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...

基本信息

化学结构

分子式

C₁₆H₂₁NO₂

分子量

259.34344

精确质量

259.15722892

电荷

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

计算属性

JChem

LogD (pH = 7.4)

0.36

LogD (pH = 5.5)

-0.61

Log P

2.58

可自由旋转的化学键

质子供体

质子受体

里宾斯基五规则

true

Acid pKa

9.67

极化表面积

41.49

极化性

30.05

摩尔折射率

76.83

LOG S

-3.70

数据来源

名称和标识

IUPAC标准名

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

别名

(R)-(+)-PROPRANOLOL HYDROCHLORIDE(S)-(-)-PROPRANOLOL HYDROCHLORIDEPropanololPropranolol HydrochlorideR,S-Propranolol HydrochloridePropanalolPropranololDl-Propranolol HydrochloridepropranololPropranolol HclPropranalolPropranolol1-(isopropylamino)-3-(1-naphthyloxy)propan-2-ol1-[(1-Methylethyl)amino]-3-(1-naphthalenyloxy)-2-propanol; 1-Isopropylamino-3-(1-naphthyloxy)-2-propanol1-((1-Methylethyl)amino)-3-(1-naphthalenyloxy)-2-propanol1-(isopropylamino)-3-(1-naphthyloxy)propan-2-olPropanololpropranololoPropranololpropranololbeta-PropranololPropanalol

IUPAC传统名

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

商标名

ApsololServanololBetachronIntermigranReducor LineBetalongInnopran XLBeta-TablinenProprasylytProphyluxObsidanMigrastatBeta-PropranololReducorEuprovasinDuranolKemi SEtalongDeralinPrano-PurenCaridololAngilolPylapronPropranurBeta-NegOposimCardinolInderideSumialRapynogenFrekvenBeta-TimeletsPropranolol Hcl IntensolInderalSagittolBedranolDocitonBepraneElbrolCorpendolInderal LaBerkololTesnolAvlocardylSloprololIndoblocPropanixEfektolol

国际非专利药品(INN)

propranololpropranololum

名称和标识

数据登录号

化合物性质

理化性质

疏水性(logP)

2.753

溶解度

0.070 mg/mL (HCl salt)

安全信息

保存条件

Room Temperature (15-30°C)

Room Temperature (15-30°C), Desiccate

MSDS下载

下载链接

药理学性质

生物活性机理

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

化合物性质

分子相关蛋白质

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分子图谱

暂无数据

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描述信息

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.

描述信息

参考文献

PubChem文献

数据源提供

• 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

• 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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

参考文献

生物活性

PubChem BioAssay

生物活性

名称和标识

IUPAC标准名

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

别名

IUPAC传统名

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

商标名

国际非专利药品(INN)

propranololpropranololum

化合物性质

理化性质

疏水性(logP)

2.753

溶解度

0.070 mg/mL (HCl salt)

安全信息

保存条件

Room Temperature (15-30°C)

Room Temperature (15-30°C), Desiccate

MSDS下载

下载链接

药理学性质

生物活性机理

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

描述信息

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.

参考文献

PubChem文献

数据源提供

• 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

• 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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

生物活性

PubChem BioAssay

化合物信息

ID:453