ALPRENOLOL

Details

Stereochemistry	RACEMIC
Molecular Formula	C15H23NO2
Molecular Weight	249.3486
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)NCC(O)COC1=CC=CC=C1CC=C

InChI

InChIKey=PAZJSJFMUHDSTF-UHFFFAOYSA-N

InChI=1S/C15H23NO2/c1-4-7-13-8-5-6-9-15(13)18-11-14(17)10-16-12(2)3/h4-6,8-9,12,14,16-17H,1,7,10-11H2,2-3H3

HIDE SMILES / InChI

Molecular Formula	C15H23NO2
Molecular Weight	249.3486
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/018240s031lbl.pdf

Alprenolol is a beta adrenoreceptor blocking agent and 5HT1A antagonist, developed by AstraZeneca and now available as generic drug. It is used for treatment of hypertension, angina pectoris due to coronary atherosclerosis and acute myocardial infarction.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Serotonin 1a (5-HT1a) receptor 177 Target ID: CHEMBL273 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8568799	Antagonist 2849	6.93 null [pKi]
Beta-1 adrenergic receptor 163 Target ID: CHEMBL213 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21870877	Antagonist 2849
Beta-2 adrenergic receptor 209 Target ID: CHEMBL210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21870877	Antagonist 2849
Beta-3 adrenergic receptor 54 Target ID: CHEMBL246 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21870877	Antagonist 2849

Conditions

Condition	Modality	Highest Phase	Product
Hypertension 575 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/018240s031lbl.pdf	Primary	Approved 8583	TENORMIN Approved Use TENORMIN is indicated in the management of hypertension. It may be used alone or concomitantly with other antihypertensive agents, particularly with a thiazide-type diuretic
Angina pectoris due to coronary atherosclerosis 4 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/018240s031lbl.pdf	Primary	Approved 8583	TENORMIN Approved Use TENORMIN is indicated for the long-term management of patients with angina pectoris
Acute myocardial infarction 37 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/018240s031lbl.pdf	Primary	Approved 8583	TENORMIN Approved Use TENORMIN is indicated in the management of hemodynamically stable patients with definite or suspected acute myocardial infarction to reduce cardiovascular mortality. Treatment can be initiated as soon as the patient's clinical condition allows.

C_max

Value	Dose	Co-administered	Analyte	Population
216.9 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/881641/	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:		ALPRENOLOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
67 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/891097/	5 mg single, intravenous dose: 5 mg route of administration: Intravenous experiment type: SINGLE co-administered:		ALPRENOLOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
706 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/891097/	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:		ALPRENOLOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/881641/	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:		ALPRENOLOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
MRP3 246 CYP2J2 33 MRP4 290 MRP2 499 OATP1B1 1079 CYP19A1 429 CYP2C19 2057 P-gp 1741 BSEP 550 OATP1B3 961 CYP1A2 2153	P-gp 2052

Drug as perpetrator

Target	Modality	Activity
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/2119#section=BioAssay-Results Page: 20.0	inconclusive [IC50 43.6486 uM]
BSEP 554	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw2MDIwIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI2NjE5NSJ9fQ==	no [IC50 >133 uM]
MRP2 625	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1NzQ4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI2NjE5NSJ9fQ==	no [IC50 >133 uM]
MRP3 326	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1OTE4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI2NjE5NSJ9fQ==	no [IC50 >133 uM]
MRP4 345	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTI4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI2NjE5NSJ9fQ==	no [IC50 >133 uM]
CYP2J2 36	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDkxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI2NjE5NSJ9fQ==	no [IC50 >50 uM]
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/2119#section=BioAssay-Results Page: 165.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/2119#section=BioAssay-Results Page: 229.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/2119#section=BioAssay-Results Page: 213.0	no
P-gp 1932	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw0MzAyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI2NjE5NSJ9fQ==	no
CYP1A2 2333	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/2119#section=BioAssay-Results Page: 13.0	yes [IC50 12.3018 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/2119#section=BioAssay-Results Page: 11.0	yes [IC50 5.495 uM]
OATP1B1 1095	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNjk3NjY4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI2NjE5NSJ9fQ==	yes [Inhibition 10 uM]
OATP1B3 970	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTIxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI2NjE5NSJ9fQ==	yes [Inhibition 10 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/2119#section=BioAssay-Results Page: 209 \| 210	no

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTI1NjE3OSJ9fQ==

PubMed

Title	Date	PubMed
Physicochemical interactions between drugs and superdisintegrants.	2008-12	19000362
Effects of a strongly adsorbed additive on process performance in chiral preparative chromatography.	2008-11-28	18962651
Putrescine modulation of acute activation of the beta-adrenergic system in the left atrium of rat.	2008-11-19	18755180
Beta-blockers alprenolol and carvedilol stimulate beta-arrestin-mediated EGFR transactivation.	2008-09-23	18787115
Enantioselective determination of alprenolol in human plasma by liquid chromatography with tandem mass spectrometry using cellobiohydrolase chiral stationary phases.	2008-09-01	18691951
Simulation-based cheminformatic analysis of organelle-targeted molecules: lysosomotropic monobasic amines.	2008-09	18338229
Effects of alcohols on CE enantioseparation of basic drugs with native gamma-CD as chiral selector.	2008-08	18623283
Enantiomeric separation by using nano-liquid chromatography with on-column focusing.	2008-08	18623279
In vitro cytotoxicity of eight beta-blockers in human corneal epithelial and retinal pigment epithelial cell lines: comparison with epidermal keratinocytes and dermal fibroblasts.	2008-06	18316173
Role of chemical structure in stereoselective recognition of beta-blockers by cyclodextrins in capillary zone electrophoresis.	2008-04-24	18022245
Noradrenergic modulation in the olfactory bulb influences spontaneous and reward-motivated discrimination, but not the formation of habituation memory.	2008-03	18364038
A unique mechanism of beta-blocker action: carvedilol stimulates beta-arrestin signaling.	2007-10-16	17925438
Detection of g protein coupled receptor mediated adenylyl cyclase activity by capillary electrophoresis using fluorescently labeled ATP.	2007-10-01	17718540
An investigation into the influence of drug lipophilicity on the in vivo absorption profiles from subcutaneous microspheres and in situ forming depots.	2007-09-11	17638603
Neuropeptide Y and glucocorticoid secretion from guinea pig adrenal gland: an in vivo and in vitro study.	2007-09	17671739
Cutaneous vasculitis induced by carvedilol.	2007-08	17659030
Multiple GPCR conformations and signalling pathways: implications for antagonist affinity estimates.	2007-08	17629959
The role of Gi proteins in reduced vasorelaxation response to beta-adrenoceptor agonists in rat aorta during maturation.	2007-06-14	17395174
Separation of basic compounds of pharmaceutical interest by using nano-liquid chromatography coupled with mass spectrometry.	2007-05-25	17069825
Medial prefrontal cortical alpha1 adrenoreceptor modulation of the nucleus accumbens dopamine response to stress in Long-Evans rats.	2007-04	17294052
Evidence for a paracrine role of endogenous adrenomedullary galanin in the regulation of glucocorticoid secretion in the rat adrenal gland.	2007-03	17273801
Bioluminescence resonance energy transfer as a screening assay: Focus on partial and inverse agonism.	2007-02	17114329
Pharmacologic characterization of the cloned human trace amine-associated receptor1 (TAAR1) and evidence for species differences with the rat TAAR1.	2007-01	17038507
Abstracts of papers presented at the 2007 pittsburgh conference.	2007	18528514
Carvedilol in the treatment of chronic heart failure: lessons from the Carvedilol Or Metoprolol European Trial.	2007	17583173
High-speed gas chromatography in doping control: fast-GC and fast-GC/MS determination of beta-adrenoceptor ligands and diuretics.	2006-12	17305237
Erythrocyte G protein as a novel target for malarial chemotherapy.	2006-12	17194200
Expression of beta-adrenergic receptor up-regulation is mediated by two different processes.	2006-09-27	16920085
Polymer-coated hollow fiber microextraction combined with on-column stacking in capillary electrophoresis.	2006-09-22	16824535
Effects of antihypertensive medication on left ventricular function during electroconvulsive therapy: study with transthoracic echocardiography.	2006-09	16980161
Coupling ligand structure to specific conformational switches in the beta2-adrenoceptor.	2006-08	16799554
Computational approaches for modeling human intestinal absorption and permeability.	2006-07	16583199
Ionic liquids versus triethylamine as mobile phase additives in the analysis of beta-blockers.	2006-06-30	16386264
Role of chemical structure in stereoselective recognition of beta-blockers and H1-antihistamines by human serum transferrin in capillary zone electrophoresis.	2006-04	16609932
Atrial natriuretic peptide enhances cortisol secretion from guinea-pig adrenal gland: evidence for an indirect paracrine mechanism probably involving the local release of medullary catecholamines.	2006-04	16525720
Catanionic mixtures involving a drug: a rather general concept that can be utilized for prolonged drug release from gels.	2006-04	16498573
Analytical characterization of chiral drug-protein interactions: comparison between the optical biosensor (surface plasmon resonance) assay and the HPLC perturbation method.	2006-03-01	16503623
UPLC/MS for the identification of beta-blockers.	2006-02-24	16413161
Investigation of chiral recognition mechanism on chicken alpha(1)-acid glycoprotein using separation system.	2006-02-17	16443457
Permanent effects of postnatal administration of beta-adrenergic ligands on the volume of sexually dimorphic nucleus of the preoptic area (SDN-POA) in rats.	2006-01-25	16648786
Putting theory into practice: James Black, receptor theory and the development of the beta-blockers at ICI, 1958-1978.	2006-01	16502872
Evidence for a secondary state of the human beta3-adrenoceptor.	2005-12	16129733
Multivariate optimization approach for chiral resolution of drugs using human serum albumin in affinity electrokinetic chromatography-partial filling technique.	2005-11	16252317
Insights into cyclodextrin interactions during sample stacking using capillary isotachophoresis with on-line microcoil NMR detection.	2005-09	16049945
Low-affinity state beta1-adrenoceptor-induced vasodilation in SHR.	2005-08	16042986
Use of vancomycin chiral stationary phase for the enantiomeric resolution of basic and acidic compounds by nano-liquid chromatography.	2005-07-15	16013606
Drug molecules as probes for studying the compatibility between gels and mucous tissue with dielectric spectroscopy.	2005-05	15793811
Effects of dexamethasone and colostrum feeding on mRNA levels and binding capacities of beta-adrenergic receptors in the liver of neonatal calves.	2005-04	15760667
The selectivity of beta-adrenoceptor antagonists at the human beta1, beta2 and beta3 adrenoceptors.	2005-02	15655528
Controlled drug release from gels using lipophilic interactions of charged substances with surfactants and polymers.	2002-04-01	16290522

Patents

Sample Use Guides

In Vivo Use Guide

For treatment of hypertension and angina pectoris the initial dose of TENORMIN is 50 mg given as one tablet. If an optimal response is not achieved, the dosage should be increased to TENORMIN 100 mg given as one tablet a day. In patients with definite or suspected acute myocardial infarction, treatment with TENORMIN I.V. Injection should be initiated as soon as possible after the patient's arrival in the hospital and after eligibility is established. Such treatment should be initiated in a coronary care or similar unit immediately after the patient's hemodynamic condition has stabilized. Treatment should begin with the intravenous administration of 5 mg TENORMIN over 5 minutes followed by another 5 mg intravenous injection 10 minutes later.

Route of Administration: Other

In Vitro Use Guide

Binding of alprenolol to beta adrenergic receptors was measured using [3H]CGP 12177 as a radioligand in the ranges of 0.71-3.14 nM, and whole CHO cells, expressing beta1, beta2 and beta3 adrenergic receptors. Alprenolol inhibits binding of log Kd of -7.95, -9.3 and -6.86 for beta1, 2 and 3 respectively.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 09:59:49 GMT 2025` Edited by `admin` on `Wed Apr 02 09:59:49 GMT 2025`
Record UNII	877K5MQ27W
Record Status	`Validated (UNII)`
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Name

Type

Language

1-(O-ALLYLPHENOXY)-3-(ISOPROPYLAMINO)-2-PROPANOL

Preferred Name

English

ALPRENOLOL

Official Name

English

ALPRENOLOL [MART.]

Common Name

English

ALPRENOLOL [MI]

Common Name

English

2-PROPANOL, 1-((1-METHYLETHYL)AMINO)-3-)2-(2-PROPENYL)PHENOXY)-

Common Name

English

Alprenolol [WHO-DD]

Common Name

English

NSC-759561

Code

English

alprenolol [INN]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QC07AA01