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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
Structure of CELIPROLOL HYDROCHLORIDE

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

HIDE SMILES / InChI

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.35 nM [Ki]
2.8 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Unknown

Approved Use

Unknown
Palliative
SELECTOL

Approved Use

Celiprolol 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.
Primary
SELECTOL

Approved Use

Celiprolol 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.
Palliative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
[Pharmacological studies of celiprolol: I. Beta-blocking effect, intrinsic sympathomimetic activity, vasodilating and hypotensive effects].
1990 Apr
Quantitative structure-retention and retention-activity relationships of beta-blocking agents by micellar liquid chromatography.
2001 Apr 6
Evidence for the binding of beta-adrenoceptor blockers to microsomal Na+/K+-ATPase in guinea pig heart preparations.
2001 Jan
A comprehensive account on the role of efflux transporters in the gastrointestinal absorption of 13 commonly used substrate drugs in humans.
2001 Mar
[The effect of celiprolol hydrochloride for lipid metabolism--especially for the low density lipoprotein particle size].
2001 May
Carvedilol versus other beta-blockers in heart failure.
2001 May
Celiprolol increases coronary blood flow and reduces severity of myocardial ischemia via nitric oxide release.
2003 Apr
Improvement of peak shape and separation performance of beta-blockers in conventional reversed-phase columns using solvent modifiers.
2003 Aug
Simultaneous determination of thirteen beta-blockers and one metabolite by gradient high-performance liquid chromatography with photodiode-array UV detection.
2004 Apr 20
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
Impact of excipients on the absorption of P-glycoprotein substrates in vitro and in vivo.
2004 Jun 18
Simultaneous determination of the acid/base antihypertensive drugs celiprolol, bisoprolol and irbesartan in human plasma by liquid chromatography.
2004 Mar 5
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
Thermodynamics of non-stoichiometric pharmaceutical hydrates.
2005 Oct 13
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
Ehlers-Danlos syndrome type IV.
2007 Jul 19
Ozonation of reverse osmosis concentrate: kinetics and efficiency of beta blocker oxidation.
2008 Jun
Natural and synthetic polymers as inhibitors of drug efflux pumps.
2008 Mar
Direct determination of celiprolol in human urine using on-line coupled ITP-CZE method with fiber-based DAD.
2008 Nov
Analysis of drug interactions involving fruit beverages and organic anion-transporting polypeptides.
2009 Dec
Acute pulmonary edema due to stress cardiomyopathy in a patient with aortic stenosis: a case report.
2009 Dec 2
[Endothelial dysfunction: role of vasodilating betablockers in hypertension and chronic heart failure].
2010 Apr
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010 Dec
Chiral separations of some beta-adrenergic agonists and antagonists on AmyCoat column by HPLC.
2010 Jan
Highly sensitive transient isotachophoresis sample stacking coupling with capillary electrophoresis-amperometric detection for analysis of doping substances.
2010 Jun 15
Evaluation of left atrial volumes using multidetector computed tomography: comparison with echocardiography.
2010 May-Jun
Fruit juice inhibition of uptake transport: a new type of food-drug interaction.
2010 Nov
Effect of celiprolol on prevention of cardiovascular events in vascular Ehlers-Danlos syndrome: a prospective randomised, open, blinded-endpoints trial.
2010 Oct 30
Patents

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
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.
Name Type Language
CELIPROLOL HYDROCHLORIDE
EP   JAN   MART.   MI   USAN   WHO-DD  
USAN  
Official Name English
UREA, N'-(3-ACETYL-4-(3-((1,1-DIMETHYLETHYL)AMINO)-2-HYDROXYPROPOXYPHENYL)-N,N-DIETHYL-, MONOHYDROCHLORIDE
Common Name English
ACER-002
Code English
CELIPROLOL HCL
Common Name English
ACER002
Code English
3-(3-ACETYL-4-((3-TERT-BUTYLAMINO)-2-HYDROXYPROPOXY)-PHENYL)-1,1-DIETHYLUREA HYDROCHLORIDE
Common Name English
CELIPROLOL HYDROCHLORIDE [USAN]
Common Name English
SELECTOL
Brand Name English
CELIPROLOL HYDROCHLORIDE [MART.]
Common Name English
CELIPROLOL HYDROCHLORIDE [MI]
Common Name English
Celiprolol hydrochloride [WHO-DD]
Common Name English
NSC-324509
Code English
CELIPROLOL HYDROCHLORIDE [JAN]
Common Name English
CELIPROLOL HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29576
Created by admin on Fri Dec 15 15:07:15 GMT 2023 , Edited by admin on Fri Dec 15 15:07:15 GMT 2023
Code System Code Type Description
SMS_ID
100000093037
Created by admin on Fri Dec 15 15:07:15 GMT 2023 , Edited by admin on Fri Dec 15 15:07:15 GMT 2023
PRIMARY
FDA UNII
G1M3398594
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PRIMARY
ChEMBL
CHEMBL27810
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PRIMARY
MERCK INDEX
m3232
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PRIMARY Merck Index
NSC
324509
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EPA CompTox
DTXSID0046850
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DRUG BANK
DBSALT002890
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EVMPD
SUB01146MIG
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ECHA (EC/EINECS)
260-752-2
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PRIMARY
PUBCHEM
42373
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NCI_THESAURUS
C81655
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RXCUI
203145
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PRIMARY RxNorm
CAS
57470-78-7
Created by admin on Fri Dec 15 15:07:15 GMT 2023 , Edited by admin on Fri Dec 15 15:07:15 GMT 2023
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