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Carteolol

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Carteolol Basic information

Product Name:
Carteolol
Synonyms:
  • 2(1H)-QUINOLINONE, 5-[3-[(1,1-DIMETHYLETHYL)AMINO]-2-HYDROXYPROPOXY]-3,4-DIHYDRO-
  • Carteolol
  • 2(H)-Quinolinone, 5-[3-[(1,1-dimethylethyl)amino]-2-hydroxypropoxy]-3,4-dihydro-
  • dl-Carteolol
  • Carteolol (base and/or unspecified salts)
  • 5-[3-(tert-Butylamino)-2-hydroxypropoxy]-3,4-dihydro-1H-quinolin-2-one
  • 5-(2-Hydroxy-3-tert-butylaminopropoxy)-3,4-dihydro-2(1H)-quinolone
  • 5-[3-(tert-Butylamino)-2-hydroxypropoxy]-3,4-dihydrocarbostyril
CAS:
51781-06-7
MF:
C16H24N2O3
MW:
292.37
Mol File:
51781-06-7.mol
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Carteolol Chemical Properties

Boiling point:
434.3°C (rough estimate)
Density 
1.0574 (rough estimate)
refractive index 
1.5800 (estimate)
pka
13.84±0.20(Predicted)
CAS DataBase Reference
51781-06-7
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Carteolol Usage And Synthesis

Originator

Mikelan,Otsuka,Japan,1981

Uses

Antiadrenergic (β-receptor).

Definition

ChEBI: Carteolol is a quinolone and a secondary alcohol. It has a role as a beta-adrenergic antagonist, an antihypertensive agent, an antiglaucoma drug, an anti-arrhythmia drug and a sympatholytic agent. It is a conjugate base of a carteolol(1+).

Manufacturing Process

A mixture of 1.63 g of 5-hydroxy-3,4-dihydrocarbostyril, 2.5 g of epibromohydrin and 2 drops of piperidine was heated at a temperature of 95°C to 100°C for a period of 4 hours with stirring. The reaction mixture was then concentrated to dryness under reduced pressure and the residue was recrystallized from acetone to obtain 1.2 g of 5-(2,3-epoxy)propoxy-3,4- dihydrocarbostyril as a colorless powder having a melting point of 172°C to 173°C.
A mixture of 0.75 g of 5-(2,3-epoxy)propoxy-3,4-dihydrocarbostyril, 1.0 g of tert-butylamine and 25 ml of ethanol was stirred at a temperature of from 50°C to 55°C for a period of 4 hours. Ethanol and unreacted tert-butylamine were distilled off under reduced pressure and the resulting residue was dissolved in acetone.

brand name

Cartrol (Abbott); Ocupress (Novartis).

Therapeutic Function

Beta-adrenergic blocker

Contact allergens

Carteolol was implicated in allergic contact dermatitis due to beta-blockers agents in eye-drops. It seems that this molecule can be safely used in some patients with hypersensitivity to other topical beta-blockers agents.

Veterinary Drugs and Treatments

Carteolol HCl is a nonspecific beta adrenergic blocking agent and it reduces aqueous humor production by decreasing cyclic-AMP synthesis in the ciliary body. Carteolol is a suitable substitute for timolol maleate or any of the other beta blocking agents although it is rarely used in veterinary medicine. In humans, similar IOP reducing effects have been shown for all members of this class. Substitutes are necessary when one particular product induces topical irritation upon application. As noted above, beta blocking agents seem to be particularly useful in the management of primary glaucoma in cats.

Metabolism

Carteolol (Cartrol) is a long-acting -blocker that is suitable for dosing once per day. It is almost completely absorbed and exhibits about 30% binding to plasma proteins. Unlike many -blockers, carteolol is not extensively metabolized. Up to

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