Propranolol

• Catalog No.: DB00571
• CAS Number: 525-66-6
• M. F.: C16H21NO2
• M. W.: 259.34344

SYNONYMS

• IUPAC name: [2-hydroxy-3-(naphthalen-1-yloxy)propyl](propan-2-yl)amine
• IUPAC Traditional name: propranolol
• Brand Name: Propranolol Hcl Intensol; Elbrol; Propranur; Migrastat; Deralin; Berkolol; Beta-Neg; Beta-Tablinen; Betachron; Caridolol; Rapynogen; Tesnol; Kemi S; Oposim; Prano-Puren; Prophylux; Angilol; Apsolol; Avlocardyl; Beprane; Beta-Propranolol; Betalong; Cardinol; Corpendol; Efektolol; Pylapron; Reducor Line; Sagittol; Euprovasin; Frekven; Inderide; Innopran XL; Intermigran; Obsidan; Propanix; Bedranol; Beta-Timelets; Dociton; Duranol; Reducor; Servanolol; Sloprolol; Sumial; Etalong; Inderal; Inderal La; Indobloc; Proprasylyt
• Synonyms: Dl-Propranolol Hydrochloride; R,S-Propranolol Hydrochloride; Propranolol Hydrochloride; Propranalol; Propanalol; Propranolol Hcl; Propanolol; propranolol

DATABASE IDS

• PubChem CID: 4946
• CAS Number: 525-66-6
• PubChem SID: 46505387

PROPERTIES

• Hydrophobicity(logP): 3
• Solubility: 0.070 mg/mL (HCl salt)

DETAILS

Description (English)

• Drug Groups: approved; investigational
• Description: A widely used non-cardioselective beta-adrenergic antagonist. Propranolol is used in the treatment or prevention of many disorders including acute myocardial infarction, arrhythmias, angina pectoris, hypertension, hypertensive emergencies, hyperthyroidism, migraine, pheochromocytoma, menopause, and anxiety. [PubChem]
• Indication: For the prophylaxis of migraine.
• Pharmacology: Propranolol, the prototype of the beta-adrenergic receptor antagonists, is a competitive, nonselective beta-blocker similar to nadolol without intrinsic sympathomimetic activity. Propanolol is a racemic compound; the l-isomer is responsible for adrenergic blocking activity.
• Toxicity: Symptoms of overdose include bradycardia, cardiac failure, hypotension, and brochospasm. LD₅₀=565 mg/kg (orally in mice).
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: Propranolol is almost completely absorbed from the GI tract; however, plasma concentrations attained are quite variable among individuals.
• Half Life: 4 hours
• Protein Binding: More than 90%
• Elimination: Propranolol is extensively metabolized with most metabolites appearing in the urine.
• Distribution: * 4 L
• References: Brunet A, Orr SP, Tremblay J, Robertson K, Nader K, Pitman RK: Effect of post-retrieval propranolol on psychophysiologic responding during subsequent script-driven traumatic imagery in post-traumatic stress disorder. J Psychiatr Res. 2007 Jun 21;. [Pubmed] ; Ohnishi ST, Sadanaga KK, Katsuoka M, Weidanz WP: Effects of membrane acting-drugs on plasmodium species and sickle cell erythrocytes. Mol Cell Biochem. 1989 Nov 23-Dec 19;91(1-2):159-65. [Pubmed] ; Singh N, Puri SK: Interaction between chloroquine and diverse pharmacological agents in chloroquine resistant Plasmodium yoelii nigeriensis. Acta Trop. 2000 Nov 2;77(2):185-93. [Pubmed] ; Murphy SC, Harrison T, Hamm HE, Lomasney JW, Mohandas N, Haldar K: Erythrocyte G protein as a novel target for malarial chemotherapy. PLoS Med. 2006 Dec;3(12):e528. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

REFERENCES

• Brunet A, Orr SP, Tremblay J, Robertson K, Nader K, Pitman RK: Effect of post-retrieval propranolol on psychophysiologic responding during subsequent script-driven traumatic imagery in post-traumatic stress disorder. J Psychiatr Res. 2007 Jun 21;. Pubmed
• Ohnishi ST, Sadanaga KK, Katsuoka M, Weidanz WP: Effects of membrane acting-drugs on plasmodium species and sickle cell erythrocytes. Mol Cell Biochem. 1989 Nov 23-Dec 19;91(1-2):159-65. Pubmed
• Singh N, Puri SK: Interaction between chloroquine and diverse pharmacological agents in chloroquine resistant Plasmodium yoelii nigeriensis. Acta Trop. 2000 Nov 2;77(2):185-93. Pubmed
• Murphy SC, Harrison T, Hamm HE, Lomasney JW, Mohandas N, Haldar K: Erythrocyte G protein as a novel target for malarial chemotherapy. PLoS Med. 2006 Dec;3(12):e528. Pubmed