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 |
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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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Evidence for the binding of beta-adrenoceptor blockers to microsomal Na+/K+-ATPase in guinea pig heart preparations. | 2001 Jan |
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Release of endothelial nitric oxide in coronary arteries by celiprolol, a beta(1)-adrenoceptor antagonist: possible clinical relevance. | 2001 Mar |
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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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Celiprolol inhibits mitogen-activated protein kinase and endothelin-1 and transforming growth factor-beta(1) gene in rats. | 2002 Dec 20 |
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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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Improvement of peak shape and separation performance of beta-blockers in conventional reversed-phase columns using solvent modifiers. | 2003 Aug |
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Itraconazole increases but grapefruit juice greatly decreases plasma concentrations of celiprolol. | 2003 Mar |
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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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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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[Vascular Ehlers-Danlos syndrome]. | 2006 Dec |
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[Identification of blockers of adrenergic beta-receptors by thin layer chromatography]. | 2006 Jan |
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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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Beta-blockers use in patients with chronic obstructive pulmonary disease and concomitant cardiovascular conditions. | 2007 |
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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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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 |
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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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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 |
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[The inhibitory effect of pluronic on P-glycoprotein drug pump]. | 2007 Sep |
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Carvedilol in hypertension treatment. | 2008 |
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Natural and synthetic polymers as inhibitors of drug efflux pumps. | 2008 Mar |
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Effect of pluronic F68 block copolymer on P-glycoprotein transport and CYP3A4 metabolism. | 2008 May 22 |
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American College of Endocrinology Pre-Diabetes Consensus Conference: part two. | 2008 Nov |
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Progress in the development of early diagnosis and a drug with unique pharmacology to improve cancer therapy. | 2008 Oct 13 |
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Acute pulmonary edema due to stress cardiomyopathy in a patient with aortic stenosis: a case report. | 2009 Dec 2 |
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Involvement of influx and efflux transport systems in gastrointestinal absorption of celiprolol. | 2009 Jul |
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Uptake/efflux transport of tramadol enantiomers and O-desmethyl-tramadol: focus on P-glycoprotein. | 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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Effect of celiprolol on prevention of cardiovascular events in vascular Ehlers-Danlos syndrome: a prospective randomised, open, blinded-endpoints trial. | 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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Record UNII |
DRB57K47QC
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Record Status |
Validated (UNII)
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QC07AB08
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456714
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C07AB08
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NCI_THESAURUS |
C29576
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