クレマスチンフマル酸塩
クレマスチンフマル酸塩 · [2R,(+)]-2-[2-[[(R)-1-(p-クロロフェニル)-1-フェニルエチル]オキシ]エチル]-1-メチルピロリジン·(E)-2-ブテン二酸 · マルスチン · マスレチン · フルミノール · マレルミンF · クレマニル · ベナンジール
識別子と物理属性
| CAS No. | 14976-57-9 |
|---|---|
| 分子式 | C25H30ClNO5 |
| 平均分子量 | 460 g/mol |
| 単同位体質量 | 459.1812508 g/mol |
| SMILES | CN1CCC[C@@H]1CCO[C@](C)(c1ccccc1)c1ccc(Cl)cc1.O=C(O)/C=C/C(=O)O |
| InChIKey | PMGQWSIVQFOFOQ-YKVZVUFRSA-N |
| PubChem CID | 5281069 |
| ChEMBL | CHEMBL1200795 |
| ChEBI | CHEBI:3739 |
| EC No. | 239-055-2 |
| DTXSID | DTXSID6047785 |
| 現地名 | クレマスチンフマル酸塩 |
化学・物理的性質
| 極性表面積 | 87.1 |
|---|---|
| 水素結合供与体数 | 2 |
| 水素結合受容体数 | 6 |
| 回転可能結合数 | 8 |
| 重原子数 | 32 |
| 形式電荷 | 0 |
| 複雑度 | 495 |
| 臭い | Odorless |
| Color/Form | Colorless to faintly yellow crystalline powder |
| 溶解度 | Very slightly soluble in water and sparingly soluble in alcohol.DMSO: 可溶5mg/mL (透明溶液加温) |
| Human Drugs | FDA approved drugs -> Active ingredient |
| 沸点 | 154 °C at 0.02 mm Hg154°C (rough estimate) |
| 融点 | 177-178 °C158-162°C |
| Other Experimental Properties | 154 °C at 0.02 mm Hg (free base) |
| 比旋光度 | D21 +16.9° (methanol) |
| 密度 | 1.0247 (rough estimate) |
| 屈折率 | 1.5790 (estimate) |
| 貯蔵条件 | 2-8°C |
| 外観・状態 | 粉 |
| 色 | 白からベージュ |
| InChIKey | PMGQWSIVQFOFOQ-YKVZVUFRSA-N |
| SMILES | [C@@](C)(OCC[C@H]1CCCN1C)(C1C=CC=CC=1)C1=CC=C(Cl)C=C1.C(/C(=O)O)=C\C(=O)O |&1:0,5,r| |
| CAS データベース | 14976-57-9(CAS DataBase Reference) |
化学的特性
White Solid
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 66.7% (12 of 18) of all reports.WarningH400 (22.2%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]P273, P391, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 18 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| FDA 要件 | Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended21 U.S.C. 321-392).The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed drug products, incl clemastine fumarate, approved on the basis of safety and effectiveness by FDA under sections 505 and 507 of the Federal Food, Drug, and Cosmetic Act. /From the Prescription Drug Product List/ |
| Hazard Classes and Categories | Aquatic Acute 1 (22.2%) |
| 体内負荷 | Following oral administration of 2.68 mg of clemastine fumarate daily for 3 days in one nursing woman, a milk clemastine concentration of about 5-10 ug/ml occurred 20 hours after the last dose of the drug. |
| Milk Concentrations | Following oral administration of 2.68 mg of clemastine fumarate daily for 3 days in one nursing woman, a milk clemastine concentration of about 5-10 ug/ml occurred 20 hours after the last dose of the drug. |
| Human Toxicity Excerpts | Usual therapeutic doses of clemastine interfere with color vision.Drowsiness, irritability, refusal to feed, and high-pitched cry occurred in one breast-fed infant (10 weeks of age) of a women who received 2.68 mg of clemastine fumarate daily for 3 days. |
| Drug Induced Liver Injury | Drug Induced Liver Injury Rank (DILIrank 2.0)Clemastine fumaratevNo-DILI-concernNo matchDOI:10.1016/j.drudis.2016.02.015 |
| Non-Human Toxicity Excerpts |
用途
用途
プロパノールアミン誘導体で す。抗ヒスタミン作用を示します。
用途
薬理研究用。
使用
Clemastine fumarate is a selective histamine H1 receptor antagonist (Ki = 0.26 nM) that also displays high affinity for muscarinic receptors (Ki = 16 nM). It has also recently been identified as a positive allosteric modulator of P2X7 receptor signaling. Clemastine fumarate has long been used to inhibit histamine-induced bronchoconstriction in asthma and airway hyperresponsive studies.
一般的な説明
Dextrorotatory clemastine, R,R-2[2[1-(4-chlorophenyl)-1-phenylethoxy]ethyl]-1- methylpyrrolidine hydrogen furnarate (1:1) (Tavist), has two chiral centers, each of which has the (R) absolute configuration. A comparison of the activities of the enantiomers indicates that the asymmetric center close to the terminal side chain nitrogen is of lesser importance to antihistaminic activity. This member of the ethanolamine series is characterized by a long duration of action, with an activity that reaches a maximum in 5 to 7 hours and persists for 10 to 12 hours. It is well absorbed when administered orally, and it is excreted primarily in the urine. The side effects are those usually encountered with this series of antihistamines. Clemastine is closely related to chlorphenoxamine, which is used for its central cholinergic-blocking activity. Therefore, it is not surprising that clemastine has significant antimuscarinic activity.