Basic information
- Standard SMILES
C=CCOc1ccccc1OCC(O)CNC(C)C- InChIKey
CEMAWMOMDPGJMB-UHFFFAOYSA-N- Molecular formula
- C15H23NO3
- Average molar mass
- 265.35 g/mol
- Monoisotopic mass
- 265.1677936
Names & identifiers
- Preferred name
- Oxprenolol
- IUPAC
- 1-(propan-2-ylamino)-3-(2-prop-2-enoxyphenoxy)propan-2-ol
- English name
- oxprenolol
- Molecular formula
- C15H23NO3
- Molecular weight
- 265.35
Names & synonyms
Show more names
Database identifiers
- CAS
6452-71-7- PubChem CID
- 4631
- DTXSID
DTXSID1043835- ChEMBL
CHEMBL546- ChEBI
CHEBI:91704- UNII
- 519MXN9YZR
- EC Number
- 229-257-9
- Nikkaji
- J318.375K、J8.410G
Properties
Computed structural properties
- XLogP
- 2.1
- Topological polar surface area
- 50.7 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 9
- Heavy atoms
- 19
- Formal charge
- 0
- Complexity
- 246
Experimental & physicochemical properties
LogP
2.1
2.10
Kovats Retention Index
1927;1925;1910;1870
1904.6;1917.6;1918.7
Physicochemical properties
- Melting point
- 78 · 78-80°
- Boiling point
- 408.57 °C · 408.57°C (rough estimate)
- Density
- 1.0479 · 1.0479 (rough estimate)
- refractive index
- 1.5 · 1.5000 (estimate)
- solubility
- Dichloromethane (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- 13.89 · 13.89±0.20(Predicted)
- color
- White to Off-White
- Stability
- Stable under recommended storage conditions., Stable Under Recommended Storage C
- FDA UNII
- 519 MXN9YZR · 519MXN9YZR
- Symbol(GHS)
- 6 · GHS06
- Signal word
- Danger
- Hazard statements
- 331 · H331-H311-H301
- Precautionary statements
- 280 · P280-P302+P352-P312-P322-P361-P363-P405-P501-P261-P271-P304+P340-P311-P321-P403+P233-P405-P501-P264-P270-P301+P310-P321-P330-P405-P501
Safety & regulation
GHS classification
GHS Classification
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral];H311 (100%): Toxic in contact with skin [Danger Acute toxicity, dermal];H331 (100%): Toxic if inhaled [Danger Acute toxicity, inhalation]
P261, P262, P264, P270, P271, P280, P301+P316, P302+P352, P304+P340, P316, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Toxicology
Regulatory information
Safety data
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- Hazard statements
- H331-H311-H301
- Precautionary statements
- P280-P302+P352-P312-P322-P361-P363-P405-P501-P261-P271-P304+P340-P311-P321-P403+P233-P405-P501-P264-P270-P301+P310-P321-P330-P405-P501
Chemistry & industry
Pharmacology
ATC Code
C - Cardiovascular system;C07 - Beta blocking agents;C07A - Beta blocking agents;C07AA - Beta blocking agents, non-selective;C07AA02 - Oxprenolol
QC - Cardiovascular system;QC07 - Beta blocking agents;QC07A - Beta blocking agents;QC07AA - Beta blocking agents, non-selective;QC07AA02 - Oxprenolol
Pharmacodynamics
Oxprenolol is a non-selective beta blocker with some intrinsic sympathomimetic activity. Oxprenolol is a lipophilic molecule and hence, it is able to cross the blood-brain barrier. As such, it is associated with a higher incidence of CNS-related side effects than hydrophilic ligands such as atenolol, sotalol and nadolol. Oxprenolol is an potent beta-blocker and should not be administered to asthmatics because it can cause irreversible airway failure and inflammation.
Mechanism of Action
Like other beta-adrenergic antagonists, oxprenolol competes with adrenergic neurotransmitters such as catecholamines for binding at sympathetic receptor sites. Like propranolol and timolol, oxprenolol binds at beta(1)-adrenergic receptors in the heart and vascular smooth muscle, inhibiting the effects of the catecholamines epinephrine and norepinephrine and decreasing heart rate, cardiac output, and systolic and diastolic blood pressure. It also blocks beta-2 adrenergic receptors located in bronchiole smooth muscle, causing vasoconstriction. By binding beta-2 receptors in the juxtaglomerular apparatus, oxprenolol inhibits the production of renin, thereby inhibiting angiotensin II and aldosterone production. Oxprenolol therefore inhibits the vasoconstriction and water retention due to angiotensin II and aldosterone, respectively.
Metabolism/Metabolites
Hepatic.
Oxoprenolol has known human metabolites that include Oxprenolol glucuronide.
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.
Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS.
Drugs that inhibit the actions of the sympathetic nervous system by any mechanism. The most common of these are the ADRENERGIC ANTAGONISTS and drugs that deplete norepinephrine or reduce the release of transmitters from adrenergic postganglionic terminals (see ADRENERGIC AGENTS). Drugs that act in the central nervous system to reduce sympathetic activity (e.g., centrally acting alpha-2 adrenergic agonists, see ADRENERGIC ALPHA-AGONISTS) are included here.
Agents that alleviate ANXIETY, tension, and ANXIETY DISORDERS, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions. ADRENERGIC BETA-ANTAGONISTS are commonly used in the symptomatic treatment of anxiety but are not included here.
Drugs used to cause dilation of the blood vessels.
Uses & manufacturing
Uses
Used as a beta-blocking agent; [Kanerva, p. 1822]
Use (kg; approx.) in Germany (2009): >50;Use (kg) in France (2004): 377;Consumption (g per capita; approx.) in Germany (2009): 0.000611;Consumption (g per capita) in France (2004): 0.00624;Calculated removal (%): 46.8
Applications
DescriptionOxprenolol induced contact dermatitis in a worker at a pharmaceutical plant, in the division for drug synthesis. Epichlorhydrin was also used for the production of both propranolol and oxprenolol.
UsesOxprenolol is a free base of Oxprenolol Hydrochloride(O870500) which is a β-Adrenergic blocker. Antihypertensive, antianginal, antiarrhythmic.
UsesVasodilator(coronary).
Upstream & downstream products
Upstream raw materials
Suppliers12 total
Additional notes
DefinitionChEBI: 1-(propan-2-ylamino)-3-(2-prop-2-enoxyphenoxy)-2-propanol is an aromatic ether.
Related reactions
Linked notes
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