Celiprolol hydrochloride Chemical Properties

Melting point:

197-200°C (dec.)

RTECS 

YR6560000

storage temp. 

Refrigerator

solubility 

Freely soluble in water and in methanol, soluble in ethanol (96 per cent), very slightly soluble in methylene chloride.

color 

White to Off-White

Water Solubility 

Soluble in ethanol, methanol and water

CAS DataBase Reference

57470-78-7(CAS DataBase Reference)

Safety Information

Toxicity

LD50 in male mice, rats (mg/kg): 56.2, 68.3 i.v.; 1834, 3826 orally (Wendtlandt, Pittner)

Celiprolol hydrochloride Usage And Synthesis

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.

Chemical Properties

White Crystalline Solid

Originator

Chemie Linz (Austria)

Uses

Cardioselective 1-adrenergic blocker. Antihypertensive, antianginal

Uses

Cardioselective β1-adrenergic blocker. Antihypertensive, antianginal.

Uses

antihypertensive antianginal;beta blocker

Definition

ChEBI: Celiprolol hydrochloride is an aromatic ketone.

brand name

Selecor (Rhone-Poulenc Rorer);SELECTOL.

in vitro

the ability of celiprolol to induce the regulation of beta adrenergic receptors was investigated in s49 lymphoma cells. results showed that celiprolol did not stimulate adenylate cyclase in membranes from wild-type (wt) s49 cells or induced the sequestration of beta adrenergic receptors on intact cells. moreover, exposure of wt s49 cells to celiprolol led to the loss of around half of the total cellular beta adrenergic receptors [1].

in vivo

in a previous study, japanese white rabbits underwent 30 min of ischemia and 48 h of reperfusion. celiprolol was administered 20 min before ischemia with or without pretreatment with n(omega)-nitro-l-arginine methylester (l-name) or 5-hydroxydecanoic acid sodium salt (5-hd). results showed that celiprolol could significantly reduce the infarct size dose-dependently. the infarct size-reducing effect of celiprolol was found to be completely blocked by l-name but not by 5-hd. in addition, celiprolol could increase the myocardial interstitial levels of nox and reduce the intensity of myocardium staining [2].

Drug interactions

Potentially hazardous interactions with other drugs
Anaesthetics: 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 flecainide
Antidepressants: 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.

Metabolism

Metabolism of celiprolol is minimal and it is mainly excreted unchanged in the urine (50%) and faeces (50%)

References

[1] reynolds ee, molinoff pb. down regulation of beta adrenergic receptors in s49 lymphoma cells induced by atypical agonists. j pharmacol exp ther. 1986 dec;239(3):654-60.
[2] chen, x. ,minatoguchi, s.,arai, m., et al. celiprolol, a selective β1-blocker, reduces the infarct size through production of nitric oxide in a rabbit model of myocardial infarction. circulation journal 71(4), 574-579 (2007).
[3] ong kt et al. 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.

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