51781-21-6

Basic information

• Product Name: 2(1H)-QUINOLINONE, 5-[3-[(1,1-DIMETHYLETHYL)AMINO]-2-HYDROXYPROPOXY]-3,4-DIHYDRO-, MONOHYDROCHLORIDE
• Synonyms: 5-(2-hydroxy-3-tert-butylamino)propoxy-3,4-dihydrocarbostyrilhydrochloride;5-(3-((1,1-dimethylethyl)amino)-2-hydroxypropoxy)-3,4-dihydro-2(1h)-quinolin;5-(3-tert-butylamino-2-hydroxy)propoxy-3,4-dihydrocarbostyrilhydrochloride;5-(3-tert-butylamino-2-hydroxy-propoxy)-3,4-dihydro-2(1h)-chinolinon-hydroch;abbott-43326;carbonolol;carteololhydrochloride;endak
• CAS NO: 51781-21-6
• Molecular Formula: C₁₆H₂₄N₂O₃*ClH
• Molecular Weight: 328.83
• EINECS: 257-415-7
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;CARTROL;API
• Mol File: 51781-21-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: 278°C
• Boiling Point: 518.6°Cat760mmHg
• Flash Point: 267.4°C
• Appearance: /
• Density: 1.13g/cm³
• Vapor Pressure: 1.4E-11mmHg at 25°C
• Storage Temp.: Refrigerator
• Solubility: Soluble in water, sparingly soluble in methanol, slightly soluble in ethanol 96 per cent, practically insoluble in methylene chloride.
• Merck: 14,1866
• CAS DataBase Reference: 2(1H)-QUINOLINONE, 5-[3-[(1,1-DIMETHYLETHYL)AMINO]-2-HYDROXYPROPOXY]-3,4-DIHYDRO-, MONOHYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2(1H)-QUINOLINONE, 5-[3-[(1,1-DIMETHYLETHYL)AMINO]-2-HYDROXYPROPOXY]-3,4-DIHYDRO-, MONOHYDROCHLORIDE(51781-21-6)
• EPA Substance Registry System: 2(1H)-QUINOLINONE, 5-[3-[(1,1-DIMETHYLETHYL)AMINO]-2-HYDROXYPROPOXY]-3,4-DIHYDRO-, MONOHYDROCHLORIDE(51781-21-6)

Safety Data

• RTECS: VC8282000
• Hazardous Substances Data: 51781-21-6(Hazardous Substances Data)

Usage

Chemical Properties

Crystalline Solid

Uses

Different sources of media describe the Uses of 51781-21-6 differently. You can refer to the following data:
1. -Adrenergic blocker. Antihypertensive; antianginal; antiarrhythmic; antiglaucoma
2. β-Adrenergic blocker. Antihypertensive; antianginal; antiarrhythmic; antiglaucoma.
3. beta-adrenergic blocker

Biological Activity

beta-adrenergic antagonist are an important class of drugs for the treatment of various heart diseases, such as high blood pressure, insufficiency of blood flow to the heart muscle, irregular heart beat, thickened heart muscle, and decreased ability of the heart to empty or fill normally. β-blockers can also be used to treat migraine headache and increased eye pressure (glaucoma). carteolol is a nonselective beta-adrenoceptor antagonist.

in vitro

previous findings demonstrate that carteolol, unlike xamoterol, is a nonconventional partial agonist, which causes agonistic effects via interaction with the low-affinity propranolol-resistant site of β1-adrenoceptors and antagonistic actions by the high-affinity site of the same receptors [1].

in vivo

both 8-oh carteolol and carteolol suppressed the water-load induced intraocular pressure (iop) rise in rabbits. 8-oh carteolol was more effective in suppressing water-load induced iop rise in rabbits compared with carteolol on equimolar basis. both 8-oh carteololand carteolol caused a significant decrease in iop in monkeys. 8-oh carteolol was estimated to be more potent than carteolol in lowering iop on equimolar basis in monkeys [2].

references

[1] maura floreani, guglielmina froldi, luigi quintieri, katia varani, pier andrea borea, maria teresa dorigo and paola dorigo. in vitro evidence that carteolol is a nonconventional partial agonist of guinea pig cardiac β1-adrenoceptors: a comparison with xamoterol. jpet 315:1386–1395, 2005[2] sugiyama k, enya t, kitazawa y. ocular hypotensive effect of 8-hydroxycarteolol, a metabolite of carteolol. int ophthalmol. 1989 jan;13(1-2):85-9.[3] trinquand c, romanet jp, nordmann jp, allaire c; groupe d'étude. efficacy and safety of long-acting carteolol 1% once daily. a double-masked, randomized study. j fr ophtalmol. 2003 feb;26(2):131-6.

InChI:InChI=1/C16H24N2O3.ClH/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);1H

Upstream product

• 51781-14-7 5-(2,3-epoxypropoxy)-3,4-dihydro-2 (1H)-quinolone 
• 75-64-9 tert-butylamine 
• 51781-13-6 5-(3-chloro-2-hydroxypropoxy)-3,4-dihydrocarbostyril 

Downstream Products

• 59826-22-1 8-Hydroxycarteolol 
• 51781-06-7 carteolol 

Relevant articles and documents

Stable carteolol hydrochloride, preparation method thereof and eye medicine combination

The invention relates to stable carteolol hydrochloride, a preparation method thereof and an eye medicine combination, in particular to a method for preparing carteolol hydrochloride. The method comprises the following steps of preparing 3-amino-2-cyclohexenone, tetrahydro-2,5(1H, 6H)-quinolinone, 5-hydroxy-3,4-dihydro-2(1H)-carbostyril and 5-(2,3-epoxypropoxy)-3,4-dihydro-2(1H)-carbostyril, and then the carteolol hydrochloride is obtained. Furthermore, the invention provides the carteolol hydrochloride crude medicine obtained according to the method, the eye medicine combination prepared by using the obtained carteolol hydrochloride as the crude medicine, and applications of the obtained carteolol hydrochloride to preparation of drugs for treating or preventing glaucoma or ocular hypertension. The method has excellent pharmaceutical characteristics, for example, the obtained crude medicine and a preparation has excellent stability.

3,4-DIHYDROCARBOSTYRIL DERIVATIVES AND PROCESS FOR PRODUCING THE SAME

Novel compounds represented by the formula STR1 wherein R. sup.1, R. sup.2, and R' and R" are defined as hereinafter, having a blocking activity on β-adrenergic nerves, novel intermediates useful for synthesis thereof and processes for preparing the same are disclosed. When substitution is at the 5-position and R 1 and R 2 are hydrogen, R' and R" are not simultaneously hydrogen and a 1 to 4 carbon atom alkyl group in the claimed compound. "