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Details

Stereochemistry RACEMIC
Molecular Formula C20H33N3O4
Molecular Weight 379.4945
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CELIPROLOL

SMILES

CCN(CC)C(=Nc1ccc(c(c1)C(=O)C)OCC(CNC(C)(C)C)O)O

InChI

InChIKey=JOATXPAWOHTVSZ-UHFFFAOYSA-N
InChI=1S/C20H33N3O4/c1-7-23(8-2)19(26)22-15-9-10-18(17(11-15)14(3)24)27-13-16(25)12-21-20(4,5)6/h9-11,16,21,25H,7-8,12-13H2,1-6H3,(H,22,26)

HIDE SMILES / InChI

Molecular Formula C20H33N3O4
Molecular Weight 379.4945
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment:: description was created based on several sources, including https://www.drugs.com/international/celiprolol.html | https://www.ncbi.nlm.nih.gov/pubmed/20825986 | http://onlinelibrary.wiley.com/doi/10.1111/j.1527-3466.1984.tb00456.x/abstract

Celiprolol is beta blocker, used to treat high blood pressure. Celiprolol is a selective β1 receptor antagonist, β2 receptor partial agonist. Celiprolol is not approved by the FDA, but is available worldwide under brand names Cardem, Selectol, Celipres, Celipro, Celol, Cordiax, Dilanorm. It is used to treat mild to moderate hypertension and angina prectoris. In 2010 celiprolol has demonstrated positive results in the prevention of vascular complications of Ehlers-Danlos syndrome. Celiprolol has fewer CNS-related side effects than other beta blockers presumably because of limited penetration through blood-brain barrier because of its solubility.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.35 nM [Ki]
2.8 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Unknown

Approved Use

Unknown
Palliative
SELECTOL

Approved Use

Celiprolol is a vasodilating beta-1 selective adrenoceptor antagonist with partial beta-2 agonist activity. The beta-2 agonist activity is thought to account for its mild vasodilating and positive inotropic properties. It lowers the blood pressure in hypertensive patients at rest and exercise. The effects on heart rate and cardiac output are dependent on the pre-existing background level of sympathetic tone.
Primary
SELECTOL

Approved Use

Celiprolol is a vasodilating beta-1 selective adrenoceptor antagonist with partial beta-2 agonist activity. The beta-2 agonist activity is thought to account for its mild vasodilating and positive inotropic properties. It lowers the blood pressure in hypertensive patients at rest and exercise. The effects on heart rate and cardiac output are dependent on the pre-existing background level of sympathetic tone.
Palliative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Anti-ischemic effects of celiprolol in patients with exercise-induced angina pectoris.
1989 Oct
[Pharmacological studies of celiprolol: III. Effects of celiprolol on the cardiovascular system and renal function, and its antiarrhythmic effects].
1990 Apr
[Pharmacological studies of celiprolol: I. Beta-blocking effect, intrinsic sympathomimetic activity, vasodilating and hypotensive effects].
1990 Apr
[Efficacy of beta-selective blocker with vasodilatating features celiprolol in patients with mild and moderate hypertension].
2003
Improvement of peak shape and separation performance of beta-blockers in conventional reversed-phase columns using solvent modifiers.
2003 Aug
Celiprolol activates eNOS through the PI3K-Akt pathway and inhibits VCAM-1 Via NF-kappaB induced by oxidative stress.
2003 Nov
Simultaneous determination of thirteen beta-blockers and one metabolite by gradient high-performance liquid chromatography with photodiode-array UV detection.
2004 Apr 20
The impact of third-generation beta-blocker antihypertensive treatment on endothelial function and the prothrombotic state: effects of smoking.
2004 Jul
Impact of excipients on the absorption of P-glycoprotein substrates in vitro and in vivo.
2004 Jun 18
Orange juice substantially reduces the bioavailability of the beta-adrenergic-blocking agent celiprolol.
2004 Mar
Screening for library-assisted identification and fully validated quantification of 22 beta-blockers in blood plasma by liquid chromatography-mass spectrometry with atmospheric pressure chemical ionization.
2004 Nov 26
Enantiomer separations on a vancomycin stationary phase and retention mechanism of pressurized capillary electrochromatography.
2004 Sep
Screening of domperidone in wastewater by high performance liquid chromatography and solid phase extraction methods.
2006 Jan 15
Beta-blockers use in patients with chronic obstructive pulmonary disease and concomitant cardiovascular conditions.
2007
Celiprolol, a selective beta1-blocker, reduces the infarct size through production of nitric oxide in a rabbit model of myocardial infarction.
2007 Apr
Separation of beta-receptor blockers and analogs by capillary liquid chromatography (CLC) and pressurized capillary electrochromatography (pCEC) using a vancomycin chiral stationary phase column.
2007 Aug
Celiprolol reduces the intimal thickening of autogenous vein grafts via an enhancement of nitric oxide function through an inhibition of superoxide production.
2007 Jul
Ehlers-Danlos syndrome type IV.
2007 Jul 19
Metabolic syndrome: treatment of hypertensive patients.
2007 Jul-Aug
[The inhibitory effect of pluronic on P-glycoprotein drug pump].
2007 Sep
Beneficial effect of combination therapy with antihypertensive drugs in patients with hypertension.
2007 Spring
Effects of the vasodilating beta-blocker nebivolol on smoking-induced endothelial dysfunction in young healthy volunteers.
2008
Carvedilol in hypertension treatment.
2008
Hesperidin in orange juice reduces the absorption of celiprolol in rats.
2008 Apr
Immune defects in Alzheimer's disease: new medications development.
2008 Dec 3
Ozonation of reverse osmosis concentrate: kinetics and efficiency of beta blocker oxidation.
2008 Jun
Simultaneous separation of eight beta-adrenergic drugs using titanium dioxide nanoparticles as additive in capillary electrophoresis.
2008 Jun
Natural and synthetic polymers as inhibitors of drug efflux pumps.
2008 Mar
Effect of pluronic F68 block copolymer on P-glycoprotein transport and CYP3A4 metabolism.
2008 May 22
Direct determination of celiprolol in human urine using on-line coupled ITP-CZE method with fiber-based DAD.
2008 Nov
American College of Endocrinology Pre-Diabetes Consensus Conference: part two.
2008 Nov
Progress in the development of early diagnosis and a drug with unique pharmacology to improve cancer therapy.
2008 Oct 13
Effects of the antioxidative beta-blocker celiprolol on endothelial progenitor cells in hypertensive rats.
2008 Sep
Chiral separation of beta-adrenergic blockers on CelluCoat column by HPLC.
2009 Apr 30
Modification of pharmacokinetics of norfloxacin following oral administration of curcumin in rabbits.
2009 Dec
Analysis of drug interactions involving fruit beverages and organic anion-transporting polypeptides.
2009 Dec
Acute pulmonary edema due to stress cardiomyopathy in a patient with aortic stenosis: a case report.
2009 Dec 2
The role of transporters in the pharmacokinetics of orally administered drugs.
2009 Sep
Uptake/efflux transport of tramadol enantiomers and O-desmethyl-tramadol: focus on P-glycoprotein.
2009 Sep
[Endothelial dysfunction: role of vasodilating betablockers in hypertension and chronic heart failure].
2010 Apr
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010 Dec
Fate of beta blockers in aquatic-sediment systems: sorption and biotransformation.
2010 Feb 1
Chiral separations of some beta-adrenergic agonists and antagonists on AmyCoat column by HPLC.
2010 Jan
Highly sensitive transient isotachophoresis sample stacking coupling with capillary electrophoresis-amperometric detection for analysis of doping substances.
2010 Jun 15
Evaluation of left atrial volumes using multidetector computed tomography: comparison with echocardiography.
2010 May-Jun
Human health risk assessment of pharmaceuticals in water: issues and challenges ahead.
2010 Nov
Fruit juice inhibition of uptake transport: a new type of food-drug interaction.
2010 Nov
Positive influence of AT(1) receptor antagonism upon the impaired celiprolol-induced vasodilatation in aorta from spontaneously hypertensive rats.
2010 Oct 10
Effect of celiprolol on prevention of cardiovascular events in vascular Ehlers-Danlos syndrome: a prospective randomised, open, blinded-endpoints trial.
2010 Oct 30
Celiprolol therapy for vascular Ehlers-Danlos syndrome.
2010 Oct 30
Patents

Patents

Sample Use Guides

The route of administration is oral. The usual dose in adults is 200 mg once daily in the morning. In the case of an inadequate response the dose may be increased to 400 mg daily. It is important to take Selectol one hour before or two hours after food with a glass of water. If the treatment is to be discontinued, reduce the dosage gradually over a period of 1-2 weeks. In hypertensive patients, additional treatment with other anti-hypertensive agents according to clinical guidelines is possible, in particular with diuretics. When a combination is initiated an increased monitoring of the blood pressure is recommended.
Route of Administration: Oral
In Vitro Use Guide
In order to quantify the affinity constants and potential partial agonist properties of beta-adrenoceptor antagonists at beta1-and beta2-adrenoceptors, competitive experiments for binding of [125I]-iodocyanopindolol (specific activity 2000 Cimmol-1) to beta-adrenoceptors were performed. Specific binding was defined as the difference in binding in the absence and in the presence of propranolol (3 umol^-1). Celiprolol at increasing concentrations (0.0001-100 umol-1) was used for binding experiments with lung, and with myocardial tissue. The experiments were performed in the presence and absence of Gpp(NH)p to evaluate agonist properties of the beta-adrenoceptor antagonists by changing the agonist affinity state of the binding site in the presence of the metabolically stable guanine nucleotide.
Substance Class Chemical
Created
by admin
on Sat Jun 26 10:17:05 UTC 2021
Edited
by admin
on Sat Jun 26 10:17:05 UTC 2021
Record UNII
DRB57K47QC
Record Status Validated (UNII)
Record Version
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Name Type Language
CELIPROLOL
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
CELIPROLOL [INN]
Common Name English
CELIPROLOL [WHO-DD]
Common Name English
UREA, N'-(3-ACETYL-4-(3-((1,1-DIMETHYLETHYL)AMINO)-2-HYDROXYPROPOXY)PHENYL)-N,N-DIETHYL-
Systematic Name English
CELIPROLOL PCH
Brand Name English
CELIPROLOL [MI]
Common Name English
CELIPROLOL [VANDF]
Common Name English
3-(3-ACETYL-4-(3-(TERT-BUTYLAMINO)-2-HYDROXYPROPOXY)PHENYL)-1,1-DIETHYLUREA
Systematic Name English
Classification Tree Code System Code
WHO-VATC QC07AB08
Created by admin on Sat Jun 26 10:17:06 UTC 2021 , Edited by admin on Sat Jun 26 10:17:06 UTC 2021
FDA ORPHAN DRUG 456714
Created by admin on Sat Jun 26 10:17:06 UTC 2021 , Edited by admin on Sat Jun 26 10:17:06 UTC 2021
WHO-ATC C07AB08
Created by admin on Sat Jun 26 10:17:06 UTC 2021 , Edited by admin on Sat Jun 26 10:17:06 UTC 2021
NCI_THESAURUS C29576
Created by admin on Sat Jun 26 10:17:06 UTC 2021 , Edited by admin on Sat Jun 26 10:17:06 UTC 2021
Code System Code Type Description
MERCK INDEX
M3232
Created by admin on Sat Jun 26 10:17:06 UTC 2021 , Edited by admin on Sat Jun 26 10:17:06 UTC 2021
PRIMARY Merck Index
INN
3979
Created by admin on Sat Jun 26 10:17:06 UTC 2021 , Edited by admin on Sat Jun 26 10:17:06 UTC 2021
PRIMARY
PUBCHEM
2663
Created by admin on Sat Jun 26 10:17:06 UTC 2021 , Edited by admin on Sat Jun 26 10:17:06 UTC 2021
PRIMARY
CAS
56980-93-9
Created by admin on Sat Jun 26 10:17:06 UTC 2021 , Edited by admin on Sat Jun 26 10:17:06 UTC 2021
PRIMARY
EVMPD
SUB07436MIG
Created by admin on Sat Jun 26 10:17:06 UTC 2021 , Edited by admin on Sat Jun 26 10:17:06 UTC 2021
PRIMARY
MESH
D017272
Created by admin on Sat Jun 26 10:17:06 UTC 2021 , Edited by admin on Sat Jun 26 10:17:06 UTC 2021
PRIMARY
DRUG BANK
DB04846
Created by admin on Sat Jun 26 10:17:06 UTC 2021 , Edited by admin on Sat Jun 26 10:17:06 UTC 2021
PRIMARY
EPA CompTox
56980-93-9
Created by admin on Sat Jun 26 10:17:06 UTC 2021 , Edited by admin on Sat Jun 26 10:17:06 UTC 2021
PRIMARY
ChEMBL
CHEMBL27810
Created by admin on Sat Jun 26 10:17:06 UTC 2021 , Edited by admin on Sat Jun 26 10:17:06 UTC 2021
PRIMARY
FDA UNII
DRB57K47QC
Created by admin on Sat Jun 26 10:17:06 UTC 2021 , Edited by admin on Sat Jun 26 10:17:06 UTC 2021
PRIMARY
WIKIPEDIA
Celiprolol
Created by admin on Sat Jun 26 10:17:06 UTC 2021 , Edited by admin on Sat Jun 26 10:17:06 UTC 2021
PRIMARY
DRUG CENTRAL
569
Created by admin on Sat Jun 26 10:17:06 UTC 2021 , Edited by admin on Sat Jun 26 10:17:06 UTC 2021
PRIMARY
ECHA (EC/EINECS)
260-497-7
Created by admin on Sat Jun 26 10:17:06 UTC 2021 , Edited by admin on Sat Jun 26 10:17:06 UTC 2021
PRIMARY
NCI_THESAURUS
C79558
Created by admin on Sat Jun 26 10:17:06 UTC 2021 , Edited by admin on Sat Jun 26 10:17:06 UTC 2021
PRIMARY
RXCUI
20498
Created by admin on Sat Jun 26 10:17:06 UTC 2021 , Edited by admin on Sat Jun 26 10:17:06 UTC 2021
PRIMARY RxNorm
Related Record Type Details
TRANSPORTER -> SUBSTRATE
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY