Grundinformationen
- Standard-SMILES
CC(C)NCC(O)COc1cccc2ccccc12- InChIKey
AQHHHDLHHXJYJD-UHFFFAOYSA-N- Summenformel
- C16H21NO2
- Durchschnittliche Molmasse
- 259,34 g/mol
- Monoisotopische Masse
- 259,15722891
Überblick
Propranolol is a propanolamine that is propan-2-ol substituted by a propan-2-ylamino group at position 1 and a naphthalen-1-yloxy group at position 3. It has a role as an anxiolytic drug, a beta-adrenergic antagonist, a vasodilator agent, an antihypertensive agent, a xenobiotic, an anti-arrhythmia drug, an environmental contaminant and a human blood serum metabolite. It is a member of naphthalenes, a secondary amine and a propanolamine. It is functionally related to a 1-naphthol.
Namen und Bezeichner
- Bevorzugter Name
- Propranolol
- IUPAC
- 1-naphthalen-1-yloxy-3-(propan-2-ylamino)propan-2-ol
- Lokaler Name
- Propranolol
- Englischer Name
- Propanolol
- Summenformel
- C16H21NO2
- Molmasse
- 259.34
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
13013-17-7、525-66-6- PubChem CID
- 4946
- DTXSID
DTXSID6023525- ChEMBL
CHEMBL27- ChEBI
CHEBI:8499- UNII
- 9Y8NXQ24VQ
- EC Number
- 208-378-0、235-867-6
- Nikkaji
- J6.653B
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 3
- Polarare Oberfläche (TPSA)
- 41,5 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 6
- Schwere Atome
- 19
- Formalladung
- 0
- Komplexität
- 257
Experimentelle und physikochemische Eigenschaften
Chemical Classes
Other Uses -> Pharmaceuticals
Pharmaceutical
Drugs
Pharmaceuticals -> Antihypertensive drugs
Pharmaceuticals -> Used in Switzerland
Pharmaceuticals
LogP
3.48
3.09
Human Drugs
Antidepressants -> Beta blockers
Breast Feeding; Lactation; Milk, Human; Antihypertensive Agents; Adrenergic Beta-Antagonists; Antiarrhythmics
EMA approved medicines: Human medicine
Pharmaceuticals
Antianginal medicines
Ionization Efficiency
Positive
3.75
2.7
Agilent XCT
Electrospray ionization
formic acid (5.3nM)
Dissociation Constants
9.53
9.45
9.42
Collision Cross Section
162.5 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID3021198]
161.5 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
162.7 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]
155.55 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physikochemische Eigenschaften
- Schmelzpunkt
- 163 · 163-164 °C
- Siedepunkt
- 402.6 °C · 402.6°C (rough estimate)
- Dichte
- 1.028 · 1.0280 (rough estimate)
- Brechungsindex
- 1.55 · 1.5500 (estimate)
- storage temp.
- -20 °C · -20°C Freezer, Under inert atmosphere
- Löslichkeit
- DMSO (Slightly), Methanol (Slightly)
- Aggregatzustand
- Solid
- pka
- 13.84 · 13.84±0.20(Predicted)
- Farbe
- White to Off-White
- Wasserlöslichkeit
- 80.99 mg/L · 80.99mg/L(25 ºC)
- 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 · 525-66-6
- NIST chemische Informationen
- Propranolol(525-66-6)
- EPA chemische Informationen
- 2 · 2-Propanol, 1-[(1-methylethyl)amino]-3-(1-naphthalenyloxy)- (525-66-6)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Warning
H302 (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.
Gefahrenhinweise
Regulatory Information
Status: Active Update: 13-09-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/20584
Propranolol: Does not have an individual approval but may be used under an appropriate group standard
Toxikologische Informationen
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 injury; the 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.
Adverse Effects
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.
Drug Induced Liver Injury
Benchmark Dataset for the Liver Toxicity Knowledge Base (LTKB)
propranolol
Inderal®
Beta blockers
3
less-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
Propranolol
Pharmaceutical
Smith, C.D. and Nowell, L.H., 2024. Health-Based Screening Levels for evaluating water-quality data (3rd ed.). DOI:10.5066/F71C1TWP
Chemie und Industrie
Pharmakologische Informationen
ATC Code
C07AA05
C - Cardiovascular system
QC - Cardiovascular system
C07AA05
Pharmacodynamics
Propranolol is a beta-adrenergic receptor antagonist used to treat hypertension. Propranolol has a long duration of action as it is given once or twice daily depending on the indication. When patients abruptly stop taking propranolol, they may experience exacerbations of angina and myocardial infarctions.
Mechanism of Action
Propranolol is a nonselective β-adrenergic receptor antagonist. Blocking of these receptors leads to vasoconstriction, inhibition of angiogenic factors like vascular endothelial growth factor (VEGF) and basic growth factor of fibroblasts (bFGF), induction of apoptosis of endothelial cells, as well as down regulation of the renin-angiotensin-aldosterone system.
Metabolism/Metabolites
Propranolol undergoes side chain oxidation to α-naphthoxylactic acid, ring oxidation to 4’-hydroxypropranolol, or glucuronidation to propranolol glucuronide. It can also be N-desisopropylated to become N-desisopropyl propranolol. 17% of a dose undergoes glucuronidation and 42% undergoes ring oxidation.
Propranolol has known human metabolites that include (2S,3S,4S,5R)-3,4,5-Trihydroxy-6-[1-naphthalen-1-yloxy-3-(propan-2-ylamino)propan-2-yl]oxyoxane-2-carboxylic acid.
FDA Pharmacological Classification
9Y8NXQ24VQ
PROPRANOLOL
Mechanisms of Action [MoA] - Adrenergic beta-Antagonists
Established Pharmacologic Class [EPC] - beta-Adrenergic Blocker
Propranolol is a beta-Adrenergic Blocker. The mechanism of action of propranolol is as an Adrenergic beta-Antagonist.
PROPRANOLOL
MeSH Pharmacological Classification
Drugs that bind to but do not activate beta-adrenergic receptors thereby blocking the actions of beta-adrenergic agonists. Adrenergic beta-antagonists are used for treatment of hypertension, cardiac arrhythmias, angina pectoris, glaucoma, migraine headaches, and anxiety.
Agents used for the treatment or prevention of cardiac arrhythmias. They may affect the polarization-repolarization phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibers. Anti-arrhythmia agents are often classed into four main groups according to their mechanism of action: sodium channel blockade, beta-adrenergic blockade, repolarization prolongation, or calcium channel blockade.
Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS.
Drugs used to cause dilation of the blood vessels.
Absorption, Distribution and Excretion
Patients taking doses of 40mg, 80mg, 160mg, and 320mg daily experienced Cmax values of 18±15ng/mL, 52±51ng/mL, 121±98ng/mL, and 245±110ng/mL respectively. Propranolol has a Tmax of approximately 2 hours, though this can range from 1 to 4 hours in fasting patients. Taking propranolol with food does not increase Tmax but does increase bioavailability.
91% of an oral dose of propranolol is recovered as 12 metabolites in the urine.
The volume of distribution of propranolol is approximately 4L/kg or 320L.
The clearance of propranolol is 2.7±0.03L/h/kg in infants <90 days and 3.3±0.35L/h/kg in infants >90 days. Propranolol clearance increases linearly with hepatic blood flow. Propranolol has a clearance in hypertensive adults of 810mL/min.
Verwendung und Herstellung
Uses
Used as a beta-blocking agent (antihypertensive drug); [Kanerva, p. 1830]
Use (kg) in Switzerland (2009): >750
Anwendungen
BeschreibungPropranolol was responsible for sensitisation of workers in drug synthesis. In one case, epichlorhydrin was used for the production of both propranolol and oxprenolol.
VerwendenCardiac depressant (anti-arrhythmic); anti-adrenergic (β-receptor).
Vor- und nachgelagerte Produkte
Nachgelagerte Produkte
Anbieter48 Anbieter
Ergänzende Hinweise
DefinitionChEBI: A propanolamine that is propan-2-ol substituted by a propan-2-ylamino group at position 1 and a naphthalen-1-yloxy group at position 3.
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