化工社化工社 化学情報印刷レポート · 研究参考用
プロプラノロール
1-イソプロピルアミノ-3-(1-ナフタレニルオキシ)-2-プロパノール · 1-(1-ナフチルオキシ)-3-(イソプロピルアミノ)プロパン-2-オール · 1-[(イソプロピルアミノ)メチル]-2-(1-ナフチルオキシ)エタノール · 1-イソプロピルアミノ-3-(1-ナフチルオキシ)-2-プロパノール · アブロカノール · 1-[(1-メチルエチル)アミノ]-3-(1-ナフタレニルオキシ)-2-プロパノール · β-プロプラノロール · 1-[(1-ナフチル)オキシ]-3-(イソプロピルアミノ)プロパン-2-オール
識別子と物理属性
| CAS No. | 13013-17-7 |
|---|---|
| 分子式 | C16H21NO2 |
| 平均分子量 | 259.34 g/mol |
| 単同位体質量 | 259.15722891 g/mol |
| SMILES | CC(C)NCC(O)COc1cccc2ccccc12 |
| InChIKey | AQHHHDLHHXJYJD-UHFFFAOYSA-N |
| PubChem CID | 4946 |
| ChEMBL | CHEMBL27 |
| ChEBI | CHEBI:8499 |
| EC No. | 208-378-0 |
| DTXSID | DTXSID6023525 |
| 現地名 | プロプラノロール |
化学・物理的性質
| XLogP | 3 |
|---|---|
| 極性表面積 | 41.5 |
| 水素結合供与体数 | 2 |
| 水素結合受容体数 | 3 |
| 回転可能結合数 | 6 |
| 重原子数 | 19 |
| 形式電荷 | 0 |
| 複雑度 | 257 |
| 物質分類 | Other Uses -> Pharmaceuticals |
| 医薬品 | Pharmaceuticals -> Antihypertensive drugsPharmaceuticals -> Used in Switzerland |
| LogP（分配係数） | 3.483.09 |
| 溶解度 | 0.0617 mg/L at 25 °CDMSO（微量）、メタノール（微量）80.99mg/L(25℃) |
| Human Drugs | Antidepressants -> Beta blockersBreast FeedingLactationMilk, HumanAntihypertensive AgentsAdrenergic Beta-AntagonistsAntiarrhythmicsEMA approved medicines: Human medicinePharmaceuticalsAntianginal medicines |
| 融点 | 96 °C163-164 °C |
| Physical Description | Solid |
| Ionization Efficiency | Positive3.752.7Agilent XCTElectrospray ionizationformic acid (5.3nM) |
| Dissociation Constants | 9.539.459.42 |
| Collision Cross Section | 162.5 Ų [M+H]+ [CCS Type: DTBuffer gas: N2Ionization: APCI+Dataset: TOXCASTSource Identifier: DTXSID3021198]161.5 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]162.7 Ų [M+H]+ [CCS Type: TWMethod: Major Mix IMS/Tof Calibration Kit (Waters)]155.55 Ų [M+H-H2O]+ [CCS Type: TW |
| 沸点 | 402.6°C (rough estimate) |
| 密度 | 1.0280 (rough estimate) |
| 屈折率 | 1.5500 (estimate) |
| 貯蔵条件 | -20°C Freezer, Under inert atmosphere |
| 外観・状態 | 個体 |
| pKa（酸解離定数） | 13.84±0.20(Predicted) |
| 色 | ホワイトからオフホワイト |
| InChI | InChI=1S/C16H21NO2/c1-12(2)17-10-14(18)11-19-16-9-5-7-13-6-3-4-8-15(13)16/h3-9,12,14,17-18H,10-11H2,1-2H3 |
| InChIKey | AQHHHDLHHXJYJD-UHFFFAOYSA-N |
| SMILES | C(NC(C)C)C(O)COC1=C2C(C=CC=C2)=CC=C1 |
| CAS データベース | 525-66-6 |
| NISTの化学物質情報 | Propranolol(525-66-6) |
| EPAの化学物質情報 | 2-Propanol, 1-[(1-methylethyl)amino]-3-(1-naphthalenyloxy)- (525-66-6) |
化学的特性
Colorless crystals.Soluble in water and alcohol; insoluble in benzene and ether.
安全性と法規制
| GHS 分類 | WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory. |
|---|---|
| 規制情報 | Status: Active Update: 13-09-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/20584Propranolol: 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 - 2-Propanol, 1-[(1-methylethyl)amino]-3-(1-naphthalenyloxy)-: Human health tier I assessment |
| 有害性の概要 | Allergic contact dermatitis reported in pharmaceutical workers[Kanerva, p. 1830] See Oxprenolol. |
| Hazard Classes and Categories | Acute Tox. 4 (100%) |
| Hepatotoxicity | Mild-to-moderate elevations in serum aminotransferase levels occur in less than 2% of patients on propranolol and are usually transient and asymptomatic, resolving even with continuation of therapy. Despite its widespread use, propranolol has not been convincingly linked to instances of clinically apparent liver injurythe few cases reported have generally occurred in patients who were receiving other well known hepatotoxic agents or were associated with elevations in serum enzymes only without jaundice. |
| 有害作用 | Skin Sensitizer - An agent that can induce an allergic reaction in the skin.Common side effects of using propranolol include bradycardia, gastrointestinal issues, abdominal pain, nausea, erectile dysfunction, and wheezing/bronchospasms. Propranolol use can also cause drowsiness, fatigue, and cold extremities. Some extreme side effects to be aware of include allergic reactions, insulin resistance, and hallucinations. Prescribers need to explain and discuss all of the side effects before giving patients a prescription for propranolol. |
| 毒性の概要 | Ingestion of greater than 1 g of propranolol in 24 hours can potentially be lethal and lead to profound bradycardia, bradyarrhythmia, hypotension, bronchospasm. |
| Drug Induced Liver Injury | Benchmark Dataset for the Liver Toxicity Knowledge Base (LTKB) |
用途
説明
Propranolol was responsible for sensitisation of workers in drug synthesis. In one case, epichlorhydrin was used for the production of both propranolol and oxprenolol.
使用
Cardiac depressant (anti-arrhythmic); anti-adrenergic (β-receptor).