Propranolol

Propranolol
Clinical data
Pronunciation	/proʊˈprænəˌlɑːl/
Trade names	Inderal, others
AHFS/Drugs.com	Monograph
License data	US DailyMed: Propranolol;
Pregnancy; category	AU: C; ;
Routes of; administration	Oral, rectal, intravenous
ATC code	C07AA05 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: WARNINGRx-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-(1-methylethylamino)-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, sold under the brand name Inderal among others, is a medication of the beta blocker class.^[2] It is used to treat high blood pressure, a number of types of irregular heart rate, thyrotoxicosis, capillary hemangiomas, performance anxiety, and essential tremors,^[2]^[3]^[4] as well to prevent migraine headaches, and to prevent further heart problems in those with angina or previous heart attacks.^[2] It can be taken orally (by mouth) or by intravenous injection (injection into a vein).^[2] The formulation that is taken orally (by mouth) comes in short-acting and long-acting versions.^[2] Propranolol appears in the blood after 30 minutes and has a maximum effect between 60 and 90 minutes when taken orally.^[2]^[5]

Common side effects include nausea, abdominal pain, and constipation.^[2] It may worsen the symptoms of asthma.^[2] Propranolol may cause harmful effects for the baby if taken during pregnancy.^[6] Its use during breastfeeding is probably safe.^[7] It is a non-selective beta blocker which works by blocking β-adrenergic receptors.^[2]

Propranolol was patented in 1962 and approved for medical use in 1964.^[8] It is on the World Health Organization's List of Essential Medicines.^[9] Propranolol is available as a generic medication.^[2] In 2021, it was the 91st most commonly prescribed medication in the United States, with more than 7 million prescriptions.^[10]^[11]

^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
^ ^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.
^ 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.
^ 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.
^ 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.
^ "Prescribing medicines in pregnancy database". Australian Government. 3 March 2014. Archived from the original on 8 April 2014. Retrieved 22 April 2014.
^ 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.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 460. ISBN 9783527607495.
^ 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.
^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
^ "Propranolol - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.

[FDA-AllBoxedWarnings-1] "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.

[AHFS2015-2] ^ ^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.

[Dav2006-3] 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.

[Chinnadurai2016-4] 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.

[5] 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.

[6] "Prescribing medicines in pregnancy database". Australian Government. 3 March 2014. Archived from the original on 8 April 2014. Retrieved 22 April 2014.

[7] 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.

[8] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 460. ISBN 9783527607495.

[WHO21st-9] 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.

[10] "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.

[11] "Propranolol - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

[11]