Basic information
- CAS
56980-93-9- Standard SMILES
CCN(CC)C(=O)Nc1ccc(OCC(O)CNC(C)(C)C)c(C(C)=O)c1- InChIKey
JOATXPAWOHTVSZ-UHFFFAOYSA-N- Molecular formula
- C20H33N3O4
- Average molar mass
- 379.5 g/mol
- Monoisotopic mass
- 379.24710654
Overview
3-[3-acetyl-4-[3-(tert-butylamino)-2-hydroxypropoxy]phenyl]-1,1-diethylurea is an aromatic ketone.
Names & identifiers
- Preferred name
- Celiprolol
- IUPAC
- 3-[3-acetyl-4-[3-(tert-butylamino)-2-hydroxypropoxy]phenyl]-1,1-diethylurea
- English name
- Celiprolol
- Molecular formula
- C20H33N3O4
- Molecular weight
- 379.49
Names & synonyms
celiprolol56980-93-9CeliprololumCeliprolol PCHUL/1677RHC-5320AACER002 FREE BASEDRB57K47QCACER-002 FREE BASEDTXSID3020259ST1396N'-(3-Acetyl-4-(3-((1,1-dimethylethyl)amino)-2-hydroxypropoxy)phenyl)-N,N-diethylurea
Show more names
EdsivoSelectol-diethyl-celiptololdl-CeliprololCeliprolol Base(R,S)-CeliprololRacemic CeliprololCeliprolol USP/EP/BP
Urea, N'-(3-acetyl-4-(3-((1,1-dimethylethyl)amino)-2-hydroxypropoxy)phenyl)-N,N-diethyl-1-{3-acetyl-4-[3-(tert-butylamino)-2-hydroxypropoxy]phenyl}-3,3-diethylureaREV 5320A1-(3-acetyl-4-(3-(tert-butylamino)-2-hydroxypropoxy)phenyl)-3,3-diethylureaRefChem:124293DTXCID90259REV5320AC07AB08
Database identifiers
- CAS
56980-93-9- PubChem CID
- 2663
- DTXSID
DTXSID3020259- ChEMBL
Properties
Computed structural properties
- XLogP
- 1.9
- Topological polar surface area
- 90.9 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 10
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 474
Experimental & physicochemical properties
DrugsPharmaceuticals
LogP1.92
Human DrugsPharmaceuticals
Melting Point120-122
Dissociation Constants9.66
Physicochemical properties
- Melting point
- 110 · 110-112°
- Boiling point
- 586.5 · 586.5±50.0 °C(Predicted)
- Density
- 1.114 · 1.114±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C Freezer, Under Inert Atmosphere
- solubility
- Chloroform (slightly), Methanol (Slightly)
- form
- Solid
- pka
- 9.7 · pKa ~9.7 (Uncertain)
- color
- Yellow
- Water Solubility
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
H412 (100%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]
P273, 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 CategoriesAquatic Chronic 3 (100%)
Toxicology
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Celiprolol
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
Chemistry & industry
Pharmacology
ATC Code
C07AB08
C - Cardiovascular system
QC - Cardiovascular system
Protein Binding25-30%.
Mechanism of Action
Celiprolol is a vasoactive beta-1 selective adrenoceptor antagonist with partial beta-2 agonist activity. The beta-2 agonist activity is thought to account for its mild vasodilating properties. It lowers blood pressure in hypertensive patients at rest and on exercise. The effects on heart rate and cardiac output are dependent on the pre-existing background level of sympathetic tone. Under conditions of stress such as exercise, celiprolol attenuates chronotropic and inotropic responses to sympathetic stimulation. However, at rest minimal impairment of cardiac function is seen.
Biological Half-Life5 hours
Metabolism/MetabolitesA 14C labelled dose was completely recovered within 48 hours. The first-pass effect in the liver is insignificant. Celiprolol is metabolized to a minor extent (1-3%).
MeSH Pharmacological Classification
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 mimic the effects of stimulating postganglionic adrenergic sympathetic nerves. Included here are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters.
Related reactions
0 records
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Compound notes
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