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
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
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 |
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 |
---|---|---|---|---|
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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Plasma analysis of celiprolol by HPTLC: a useful technique for pharmacokinetic studies. | 2001 Jul-Aug |
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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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CYP3A4, CYP3A5, and MDR1 in human small and large intestinal cell lines suitable for drug transport studies. | 2001 Nov |
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Acute hemodynamic effects of beta-blockers in patients with severe congestive heart failure: comparison of celiprolol and esmolol. | 2001 Nov |
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Cardioselective beta-blockers for reversible airway disease. | 2002 |
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[Efficacy of beta-selective blocker with vasodilatating features celiprolol in patients with mild and moderate hypertension]. | 2003 |
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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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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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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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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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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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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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Celiprolol-induced lupus-like syndrome. | 2006 Dec |
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[Vascular Ehlers-Danlos syndrome]. | 2006 Dec |
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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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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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Metabolic syndrome: treatment of hypertensive patients. | 2007 Jul-Aug |
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Carvedilol in hypertension treatment. | 2008 |
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Ozonation of reverse osmosis concentrate: kinetics and efficiency of beta blocker oxidation. | 2008 Jun |
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Simultaneous separation of eight beta-adrenergic drugs using titanium dioxide nanoparticles as additive in capillary electrophoresis. | 2008 Jun |
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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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Acute pulmonary edema due to stress cardiomyopathy in a patient with aortic stenosis: a case report. | 2009 Dec 2 |
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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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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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Human health risk assessment of pharmaceuticals in water: issues and challenges ahead. | 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 |
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
by
admin
on
Edited
Fri Dec 15 15:07:15 GMT 2023
by
admin
on
Fri Dec 15 15:07:15 GMT 2023
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Record UNII |
G1M3398594
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Record Status |
Validated (UNII)
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Record Version |
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C29576
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