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
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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[Pharmacological studies of celiprolol: I. Beta-blocking effect, intrinsic sympathomimetic activity, vasodilating and hypotensive effects]. | 1990 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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Evidence for the binding of beta-adrenoceptor blockers to microsomal Na+/K+-ATPase in guinea pig heart preparations. | 2001 Jan |
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A comprehensive account on the role of efflux transporters in the gastrointestinal absorption of 13 commonly used substrate drugs in humans. | 2001 Mar |
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[The effect of celiprolol hydrochloride for lipid metabolism--especially for the low density lipoprotein particle size]. | 2001 May |
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Carvedilol versus other beta-blockers in heart failure. | 2001 May |
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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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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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Impact of excipients on the absorption of P-glycoprotein substrates in vitro and in vivo. | 2004 Jun 18 |
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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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Thermodynamics of non-stoichiometric pharmaceutical hydrates. | 2005 Oct 13 |
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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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Ehlers-Danlos syndrome type IV. | 2007 Jul 19 |
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Ozonation of reverse osmosis concentrate: kinetics and efficiency of beta blocker oxidation. | 2008 Jun |
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Natural and synthetic polymers as inhibitors of drug efflux pumps. | 2008 Mar |
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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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Analysis of drug interactions involving fruit beverages and organic anion-transporting polypeptides. | 2009 Dec |
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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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[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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Chiral separations of some beta-adrenergic agonists and antagonists on AmyCoat column by HPLC. | 2010 Jan |
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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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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.
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NCI_THESAURUS |
C29576
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G1M3398594
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m3232
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ACTIVE MOIETY
SUBSTANCE RECORD