Basic information
- CAS
47141-42-4- Standard SMILES
CC(C)(C)NC[C@H](O)COc1cccc2c1CCCC2=O- InChIKey
IXHBTMCLRNMKHZ-LBPRGKRZSA-N- Molecular formula
- C17H25NO3
- Average molar mass
- 291.4 g/mol
- Monoisotopic mass
- 291.18344366
Overview
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.
Names & identifiers
- Preferred name
- Levobunolol
- IUPAC
- 5-[(2S)-3-(tert-butylamino)-2-hydroxypropoxy]-3,4-dihydro-2H-naphthalen-1-one
- English name
- LEVOBUNOLOL
- Molecular formula
- C17H25NO3
- Molecular weight
- 291.39
Names & synonyms
LEVOBUNOLOL47141-42-4Levobunololum(-)-BunololBunolol, (s)-Bunolol, (-)-G6317AOI7K(S)-5-(3-((1,1-dimethylethyl)amino)-2-hydroxypropoxy)-3,4-dihydro-1(2H)-naphthalenoneCHEBI:6438DTXSID10438335-[(2S)-3-(tert-butylamino)-2-hydroxypropoxy]-1,2,3,4-tetrahydronaphthalen-1-one1(2H)-Naphthalenone, 5-(3-((1,1-dimethylethyl)amino)-2-hydroxypropoxy)-3,4-dihydro-, (S)-
Show more names
W 6421AAK-BetaBeteganl-BunololLiquifilmLEVOBUNOLOL USP/EP/BP[(-)-5-[3,(t-Butylamino)-2-hydroxy-propoxy]-3,4-di,HCl5-[3-(tert-Butylamino)-2β-hydroxypropyloxy]-3,4-dihydronaphthalen-1(2H)-one
levobunololoApoLevobunololNovoLevobunololPMSLevobunololApo LevobunololNovo LevobunololPMS Levobunololratio Levobunolol
Database identifiers
- CAS
47141-42-4- PubChem CID
- 39468
- DTXSID
DTXSID1043833- ChEMBL
CHEMBL1201237- ChEBI
CHEBI:6438- UNII
- G6317AOI7K
- Nikkaji
- J237.992I
Properties
Computed structural properties
- XLogP
- 2.4
- Topological polar surface area
- 58.6 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 6
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 350
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LogP2.1
Solubility2.51e-01 g/L
Human Drugs
Breast Feeding; Lactation; Milk, Human; Antihypertensive Agents; Adrenergic Beta-Antagonists; Antiglaucoma Agents; Antiarrhythmics
Pharmaceuticals
Melting Point
209-211 °C
209 - 211 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 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 DataBase Reference
- 47141 · 47141-42-4(CAS DataBase Reference)
- FDA UNII
- 6317 AOI7K · G6317AOI7K
- ATC code
- 1 ED03 · S01ED03
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302
- Precautionary statements
- 301 · P301+P312+P330
- WGK Germany
- 3 · WGK 3
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 Oral · Acute Tox. 4 Oral
- Toxicity
- 50 in · 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)
Safety & regulation
Toxicology
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Safety data
- wgk
- WGK 3
- Toxicity
- 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)
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302
- Hazard Classifications
- Acute Tox. 4 Oral
- Precautionary statements
- P301+P312+P330
Chemistry & industry
Pharmacology
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.
Biological Half-Life20 hours
Metabolism/MetabolitesHepatic
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.
Absorption, Distribution and Excretion80%
Cellular LocationsMembrane
Metabolite PathwaysLevobunolol Action Pathway
Uses & manufacturing
Use ClassificationPharmaceuticals
Applications
UsesLevobunolol hydrochloride is an antiglaucoma agent in ophthalmie solutions.
UsesAs a non-selective adrenoceptor antagonist, Levobunolol is used as an anticonvulsant.
Upstream & downstream products
Upstream raw materials
Suppliers14 total
北京华美互利生物化工010-56205725 · [email protected]
杭州摩库生物医药科技有限公司+86-057181025280; +8617767106207 · [email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
安耐吉化学&3A（安徽泽升科技有限公司）021-58432009 400-005-6266 · [email protected]
凯试(上海)科技有限公司021-50135380 · [email protected]
BOC Sciences1-631-485-4226; 16314854226 · [email protected]
陕西缔都医药化工有限公司+86-29-81139210 +86-17392587031 · [email protected]
上海陶术生物科技股份有限公司13564774135 · [email protected]
上海相辉医药科技有限公司[email protected]
厦门盈融达化工有限公司+86-0592-6210733 · [email protected]
上海瀚香生物科技有限公司17754423994 · [email protected]
TargetMol中国（陶术生物）15002134094 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354 · [email protected]
山东子易医药有限公司13173053288 · [email protected]
Additional notes
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.
Related reactions
2 records
Compound notes
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