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Levobunolol

Levobunolol structure

CAS No:
47141-42-4
Formula:
C17H25NO3
Chemical Name:
Levobunolol
Synonyms:
1(2H)-Naphthalenone,5-[(2S)-3-[(1,1-dimethylethyl)amino]-2-hydroxypropoxy]-3,4-dihydro-;1(2H)-Naphthalenone,5-[3-[(1,1-dimethylethyl)amino]-2-hydroxypropoxy]-3,4-dihydro-,(S)-;5-[(2S)-3-[(1,1-Dimethylethyl)amino]-2-hydroxypropoxy]-3,4-dihydro-1(2H)-naphthalenone;l-Bunolol;Levobunolol;(-)-Bunolol;W 6421A;Bunolgan;(S)-5-(3-(tert-Butylamino)-2-hydroxypropoxy)-3,4-dihydronaphthalen-1(2H)-one
Categories:
Organic Chemistry > Amides

Description

White Solid

Solid

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 an antiglaucoma drug and a beta-adrenergic antagonist. It is a propanolamine, a cyclic ketone and an aromatic ether. It is a conjugate acid of a levobunolol(1+). It derives from a hydride of a tetralin.|A nonselective beta-adrenoceptor antagonist used in the treatment of glaucoma.|Levobunolol is a beta-Adrenergic Blocker. The mechanism of action of levobunolol is as an Adrenergic beta-Antagonist.|Levobunolol is a naphthalenone and non-cardioselective adrenergic beta-receptor antagonist with anti-glaucoma activity. Upon administration in the eye, levobunolol blocks beta-adrenergic receptors, thereby causing vasoconstriction. Levobunolol also decreases ciliary's body production of aqueous humor, leading to a decrease in aqueous humor.|The L-Isomer of bunolol.

Levobunolol Basic Attributes

Molecular Weight：

291.39

Exact Mass：

291.39

UNII：

G6317AOI7K

DSSTox ID：

DTXSID1043833

NCI Thesaurus Code：

C62043

ATC Code：

S01ED03|S - Sensory organs

HScode：

2922509090

Characteristics

PSA：

58.6

XLogP3：

2.1

Appearance：

Solid

Melting Point：

209-211°C

Water Solubility：

2.51e-01 g/L

Storage Conditions：

-20°C Freezer, Under Inert Atmosphere

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)

Toxicity

Toxicity Summary：

Bradycardia, hypotension, bronchospasm, and acute cardiac failure, LD50=700 mg/kg (orally in rat).

Drug Information

Drug Indication：

For lowering intraocular pressure (IOP) and may be used in patients with chronic open-angle glaucoma or ocular hypertension.|FDA Label

Pharmacology：

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.

MeSH：

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. (See all compounds classified as Adrenergic beta-Antagonists.)|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. (See all compounds classified as Sympatholytics.)

Absorption：

80%

Metabolism/Metabolites：

Hepatic

Biological Half-Life：

20 hours

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.

MeSH Entry Terms：

AKBeta

Levobunolol Use and Manufacturing

Uses

A non-selective ?-adrenoceptor antagonist used as an anticonvulsant.

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Pharmaceuticals

Computed Properties

Molecular Weight:291.4
XLogP3:2.4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:6
Exact Mass:291.18344366
Monoisotopic Mass:291.18344366
Topological Polar Surface Area:58.6
Heavy Atom Count:21
Complexity:350
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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CAS No.: 47141-42-4

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