Oxprenolol

HCID 4631CAS 6452-71-7

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

oxprenolol6452-71-7CoretalOxprenololum519MXN9YZRDTXSID10438352-Propanol, 1-((1-methylethyl)amino)-3-(2-(2-propenyloxy)phenoxy)-2-Propanol, 1-[(1-methylethyl)amino]-3-[2-(2-propenyloxy)phenoxy]-{2-hydroxy-3-[2-(prop-2-en-1-yloxy)phenoxy]propyl}(propan-2-yl)amineoxprenololo(2-hydroxy-3-(2-(prop-2-en-1-yloxy)phenoxy)propyl)(propan-2-yl)amineTrasicor, Slow
Show more names
TevacorOxenalolAids001596Aids-001596Oxprenolol-d7oxprenolol USP/EP/BPCoretal (hydrochloride)1-(2-allyloxyphenoxy)-3-isopropylaminopropan-2-ol
RefChem:857811DTXCID9023835C07AA02229-257-9245-359-6dl-Oxprenolol(+-)-OxprenololOsprenololo [DCIT]

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

Experimental & physicochemical properties

LogP · 2 items

2.1

2.10

Solubility6.80e-01 g/L
Caco2 Permeability-4.68
Physical DescriptionSolid
Dissociation Constants9.57
Kovats Retention Index · 2 items

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

Safety & regulation

GHS classification

GHS Classification · 5 items

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

Regulatory Information2-Propanol, 1-(1-methylethyl)amino-3-2-(2-propenyloxy)phenoxy-: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryAllergic contact dermatitis reported in a pharmaceutical worker; [Kanerva, p. 1822] See Propranolol.
Hazard Classes and CategoriesAcute Tox. 3 (100%);Acute Tox. 3 (100%);Acute Tox. 3 (100%)

Toxicology

Adverse EffectsSkin Sensitizer - An agent that can induce an allergic reaction in the skin.

Regulatory information

Regulatory Information2-Propanol, 1-(1-methylethyl)amino-3-2-(2-propenyloxy)phenoxy-: Does not have an individual approval but may be used under an appropriate group standard

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 · 2 items

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 · 1 item

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 · 1 item

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.

Biological Half-Life1-2 hours
Metabolism/Metabolites · 2 items

Hepatic.

Oxoprenolol has known human metabolites that include Oxprenolol glucuronide.

MeSH Pharmacological Classification · 6 items

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 · 2 items

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

Use ClassificationPharmaceuticals
Applications · 3 items

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

Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
杭州摩库生物医药科技有限公司+86-057181025280; +8617767106207 · [email protected]
西安美科生物科技有限公司029-18710438009 18710438009 · [email protected]
湖北扬信医药科技有限公司15347293736 · [email protected]
武汉鹏胤药业有限公司13163333255 · [email protected]

Additional notes

DefinitionChEBI: 1-(propan-2-ylamino)-3-(2-prop-2-enoxyphenoxy)-2-propanol is an aromatic ether.

Related reactions

1 records

Linked notes

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