Basic information
- CAS
14556-46-8- Standard SMILES
Cc1ccc(Cl)c(OCC(O)CNC(C)(C)C)c1- InChIKey
HQIRNZOQPUAHHV-UHFFFAOYSA-N- Molecular formula
- C14H22ClNO2
- Average molar mass
- 271.78 g/mol
- Monoisotopic mass
- 271.1339066
Overview
Bupranolol is an aromatic ether.
Names & identifiers
- Preferred name
- Bupranolol
- IUPAC
- 1-(tert-butylamino)-3-(2-chloro-5-methylphenoxy)propan-2-ol
- English name
- Bupranolol
- Molecular formula
- C14H22ClNO2
- Molecular weight
- 271.78
Names & synonyms
BUPRANOLOL14556-46-8OphtoreninBupranolBupranololumKL 255DTXSID7022704BRN 2272923858YGI5PITKL-255 FREE BASEB 1312 FREE BASEB-1312 FREE BASE
Show more names
(±)-BupranololKL 255OphtoreninBupranolol, 10 mM in DMSOBupranolol, beta adrenoceptor antagonistB 1312KL 255OPHTORENIN
DTXCID202704tert-butyl[3-(2-chloro-5-methylphenoxy)-2-hydroxypropyl]amineKL-255 (AS HYDROCHLORIDE)KL-255 [AS HYDROCHLORIDE]bupranololotert-butyl(3-(2-chloro-5-methylphenoxy)-2-hydroxypropyl)amine(+-)-Bupranolol2-Propanol, 1-(2-chloro-5-methylphenoxy)-3-((1,1-dimethylethyl)amino)-, hydrochloride, (+-)-
Database identifiers
- CAS
14556-46-8、23284-25-5- PubChem CID
- 2475
- DTXSID
DTXSID7022704- ChEMBL
CHEMBL305380- ChEBI
CHEBI:135123- UNII
- 858YGI5PIT
- EC Number
- 977-806-2
Properties
Computed structural properties
- XLogP
- 2.8
- Topological polar surface area
- 41.5 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 6
- Heavy atoms
- 18
- Formal charge
- 0
- Complexity
- 242
Experimental & physicochemical properties
LogP2.8
Human DrugsPharmaceuticals
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 71 · 71-74°C
- Boiling point
- 396.3 · 396.3±42.0 °C(Predicted)
- Density
- 1.098 · 1.098±0.06 g/cm3(Predicted)
- storage temp.
- Hygroscopic, Refrigerator, Under Inert Atmosphere
- solubility
- DMSO (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- 13.82 · 13.82±0.20(Predicted)
- color
- White to Off-White
- FDA UNII
- 858 YGI5PIT · 858YGI5PIT
- ATC code
- 7 AA19 · C07AA19
- Symbol(GHS)
- 7 · GHS07
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+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
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501
Chemistry & industry
Pharmacology
ATC Code
C - Cardiovascular system
QC - Cardiovascular system
Protein Binding76%
PharmacodynamicsBupranolol is a competitive, nonselective beta-blocker similar to propanolol without intrinsic sympathomimetic activity.
Mechanism of Action
Bupranolol competes with sympathomimetic neurotransmitters such as catecholamines for binding at beta(1)-adrenergic receptors in the heart, inhibiting sympathetic stimulation. This results in a reduction in resting heart rate, cardiac output, systolic and diastolic blood pressure, and reflex orthostatic hypotension.
Biological Half-Life2-4 hours
Metabolism/MetabolitesOver 90% undergoes first-pass metabolism. The main metabolite is carboxybupranolol, 4-chloro-3-[3-(1,1-dimethylethylamino)-2-hydroxy-propyloxy]benzoic acid, of which 88% are eliminated renally within 24 hours.
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.
Related reactions
1 records
Compound notes
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