Grundinformationen
- Standard-SMILES
CC(C)(C)NC[C@H](O)COc1cccc2c1CCCC2=O- InChIKey
IXHBTMCLRNMKHZ-LBPRGKRZSA-N- Summenformel
- C17H25NO3
- Durchschnittliche Molmasse
- 291,4 g/mol
- Monoisotopische Masse
- 291,18344366
Überblick
Levobunolol is a cyclic ketone that is 3,4-dihydronaphthalen-1-one substituted at position 5 by a 3-(tert-butylamino)-2-hydroxypropoxy group (the S-enantiomer). A non-selective beta-adrenergic antagonist used (as its hydrochloride salt) for treatment of glaucoma. It has a role as a beta-adrenergic antagonist and an antiglaucoma drug. It is a propanolamine, an aromatic ether and a cyclic ketone. It is a conjugate base of a levobunolol(1+). It derives from a hydride of a tetralin.
Namen und Bezeichner
- Bevorzugter Name
- Levobunolol
- IUPAC
- 5-[(2S)-3-(tert-butylamino)-2-hydroxypropoxy]-3,4-dihydro-2H-naphthalen-1-one
- Englischer Name
- LEVOBUNOLOL
- Summenformel
- C17H25NO3
- Molmasse
- 291.39
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
47141-42-4- PubChem CID
- 39468
- DTXSID
DTXSID1043833- ChEMBL
CHEMBL1201237- ChEBI
CHEBI:6438- UNII
- G6317AOI7K
- Nikkaji
- J237.992I
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 2,4
- Polarare Oberfläche (TPSA)
- 58,6 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 6
- Schwere Atome
- 21
- Formalladung
- 0
- Komplexität
- 350
Experimentelle und physikochemische Eigenschaften
Human Drugs
Breast Feeding; Lactation; Milk, Human; Antihypertensive Agents; Adrenergic Beta-Antagonists; Antiglaucoma Agents; Antiarrhythmics
Pharmaceuticals
Melting Point
209-211 °C
209 - 211 °C
Physikochemische Eigenschaften
- Schmelzpunkt
- 209 · 209-211°C
- storage temp.
- -20 °C · -20°C Freezer, Under Inert Atmosphere
- Major Application
- pharmaceutical (small molecule)
- InChI
- 1S/C17H25NO3/c1-17(2,3)18-10-12(19)11-21-16-9-5-6-13-14(16)7-4-8-15(13)20/h5-6,9,12,18-19H,4,7-8,10-11H2,1-3H3/t12-/m0/s1
- InChIKey
- IXHBTMCLRNMKHZ-LBPRGKRZSA-N
- SMILES
- N(C[C@H](O)COc1c2c(ccc1)C(=O)CCC2)C(C)(C)C
- CAS Datenbank
- 47141 · 47141-42-4(CAS DataBase Reference)
Sicherheit und Regulatorisches
Toxikologische Informationen
Sicherheitsdaten
- wgk
- WGK 3
- Toxizität
- LD50 in male, female rats, mice (mg/kg): 700, 800, 1530, 1220 orally; 25, 28, 78, 84 i.v.; LD50 in male, female hamsters, dogs (mg/kg): 435, 500, 100, 100 orally (Kaplan, 1980)
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Acute Tox. 4 Oral
Chemie und Industrie
Pharmakologische Informationen
ATC Code
S01ED03
S - Sensory organs
QS - Sensory organs
Pharmacodynamics
Levobunolol is an ophthalmic beta-blocker, equally effective at β(1)- and β(2)-receptor sites. Levobunolol reduces both elevated and normal IOP in patients with or without glaucoma. In patients with elevated IOP, levobunolol reduces mean IOP by approximately 25-40% from baseline. As the drug is a nonselective &beta-adrenergic blocking agent, it can produce both systemic pulmonary and cardiovascular effects following topical application to the eye. These effects include adverse pulmonary effects (eg. bronchoconstriction, increased airway resistance), and a decrease in blood pressure and heart rate.
Mechanism of Action
Levobunolol's mechanism of action in reducing IOP is not clearly defined, but is believed to be due to a reduction of the production of aqueous humor via blockage of endogenous catecholamine-stimulated increases in cyclic adenosine monophosphate (AMP) concentrations within the ciliary processes.
FDA Pharmacological Classification
G6317AOI7K
LEVOBUNOLOL
Mechanisms of Action [MoA] - Adrenergic beta-Antagonists
Established Pharmacologic Class [EPC] - beta-Adrenergic Blocker
Levobunolol is a beta-Adrenergic Blocker. The mechanism of action of levobunolol 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.
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.
Verwendung und Herstellung
Anwendungen
VerwendenAs a non-selective adrenoceptor antagonist, Levobunolol is used as an anticonvulsant.
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Anbieter14 Anbieter
Ergänzende Hinweise
DefinitionChEBI: A cyclic ketone that is 3,4-dihydronaphthalen-1-one substituted at position 5 by a 3-(tert-butylamino)-2-hydroxypropoxy group (the S-enantiomer). A non-selective beta-adrenergic antagonist used (as its hydrochlo ide salt) for treatment of glaucoma.
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