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
Show more names
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
- Formal charge
- 0
- Complexity
- 354
Experimental & physicochemical properties
LogP
1.1
1.49
Human Drugs
Breast Feeding; Lactation; Milk, Human; Adrenergic Beta-Antagonists; Antiglaucoma Agents
Pharmaceuticals
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
- ATC code
- 7 AA15,S01ED05,S01ED55 · C07AA15,S01ED05,S01ED55
Safety & regulation
Toxicology
Chemistry & industry
Pharmacology
ATC Code
S01ED05
C - Cardiovascular system
S - Sensory organs
QS - Sensory organs
QC - Cardiovascular system
Pharmacodynamics
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
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.
FDA Pharmacological Classification
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
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
Applications
UsesAntiadrenergic (β-receptor).
Upstream & downstream products
Upstream raw materials
Suppliers9 total
Additional notes
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
No reaction records under the current filter.
Compound notes
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