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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
Structure of CELIPROLOL

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)

HIDE SMILES / InChI

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 ( + / - )

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
Evidence for the binding of beta-adrenoceptor blockers to microsomal Na+/K+-ATPase in guinea pig heart preparations.
2001 Jan
Release of endothelial nitric oxide in coronary arteries by celiprolol, a beta(1)-adrenoceptor antagonist: possible clinical relevance.
2001 Mar
Carvedilol versus other beta-blockers in heart failure.
2001 May
CYP3A4, CYP3A5, and MDR1 in human small and large intestinal cell lines suitable for drug transport studies.
2001 Nov
[Use of selective long-acting beta-blocker with vasodilating activity celiprolol in patients with essential hypertension].
2002
Celiprolol inhibits mitogen-activated protein kinase and endothelin-1 and transforming growth factor-beta(1) gene in rats.
2002 Dec 20
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
Itraconazole increases but grapefruit juice greatly decreases plasma concentrations of celiprolol.
2003 Mar
The impact of third-generation beta-blocker antihypertensive treatment on endothelial function and the prothrombotic state: effects of smoking.
2004 Jul
Simultaneous determination of the acid/base antihypertensive drugs celiprolol, bisoprolol and irbesartan in human plasma by liquid chromatography.
2004 Mar 5
[Vascular Ehlers-Danlos syndrome].
2006 Dec
[Identification of blockers of adrenergic beta-receptors by thin layer chromatography].
2006 Jan
Non-neuroleptic catecholaminergic drugs for neuroleptic-induced tardive dyskinesia.
2006 Jan 25
Effects of celiprolol and simvastatin on the calculated risk of coronary heart disease (the Celisimva study).
2006 Jun
Concurrent dolichoectasia of basilar and coronary arteries.
2006 May 9
Beta-blockers use in patients with chronic obstructive pulmonary disease and concomitant cardiovascular conditions.
2007
Celiprolol, a selective beta1-blocker, reduces the infarct size through production of nitric oxide in a rabbit model of myocardial infarction.
2007 Apr
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
Impact of curcumin-induced changes in P-glycoprotein and CYP3A expression on the pharmacokinetics of peroral celiprolol and midazolam in rats.
2007 Jan
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
[The inhibitory effect of pluronic on P-glycoprotein drug pump].
2007 Sep
Carvedilol in hypertension treatment.
2008
Natural and synthetic polymers as inhibitors of drug efflux pumps.
2008 Mar
Effect of pluronic F68 block copolymer on P-glycoprotein transport and CYP3A4 metabolism.
2008 May 22
American College of Endocrinology Pre-Diabetes Consensus Conference: part two.
2008 Nov
Progress in the development of early diagnosis and a drug with unique pharmacology to improve cancer therapy.
2008 Oct 13
Acute pulmonary edema due to stress cardiomyopathy in a patient with aortic stenosis: a case report.
2009 Dec 2
Involvement of influx and efflux transport systems in gastrointestinal absorption of celiprolol.
2009 Jul
Uptake/efflux transport of tramadol enantiomers and O-desmethyl-tramadol: focus on P-glycoprotein.
2009 Sep
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010 Dec
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:12:29 UTC 2023
Edited
by admin
on Fri Dec 15 16:12:29 UTC 2023
Record UNII
DRB57K47QC
Record Status Validated (UNII)
Record Version
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Name Type Language
CELIPROLOL
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
Celiprolol [WHO-DD]
Common Name English
celiprolol [INN]
Common Name English
ACER-002 FREE BASE
Code English
N-[3-acetyl-4-[(2RS)-3-(tert-butylamino)-2-hydroxypropoxy]phenyl]-N′-tert-butylurea
Systematic Name English
UREA, N'-(3-ACETYL-4-(3-((1,1-DIMETHYLETHYL)AMINO)-2-HYDROXYPROPOXY)PHENYL)-N,N-DIETHYL-
Systematic Name English
CELIPROLOL PCH
Brand Name English
CELIPROLOL [MI]
Common Name English
ACER002 FREE BASE
Code English
CELIPROLOL [VANDF]
Common Name English
3-(3-ACETYL-4-(3-(TERT-BUTYLAMINO)-2-HYDROXYPROPOXY)PHENYL)-1,1-DIETHYLUREA
Systematic Name English
CELIPROLOL HYDROCHLORIDE IMPURITY C [EP IMPURITY]
Common Name English
Classification Tree Code System Code
WHO-VATC QC07AB08
Created by admin on Fri Dec 15 16:12:29 UTC 2023 , Edited by admin on Fri Dec 15 16:12:29 UTC 2023
FDA ORPHAN DRUG 456714
Created by admin on Fri Dec 15 16:12:29 UTC 2023 , Edited by admin on Fri Dec 15 16:12:29 UTC 2023
WHO-ATC C07AB08
Created by admin on Fri Dec 15 16:12:29 UTC 2023 , Edited by admin on Fri Dec 15 16:12:29 UTC 2023
NCI_THESAURUS C29576
Created by admin on Fri Dec 15 16:12:29 UTC 2023 , Edited by admin on Fri Dec 15 16:12:29 UTC 2023
Code System Code Type Description
MERCK INDEX
m3232
Created by admin on Fri Dec 15 16:12:29 UTC 2023 , Edited by admin on Fri Dec 15 16:12:29 UTC 2023
PRIMARY Merck Index
INN
3979
Created by admin on Fri Dec 15 16:12:29 UTC 2023 , Edited by admin on Fri Dec 15 16:12:29 UTC 2023
PRIMARY
PUBCHEM
2663
Created by admin on Fri Dec 15 16:12:29 UTC 2023 , Edited by admin on Fri Dec 15 16:12:29 UTC 2023
PRIMARY
CAS
56980-93-9
Created by admin on Fri Dec 15 16:12:29 UTC 2023 , Edited by admin on Fri Dec 15 16:12:29 UTC 2023
PRIMARY
EVMPD
SUB07436MIG
Created by admin on Fri Dec 15 16:12:29 UTC 2023 , Edited by admin on Fri Dec 15 16:12:29 UTC 2023
PRIMARY
MESH
D017272
Created by admin on Fri Dec 15 16:12:29 UTC 2023 , Edited by admin on Fri Dec 15 16:12:29 UTC 2023
PRIMARY
DRUG BANK
DB04846
Created by admin on Fri Dec 15 16:12:29 UTC 2023 , Edited by admin on Fri Dec 15 16:12:29 UTC 2023
PRIMARY
EPA CompTox
DTXSID3020259
Created by admin on Fri Dec 15 16:12:29 UTC 2023 , Edited by admin on Fri Dec 15 16:12:29 UTC 2023
PRIMARY
ChEMBL
CHEMBL27810
Created by admin on Fri Dec 15 16:12:29 UTC 2023 , Edited by admin on Fri Dec 15 16:12:29 UTC 2023
PRIMARY
FDA UNII
DRB57K47QC
Created by admin on Fri Dec 15 16:12:29 UTC 2023 , Edited by admin on Fri Dec 15 16:12:29 UTC 2023
PRIMARY
WIKIPEDIA
Celiprolol
Created by admin on Fri Dec 15 16:12:29 UTC 2023 , Edited by admin on Fri Dec 15 16:12:29 UTC 2023
PRIMARY
DRUG CENTRAL
569
Created by admin on Fri Dec 15 16:12:29 UTC 2023 , Edited by admin on Fri Dec 15 16:12:29 UTC 2023
PRIMARY
ECHA (EC/EINECS)
260-497-7
Created by admin on Fri Dec 15 16:12:29 UTC 2023 , Edited by admin on Fri Dec 15 16:12:29 UTC 2023
PRIMARY
SMS_ID
100000082044
Created by admin on Fri Dec 15 16:12:29 UTC 2023 , Edited by admin on Fri Dec 15 16:12:29 UTC 2023
PRIMARY
NCI_THESAURUS
C79558
Created by admin on Fri Dec 15 16:12:29 UTC 2023 , Edited by admin on Fri Dec 15 16:12:29 UTC 2023
PRIMARY
RXCUI
20498
Created by admin on Fri Dec 15 16:12:29 UTC 2023 , Edited by admin on Fri Dec 15 16:12:29 UTC 2023
PRIMARY RxNorm
Related Record Type Details
SALT/SOLVATE -> PARENT
TRANSPORTER -> SUBSTRATE
Related Record Type Details
PARENT -> IMPURITY
Related Record Type Details
ACTIVE MOIETY