Nadolol

Bezeichnung:Nadolol

CAS-Nr42200-33-9

Englisch Name:NADOLOL

CBNumberCB2494641

SummenformelC17H27NO4

Molgewicht309.4

MOL-Datei42200-33-9.mol

Synonyma

Nadolol

Nadolol physikalisch-chemischer Eigenschaften

Schmelzpunkt	125-130°C
Siedepunkt	449.67°C (rough estimate)
Dichte	1.0449 (rough estimate)
Brechungsindex	1.5420 (estimate)
storage temp.	Refrigerator
Löslichkeit	Slightly soluble in water, freely soluble in ethanol (96 per cent), practically insoluble in acetone.
pka	9.67(at 25℃)
Aggregatzustand	Solid
Farbe	White to Off-White
Wasserlöslichkeit	8.30g/L(25 ºC)
BCS Class	3
EPA chemische Informationen	2,3-Naphthalenediol, 5-[3-[(1,1-dimethylethyl)amino]-2-hydroxypropoxy]-1,2,3,4-tetrahydro- (42200-33-9)

Sicherheit

WGK Germany	2
RTECS-Nr.	QJ4870000
HS Code	2922190900
Giftige Stoffe Daten	42200-33-9(Hazardous Substances Data)
Toxizität	LD50 in mice, rats (mg/kg): 4500, 5300 orally (Antonaccio, Evans)

Gefahreninformationscode (GHS)

NADOLOL Chemische Eigenschaften,Einsatz,Produktion Methoden

Chemische Eigenschaften
White Solid
Originator
Solgol,Heyden,W. Germany,1978
Verwenden
CNS stimulant
Verwenden
Labeled Nadolol, intended for use as an internal standard for the quantification of Nadolol by GC- or LC-mass spectrometry.
Verwenden
Labelled Nadolol (N201052). β-Adrenergic
Manufacturing Process
(a) cis-5,6,7,8-Tetrahydro-1,6,7-naphthalenetriol: A solution of 29.2 g (0.2 mol) of 5,8-dihydro-1-naphthol and 40 ml of acetic anhydride in 100 ml of pyridine is prepared. After 16 hours the solvent is removed in vacuo and the residue dissolved in ether and washed with 200 ml of 5% hydrochloric acid, water, 200 ml of 10% sodium hydroxide, saturated salt solution and dried. Solvent removal gives 34.2 g (90.5%) of crude acetate which is dissolved in 900 ml of acetic acid and 36 ml of water. 53.3 g (0.32 mol) of silver acetate is added followed by 40.6 g (0.16 g-atom) of iodine. The slurry is heated with good stirring at 85°10°C for 3 hours under nitrogen, cooled and filtered. The filtrate is evaporated in vacuo and the residue dissolved in 250 ml of methanol and cooled to 0°C.
A solution of 40 g of sodium hydroxide in 200 ml of water is added under nitrogen and the mixture stirred overnight. The bulk of the methanol is removed in vacuo whereupon a solid forms. The solid is separated by filtration, dissolved in 150 ml of water and acidified with 20 ml of concentrated hydrochloric acid. Cooling gives a solid which is filtered and dried to give 16.5 g cis-5,6,7,8-tetrahydro-1,6,7-naphthalenetriol, melting point 184.5°C to 187°C. Three recrystallizations from absolute ethanol give the analytical sample, melting point 188°C to 188.5°C.
(b) 2,3-cis-1,2,3,4-Tetrahydro-5-[2,3-(epoxy)-propoxy]-2,3-naphthalenediol: A solution of 1.20 g (0.03 mol) of sodium methoxide and 5.4 g (0.03 mol) of cis-5,6,7,8-tetrahydro-1,6,7-naphthalenetriol in 200 ml of methanol is prepared under nitrogen. The residue obtained upon solvent removal is stirred overnight with 200 ml of dimethylsulfoxide and 4.65 g (0.05 mol) of epichlorohydrin under nitrogen. The bulk of the solvent is removed at 50°C at 0.1 mm and the residue dissolved in 100 ml of water. Extraction with chloroform (10 x 200 ml) gives a solid which is recrystallized from 150 ml of hexane-ethyl acetate to give epoxy diol of the above title.
(c)2,3-cis-1,2,3,4-Tetrahydro-5-[2-hydroxy-3-(tert-butylamino)propoxy]-2,3- naphthalenediol: A mixture of 2,3-cis-1,2,3,4-tetrahydro-5-[2,3- (epoxy)propoxy]-2,3-naphthalenediol (melting point 104°C to 107°C, one spot on TLC-alumina, 5% methanol in chloroform, iodine visualization) and 22 ml of tert-butylamine is heated at 85°C to 95°C for 15 hours in a Parr bomb and the excess amine removed in vacuo. The solid obtained by trituration of the residue with ether is filtered and recrystallized from benzene to give 3.4 g, melting point 124°C to 136°C.
Trademarks
Corgard (King).
Therapeutic Function
Antiarrhythmic
Clinical Use
Beta-adrenoceptor blocker:
Hypertension
Angina
Arrhythmias
Migraine
Thyrotoxicosis
Arzneimittelwechselwirkung
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.
Stoffwechsel
Nadolol (Corgard) is slowly and incompletely absorbed from the gastrointestinal tract, and only 30% of an orally administered dose is absorbed. Appreciable metabolism does not seem to occur; nadolol is excreted primarily unchanged in the urine and feces.The plasma half-life is quite long, approaching 24 hours, which permits dosing once per day.

NADOLOL Upstream-Materialien And Downstream Produkte

Nadolol Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

42200-33-9, NADOLOL Verwandte Suche:

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