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Identification
- Summary
Celiprolol is a beta-blocker for the management of hypertension and angina pectoris.
- Generic Name
- Celiprolol
- DrugBank Accession Number
- DB04846
- Background
Celiprolol is indicated for the management of mild to moderate hypertension and effort-induced angina pectoris. It is simultaneously a selective β1 receptor antagonist, a β2 receptor partial agonist and a weak α2 receptor antagonist. In 2010 a clinical trial has suggested a use for this medication in the prevention of vascular complications of a rare inherited disease called vascular Ehlers–Danlos syndrome. This study demonstrated decreased incidence of arterial rupture or dissection (a specific type of arterial rupture in which the layers of the vessel separate prior to complete failure of the artery wall). Celiprolol is not approved for use by the FDA in the treatment of vascular Ehlers–Danlos syndrome.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Celiprolol (DB04846)
- Weight
- Average: 379.501
Monoisotopic: 379.247106555 - Chemical Formula
- C20H33N3O4
- Synonyms
- Celiprolol
- Celiprololum
- RS)-N'-{3-acetyl-4-[3-(tert-butylamino)-2-hydroxypropoxy]phenyl}-N,N-diethylurea
- External IDs
- REV 5320 A
- RHC 5320 A
- RHC-5320A
- ST 1396
- UL/1677
Pharmacology
- Indication
Celiprolol is indicated for the management of mild to moderate hypertension and effort-induced angina pectoris.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Angina pectoris •••••••••••• ••••••• ••••••• •••••• Treatment of High blood pressure (hypertension) •••••••••••• ••••••• ••••••• •••••• - Contraindications & Blackbox Warnings
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Not Available
- Mechanism of action
Celiprolol is a vasoactive beta-1 selective adrenoceptor antagonist with partial beta-2 agonist activity. The beta-2 agonist activity is thought to account for its mild vasodilating properties. It lowers blood pressure in hypertensive patients at rest and on exercise. The effects on heart rate and cardiac output are dependent on the pre-existing background level of sympathetic tone. Under conditions of stress such as exercise, celiprolol attenuates chronotropic and inotropic responses to sympathetic stimulation. However, at rest minimal impairment of cardiac function is seen.
Target Actions Organism ABeta-1 adrenergic receptor antagonistHumans ABeta-2 adrenergic receptor agonistHumans UBeta-3 adrenergic receptor agonistHumans UAlpha-2A adrenergic receptor antagonistHumans UAlpha-2B adrenergic receptor antagonistHumans UAlpha-2C adrenergic receptor antagonistHumans - Absorption
Absorption of an oral dose is rapid and consistent but incomplete (55% for 200 mg dose and 74% for 400 mg dose) from the gastrointestinal tract. The bioavailability of celiprolol has been shown to be markedly affected by food and one should avoid administration of celiprolol with food. Coadministration of chlorthalidone, hydrochlorothiazide and theophylline also reduces the bioavailability of celiprolol. Following oral dosing, maximal blood concentrations are reached between 2 and 3 hours.
- Volume of distribution
The distribution volume is 4.5L/kg. Celiprolol is hydrophilic and does not cross the blood-brain barrier. The binding to plasma proteins is about 25-30%.
- Protein binding
25-30%.
- Metabolism
A 14C labelled dose was completely recovered within 48 hours. The first-pass effect in the liver is insignificant. Celiprolol is metabolized to a minor extent (1-3%).
- Route of elimination
Not Available
- Half-life
5 hours
- Clearance
Cleared by both renal and non-renal excretory pathways. Celiprolol is not recommended for patients with creatinine clearance less than 15 mL per minute.
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
No data are available regarding celiprolol overdose in humans. The most common symptoms to be expected following overdosage with beta-adrenoceptor blocking agents are bradycardia, hypotension, bronchospasm and acute cardiac insufficiency.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbaloparatide Abaloparatide may increase the hypotensive activities of Celiprolol. Abatacept The metabolism of Celiprolol can be increased when combined with Abatacept. Abiraterone The metabolism of Celiprolol can be decreased when combined with Abiraterone. Acarbose The therapeutic efficacy of Acarbose can be increased when used in combination with Celiprolol. Acebutolol Acebutolol may increase the arrhythmogenic activities of Celiprolol. - Food Interactions
- Avoid fruit juice. Orange juice may reduce the absorption of celiprolol.
- Avoid grapefruit products. Grapefruit juice may reduce the absorption of celiprolol.
- Take with or without food. The bioavailability of celiprolol may be reduced when taken with food, however, it is unlikely that this reduction is clinically relevant.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Celiprolol hydrochloride G1M3398594 57470-78-7 VKJHTUVLJYWAEY-UHFFFAOYSA-N - International/Other Brands
- Selectol (Sanofi)
Categories
- ATC Codes
- C07AB08 — Celiprolol
- Drug Categories
- Adrenergic Agents
- Adrenergic Agonists
- Adrenergic Antagonists
- Adrenergic beta-1 Receptor Antagonists
- Adrenergic beta-2 Receptor Agonists
- Adrenergic beta-3 Receptor Agonists
- Adrenergic beta-Agonists
- Adrenergic beta-Antagonists
- Agents causing hyperkalemia
- Alcohols
- Amides
- Amines
- Amino Alcohols
- Antiarrhythmic agents
- Antihypertensive Agents
- Autonomic Agents
- Benzene Derivatives
- Beta Blocking Agents, Selective
- Beta-Blockers (Beta1 Selective)
- Bradycardia-Causing Agents
- Cardiovascular Agents
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 Substrates
- Neurotransmitter Agents
- Peripheral Nervous System Agents
- Phenoxypropanolamines
- Phenylurea Compounds
- Potential QTc-Prolonging Agents
- Propanolamines
- Propanols
- QTc Prolonging Agents
- Sympathomimetics
- Vasodilating Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
- Kingdom
- Organic compounds
- Super Class
- Organic oxygen compounds
- Class
- Organooxygen compounds
- Sub Class
- Carbonyl compounds
- Direct Parent
- Alkyl-phenylketones
- Alternative Parents
- N-phenylureas / Acetophenones / Phenoxy compounds / Phenol ethers / Benzoyl derivatives / Aryl alkyl ketones / Alkyl aryl ethers / Ureas / Secondary alcohols / 1,2-aminoalcohols show 4 more
- Substituents
- 1,2-aminoalcohol / Acetophenone / Alcohol / Alkyl aryl ether / Alkyl-phenylketone / Amine / Aromatic homomonocyclic compound / Aryl alkyl ketone / Benzenoid / Benzoyl show 15 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- DRB57K47QC
- CAS number
- 56980-93-9
- InChI Key
- JOATXPAWOHTVSZ-UHFFFAOYSA-N
- InChI
- 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)
- IUPAC Name
- 1-{3-acetyl-4-[3-(tert-butylamino)-2-hydroxypropoxy]phenyl}-3,3-diethylurea
- SMILES
- CCN(CC)C(=O)NC1=CC=C(OCC(O)CNC(C)(C)C)C(=C1)C(C)=O
References
- Synthesis Reference
Zolss, G., Pittner, H., Stormann-Menninger-Lerchenthal, H. and Lindner, I.; US. Patent 3,983,169; September 28,1976; assigned to Chemie Linz AG (Austria).
- General References
- Ong KT, Perdu J, De Backer J, Bozec E, Collignon P, Emmerich J, Fauret AL, Fiessinger JN, Germain DP, Georgesco G, Hulot JS, De Paepe A, Plauchu H, Jeunemaitre X, Laurent S, Boutouyrie P: Effect of celiprolol on prevention of cardiovascular events in vascular Ehlers-Danlos syndrome: a prospective randomised, open, blinded-endpoints trial. Lancet. 2010 Oct 30;376(9751):1476-84. doi: 10.1016/S0140-6736(10)60960-9. Epub 2010 Sep 7. [Article]
- External Links
- KEGG Drug
- D07660
- PubChem Compound
- 2663
- PubChem Substance
- 310264853
- ChemSpider
- 2563
- BindingDB
- 50470842
- 20498
- ChEBI
- 94461
- ChEMBL
- CHEMBL27810
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Celiprolol
- MSDS
- Download (80.4 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data4 Completed Treatment CHROMOSOME 2q31.2 DELETION SYNDROME / Ehlers-danlos syndrome, type IV, autosomal dominant 1 somestatus stop reason just information to hide 4 Completed Treatment Chronic Obstructive Pulmonary Disease (COPD) 1 somestatus stop reason just information to hide 3 Recruiting Treatment Ehlers-Danlos Syndrome, Vascular Type 1 somestatus stop reason just information to hide 2 Unknown Status Prevention Complications; Cardiac, Postoperative 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet, film coated Oral 200 mg/1 Tablet, film coated Oral 200 MG Tablet, film coated Oral 400 MG Tablet, coated Oral 200 MG Tablet, coated Oral - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 120-122 Zolss, G., Pittner, H., Stormann-Menninger-Lerchenthal, H. and Lindner, I.; US. Patent 3,983,169; September 28,1976; assigned to Chemie Linz AG (Austria). - Predicted Properties
Property Value Source Water Solubility 0.174 mg/mL ALOGPS logP 2.29 ALOGPS logP 1.5 Chemaxon logS -3.3 ALOGPS pKa (Strongest Acidic) 13.55 Chemaxon pKa (Strongest Basic) 9.66 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 90.9 Å2 Chemaxon Rotatable Bond Count 10 Chemaxon Refractivity 108.25 m3·mol-1 Chemaxon Polarizability 43.18 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 187.72368 predictedDeepCCS 1.0 (2019) [M+H]+ 190.15547 predictedDeepCCS 1.0 (2019) [M+Na]+ 197.64699 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately equal affinity. Mediates Ras activation through G(s)-alpha- and cAMP-mediated signaling. Involved in the regulation of sleep/wake behaviors (PubMed:31473062)
- Specific Function
- alpha-2A adrenergic receptor binding
- Gene Name
- ADRB1
- Uniprot ID
- P08588
- Uniprot Name
- Beta-1 adrenergic receptor
- Molecular Weight
- 51222.97 Da
References
- Chen X, Minatoguchi S, Arai M, Wang N, Lu C, Narentuoya B, Uno Y, Misao Y, Takemura G, Fujiwara T, Fujiwara H: Celiprolol, a selective beta1-blocker, reduces the infarct size through production of nitric oxide in a rabbit model of myocardial infarction. Circ J. 2007 Apr;71(4):574-9. [Article]
- Hayashi T, Juliet PA, Miyazaki-Akita A, Funami J, Matsui-Hirai H, Fukatsu A, Iguchi A: beta1 antagonist and beta2 agonist, celiprolol, restores the impaired endothelial dependent and independent responses and decreased TNFalpha in rat with type II diabetes. Life Sci. 2007 Jan 16;80(6):592-9. Epub 2006 Dec 1. [Article]
- Yao EH, Fukuda N, Matsumoto T, Katakawa M, Yamamoto C, Han Y, Ueno T, Kobayashi N, Matsumoto K: Effects of the antioxidative beta-blocker celiprolol on endothelial progenitor cells in hypertensive rats. Am J Hypertens. 2008 Sep;21(9):1062-8. doi: 10.1038/ajh.2008.233. Epub 2008 Jul 17. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine
- Specific Function
- adenylate cyclase binding
- Gene Name
- ADRB2
- Uniprot ID
- P07550
- Uniprot Name
- Beta-2 adrenergic receptor
- Molecular Weight
- 46458.32 Da
References
- Hayashi T, Juliet PA, Miyazaki-Akita A, Funami J, Matsui-Hirai H, Fukatsu A, Iguchi A: beta1 antagonist and beta2 agonist, celiprolol, restores the impaired endothelial dependent and independent responses and decreased TNFalpha in rat with type II diabetes. Life Sci. 2007 Jan 16;80(6):592-9. Epub 2006 Dec 1. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. Beta-3 is involved in the regulation of lipolysis and thermogenesis
- Specific Function
- beta-3 adrenergic receptor binding
- Gene Name
- ADRB3
- Uniprot ID
- P13945
- Uniprot Name
- Beta-3 adrenergic receptor
- Molecular Weight
- 43518.615 Da
References
- Nawarskas JJ, Cheng-Lai A, Frishman WH: Celiprolol: A Unique Selective Adrenoceptor Modulator. Cardiol Rev. 2017 Sep/Oct;25(5):247-253. doi: 10.1097/CRD.0000000000000159. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
- Specific Function
- alpha-1B adrenergic receptor binding
- Gene Name
- ADRA2A
- Uniprot ID
- P08913
- Uniprot Name
- Alpha-2A adrenergic receptor
- Molecular Weight
- 50646.17 Da
References
- Nawarskas JJ, Cheng-Lai A, Frishman WH: Celiprolol: A Unique Selective Adrenoceptor Modulator. Cardiol Rev. 2017 Sep/Oct;25(5):247-253. doi: 10.1097/CRD.0000000000000159. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phentolamine > mianserine > spiperone > prazosin > alprenolol > propanolol > pindolol
- Specific Function
- alpha2-adrenergic receptor activity
- Gene Name
- ADRA2B
- Uniprot ID
- P18089
- Uniprot Name
- Alpha-2B adrenergic receptor
- Molecular Weight
- 49953.145 Da
References
- Nawarskas JJ, Cheng-Lai A, Frishman WH: Celiprolol: A Unique Selective Adrenoceptor Modulator. Cardiol Rev. 2017 Sep/Oct;25(5):247-253. doi: 10.1097/CRD.0000000000000159. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins
- Specific Function
- alpha-2A adrenergic receptor binding
- Gene Name
- ADRA2C
- Uniprot ID
- P18825
- Uniprot Name
- Alpha-2C adrenergic receptor
- Molecular Weight
- 49521.585 Da
References
- Nawarskas JJ, Cheng-Lai A, Frishman WH: Celiprolol: A Unique Selective Adrenoceptor Modulator. Cardiol Rev. 2017 Sep/Oct;25(5):247-253. doi: 10.1097/CRD.0000000000000159. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of fatty acids, steroids and retinoids (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:19965576, PubMed:20972997). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 20-hydroxyeicosatetraenoic acid ethanolamide (20-HETE-EA) and 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:18698000, PubMed:21289075). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Catalyzes the oxidative transformations of all-trans retinol to all-trans retinal, a precursor for the active form all-trans-retinoic acid (PubMed:10681376). Also involved in the oxidative metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants
- Specific Function
- anandamide 11,12 epoxidase activity
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Sternieri E, Coccia CP, Pinetti D, Guerzoni S, Ferrari A: Pharmacokinetics and interactions of headache medications, part II: prophylactic treatments. Expert Opin Drug Metab Toxicol. 2006 Dec;2(6):981-1007. doi: 10.1517/17425255.2.6.981 . [Article]
- Brodde OE, Kroemer HK: Drug-drug interactions of beta-adrenoceptor blockers. Arzneimittelforschung. 2003;53(12):814-22. [Article]
- Iwaki M, Niwa T, Bandoh S, Itoh M, Hirose H, Kawase A, Komura H: Application of substrate depletion assay to evaluation of CYP isoforms responsible for stereoselective metabolism of carvedilol. Drug Metab Pharmacokinet. 2016 Dec;31(6):425-432. doi: 10.1016/j.dmpk.2016.08.007. Epub 2016 Sep 2. [Article]
Drug created at October 18, 2007 15:59 / Updated at June 19, 2021 00:26