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Also known as propranolol hydrochloride, Propanolol, 1-(isopropylamino)-3-(1-naphthyloxy)propan-2-ol, beta-Propranolol, 1-((1-Methylethyl)amino)-3-(1-naphthalenyloxy)-2-propanol, Propanalol, Euprovasin, [2-hydroxy-3-(naphthalen-1-yloxy)propyl](propan-2-yl)amine

Propranolol is a medication of the beta blocker class. It is used to treat high blood pressure, some types of irregular heart rate, thyrotoxicosis, capillary hemangiomas, akathisia, performance anxiety, and essential tremors, as well as to prevent migraine headaches, and to prevent further heart problems in those with angina or previous heart attacks. It can be taken orally, rectally, or by intravenous injection. The formulation that is taken orally comes in short-acting and long-acting versions. Propranolol appears in the blood after 30 minutes and has a maximum effect between 60 and 90 minut

OverviewAI-generated

Propranolol is a chemical compound with the formula C₁₆H₂₁NO₂. Its IUPAC name is 1-naphthalen-1-yloxy-3-(propan-2-ylamino)propan-2-ol. The substance has a mass of 259.157229 and a weight of 259.34. It possesses a charge of 0, an xlogp of 3, and a topological polar surface area of 41.5.

The molecule contains two hydrogen bond donors and three hydrogen bond acceptors. Its canonical SMILES representation is CC(C)NCC(COC1=CC=CC2=CC=CC=C21)O. In scientific literature, propranolol is the subject of 47,785 PubMed entries. Additionally, the compound is referenced by 2,352 other encyclopedia articles.

Synthesized by Vinony from 17 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.

Key facts

Drug.legal_UK: POM
Drug.legal_US: Rx-only
Drug.image: Propranolol.svg
Drug.image_class: skin-invert-image
Drug.width: 250
Drug.image2: Propranolol-from-1977-crystal-structure-3D-balls-side.png
Drug.image_class2: bg-transparent
Drug.width2: 250
Drug.chirality: Racemic mixture
Drug.USAN: propranolol hydrochloride
Drug.tradename: Inderal, others
Drug.MedlinePlus: a682607
Drug.DailyMedID: Propranolol
Drug.pregnancy_AU: C
Drug.routes_of_administration: By mouth, rectal, intravenous
Drug.class: Beta blocker
Drug.ATC_prefix: C07
Drug.ATC_suffix: AA05

via Wikipedia infobox

Chemical data

Formula: C16H21NO2
Molecular weight: 259.34 g/mol
IUPAC name: 1-naphthalen-1-yloxy-3-(propan-2-ylamino)propan-2-ol
SMILES: CC(C)NCC(COC1=CC=CC2=CC=CC=C21)O
InChIKey: AQHHHDLHHXJYJD-UHFFFAOYSA-N
XLogP: 3
Polar surface area: 41.5 Å²
H-bond donors: 2
H-bond acceptors: 3
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 1967
Admin. routes: oral, parenteral
Indications: hepatocellular carcinoma, cardiovascular disease, chronic obstructive pulmonary disease, hypertension

via ChEMBL · EBI