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Details

Stereochemistry RACEMIC
Molecular Formula C20H33N3O4.ClH
Molecular Weight 415.955
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CELIPROLOL HYDROCHLORIDE

SMILES

Cl.CCN(CC)C(=O)NC1=CC(C(C)=O)=C(OCC(O)CNC(C)(C)C)C=C1

InChI

InChIKey=VKJHTUVLJYWAEY-UHFFFAOYSA-N
InChI=1S/C20H33N3O4.ClH/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);1H

HIDE SMILES / InChI

Molecular Formula C20H33N3O4
Molecular Weight 379.4937
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Plasma analysis of celiprolol by HPTLC: a useful technique for pharmacokinetic studies.
2001 Jul-Aug
Release of endothelial nitric oxide in coronary arteries by celiprolol, a beta(1)-adrenoceptor antagonist: possible clinical relevance.
2001 Mar
CYP3A4, CYP3A5, and MDR1 in human small and large intestinal cell lines suitable for drug transport studies.
2001 Nov
Acute hemodynamic effects of beta-blockers in patients with severe congestive heart failure: comparison of celiprolol and esmolol.
2001 Nov
Cardioselective beta-blockers for reversible airway disease.
2002
[Efficacy of beta-selective blocker with vasodilatating features celiprolol in patients with mild and moderate hypertension].
2003
Quantitation of talinolol and other beta-blockers by capillary electrophoresis for in vitro drug absorption studies.
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
Celiprolol, a vasodilatory beta-blocker, inhibits pressure overload-induced cardiac hypertrophy and prevents the transition to heart failure via nitric oxide-dependent mechanisms in mice.
2004 Aug 10
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
Influence of the nature of the electrolyte on the chiral separation of basic compounds in nonaqueous capillary electrophoresis using heptakis(2,3-di-O-methyl-6-O-sulfo)-beta-cyclodextrin.
2005 Mar 11
Celiprolol-induced lupus-like syndrome.
2006 Dec
[Vascular Ehlers-Danlos syndrome].
2006 Dec
Non-neuroleptic catecholaminergic drugs for neuroleptic-induced tardive dyskinesia.
2006 Jan 25
Effects of celiprolol and simvastatin on the calculated risk of coronary heart disease (the Celisimva study).
2006 Jun
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
Impact of curcumin-induced changes in P-glycoprotein and CYP3A expression on the pharmacokinetics of peroral celiprolol and midazolam in rats.
2007 Jan
beta1 antagonist and beta2 agonist, celiprolol, restores the impaired endothelial dependent and independent responses and decreased TNFalpha in rat with type II diabetes.
2007 Jan 16
Metabolic syndrome: treatment of hypertensive patients.
2007 Jul-Aug
Carvedilol in hypertension treatment.
2008
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
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
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
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
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
Positive influence of AT(1) receptor antagonism upon the impaired celiprolol-induced vasodilatation in aorta from spontaneously hypertensive rats.
2010 Oct 10
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 Fri Dec 15 15:07:15 GMT 2023
Edited
by admin
on Fri Dec 15 15:07:15 GMT 2023
Record UNII
G1M3398594
Record Status Validated (UNII)
Record Version
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Name Type Language
CELIPROLOL HYDROCHLORIDE
EP   JAN   MART.   MI   USAN   WHO-DD  
USAN  
Official Name English
UREA, N'-(3-ACETYL-4-(3-((1,1-DIMETHYLETHYL)AMINO)-2-HYDROXYPROPOXYPHENYL)-N,N-DIETHYL-, MONOHYDROCHLORIDE
Common Name English
ACER-002
Code English
CELIPROLOL HCL
Common Name English
ACER002
Code English
3-(3-ACETYL-4-((3-TERT-BUTYLAMINO)-2-HYDROXYPROPOXY)-PHENYL)-1,1-DIETHYLUREA HYDROCHLORIDE
Common Name English
CELIPROLOL HYDROCHLORIDE [USAN]
Common Name English
SELECTOL
Brand Name English
CELIPROLOL HYDROCHLORIDE [MART.]
Common Name English
CELIPROLOL HYDROCHLORIDE [MI]
Common Name English
Celiprolol hydrochloride [WHO-DD]
Common Name English
NSC-324509
Code English
CELIPROLOL HYDROCHLORIDE [JAN]
Common Name English
CELIPROLOL HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29576
Created by admin on Fri Dec 15 15:07:15 GMT 2023 , Edited by admin on Fri Dec 15 15:07:15 GMT 2023
Code System Code Type Description
SMS_ID
100000093037
Created by admin on Fri Dec 15 15:07:15 GMT 2023 , Edited by admin on Fri Dec 15 15:07:15 GMT 2023
PRIMARY
FDA UNII
G1M3398594
Created by admin on Fri Dec 15 15:07:15 GMT 2023 , Edited by admin on Fri Dec 15 15:07:15 GMT 2023
PRIMARY
ChEMBL
CHEMBL27810
Created by admin on Fri Dec 15 15:07:15 GMT 2023 , Edited by admin on Fri Dec 15 15:07:15 GMT 2023
PRIMARY
MERCK INDEX
m3232
Created by admin on Fri Dec 15 15:07:15 GMT 2023 , Edited by admin on Fri Dec 15 15:07:15 GMT 2023
PRIMARY Merck Index
NSC
324509
Created by admin on Fri Dec 15 15:07:15 GMT 2023 , Edited by admin on Fri Dec 15 15:07:15 GMT 2023
PRIMARY
EPA CompTox
DTXSID0046850
Created by admin on Fri Dec 15 15:07:15 GMT 2023 , Edited by admin on Fri Dec 15 15:07:15 GMT 2023
PRIMARY
DRUG BANK
DBSALT002890
Created by admin on Fri Dec 15 15:07:15 GMT 2023 , Edited by admin on Fri Dec 15 15:07:15 GMT 2023
PRIMARY
EVMPD
SUB01146MIG
Created by admin on Fri Dec 15 15:07:15 GMT 2023 , Edited by admin on Fri Dec 15 15:07:15 GMT 2023
PRIMARY
ECHA (EC/EINECS)
260-752-2
Created by admin on Fri Dec 15 15:07:15 GMT 2023 , Edited by admin on Fri Dec 15 15:07:15 GMT 2023
PRIMARY
PUBCHEM
42373
Created by admin on Fri Dec 15 15:07:15 GMT 2023 , Edited by admin on Fri Dec 15 15:07:15 GMT 2023
PRIMARY
NCI_THESAURUS
C81655
Created by admin on Fri Dec 15 15:07:15 GMT 2023 , Edited by admin on Fri Dec 15 15:07:15 GMT 2023
PRIMARY
RXCUI
203145
Created by admin on Fri Dec 15 15:07:15 GMT 2023 , Edited by admin on Fri Dec 15 15:07:15 GMT 2023
PRIMARY RxNorm
CAS
57470-78-7
Created by admin on Fri Dec 15 15:07:15 GMT 2023 , Edited by admin on Fri Dec 15 15:07:15 GMT 2023
PRIMARY
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