Details
| Stereochemistry | EPIMERIC |
| Molecular Formula | C15H23NO2.C4H6O6 |
| Molecular Weight | 399.4355 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O[C@H]([C@@H](O)C(O)=O)C(O)=O.CC(C)NCC(O)COC1=CC=CC=C1CC=C
InChI
InChIKey=MADUQKMQKQDWJH-LREBCSMRSA-N
InChI=1S/C15H23NO2.C4H6O6/c1-4-7-13-8-5-6-9-15(13)18-11-14(17)10-16-12(2)3;5-1(3(7)8)2(6)4(9)10/h4-6,8-9,12,14,16-17H,1,7,10-11H2,2-3H3;1-2,5-6H,(H,7,8)(H,9,10)/t;1-,2-/m.1/s1
| 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 | ( + / - ) |
| Molecular Formula | C4H6O6 |
| Molecular Weight | 150.0868 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL273 |
6.93 null [pKi] | ||
Target ID: CHEMBL213 |
|||
Target ID: CHEMBL210 |
|||
Target ID: CHEMBL246 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | TENORMIN Approved UseTENORMIN is indicated in the management of hypertension. It may be used alone or concomitantly with other antihypertensive agents, particularly with a thiazide-type diuretic |
|||
| Primary | TENORMIN Approved UseTENORMIN is indicated for the long-term management of patients with angina pectoris |
|||
| Primary | TENORMIN Approved UseTENORMIN 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. |
Cmax
| 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 |
T1/2
| 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 |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| inconclusive [IC50 43.6486 uM] | ||||
| no [IC50 >133 uM] | ||||
| no [IC50 >133 uM] | ||||
| no [IC50 >133 uM] | ||||
| no [IC50 >133 uM] | ||||
| no [IC50 >50 uM] | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| yes [IC50 12.3018 uM] | ||||
| yes [IC50 5.495 uM] | ||||
| yes [Inhibition 10 uM] | ||||
| yes [Inhibition 10 uM] |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Page: 209 | 210 |
no |
Tox targets
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| Physicochemical interactions between drugs and superdisintegrants. | 2008-12 |
|
| Effects of a strongly adsorbed additive on process performance in chiral preparative chromatography. | 2008-11-28 |
|
| Putrescine modulation of acute activation of the beta-adrenergic system in the left atrium of rat. | 2008-11-19 |
|
| Beta-blockers alprenolol and carvedilol stimulate beta-arrestin-mediated EGFR transactivation. | 2008-09-23 |
|
| Enantioselective determination of alprenolol in human plasma by liquid chromatography with tandem mass spectrometry using cellobiohydrolase chiral stationary phases. | 2008-09-01 |
|
| Simulation-based cheminformatic analysis of organelle-targeted molecules: lysosomotropic monobasic amines. | 2008-09 |
|
| Effects of alcohols on CE enantioseparation of basic drugs with native gamma-CD as chiral selector. | 2008-08 |
|
| Enantiomeric separation by using nano-liquid chromatography with on-column focusing. | 2008-08 |
|
| 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 |
|
| Role of chemical structure in stereoselective recognition of beta-blockers by cyclodextrins in capillary zone electrophoresis. | 2008-04-24 |
|
| Noradrenergic modulation in the olfactory bulb influences spontaneous and reward-motivated discrimination, but not the formation of habituation memory. | 2008-03 |
|
| A unique mechanism of beta-blocker action: carvedilol stimulates beta-arrestin signaling. | 2007-10-16 |
|
| Detection of g protein coupled receptor mediated adenylyl cyclase activity by capillary electrophoresis using fluorescently labeled ATP. | 2007-10-01 |
|
| 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 |
|
| Neuropeptide Y and glucocorticoid secretion from guinea pig adrenal gland: an in vivo and in vitro study. | 2007-09 |
|
| Cutaneous vasculitis induced by carvedilol. | 2007-08 |
|
| Multiple GPCR conformations and signalling pathways: implications for antagonist affinity estimates. | 2007-08 |
|
| The role of Gi proteins in reduced vasorelaxation response to beta-adrenoceptor agonists in rat aorta during maturation. | 2007-06-14 |
|
| Separation of basic compounds of pharmaceutical interest by using nano-liquid chromatography coupled with mass spectrometry. | 2007-05-25 |
|
| Medial prefrontal cortical alpha1 adrenoreceptor modulation of the nucleus accumbens dopamine response to stress in Long-Evans rats. | 2007-04 |
|
| Evidence for a paracrine role of endogenous adrenomedullary galanin in the regulation of glucocorticoid secretion in the rat adrenal gland. | 2007-03 |
|
| Bioluminescence resonance energy transfer as a screening assay: Focus on partial and inverse agonism. | 2007-02 |
|
| Pharmacologic characterization of the cloned human trace amine-associated receptor1 (TAAR1) and evidence for species differences with the rat TAAR1. | 2007-01 |
|
| Abstracts of papers presented at the 2007 pittsburgh conference. | 2007 |
|
| Carvedilol in the treatment of chronic heart failure: lessons from the Carvedilol Or Metoprolol European Trial. | 2007 |
|
| High-speed gas chromatography in doping control: fast-GC and fast-GC/MS determination of beta-adrenoceptor ligands and diuretics. | 2006-12 |
|
| Erythrocyte G protein as a novel target for malarial chemotherapy. | 2006-12 |
|
| Expression of beta-adrenergic receptor up-regulation is mediated by two different processes. | 2006-09-27 |
|
| Polymer-coated hollow fiber microextraction combined with on-column stacking in capillary electrophoresis. | 2006-09-22 |
|
| Effects of antihypertensive medication on left ventricular function during electroconvulsive therapy: study with transthoracic echocardiography. | 2006-09 |
|
| Coupling ligand structure to specific conformational switches in the beta2-adrenoceptor. | 2006-08 |
|
| Computational approaches for modeling human intestinal absorption and permeability. | 2006-07 |
|
| Ionic liquids versus triethylamine as mobile phase additives in the analysis of beta-blockers. | 2006-06-30 |
|
| Role of chemical structure in stereoselective recognition of beta-blockers and H1-antihistamines by human serum transferrin in capillary zone electrophoresis. | 2006-04 |
|
| 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 |
|
| Catanionic mixtures involving a drug: a rather general concept that can be utilized for prolonged drug release from gels. | 2006-04 |
|
| Analytical characterization of chiral drug-protein interactions: comparison between the optical biosensor (surface plasmon resonance) assay and the HPLC perturbation method. | 2006-03-01 |
|
| UPLC/MS for the identification of beta-blockers. | 2006-02-24 |
|
| Investigation of chiral recognition mechanism on chicken alpha(1)-acid glycoprotein using separation system. | 2006-02-17 |
|
| 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 |
|
| Putting theory into practice: James Black, receptor theory and the development of the beta-blockers at ICI, 1958-1978. | 2006-01 |
|
| Evidence for a secondary state of the human beta3-adrenoceptor. | 2005-12 |
|
| Multivariate optimization approach for chiral resolution of drugs using human serum albumin in affinity electrokinetic chromatography-partial filling technique. | 2005-11 |
|
| Insights into cyclodextrin interactions during sample stacking using capillary isotachophoresis with on-line microcoil NMR detection. | 2005-09 |
|
| Low-affinity state beta1-adrenoceptor-induced vasodilation in SHR. | 2005-08 |
|
| Use of vancomycin chiral stationary phase for the enantiomeric resolution of basic and acidic compounds by nano-liquid chromatography. | 2005-07-15 |
|
| Drug molecules as probes for studying the compatibility between gels and mucous tissue with dielectric spectroscopy. | 2005-05 |
|
| Effects of dexamethasone and colostrum feeding on mRNA levels and binding capacities of beta-adrenergic receptors in the liver of neonatal calves. | 2005-04 |
|
| The selectivity of beta-adrenoceptor antagonists at the human beta1, beta2 and beta3 adrenoceptors. | 2005-02 |
|
| Controlled drug release from gels using lipophilic interactions of charged substances with surfactants and polymers. | 2002-04-01 |
Patents
Sample Use Guides
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
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
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admin
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Edited
Mon Mar 31 22:48:58 GMT 2025
by
admin
on
Mon Mar 31 22:48:58 GMT 2025
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| Record UNII |
S1AJV61HCH
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| Record Status |
Validated (UNII)
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| Record Version |
|
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Common Name | English | ||
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Preferred Name | English |
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S1AJV61HCH
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91810505
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21378-88-1
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