Propranolol

Propranolol
Clinical data
Pronunciation	/proʊˈprænəˌlɒl/
Trade names	Inderal, others
AHFS/Drugs.com	Monograph
License data	US DailyMed: Propranolol;
Pregnancy; category	AU: C;
Routes of; administration	By mouth, rectal, intravenous
Drug class	Beta blocker
ATC code	C07AA05 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: ℞-only; EU: Rx-only;
Pharmacokinetic data
Bioavailability	26%
Protein binding	90%
Metabolism	Liver (extensive) CYP1A2, CYP2D6; minor: CYP2C19, CYP3A4
Metabolites	N-desisopropylpropranolol, 4'-hydroxypropanolol
Elimination half-life	4–5 hours
Excretion	Kidney (<1%)
Identifiers
	IUPAC name (RS)-1-(propan-2-ylamino)-3-(1-naphthyloxy)propan-2-ol;
CAS Number	525-66-6 ;
PubChem CID	4946;
IUPHAR/BPS	564;
DrugBank	DB00571 ;
ChemSpider	4777 ;
UNII	9Y8NXQ24VQ;
KEGG	D08443 ; as HCl: D00483 ;
ChEBI	CHEBI:8499 ;
ChEMBL	ChEMBL27 ;
CompTox Dashboard (EPA)	DTXSID6023525 ;
ECHA InfoCard	100.007.618
Chemical and physical data
Formula	C16H21NO2
Molar mass	259.349 g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Racemic mixture
Melting point	96 °C (205 °F)
	SMILES OC(COC1=C2C=CC=CC2=CC=C1)CNC(C)C;
	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 ; Key:AQHHHDLHHXJYJD-UHFFFAOYSA-N ;
	(verify)

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 to prevent migraine headaches, and to prevent further heart problems in those with angina or previous heart attacks. It can be taken orally 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 minutes when taken orally.

Common side effects include nausea, abdominal pain, and constipation. It may worsen the symptoms of asthma. Propranolol may cause harmful effects for the baby if taken during pregnancy; however, its use during breastfeeding is generally considered to be safe. It is a non-selective beta blocker which works by blocking β-adrenergic receptors.

Propranolol was patented in 1962 and approved for medical use in 1964. It is on the World Health Organization's List of Essential Medicines. Propranolol is available as a generic medication. In 2022, it was the 77th most commonly prescribed medication in the United States, with more than 8 million prescriptions.