51781-06-7

Basic information

• Product Name: 5-[3-(tert-Butylamino)-2-hydroxypropoxy]-3,4-dihydro-1H-quinolin-2-one
• 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 NO: 51781-06-7
• Molecular Formula: C₁₆H₂₄N₂O₃
• Molecular Weight: 292.37
• Mol File: 51781-06-7.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 434.3°C (rough estimate)
• Flash Point: 267.4 °C
• Appearance: /
• Density: 1.0574 (rough estimate)
• Refractive Index: 1.5800 (estimate)
• PKA: 13.84±0.20(Predicted)
• CAS DataBase Reference: 5-[3-(tert-Butylamino)-2-hydroxypropoxy]-3,4-dihydro-1H-quinolin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5-[3-(tert-Butylamino)-2-hydroxypropoxy]-3,4-dihydro-1H-quinolin-2-one(51781-06-7)
• EPA Substance Registry System: 5-[3-(tert-Butylamino)-2-hydroxypropoxy]-3,4-dihydro-1H-quinolin-2-one(51781-06-7)

Safety Data

• Hazardous Substances Data: 51781-06-7(Hazardous Substances Data)

Usage

Originator

Mikelan,Otsuka,Japan,1981

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

InChI:InChI=1/C16H24N2O3/c1-16(2,3)17-9-11(19)10-21-14-6-4-5-13-12(14)7-8-15(20)18-13/h4-6,11,17,19H,7-10H2,1-3H3,(H,18,20)

Upstream product

• 51781-21-6 carteolol hydrochloride 

Downstream Products

• 75331-19-0 -(+)-carteolol 
• 81102-77-4 -(-)-carteolol 

Relevant articles and documents

COMPOSITIONS AND METHODS FOR DIAGNOSING AND TREATING SALT SENSITIVITY OF BLOOD PRESSURE

To characterize the urinary exosome miRNome, microarrays were used to identify the miRNA spectrum present within urinary exosomes from ten individuals that were previously classified for their salt sensitivity status. The present application discloses distinct patterns of selected exosomal miRNA expression that were different between salt-sensitive (SS), salt-resistant (SR), and inverse salt-sensitive (ISS) individuals. These miRNAs can be useful as biomarkers either individually or as panels comprising multiple miRNAs. The present invention provides compositions and methods for identifying, diagnosing, monitoring, and treating subjects with salt sensitivity of blood pressure. The applications discloses panels of miRNAs useful for comparing profiles, and in some cases one or more of the miRNAs in a panel can be used. The miRNAs useful for distinguishing SS and SR or ISS and SR subjects. One or more of the 45 miRNAs can be used. Some of the miRNAs have not been previously reported to be circulating. See those miRNAs with asterisks in FIG. 1 and below. The present invention encompasses the use of one or more of these markers for identifying and diagnosing SR, SS, and ISS subjects.

Designing dendrimers for ocular drug delivery

New series of phosphorus-containing dendrimers, having one quaternary ammonium salt as core and carboxylic acid terminal groups have been synthesized from generation 0 (3 carboxylic acid terminal groups) to generation 2 (12 carboxylic acid terminal groups). These dendrimers react with the neutral form of carteolol (an ocular anti-hypertensive drug used to treat glaucoma) to afford ion pair (saline) species. The solubility in water of these charged dendrimers depends on the generation considered: generation 0 (3 carteolol) is well soluble, whereas generation 1 (6 carteolol) and generation 2 (12 carteolol) are poorly soluble. These dendrimers have been tested in vivo, as vehicle for ocular drug delivery of carteolol to rabbits.

ANTIHYPERTENSIVE THERAPY

A new use of darusentan is provided in preparation of a pharmaceutical composition for lowering blood pressure in a patient exhibiting resistance to a baseline antihypertensive therapy with one or more drugs. The composition comprises darusentan in an amount providing a therapeutically effective daily dose; wherein (a) the composition is orally deliverable and/or (b) the daily dose of darusentan is effective to provide a reduction of at least about 3 mmHg in one or more blood pressure parameters selected from trough sitting systolic, trough sitting diastolic, 24-hour ambulatory systolic, 24-hour ambulatory diastolic, maximum diurnal systolic and maximum diurnal diastolic blood pressures. Further provided is a new use of darusentan in preparation of a pharmaceutical composition for lowering blood pressure in a patient exhibiting resistance to a baseline antihypertensive therapy, wherein the composition is administered adjunctively with at least one diuretic and at least one antihypertensive drug selected from ACE inhibitors, angiotensin II receptor blockers, beta-adrenergic receptor blockers and calcium channel blockers.