Absorption, Distribution and Excretion
80%

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Metabolism / Metabolites
Hepatic

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Biological Half-Life
20 hours

Effects During Pregnancy and Lactation
◉ Summary of Use during Lactation
Based on its physicochemical properties and its ophthalmic route of administration, levobunolol appears to present a moderately low risk to the breastfed infant. Some guidelines state that gel formulations are preferred over solutions. To substantially diminish the amount of drug that reaches the breastmilk after using eye drops, place pressure over the tear duct by the corner of the eye for 1 minute or more, then remove the excess solution with an absorbent tissue.
◉ Effects in Breastfed Infants
A study of mothers taking beta-blockers during nursing found a numerically, but not statistically significant increased number of adverse reactions in those taking any beta-blocker. Although the ages of infants were matched to control infants, the ages of the affected infants were not stated. None of the mothers were taking levobunolol.
◉ Effects on Lactation and Breastmilk
Relevant published information on the effects of beta-blockade or levobunolol during normal lactation was not found as of the revision date. A study in 6 patients with hyperprolactinemia and galactorrhea found no changes in serum prolactin levels following beta-adrenergic blockade with propranolol.

[1]. Injectable drug depot engineered to release multiple ophthalmic therapeutic agents with precise time profiles for postoperative treatment following ocular surgery. Acta Biomater. 2018 Jun;73:90-102.

[2]. Extended levobunolol release from Eudragit nanoparticle-laden contact lenses for glaucoma therapy. Futur J Pharm Sci 6, 109 (2020).

[3]. Superior oblique myokymia treated with levobunolol. J AAPOS. 2018 Feb;22(1):67-69.e2.

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.
See also: Levobunolol Hydrochloride (has salt form).

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

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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.

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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.

C17H25NO3.HCL

327.84624

327.16

27912-14-7

Levobunolol;47141-42-4

39468

White to off-white solid powder

464.4ºC at 760mmHg

209-211°

234.7ºC

2.01E-09mmHg at 25°C

3.526

2

4

6

21

350

1

O=C1CCCC2=C1C=CC=C2OC[C@@H](O)CNC(C)(C)C.[H]Cl

IXHBTMCLRNMKHZ-LBPRGKRZSA-N

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

5-[(2S)-3-(tert-butylamino)-2-hydroxypropoxy]-3,4-dihydro-2H-naphthalen-1-one

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment, avoid exposure to moisture.

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

DMSO : ≥ 62.5 mg/mL (~190.64 mM)
H2O : ~50 mg/mL (~152.51 mM)

Solubility in Formulation 1: ≥ 2.08 mg/mL (6.34 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

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Solubility in Formulation 2: ≥ 2.08 mg/mL (6.34 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.08 mg/mL (6.34 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

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Solubility in Formulation 4: 50 mg/mL (152.51 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication.

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 (Please use freshly prepared in vivo formulations for optimal results.)