CAS 4199-10-4|CAS 13071-11-9|CAS 525-66-6|[2-hydroxy-3-(naphthalen-1-yloxy)propyl](propan-2-yl)amine|(R)-(+)-PROPRANOLOL HYDROCHLORIDE|propranolol|(S)-(-)-PROPRANOLOL HYDROCHLORIDE|Apsolol|Propanolo...

General Information

Structure

Molecular Formula

C₁₆H₂₁NO₂

Molecular Mass

259.34344

Exact Mass

259.15722892

Charge

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

Canonic Smiles

OC(COc1cccc2c1cccc2)CNC(C)C

Isomeric Smiles

O(CC(O)CNC(C)C)c1c2c(ccc1)cccc2

Calculated Properties

JChem

LogD (pH = 7.4)

0.36

LogD (pH = 5.5)

-0.61

Log P

2.58

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

9.67

Polar Surface Area

41.49

Polarizability

30.05

Molar Refractivity

76.83

LOG S

-3.70

Data Source

Names and Identifiers

IUPAC name

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

IUPAC Traditional name

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

Synonyms

(S)-(-)-PROPRANOLOL HYDROCHLORIDE(R)-(+)-PROPRANOLOL HYDROCHLORIDEPropranolol HydrochloridePropanololPropranololDl-Propranolol HydrochlorideR,S-Propranolol HydrochloridePropanalolpropranololPropranalolPropranolol HclPropranolol1-(isopropylamino)-3-(1-naphthyloxy)propan-2-ol1-[(1-Methylethyl)amino]-3-(1-naphthalenyloxy)-2-propanol; 1-Isopropylamino-3-(1-naphthyloxy)-2-propanolbeta-Propranolol1-((1-Methylethyl)amino)-3-(1-naphthalenyloxy)-2-propanolPropranololPropanalolpropranololo1-(isopropylamino)-3-(1-naphthyloxy)propan-2-olpropranololPropanolol

Brand Name

IntermigranServanololReducorEtalongApsololProphyluxProprasylytReducor LineInnopran XLBeta-PropranololEuprovasinBetalongKemi SObsidanBeta-TablinenBetachronDuranolMigrastatPylapronOposimFrekvenCaridololSumialAngilolCardinolRapynogenPropranurPrano-PurenInderideBeta-NegBeta-TimeletsDeralinSagittolBepraneBerkololPropranolol Hcl IntensolDocitonIndoblocEfektololElbrolBedranolInderal LaTesnolPropanixAvlocardylInderalSloprololCorpendol

International Nonproprietary Name (INN)

propranololpropranololum

Names and Identifiers

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

2.753

Solubility

0.070 mg/mL (HCl salt)

Safety Information

Storage Condition

Room Temperature (15-30°C)

Room Temperature (15-30°C), Desiccate

MSDS Link

Download link

Pharmacology Properties

Mechanism of Action

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.

Beta-Adrenergic blocking agent

Only L-propranolol is a powerful adrenoceptor antagonist, whereas D-propranolol is not

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

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]

MP Biomedicals

02156412

Hydrochloride

02156413

Hydrochloride
5-HT₁ antagonist and β adrenergic blocker.

ChEBI

CHEBI:8499

A propanolamine that is propan-2-ol substituted by a propan-2-ylamino group at position 1 and a naphthalen-1-yloxy group at position 3.

Molecule Details

References

PubChem Literature

From Data Sources

• 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

• 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

• 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

• Howe, R. et al., Nature (London), 1965, 207, 594; 1966, 210, 1336, (synth, resoln)

• U.K. Pat., 1965, 994 918; CA, 63, 8130d, (synth)

• Klunder, J.M. et al., J.O.C., 1986, 51, 3710, (synth)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 4064

• Matchett, M.W. et al., Chirality, 1996, 8, 126-130, (resoln)

• Dukes, M. et al., J. Med. Chem., 1971, 14, 326

• Alkondon, M. et al., Can. J. Physiol. Pharmacol., 1986, 64, 1455, (rev, pharmacol)

• Abe, Y. et al., Chem. Pharm. Bull., 1996, 44, 1521, (resoln)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 633C; 634A, (nmr)

• Routledge, P.A. et al., Appl. Pharmacokinet., 1980, 464, (rev, metab, pharmacol)

• Tsuda, Y. et al., Chem. Pharm. Bull., 1981, 29, 3593, (synth, deriv)

• Imuchijima, S. et al., Agric. Biol. Chem., 1982, 46, 1153, (metab, synth)

• Sakuraba, S. et al., Chem. Pharm. Bull., 1995, 43, 738, (synth)

• Katsuki, T., Tet. Lett., 1984, 25, 2821, (synth)

• Okamoto, Y. et al., Chem. Lett., 1986, 7, 1237, (resoln)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, ICB000; ICC000; PNB790; PNB800

• Thompson, J.A. et al., J. Chromatogr., 1982, 238, 470, (synth, sepn)

• Barrans, Y. et al., Acta Cryst. B, 1973, 29, 1264, (cryst struct)

• Fitzgerald, J.D., Pharmacol. Antihypertens. Drugs, 1980, 195, (rev, pharmacol)

• Mishriki, A. et al., Pharmacotherapy (Carlisle, Mass.), 1983, 3, 334-341, (rev)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 638

• Paul, R. et al., J.O.C., 1975, 40, 1653, (abs config)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC name

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

IUPAC Traditional name

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

Synonyms

Brand Name

International Nonproprietary Name (INN)

propranololpropranololum

Properties

Physical Property

Hydrophobicity(logP)

2.753

Solubility

0.070 mg/mL (HCl salt)

Safety Information

Storage Condition

Room Temperature (15-30°C)

Room Temperature (15-30°C), Desiccate

MSDS Link

Download link

Pharmacology Properties

Mechanism of Action

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.

Beta-Adrenergic blocking agent

Only L-propranolol is a powerful adrenoceptor antagonist, whereas D-propranolol is not

Molecule Details

DrugBank

DB00571

Drug Groups

approved; investigational

Description

Indication

For the prophylaxis of migraine.

Pharmacology

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

• 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]

MP Biomedicals

02156412

Hydrochloride

02156413

Hydrochloride
5-HT₁ antagonist and β adrenergic blocker.

ChEBI

CHEBI:8499

A propanolamine that is propan-2-ol substituted by a propan-2-ylamino group at position 1 and a naphthalen-1-yloxy group at position 3.

References

PubChem Literature

From Data Sources

• 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

• 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

• 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

• Howe, R. et al., Nature (London), 1965, 207, 594; 1966, 210, 1336, (synth, resoln)

• U.K. Pat., 1965, 994 918; CA, 63, 8130d, (synth)

• Klunder, J.M. et al., J.O.C., 1986, 51, 3710, (synth)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 4064

• Matchett, M.W. et al., Chirality, 1996, 8, 126-130, (resoln)

• Dukes, M. et al., J. Med. Chem., 1971, 14, 326

• Alkondon, M. et al., Can. J. Physiol. Pharmacol., 1986, 64, 1455, (rev, pharmacol)

• Abe, Y. et al., Chem. Pharm. Bull., 1996, 44, 1521, (resoln)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 633C; 634A, (nmr)

• Routledge, P.A. et al., Appl. Pharmacokinet., 1980, 464, (rev, metab, pharmacol)

• Tsuda, Y. et al., Chem. Pharm. Bull., 1981, 29, 3593, (synth, deriv)

• Imuchijima, S. et al., Agric. Biol. Chem., 1982, 46, 1153, (metab, synth)

• Sakuraba, S. et al., Chem. Pharm. Bull., 1995, 43, 738, (synth)

• Katsuki, T., Tet. Lett., 1984, 25, 2821, (synth)

• Okamoto, Y. et al., Chem. Lett., 1986, 7, 1237, (resoln)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, ICB000; ICC000; PNB790; PNB800

• Thompson, J.A. et al., J. Chromatogr., 1982, 238, 470, (synth, sepn)

• Barrans, Y. et al., Acta Cryst. B, 1973, 29, 1264, (cryst struct)

• Fitzgerald, J.D., Pharmacol. Antihypertens. Drugs, 1980, 195, (rev, pharmacol)

• Mishriki, A. et al., Pharmacotherapy (Carlisle, Mass.), 1983, 3, 334-341, (rev)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 638

• Paul, R. et al., J.O.C., 1975, 40, 1653, (abs config)

Bioactivity

PubChem BioAssay

Molecule

ID:453