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13071-11-9 molecular structure
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[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 and InChIs

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

Cite this record

CBID:453 http://www.chembase.cn/molecule-453.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

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

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 14.08793  H Acceptors
H Donor LogD (pH = 5.5) -0.6095358 
LogD (pH = 7.4) 0.3584574  Log P 2.583696 
Molar Refractivity 76.8257 cm3 Polarizability 31.766071 Å3
Polar Surface Area 41.49 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 3.03  LOG S -3.51 
Solubility (Water) 7.94e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
0.070 mg/mL (HCl salt) expand Show data source
Hydrophobicity(logP)
2.753 expand Show data source
3 expand Show data source
Storage Condition
Room Temperature (15-30°C) expand Show data source
Room Temperature (15-30°C), Desiccate expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Mechanism of Action
Beta-Adrenergic blocking agent expand Show data source
It has little intrinsic sympathomimetic activity (ISA) but has strong membrane stabilizing activity (only at high blood concentrations, eg overdosage). expand Show data source
It is a non-selective beta blocker, that is, it blocks the action of epinephrine on both beta1- and beta2-adrenergic receptors. expand Show data source
Only L-propranolol is a powerful adrenoceptor antagonist, whereas D-propranolol is not expand Show data source
Purity
95% expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Application(s)
Antiarrhythmic agent expand Show data source
Hypotensives expand Show data source
Local anesthetic expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank
MP Biomedicals - 02156412 external link
Hydrochloride
MP Biomedicals - 02156413 external link
Hydrochloride
5-HT1 antagonist and β adrenergic blocker.
DrugBank - DB00571 external link
Item Information
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

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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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PATENTS

PATENTS

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INTERNET

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