Details
Stereochemistry | RACEMIC |
Molecular Formula | C20H33N3O4 |
Molecular Weight | 379.4937 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCN(CC)C(=O)NC1=CC(C(C)=O)=C(OCC(O)CNC(C)(C)C)C=C1
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)
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 | ( + / - ) |
DescriptionCurator'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
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.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL213 |
0.35 nM [Ki] | ||
Target ID: CHEMBL210 |
2.8 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Palliative | Unknown Approved UseUnknown |
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Palliative | SELECTOL Approved UseCeliprolol 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. |
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Primary | SELECTOL Approved UseCeliprolol 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. |
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Palliative | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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[Pharmacological studies of celiprolol: III. Effects of celiprolol on the cardiovascular system and renal function, and its antiarrhythmic effects]. | 1990 Apr |
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[Pharmacological studies of celiprolol: I. Beta-blocking effect, intrinsic sympathomimetic activity, vasodilating and hypotensive effects]. | 1990 Apr |
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Celiprolol stimulates endothelial nitric oxide synthase expression and improves myocardial remodeling in deoxycorticosterone acetate-salt hypertensive rats. | 2001 Apr |
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Quantitative structure-retention and retention-activity relationships of beta-blocking agents by micellar liquid chromatography. | 2001 Apr 6 |
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A functional assay for quantitation of the apparent affinities of ligands of P-glycoprotein in Caco-2 cells. | 2001 Feb |
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Carvedilol versus other beta-blockers in heart failure. | 2001 May |
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CYP3A4, CYP3A5, and MDR1 in human small and large intestinal cell lines suitable for drug transport studies. | 2001 Nov |
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[Use of selective long-acting beta-blocker with vasodilating activity celiprolol in patients with essential hypertension]. | 2002 |
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Interactions of sildenafil with various coronary vasodilators in isolated porcine coronary artery. | 2002 Feb 22 |
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Celiprolol increases coronary blood flow and reduces severity of myocardial ischemia via nitric oxide release. | 2003 Apr |
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Quantitation of talinolol and other beta-blockers by capillary electrophoresis for in vitro drug absorption studies. | 2003 Aug |
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Itraconazole increases but grapefruit juice greatly decreases plasma concentrations of celiprolol. | 2003 Mar |
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Celiprolol activates eNOS through the PI3K-Akt pathway and inhibits VCAM-1 Via NF-kappaB induced by oxidative stress. | 2003 Nov |
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Angiotensinogen gene M235T polymorphism and reduction in wall thickness in response to antihypertensive treatment. | 2003 Nov |
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Simultaneous determination of thirteen beta-blockers and one metabolite by gradient high-performance liquid chromatography with photodiode-array UV detection. | 2004 Apr 20 |
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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 |
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Rifampicin reduces plasma concentrations of celiprolol. | 2004 Jan |
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The impact of third-generation beta-blocker antihypertensive treatment on endothelial function and the prothrombotic state: effects of smoking. | 2004 Jul |
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Impact of excipients on the absorption of P-glycoprotein substrates in vitro and in vivo. | 2004 Jun 18 |
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Orange juice substantially reduces the bioavailability of the beta-adrenergic-blocking agent celiprolol. | 2004 Mar |
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Simultaneous determination of the acid/base antihypertensive drugs celiprolol, bisoprolol and irbesartan in human plasma by liquid chromatography. | 2004 Mar 5 |
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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 |
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Enantiomer separations on a vancomycin stationary phase and retention mechanism of pressurized capillary electrochromatography. | 2004 Sep |
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Oxidative-nitrosative stress in hypertension. | 2005 Jul |
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Thermodynamics of non-stoichiometric pharmaceutical hydrates. | 2005 Oct 13 |
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[Identification of blockers of adrenergic beta-receptors by thin layer chromatography]. | 2006 Jan |
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Screening of domperidone in wastewater by high performance liquid chromatography and solid phase extraction methods. | 2006 Jan 15 |
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Non-neuroleptic catecholaminergic drugs for neuroleptic-induced tardive dyskinesia. | 2006 Jan 25 |
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Effects of celiprolol and simvastatin on the calculated risk of coronary heart disease (the Celisimva study). | 2006 Jun |
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Concurrent dolichoectasia of basilar and coronary arteries. | 2006 May 9 |
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Celiprolol, a selective beta1-blocker, reduces the infarct size through production of nitric oxide in a rabbit model of myocardial infarction. | 2007 Apr |
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Impact of curcumin-induced changes in P-glycoprotein and CYP3A expression on the pharmacokinetics of peroral celiprolol and midazolam in rats. | 2007 Jan |
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Beneficial effect of combination therapy with antihypertensive drugs in patients with hypertension. | 2007 Spring |
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Effects of the vasodilating beta-blocker nebivolol on smoking-induced endothelial dysfunction in young healthy volunteers. | 2008 |
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American College of Endocrinology Pre-Diabetes Consensus Conference: part two. | 2008 Nov |
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Chiral separation of beta-adrenergic blockers on CelluCoat column by HPLC. | 2009 Apr 30 |
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Involvement of influx and efflux transport systems in gastrointestinal absorption of celiprolol. | 2009 Jul |
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The role of transporters in the pharmacokinetics of orally administered drugs. | 2009 Sep |
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Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method. | 2010 Dec |
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Fate of beta blockers in aquatic-sediment systems: sorption and biotransformation. | 2010 Feb 1 |
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Highly sensitive transient isotachophoresis sample stacking coupling with capillary electrophoresis-amperometric detection for analysis of doping substances. | 2010 Jun 15 |
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Evaluation of left atrial volumes using multidetector computed tomography: comparison with echocardiography. | 2010 May-Jun |
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Fruit juice inhibition of uptake transport: a new type of food-drug interaction. | 2010 Nov |
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Positive influence of AT(1) receptor antagonism upon the impaired celiprolol-induced vasodilatation in aorta from spontaneously hypertensive rats. | 2010 Oct 10 |
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Celiprolol therapy for vascular Ehlers-Danlos syndrome. | 2010 Oct 30 |
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7858847
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
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admin
on
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Record UNII |
DRB57K47QC
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Record Status |
Validated (UNII)
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C07AB08
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C29576
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