soluble in water1 g soluble in 150 mL alcohol, in 200 mL chloroformslightly soluble in methanol1.11e-01 g/L水にほとんど溶けず、エタノール (96%) およびジクロロメタンに溶けにくい。115mg/L(25℃) |
| Decomposition | Hazardous decomposition products formed under fire conditions - Carbon oxides.When heated to decomposition it emits acrid smoke and irritating fumes. |
| 融点 | 451 to 455 °F (DEC) (NTP, 1992)230234 °C (decomposes)233 - 235 °C236-238 °C(lit.) |
| Optical Rotation | Specific optical rotation: +172 deg at 25 °C/D (dioxane)max absorption (methanol): 238 nm (e = 15,500) |
| Physical Description | Prednisone is an odorless white crystalline powder. (NTP, 1992)Solid |
| Stability/Shelf Life | Stable under recommended storage conditions. |
| Collision Cross Section | 253.9 Ų [M-H]- [CCS Type: DTBuffer gas: N2Ionization: ESI-Dataset: TOXCASTSource Identifier: DTXSID4021185]184.1 Ų [M+H]+ [CCS Type: DTIonization: APCI+192.2 Ų [M+Na]+ [CCS Type: DTIonization: ESI+181.8 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]174.8 Ų [M+H-H2O]+ [CCS Type: TW180.52 Ų [M+H]+ [CCS Type: TW180.1 Ų [M+H]+ [CCS Type: TW] |
| 比旋光度 | 169 º (c=0.5, dioxane) |
| 沸点 | 410.86°C (rough estimate) |
| 密度 | 1.1121 (rough estimate) |
| 屈折率 | 170 ° (C=0.5, Dioxane) |
| 引火点 | >200℃ |
| 貯蔵条件 | 2-8°C |
| pKa(酸解離定数) | 12.36±0.60(Predicted) |
| 外観・状態 | 個体 |
| 色 | ホワイトからオフホワイト |
| Merck | 7722 |
| BRN | 2065301 |
| ヘンリー定数 | 3.5×104 mol/(m3Pa) at 25℃, HSDB (2015) |
| BCS Class | 1 |
| 安定性 | 安定。強力な酸化剤とは相容れない。 |
| 主な用途 | 臨床検査 |
| InChIKey | XOFYZVNMUHMLCC-ZPOLXVRWSA-N |
| SMILES | O[C@]1([C@@]2([C@H]([C@H]3[C@@H]([C@@]4(C(=CC(=O)C=C4)CC3)C)C(=O)C2)CC1)C)C(=O)CO |
| CAS データベース | 53-03-2(CAS DataBase Reference) |
| NISTの化学物質情報 | Prednisone(53-03-2) |
| EPAの化学物質情報 | Prednisone (53-03-2) |
化学的特性
White or almost white, crystalline powder.
安全性と法規制
| GHS 分類 | DangerH360 (33.7%): May damage fertility or the unborn child [Danger Reproductive toxicity]H361 (65.1%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]H372 (32%): Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]H373 (20.1%): May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]P203, P260, P264, P270, P280, P318, P319, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 169 reports by companies from 21 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| 規制情報 | Prednisone: Does not have an individual approval but may be used under an appropriate group standard |
| その他の安全情報 | IMAP assessments - Pregna-1,4-diene-3,11,20-trione, 17,21-dihydroxy-: Environment tier I assessmentIMAP assessments - Pregna-1,4-diene-3,11,20-trione, 17,21-dihydroxy-: Human health tier I assessment |
| 健康有害性 | SYMPTOMS: Implicated in aplastic anemia.ACUTE/CHRONIC HAZARDS: Toxic. (NTP, 1992) |
| FDA 要件 | The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including prednisone, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.The Generic Animal Drug and Patent Restoration act requires that each sponsor of an approved animal drug must submit to the FDA certain information regarding patents held for the animal drug or its method of use. The Act requires that this information, as well as a list of all animal drug products approved for safety and effectiveness, be made available to the public. Prednisone is included on this list.Implantation or injectable dosage form new animal drugs. Sterile prednisone suspension. ... Indications for use: It is used /in horses, dogs and cats/ for conditions requiring an anti-inflammatory agent. ... Do not use in horses intended for human consumption. Federal law restricts this drug to use by or on the order of a licensed veterinarian. |
用途
解説
プレドニソン,白色の結晶.分解点226~232 ℃.[α]D25"+186°(ジオキサン).λmax 238 nm(ε 16100).水に難溶,エタノール,クロロホルムに可溶.副じん皮質ホルモン作用のうち,糖質コルチコイド作用が強く抗アレルギー作用,抗炎症作用を呈する.リウマチ性疾患,皮膚疾患,ぜん息などの治療薬に用いられる.森北出版「化学辞典(第2版)
用途
薬理研究用。
来歴
The first isolation and structure identifications of prednisone and prednisolone were done in 1950 by Arthur Nobile. The first commercially feasible synthesis of prednisone was carried out in 1955 in the laboratories of Schering Corporation, which later became Schering-Plough Corporation, by Arthur Nobile and coworkers. They discovered that cortisone could be microbiologically oxidized to prednisone by the bacterium Corynebacterium simplex. Prednisone was introduced in 1955 by Schering, under the brand name Meticorten.Prednisone was patented in 1954 and approved for medical use in the United States in 1955. In 2023, it was the 38th most commonly prescribed medication in the United States, with more than 15 million prescriptions.
使用
Prednisone is used for the same indications as cortisone for inflammatory processes, allergies, and adrenal gland insufficiency; however, it is somewhat more active than cortisone and has less of an effect on mineral volume.
一般的な説明
Prednisone, Δ1-cortisone, 17,21-dihydroxypregna-1,4-diene-3,11,20-trione, has systemic activityvery similar to that of prednisolone, and because of itslower salt-retention activity, it is often preferred over cortisoneor hydrocortisone. Prednisone must be reduced in vivoto prednisolone to provide the active GC.
製法・合成法
純化方法
Crystallise prednisone from acetone/hexane, then recrystallise it from Me2CO. The monoacetate crystallises from Me2CO/hexane with m 227-233o(dec), [] D +186o (c 1, dioxane), and the diacetate crystallises from 25Me2CO/hexane with m 219-221o(dec), [] D +125o (c 1, CHCl3). [Hertzog et al. Tetrahedron 18 581 1962, Beilstein 8 IV 3531.]