Propranolol

HCID 4946CAS 13013-17-7

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

propranolol525-66-6Propanololbeta-PropranololBetalongEuprovasinProprasylytReducorPropanalolAnaprilinepropranololodl-propranolol
Weitere Namen anzeigen
Avlocardylrac-PropanololAvlocanol208-378-0
Propranololum1-naphthalen-1-yloxy-3-(propan-2-ylamino)propan-2-ol1-(isopropylamino)-3-(1-naphthyloxy)propan-2-ol9Y8NXQ24VQ1-((1-Methylethyl)amino)-3-(1-naphthalenyloxy)-2-propanol2-Propanol, 1-[(1-methylethyl)amino]-3-(1-naphthalenyloxy)-CHEBI:8499DTXSID6023525

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

Experimentelle und physikochemische Eigenschaften

Chemical Classes · 2 Einträge

Other Uses -> Pharmaceuticals

Pharmaceutical

Drugs · 3 Einträge

Pharmaceuticals -> Antihypertensive drugs

Pharmaceuticals -> Used in Switzerland

Pharmaceuticals

LogP · 2 Einträge

3.48

3.09

Solubility0.0617 mg/L at 25 °C
Human Drugs · 5 Einträge

Antidepressants -> Beta blockers

Breast Feeding; Lactation; Milk, Human; Antihypertensive Agents; Adrenergic Beta-Antagonists; Antiarrhythmics

EMA approved medicines: Human medicine

Pharmaceuticals

Antianginal medicines

Melting Point96 °C

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)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

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 · 2 Einträge

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

Other Safety InformationIMAP assessments - 2-Propanol, 1-[(1-methylethyl)amino]-3-(1-naphthalenyloxy)-: Human health tier I assessment
Hazards SummaryAllergic contact dermatitis reported in pharmaceutical workers; [Kanerva, p. 1830] See Oxprenolol.
Hazard Classes and CategoriesAcute Tox. 4 (100%)

Toxikologische Informationen

Hepatotoxicity · 1 Eintrag

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 · 2 Einträge

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.

Toxicity SummaryIngestion 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 · 6 Einträge

Benchmark Dataset for the Liver Toxicity Knowledge Base (LTKB)

propranolol

Inderal®

Beta blockers

3

less-DILI-concern drugs

Effects During Pregnancy and Lactation · 2 Einträge

◉ Summary of Use during Lactation

◈ What is propranolol?

USGS Health-Based Screening Levels for Evaluating Water-Quality · 3 Einträge

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 · 4 Einträge

C07AA05

C - Cardiovascular system

QC - Cardiovascular system

C07AA05

Protein BindingApproximately 90% of propranolol is protein bound in plasma. Other studies have reported ranges of 85-96%.
Pharmacodynamics · 1 Eintrag

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 · 1 Eintrag

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.

Biological Half-LifeThe elimination half-life of propranolol is approximately 8 hours. The plasma half-life of propranolol is 3 to 6 hours.
Metabolism/Metabolites · 2 Einträge

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.

Verwendung und Herstellung

Uses · 2 Einträge

Used as a beta-blocking agent (antihypertensive drug); [Kanerva, p. 1830]

Use (kg) in Switzerland (2009): >750

Use ClassificationPharmaceuticals

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

Anbieter48 Anbieter

北京华美互利生物化工010-56205725 · [email protected]
Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
盐城通铭生物科技有限公司15195160625 · [email protected]
艾吉析科技(上海)有限公司17717235263 · [email protected]
江苏艾康生物医药研发有限公司025-58851090 19370895928 · [email protected]

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.

Zugehörige Reaktionen

17

Verknüpfte Notizen

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