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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Anti-ischemic effects of celiprolol in patients with exercise-induced angina pectoris. | 1989 Oct |
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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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Improvement of peak shape and separation performance of beta-blockers in conventional reversed-phase columns using solvent modifiers. | 2003 Aug |
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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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Determination of stability constants of the inclusion complexes of beta-blockers in heptakis (2,3-dimethyl-6-sulfato)-beta-cyclodextrin. | 2004 Dec |
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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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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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[Celiprolol poisoning: two case reports]. | 2005 Jan-Feb |
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Oxidative-nitrosative stress in hypertension. | 2005 Jul |
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Detrimental effects of beta-blockers in COPD: a concern for nonselective beta-blockers. | 2005 Mar |
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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 |
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Mechanisms of combined treatment with celiprolol and candesartan for ventricular remodeling in experimental heart failure. | 2005 May |
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Thermodynamics of non-stoichiometric pharmaceutical hydrates. | 2005 Oct 13 |
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Celiprolol-induced lupus-like syndrome. | 2006 Dec |
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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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Celiprolol reduces the intimal thickening of autogenous vein grafts via an enhancement of nitric oxide function through an inhibition of superoxide production. | 2007 Jul |
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Ehlers-Danlos syndrome type IV. | 2007 Jul 19 |
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Metabolic syndrome: treatment of hypertensive patients. | 2007 Jul-Aug |
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[The inhibitory effect of pluronic on P-glycoprotein drug pump]. | 2007 Sep |
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Hesperidin in orange juice reduces the absorption of celiprolol in rats. | 2008 Apr |
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Immune defects in Alzheimer's disease: new medications development. | 2008 Dec 3 |
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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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Direct determination of celiprolol in human urine using on-line coupled ITP-CZE method with fiber-based DAD. | 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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Effects of the antioxidative beta-blocker celiprolol on endothelial progenitor cells in hypertensive rats. | 2008 Sep |
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Chiral separation of beta-adrenergic blockers on CelluCoat column by HPLC. | 2009 Apr 30 |
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Analysis of drug interactions involving fruit beverages and organic anion-transporting polypeptides. | 2009 Dec |
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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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Uptake/efflux transport of tramadol enantiomers and O-desmethyl-tramadol: focus on P-glycoprotein. | 2009 Sep |
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[Endothelial dysfunction: role of vasodilating betablockers in hypertension and chronic heart failure]. | 2010 Apr |
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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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Chiral separations of some beta-adrenergic agonists and antagonists on AmyCoat column by HPLC. | 2010 Jan |
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Human health risk assessment of pharmaceuticals in water: issues and challenges ahead. | 2010 Nov |
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Fruit juice inhibition of uptake transport: a new type of food-drug interaction. | 2010 Nov |
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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C29576
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