Carteolol

HCID 2583

Basic information

CAS
51781-06-7
Standard SMILES
CC(C)(C)NCC(O)COc1cccc2c1CCC(=O)N2
InChIKey
LWAFSWPYPHEXKX-UHFFFAOYSA-N
Molecular formula
C16H24N2O3
Average molar mass
292.37 g/mol
Monoisotopic mass
292.17869263

Overview

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

Names & identifiers

Preferred name
Carteolol
IUPAC
5-[3-(tert-butylamino)-2-hydroxypropoxy]-3,4-dihydro-1H-quinolin-2-one
English name
Carteolol
Molecular formula
C16H24N2O3
Molecular weight
292.37

Names & synonyms

CARTEOLOL51781-06-7Carteololum8NF31401XG2(1H)-Quinolinone, 5-(3-((1,1-dimethylethyl)amino)-2-hydroxypropoxy)-3,4-dihydro-CHEBI:3437DTXSID30227465-[3-(tert-butylamino)-2-hydroxypropoxy]-1,2,3,4-tetrahydroquinolin-2-onecarteololo5-(3-(tert-butylamino)-2-hydroxypropoxy)-3,4-dihydroquinolin-2-ol5-[3-(tert-butylamino)-2-hydroxypropoxy]-3,4-dihydroquinolin-2-ol5-(3-(tert-butylamino)-2-hydroxypropoxy)-1,2,3,4-tetrahydroquinolin-2-one
Show more names
C06874dl-CarteololCarteolol USP/EP/BPCarteolol Impurities1808Carteolol (base and/or unspecified salts)5-[3-(tert-Butylamino)-2-hydroxypropoxy]-3,4-dihydrocarbostyril5-(2-Hydroxy-3-tert-butylaminopropoxy)-3,4-dihydro-2(1H)-quinolone5-[3-(tert-Butylamino)-2-hydroxypropoxy]-3,4-dihydroquinolin-2(1H)-one
RefChem:58563DTXCID202746C07AA15S01ED05Carteololum [INN-Latin]5-(3-(tert-Butylamino)-2-hydroxypropoxy)-3,4-dihydroquinolin-2(1H)-one5-[3-(tert-butylamino)-2-hydroxypropoxy]-3,4-dihydro-1H-quinolin-2-oneCarteolol (INN)

Database identifiers

CAS
51781-06-7
PubChem CID
2583
DTXSID
DTXSID3022746
ChEMBL
CHEMBL839
ChEBI
CHEBI:3437
UNII
8NF31401XG
Nikkaji
J13.087G

Properties

Computed structural properties

XLogP
1
Topological polar surface area
70.6 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
4
Rotatable bonds
6
Heavy atoms
21

Experimental & physicochemical properties

LogP · 2 items

1.1

1.49

Solubility4.21e-01 g/L
Human Drugs · 2 items

Breast Feeding; Lactation; Milk, Human; Adrenergic Beta-Antagonists; Antiglaucoma Agents

Pharmaceuticals

Physical DescriptionSolid

Physicochemical properties

Boiling point
434.3 °C · 434.3°C (rough estimate)
Density
1.0574 · 1.0574 (rough estimate)
refractive index
1.58 · 1.5800 (estimate)
pka
13.84 · 13.84±0.20(Predicted)
CAS DataBase Reference
51781 · 51781-06-7
FDA UNII
8 NF31401XG · 8NF31401XG

Safety & regulation

Toxicology

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Chemistry & industry

Pharmacology

ATC Code · 5 items

S01ED05

C - Cardiovascular system

S - Sensory organs

QS - Sensory organs

QC - Cardiovascular system

Pharmacodynamics · 1 item

Carteolol is a beta1 and beta2 (non-selective) adrenergic receptor-blocking agent that does not have significant intrinsic sympathomimetic, direct myocardial depressant, or local anesthetic (membrane-stabilizing) activity. Carteolol, when applied topically to the eye, has the action of reducing elevated, as well as normal, intraocular pressure, whether or not accompanied by glaucoma. Elevated intraocular pressure is a major risk factor in the pathogenesis of glaucomatous visual field loss and optic nerve damage. Carteolol reduces intraocular pressure with little or no effect on pupil size or accommodation in contrast to the miosis which cholinergic agents are known to produce.

Mechanism of Action · 1 item

The primary mechanism of the ocular hypotensive action of carteolol in reducing intraocular pressure is most likely a decrease in aqueous humor production. This process is initiated by the non-selective beta1 and beta2 adrenergic receptor blockade.

Metabolism/MetabolitesHepatic.
FDA Pharmacological Classification · 5 items

8NF31401XG

CARTEOLOL

Mechanisms of Action [MoA] - Adrenergic beta-Antagonists

Established Pharmacologic Class [EPC] - beta-Adrenergic Blocker

Carteolol is a beta-Adrenergic Blocker. The mechanism of action of carteolol is as an Adrenergic beta-Antagonist.

MeSH Pharmacological Classification · 4 items

Drugs that bind to but do not activate beta-adrenergic receptors thereby blocking the actions of beta-adrenergic agonists. Adrenergic beta-antagonists are used for treatment of hypertension, cardiac arrhythmias, angina pectoris, glaucoma, migraine headaches, and anxiety.

Agents used for the treatment or prevention of cardiac arrhythmias. They may affect the polarization-repolarization phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibers. Anti-arrhythmia agents are often classed into four main groups according to their mechanism of action: sodium channel blockade, beta-adrenergic blockade, repolarization prolongation, or calcium channel blockade.

Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS.

Drugs that inhibit the actions of the sympathetic nervous system by any mechanism. The most common of these are the ADRENERGIC ANTAGONISTS and drugs that deplete norepinephrine or reduce the release of transmitters from adrenergic postganglionic terminals (see ADRENERGIC AGENTS). Drugs that act in the central nervous system to reduce sympathetic activity (e.g., centrally acting alpha-2 adrenergic agonists, see ADRENERGIC ALPHA-AGONISTS) are included here.

Uses & manufacturing

Use ClassificationPharmaceuticals

Applications

UsesAntiadrenergic (β-receptor).

Upstream & downstream products

Suppliers9 total

北京华美互利生物化工010-56205725 · [email protected]
銳迪國際科技有限公司18024082417 · [email protected]
南京生利德生物科技有限公司025-57798810 18652991625 · [email protected]
南京伶亚生物医药科技有限公司18068075658 · [email protected]
深圳市华信医药科技有限公司15671363360 · [email protected]
Additional notes · 1 item

DefinitionChEBI: 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+).

Related reactions

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Compound notes

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