Alprenolol
Basic information
- CAS
13655-52-2- Standard SMILES
C=CCc1ccccc1OCC(O)CNC(C)C- InChIKey
PAZJSJFMUHDSTF-UHFFFAOYSA-N- Molecular formula
- C15H23NO2
- Average molar mass
- 249.35 g/mol
- Monoisotopic mass
- 249.17287898
Overview
Alprenolol is a secondary alcohol that is propan-2-ol substituted by a 2-allylphenoxy group at position 1 and an isopropylamino group at position 3. It is a beta-adrenergic antagonist used as a antihypertensive, anti-arrhythmia and a sympatholytic agent. It has a role as a beta-adrenergic antagonist, an antihypertensive agent, an anti-arrhythmia drug and a sympatholytic agent. It is a secondary alcohol and a secondary amino compound.
Names & identifiers
- Preferred name
- Alprenolol
- IUPAC
- 1-(propan-2-ylamino)-3-(2-prop-2-enylphenoxy)propan-2-ol
- English name
- Alprenolol
- Molecular formula
- C15H23NO2
- Molecular weight
- 249.35
Names & synonyms
alprenolol13655-52-2AlfeprolAlprenololum1-(o-Allylphenoxy)-3-(isopropylamino)-2-propanol1-(2-Allylphenoxy)-3-isopropylamino-2-propanol1-(propan-2-ylamino)-3-(2-prop-2-enylphenoxy)propan-2-olDTXSID00451272-Propanol, 1-[(1-methylethyl)amino]-3-[2-(2-propenyl)phenoxy]-877K5MQ27WNSC-759561DTXCID8025127
Show more names
1-Isopropylamino-3-(2-allyl)phenoxypropan-2-olAlpheprolALLPRENOLOLdl-Alprenolol(RS)-AlprenololAlprenolol USP/EP/BP(-)-Alprenolol hydrate D-tartrate3-(o-Allylphenoxy)-1-isopropylamino-2-propanol1-(2-Allylphenoxy)-3-(isopropylamino)-2-propanol
CHEBI:512112-Propanol, 1-((1-methylethyl)amino)-3-(2-(2-propenyl)phenoxy)-{2-hydroxy-3-[2-(prop-2-en-1-yl)phenoxy]propyl}(propan-2-yl)aminealprenololoAptinDurilesAptin DurilesAptin-Duriles(2-hydroxy-3-(2-(prop-2-en-1-yl)phenoxy)propyl)(propan-2-yl)amine
Database identifiers
Properties
Computed structural properties
- XLogP
- 3.1
- Topological polar surface area
- 41.5 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 8
- Heavy atoms
- 18
- Formal charge
- 0
- Complexity
- 231
Experimental & physicochemical properties
Chemical ClassesOther Uses -> Pharmaceuticals
LogP2.8
Solubility1.88e-01 g/L
Human DrugsPharmaceuticals
Melting Point
107-109 °C
107 - 109 °C
Physical DescriptionSolid
Dissociation Constants
9.51
9.6
Collision Cross Section
159.5 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]
163.63 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
158.6 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Other Safety InformationIMAP assessments - 2-Propanol, 1-[(1-methylethyl)amino]-3-[2-(2-propen-1-yl)phenoxy]-: Environment tier I assessment
Hazards SummaryAllergic contact dermatitis reported in pharmaceutical workers; [Kanerva, p. 1181-2]
Toxicology
Adverse EffectsSkin Sensitizer - An agent that can induce an allergic reaction in the skin.
Safety data
- ridadr
- 3249
- Toxicity
- mammal (species unspecified),LD50,intraperitoneal,102mg/kg (102mg/kg),Pharmaceutical Chemistry Journal Vol. 8, Pg. 137, 1974.
- risk_code
- 23/24/25-43
- hazard_code
- T
- safety_code
- 36/37/39-45
- hazard_class
- 6.1(b)
- packing_group
- III
Chemistry & industry
Pharmacology
ATC Code
C - Cardiovascular system
QC - Cardiovascular system
Protein Binding80-90%
Pharmacodynamics
Alprenolol is a non-selective beta-blocker used in the treatment of hypertension, edema, ventricular tachycardias, and atrial fibrillation. Alprenolol impairs AV node conduction and decreases sinus rate and may also increase plasma triglycerides and decrease HDL-cholesterol levels. Alprenolol is nonpolar and hydrophobic, with low to moderate lipid solubility. Alprenolol has little to no intrinsic sympathomimetic activity and, unlike some other beta-adrenergic blocking agents, alprenolol has little direct myocardial depressant activity and does not have an anesthetic-like membrane-stabilizing action.
Mechanism of Action
Alprenolol non-selectively blocks beta-1 adrenergic receptors mainly in the heart, inhibiting the effects of epinephrine and norepinephrine resulting in a decrease in heart rate and blood pressure. Also, with a more minor effect, by binding beta-2 receptors in the juxtaglomerular apparatus, alprenolol inhibits the production of renin, thereby inhibiting angiotensin II and aldosterone production and therefore inhibits the vasoconstriction and water retention due to angiotensin II and aldosterone, respectively.
Biological Half-Life2-3 hours
Metabolism/MetabolitesHepatic. One of the active metabolites, 4-OH-alprenolol, is an active beta-blocker.
MeSH Pharmacological Classification
Drugs that bind to but do not activate beta-adrenergic receptors thereby blocking the actions of beta-adrenergic agonists. Adrenergic beta-antagonists are used for treatment of hypertension, cardiac arrhythmias, angina pectoris, glaucoma, migraine headaches, and anxiety.
Agents used for the treatment or prevention of cardiac arrhythmias. They may affect the polarization-repolarization phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibers. Anti-arrhythmia agents are often classed into four main groups according to their mechanism of action: sodium channel blockade, beta-adrenergic blockade, repolarization prolongation, or calcium channel blockade.
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