Propranolol

Not to be confused with Propanol or Propofol.

Propranolol
Clinical data
Pronunciation/proʊˈprænəˌlɒl/
Trade namesInderal, others
Other namesAY-20694; AY20694
AHFS/Drugs.comMonograph
License data
Pregnancy
category
  • AU: C
Routes of
administration		By mouth, rectal, intravenous[1][2]
Drug classBeta blocker
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability25%[1][3]
Protein binding90% (albumin and α1-acid glycoprotein)[1][2]
MetabolismLiver (extensive) CYP1A2, CYP2D6; minor: CYP2C19, CYP3A4; aromatic hydroxylation (mainly 4-hydroxylation), N-dealkylation, side-chain oxidation, glucuronidation[1][2]
MetabolitesN-Desisopropylpropranolol; 4'-Hydroxypropanolol[2]
Elimination half-life~4 hours (range 3–8 hours)[1][4][2]
Duration of actionUp to 12 hours[5]
ExcretionUrine: 91%[4][2]
Identifiers
IUPAC name
  • (RS)-1-(propan-2-ylamino)-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)
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 Y
  • Key:AQHHHDLHHXJYJD-UHFFFAOYSA-N Y
  (verify)

Propranolol is a medication of the beta blocker class.[3][6][1] It is used to treat high blood pressure, some types of irregular heart rate, thyrotoxicosis, capillary hemangiomas, akathisia, performance anxiety, and essential tremors,[6][7][8][9] as well to prevent migraine headaches, and to prevent further heart problems in those with angina or previous heart attacks.[6] It can be taken orally, rectally, or by intravenous injection.[6][2] The formulation that is taken orally comes in short-acting and long-acting versions.[6] Propranolol appears in the blood after 30 minutes and has a maximum effect between 60 and 90 minutes when taken orally.[6][10]

Common side effects include nausea, abdominal pain, and constipation.[6] It may worsen the symptoms of asthma.[6] Propranolol may cause harmful effects for the baby if taken during pregnancy;[11] however, its use during breastfeeding is generally considered to be safe.[12] It is a non-selective beta blocker which works by blocking β-adrenergic receptors.[6]

Propranolol was patented in 1962 and approved for medical use in 1964.[13] It is on the World Health Organization's List of Essential Medicines.[14] Propranolol is available as a generic medication.[6] In 2022, it was the 77th most commonly prescribed medication in the United States, with more than 8 million prescriptions.[15][16]

  1. ^ a b c d e f "Inderal (propranolol hydrochloride) Tablets" (PDF). www.accessdata.fda.gov.
  2. ^ a b c d e f g Cite error: The named reference KalamRasoolRehman2020 was invoked but never defined (see the help page).
  3. ^ a b Srinivasan AV (2019). "Propranolol: A 50-Year Historical Perspective". Ann Indian Acad Neurol. 22 (1): 21–26. doi:10.4103/aian.AIAN_201_18. PMC 6327687. PMID 30692755.
  4. ^ a b Cite error: The named reference DrugBank was invoked but never defined (see the help page).
  5. ^ Cite error: The named reference PubChem was invoked but never defined (see the help page).
  6. ^ a b c d e f g h i j "Propranolol hydrochloride". Monograph. The American Society of Health-System Pharmacists. Archived from the original on 1 January 2015. Retrieved 1 January 2015.
  7. ^ Davidson JR (2006). "Pharmacotherapy of social anxiety disorder: what does the evidence tell us?". The Journal of Clinical Psychiatry. 67 (Suppl 12): 20–26. doi:10.1016/j.genhosppsych.2005.07.002. PMID 17092192.
  8. ^ Chinnadurai S, Fonnesbeck C, Snyder KM, Sathe NA, Morad A, Likis FE, et al. (February 2016). "Pharmacologic Interventions for Infantile Hemangioma: A Meta-analysis" (PDF). Pediatrics. 137 (2) e20153896. doi:10.1542/peds.2015-3896. PMID 26772662. S2CID 30459652.
  9. ^ Blaisdell GD (July 1994). "Akathisia: A Comprehensive Review and Treatment Summary". Pharmacopsychiatry. 27 (4): 139–146. doi:10.1055/s-2007-1014294. ISSN 0176-3679. PMID 7972345.
  10. ^ Bryson PD (1997). Comprehensive review in toxicology for emergency clinicians (3 ed.). Washington, DC: Taylor & Francis. p. 167. ISBN 9781560326120. Archived from the original on 24 March 2017.
  11. ^ "Prescribing medicines in pregnancy database". Australian Government. 3 March 2014. Archived from the original on 8 April 2014. Retrieved 22 April 2014.
  12. ^ Briggs GG, Freeman RK, Yaffe SJ (2011). Drugs in pregnancy and lactation: a reference guide to fetal and neonatal risk (9th ed.). Philadelphia: Wolters Kluwer Health/Lippincott Williams & Wilkins. p. 1226. ISBN 9781608317080. Archived from the original on 14 February 2017.
  13. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 460. ISBN 9783527607495.
  14. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  15. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  16. ^ "Propranolol Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
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