[2-hydroxy-3-(naphthalen-1-yloxy)propyl](propan-2-yl)amine

• ChemBase ID: 453
• Molecular Formular: C16H21NO2
• Molecular Mass: 259.34344
• Monoisotopic Mass: 259.15722892
• SMILES: O(CC(O)CNC(C)C)c1c2c(ccc1)cccc2
• Canonical SMILES: OC(COc1cccc2c1cccc2)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
• InChIKey: AQHHHDLHHXJYJD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 525-66-6; 13071-11-9; 4199-10-4
• EC Number: 224-096-0; 235-961-7
• MDL Number: MFCD00062560
• PubChem SID: 46505387; 160963916
• PubChem CID: 4946

CALCULATED PROPERTIES

JChem

• Acid pKa: 14.08793
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.6095358
• LogD (pH = 7.4): 0.3584574
• Log P: 2.583696
• Molar Refractivity: 76.8257 cm^3
• Polarizability: 31.766071 Å^3
• Polar Surface Area: 41.49 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.03
• LOG S: -3.51
• Solubility (Water): 7.94e-02 g/l

PROPERTIES

Physical Property

• Solubility: 0.070 mg/mL (HCl salt)
• Hydrophobicity(logP): 2.753; 3

Safety Information

• Storage Condition: Room Temperature (15-30°C); Room Temperature (15-30°C), Desiccate

Pharmacology Properties

• Mechanism of Action: Beta-Adrenergic blocking agent; It has little intrinsic sympathomimetic activity (ISA) but has strong membrane stabilizing activity (only at high blood concentrations, eg overdosage).; It is a non-selective beta blocker, that is, it blocks the action of epinephrine on both beta1- and beta2-adrenergic receptors.; Only L-propranolol is a powerful adrenoceptor antagonist, whereas D-propranolol is not

Product Information

• Purity: 95%
• Application(s): Antiarrhythmic agent; Hypotensives; Local anesthetic

DETAILS

MP Biomedicals - 02156412

Hydrochloride

MP Biomedicals - 02156413

Hydrochloride
5-HT₁ antagonist and β adrenergic blocker.

DrugBank - DB00571

• 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
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