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Propranolol
PROPANALOL · Avlocardyl · rac-Propanolol · 1-naphthalen-1-yloxy-3-(propan-2-ylamino)propan-2-ol · Reducor · Betalong · Avlocanol · 208-378-0
Identifikatoren & physikalische Daten
| CAS No. | 13013-17-7 |
|---|---|
| Summenformel | C16H21NO2 |
| Durchschnittliche Molmasse | 259,34 g/mol |
| Monoisotopische Masse | 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 |
| Lokaler Name | Propranolol |
Chemische & physikalische Eigenschaften
| XLogP | 3 |
|---|---|
| Polarare Oberfläche (TPSA) | 41,5 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 6 |
| Schwere Atome | 19 |
| Formalladung | 0 |
| Komplexität | 257 |
| Stoffklassen | Other Uses -> Pharmaceuticals |
| Arzneimittel | Pharmaceuticals -> Antihypertensive drugsPharmaceuticals -> Used in Switzerland |
| LogP (Verteilungskoeffizient) | 3.483.09 |
| Löslichkeit | 0.0617 mg/L at 25 °CDMSO (Slightly), Methanol (Slightly)80.99mg/L(25 ºC) |
| Human Drugs | Antidepressants -> Beta blockersBreast FeedingLactationMilk, HumanAntihypertensive AgentsAdrenergic Beta-AntagonistsAntiarrhythmicsEMA approved medicines: Human medicinePharmaceuticalsAntianginal medicines |
| Schmelzpunkt | 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 |
| Siedepunkt | 402.6°C (rough estimate) |
| Dichte | 1.0280 (rough estimate) |
| Brechungsindex | 1.5500 (estimate) |
| Lagerbedingungen | -20°C Freezer, Under inert atmosphere |
| Aggregatzustand | Solid |
| pKa (Säurekonstante) | 13.84±0.20(Predicted) |
| Farbe | White to Off-White |
| 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 Datenbank | 525-66-6 |
| NIST chemische Informationen | Propranolol(525-66-6) |
| EPA chemische Informationen | 2-Propanol, 1-[(1-methylethyl)amino]-3-(1-naphthalenyloxy)- (525-66-6) |
Sicherheit & Vorschriften
| GHS-Einstufung | 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. |
|---|---|
| Regulatorische Informationen | 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 |
| Weitere Sicherheitsinformationen | IMAP assessments - 2-Propanol, 1-[(1-methylethyl)amino]-3-(1-naphthalenyloxy)-: Human health tier I assessment |
| Gefahrenübersicht | 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. |
| Unerwünschte Wirkungen | 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. |
| Toxizitätsübersicht | 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)propranololInderal®Beta blockers3less-DILI-concern drugs |
| Effects During Pregnancy and Lactation | ◉ Summary of Use during Lactation◈ What is propranolol? |
| USGS Health-Based Screening Levels for Evaluating Water-Quality | PropranololPharmaceuticalSmith, C.D. and Nowell, L.H., 2024. Health-Based Screening Levels for evaluating water-quality data (3rd ed.). DOI:10.5066/F71C1TWP |
Anwendungen & Verwendung
Beschreibung
Propranolol was responsible for sensitisation of workers in drug synthesis. In one case, epichlorhydrin was used for the production of both propranolol and oxprenolol.
Verwenden
Cardiac depressant (anti-arrhythmic); anti-adrenergic (β-receptor).