Dexpropranolol
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Basic information
- CAS
5051-22-9- Standard SMILES
CC(C)NC[C@@H](O)COc1cccc2ccccc12- InChIKey
AQHHHDLHHXJYJD-CQSZACIVSA-N- Molecular formula
- C16H21NO2
- Average molar mass
- 259.34 g/mol
- Monoisotopic mass
- 259.15722891
Overview
(R)-(+)-propranolol is a propranolol.
Names & identifiers
- Preferred name
- Dexpropranolol
- IUPAC
- (2R)-1-naphthalen-1-yloxy-3-(propan-2-ylamino)propan-2-ol
- English name
- R(+)-PROPRANOLOL HCL
- Molecular formula
- C16H21NO2
- Molecular weight
- 259.34
Names & synonyms
DEXPROPRANOLOL5051-22-9(+)-PropranololD-Propranolol2R-PropranololR-(+)-PropranololDextropropranolol(R)-(+)-propranololDexpropranololumR (+)-PropanololDespropranoloPropranolol, (r)-
Show more names
(+)-2-propano(r)-2-propanod-(+)-propranololR(+)-PROPRANOLOL HCLR(+)-PROPRANOLOL HCL USP/EP/BP
(2R)-1-naphthalen-1-yloxy-3-(propan-2-ylamino)propan-2-ol(+)-1-Isopropylamino-3-(1-naphthyloxy)-2-propanolDTXSID3045304PG6KY07UD7CHEBI:8736DTXCID1025304(2R)-3-(naphthalen-1-yloxy)-1-(propan-2-ylamino)propan-2-olRefChem:585865
Database identifiers
- CAS
5051-22-9- PubChem CID
- 21138
- DTXSID
DTXSID3045304- ChEMBL
CHEMBL275742- ChEBI
CHEBI:8736- UNII
- PG6KY07UD7
- EC Number
- 225-749-2
- Nikkaji
- J8.801C
Properties
Computed structural propertiesFilling in
- XLogP
- 3
- Topological polar surface area
- 41.5 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 6
- Heavy atoms
- 19
- Formal charge
- 0
- Complexity
- 257
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Collision Cross Section160.31 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 96 °C · 96 °C
- Boiling point
- 434.9 · 434.9±30.0 °C(Predicted)
- Density
- 1.093 · 1.093±0.06 g/cm3(Predicted)
- storage temp.
- Store at RT
- pka
- 9.53 · pKa 9.53±0.01(H2O,t=25±0.5,I=0.15(KCl))(Approximate)
- FDA UNII
- 6 KY07UD7 · PG6KY07UD7
- ATC code
- 7 AA05 · C07AA05
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-(1-naphthalenyloxy)-, (R)-: Environment tier I assessment
Chemistry & industry
Pharmacology
Metabolism/MetabolitesDexpropranolol (propranolol) has known human metabolites that include 5-Hydroxypropranolol, N-Desisopropylpropranolol, and 4-Hydroxypropranolol.
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 used to cause dilation of the blood vessels.
Applications
HistoryScottish scientist James W. Black developed propranolol in the 1960s. It was the first beta-blocker effectively used in the treatment of coronary artery disease and hypertension.Propranolol was patented in 1962 and approved for medical use in 1964. It is on the World Health Organization's List of Essential Medicines. In 2023, it was the 69th most commonly prescribed medication in the United States, with more than 9 million prescriptions.
UsesPropranolol is used for treating hypertension, angina pectoris, supraventricular arrhythmia, ventricular tachycardia, migraines, hypertrophic subaortal stenosis, and pheochromocytosis. It is used following a myocardial infraction.
UsesPropranolol has been studied most carefully in experiments and in clinics. It is used for ventricular tachycardia, arrhythmia caused by digitalis drug overdose, or as a result of thyrotoxosis or excess catecholamine activity. Despite the fact that there are a number of β-adrenoblockers, propranolol is considered the first choice of drugs although other blockers of calcium blockers can be just as effective.
Related reactions
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Compound notes
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