Propranolol

Propranolol, sold under the brand name Inderal among others, is a medication of the beta blocker class. It is used to treat high blood pressure, a number of types of irregular heart rate, thyrotoxicosis, capillary hemangiomas, 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 (by mouth) or by intravenous injection (injection into a vein). The formulation that is taken orally (by mouth) 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.

Not to be confused with Propanol or Propofol.

Propranolol
Clinical data
Pronunciation/proʊˈprænəˌlɑːl/
Trade namesInderal, others
AHFS/Drugs.comMonograph
License data
Pregnancy
category
  • AU: C
Routes of
administration		Oral, rectal, intravenous
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability26%
Protein binding90%
MetabolismLiver (extensive) 1A2, 2D6; minor: 2C19, 3A4
MetabolitesN-desisopropylpropranolol, 4'-hydroxypropanolol
Elimination half-life4–5 hours
ExcretionKidney (<1%)
Identifiers
  • (RS)-1-(1-methylethylamino)-3-(1-naphthyloxy)propan-2-ol
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.007.618
Chemical and physical data
FormulaC16H21NO2
Molar mass259.349 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
Melting point96 °C (205 °F)
  • OC(COC1=C2C=CC=CC2=CC=C1)CNC(C)C
  • 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 Y
  • Key:AQHHHDLHHXJYJD-UHFFFAOYSA-N Y
  (verify)

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. Its use during breastfeeding is probably 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 2021, it was the 91st most commonly prescribed medication in the United States, with more than 7 million prescriptions.

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