Celiprolol hydrochloride

Base Information

• Chemical Name: Celiprolol hydrochloride
• CAS No.: 57470-78-7
• Molecular Formula: C20H33N3O4^.HCl
• Molecular Weight: 415.961
• European Community (EC) Number: 260-752-2
• NSC Number: 324509
• UNII: G1M3398594
• DSSTox Substance ID: DTXSID0046850
• Wikidata: Q27278610
• NCI Thesaurus Code: C81655
• ChEMBL ID: CHEMBL1742424
• Mol file: 57470-78-7.mol

Synonyms:Celiprolol;Celiprolol Hydrochloride;Celiprolol Monohydrochloride;Celiprolol, (+,-)-Isomer;Celiprolol, (R)-Isomer;Celiprolol, (S)-Isomer;Celiprolol, Monohydrochloride, (R)-Isomer;Celiprolol, Monohydrochloride, (S)-Isomer;Hydrochloride, Celiprolol;Monohydrochloride, Celiprolol;N'-(3-Acetyl-4-(3-((1,1-dimethylethyl)amino)-2-hydroxypropoxy)phenyl)-N,N-diethylurea;REV 5320A;REV-5320A;REV5320A;Selectol;ST 1396;ST-1396;ST1396

Chemical Property of Celiprolol hydrochloride

Chemical Property:

• Appearance/Colour: White crystalline solid
• Vapor Pressure: 1.34E-14mmHg at 25°C
• Melting Point: 197-200 °C (dec.)
• Boiling Point: 586.5 °C at 760 mmHg
• Flash Point: 308.5 °C
• PSA: 90.90000
• Density: 1.114g/cm3
• LogP: 4.15660
• Storage Temp.: Refrigerator
• Solubility.: Freely soluble in water and in methanol, soluble in ethanol (96 per cent), very slightly soluble in methylene chloride.
• Water Solubility.: Soluble in ethanol, methanol and water
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 415.2237843
• Heavy Atom Count: 28
• Complexity: 474

Purity/Quality:

99% ^*data from raw suppliers

Celiprolol hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN(CC)C(=O)NC1=CC(=C(C=C1)OCC(CNC(C)(C)C)O)C(=O)C.Cl
• Recent EU Clinical Trials: Proof of concept study to assess the differential effects of chronic beta-blockade (celiprolol versus bisoprolol) on cardiopulmonary outcomes at rest and during exercise in chronic obstructive pulmonary disease.
• Description: Celiprolol hydrochloride is a once-daily, cardioselective β-adrenergic blocker useful in the management of hypertension, angina pectoris and hyperkinetic heart syndrome. It is also being evaluated in glaucoma.
• Uses: Cardioselective 1-adrenergic blocker. Antihypertensive, antianginal antihypertensive antianginal;beta blocker
• Clinical Use: #N/A
• Drug interactions: Potentially hazardous interactions with other drugsAnaesthetics: enhanced hypotensive effect.Analgesics: NSAIDs antagonise hypotensive effect.Anti-arrhythmics: increased risk of myocardial depression and bradycardia; increased risk of bradycardia, myocardial depression and AV block with amiodarone; increased risk of myocardial depression and bradycardia with flecainideAntidepressants: enhanced hypotensive effect with MAOIs.Antihypertensives; enhanced hypotensive effect; increased risk of withdrawal hypertension with clonidine; increased risk of first dose hypotensive effect with post-synaptic alpha-blockers such as prazosin.Antimalarials: increased risk of bradycardia with mefloquine.Antipsychotics enhanced hypotensive effect with phenothiazines.Calcium-channel blockers: increased risk of bradycardia and AV block with diltiazem; hypotension and heart failure possible with nifedipine and nisoldipine; asystole, severe hypotension and heart failure with verapamil.Cytotoxics: possible increased risk of bradycardia with crizotinib.Diuretics: enhanced hypotensive effect.Fingolimod: possibly increased risk of bradycardia.Moxisylyte: possible severe postural hypotension.Sympathomimetics: severe hypertension with adrenaline and noradrenaline and possibly with dobutamine.

Technology Process of Celiprolol hydrochloride

There total 11 articles about Celiprolol hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 81.3%

celiprolol (56980-93-9) → (+/-)-celiprolol hydrochloride (57470-78-7)

Guidance literature:

With hydrogenchloride; In acetone; pH=5.5 - 6;

DOI:10.3184/174751911X13192995267028

Reference yield:

4-nitrophenol acetate (830-03-5) → (+/-)-celiprolol hydrochloride (57470-78-7)

Guidance literature:

Multi-step reaction with 6 steps

1: aluminum (III) chloride / nitrobenzene / 6.5 h / 20 - 140 °C

2: potassium carbonate; N-benzyl-N,N,N-triethylammonium chloride / 10 h / 75 °C

3: water / 12 h / 20 °C

4: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 1034.32 Torr

5: triethylamine / tetrahydrofuran / 48 h / 40 °C

6: hydrogenchloride / acetone / 1.5 h / 20 °C / pH 5.5 - 6

With hydrogenchloride; aluminum (III) chloride; palladium 10% on activated carbon; N-benzyl-N,N,N-triethylammonium chloride; hydrogen; potassium carbonate; triethylamine; In tetrahydrofuran; methanol; water; nitrobenzene; acetone;

DOI:10.1021/op000297l

Reference yield:

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) → (+/-)-celiprolol hydrochloride (57470-78-7)

Guidance literature:

Multi-step reaction with 7 steps

1: sodium hydroxide / water / 0.17 h / 90 - 95 °C

2: aluminum (III) chloride / nitrobenzene / 6.5 h / 20 - 140 °C

3: potassium carbonate; N-benzyl-N,N,N-triethylammonium chloride / 10 h / 75 °C

4: water / 12 h / 20 °C

5: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 1034.32 Torr

6: triethylamine / tetrahydrofuran / 48 h / 40 °C

7: hydrogenchloride / acetone / 1.5 h / 20 °C / pH 5.5 - 6

With hydrogenchloride; aluminum (III) chloride; palladium 10% on activated carbon; N-benzyl-N,N,N-triethylammonium chloride; hydrogen; potassium carbonate; triethylamine; sodium hydroxide; In tetrahydrofuran; methanol; water; nitrobenzene; acetone;

DOI:10.1021/op000297l

upstream raw materials:

4-(3,3-diethylureido)phenyl acetate

3-(3-Acetyl-4-hydroxy-phenyl)-1,1-diethylharnstoff

celiprolol

4-chlorobenzonitrile

Refernces

• 1、 Joshi, Ramesh A.,Gurjar, Mukund K.,Tripathy, Narendra K.,Chorghade, Mukund S.. "A new and improved process for celiprolol hydrochloride". . p. 176 - 178. Retrieved 2013/09/07.