Levobunolol | CAS#47141-42-4

MedKoo Cat#: 318095 | Name: Levobunolol

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Levobunolol is a non-selective beta blocker. It is used topically to manage glaucoma.

Chemical Structure

Levobunolol

CAS#47141-42-4

Theoretical Analysis

MedKoo Cat#: 318095

Name: Levobunolol

CAS#: 47141-42-4

Chemical Formula: C17H25NO3

Exact Mass: 291.1834

Molecular Weight: 291.39

Elemental Analysis: C, 70.07; H, 8.65; N, 4.81; O, 16.47

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Related CAS #

47141-42-4 27912-14-7 (HCl)

Synonym

Levobunolol, Levobunololum, AK-Beta, Liquifilm, Betegan

IUPAC/Chemical Name

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

InChi Key

IXHBTMCLRNMKHZ-LBPRGKRZSA-N

InChi Code

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

SMILES Code

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

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Levobunolol (l-Bunolol) is a potent and nonselective β-adrenergic receptor antagonist.

In vitro activity:

Timolol (100 nM, 10 microM) and levobunolol (10 microM) produced cAMP-independent inhibition of the regulatory volume increase (RVI) in PE (pigmented ciliary epithelial) cells and increased intracellular Ca(2+) and pH. Reference: Am J Physiol Cell Physiol. 2001 Sep;281(3):C865-75. https://pubmed.ncbi.nlm.nih.gov/11502564/

In vivo activity:

Levobunolol and ICI 118, 551 impaired corneal wound healing, decreased the expressions of CK3, CK14, and CK19 after limbal region scraping in mice. Moreover, levobunolol and ICI 118, 551 inhibited corneal wound healing by mediating the expression of Ki67, and the phosphorylation of EGFR and ERK1/2 in the limbal and regenerated corneal epithelium. Reference: BMC Ophthalmol. 2021 Dec 5;21(1):419. https://pubmed.ncbi.nlm.nih.gov/34863129/

Preparing Stock Solutions

The following data is based on the product molecular weight 291.39 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. McLaughlin CW, Peart D, Purves RD, Carré DA, Peterson-Yantorno K, Mitchell CH, Macknight AD, Civan MM. Timolol may inhibit aqueous humor secretion by cAMP-independent action on ciliary epithelial cells. Am J Physiol Cell Physiol. 2001 Sep;281(3):C865-75. doi: 10.1152/ajpcell.2001.281.3.C865. PMID: 11502564. 2. Wang HZ, Hong SJ, Wu KY. Change of calcium and cAMP concentration by adrenoceptor agents in cultured porcine corneal endothelial cells. J Ocul Pharmacol Ther. 2000 Aug;16(4):299-309. doi: 10.1089/jop.2000.16.299. PMID: 10977125. 3. Yuan X, Ma X, Yang L, Zhou Q, Li Y. β-blocker eye drops affect ocular surface through β2 adrenoceptor of corneal limbal stem cells. BMC Ophthalmol. 2021 Dec 5;21(1):419. doi: 10.1186/s12886-021-02186-w. PMID: 34863129; PMCID: PMC8645087. 4. Dong Y, Ishikawa H, Wu Y, Yoshitomi T. Vasodilatory mechanism of levobunolol on vascular smooth muscle cells. Exp Eye Res. 2007 Jun;84(6):1039-46. doi: 10.1016/j.exer.2007.01.010. Epub 2007 Jan 27. PMID: 17459374.

In vitro protocol:

In vivo protocol:

1. Yuan X, Ma X, Yang L, Zhou Q, Li Y. β-blocker eye drops affect ocular surface through β2 adrenoceptor of corneal limbal stem cells. BMC Ophthalmol. 2021 Dec 5;21(1):419. doi: 10.1186/s12886-021-02186-w. PMID: 34863129; PMCID: PMC8645087. 2. Dong Y, Ishikawa H, Wu Y, Yoshitomi T. Vasodilatory mechanism of levobunolol on vascular smooth muscle cells. Exp Eye Res. 2007 Jun;84(6):1039-46. doi: 10.1016/j.exer.2007.01.010. Epub 2007 Jan 27. PMID: 17459374.

1: Horcajada-Reales C, Rodríguez-Soria VJ, Suárez-Fernández R. Allergic contact dermatitis caused by timolol with cross-sensitivity to levobunolol. Contact Dermatitis. 2015 Dec;73(6):368-9. doi: 10.1111/cod.12448. Epub 2015 Jul 31. PubMed PMID: 26227808. 2: Lin L, Wang Y, Chen Y, Liu M. Bradyarrhythmias secondary to topical levobunolol hydrochloride solution. Clin Interv Aging. 2014 Oct 13;9:1741-5. doi: 10.2147/CIA.S69420. eCollection 2014. PubMed PMID: 25342892; PubMed Central PMCID: PMC4206249. 3: Scardillo A, Pugliese M, De Majo M, Niutta PP, Pugliese A. Effects of topical 0.5% levobunolol alone or in association with 2% dorzolamide compared with a fixed combination of 0.5% timolol and 2% dorzolamide on intraocular pressure and heart rate in dogs without glaucoma. Vet Ther. 2010 Fall;11(3):E1-6. PubMed PMID: 20960417. 4: Pugliese M, Scardillo A, Niutta PP, Pugliese A. Comparison of effects of topical levobunolol to a combination of timolol-dorzolamide on intraocular pressure and pulse rate of healthy dogs. Vet Res Commun. 2009 Sep;33 Suppl 1:205-7. doi: 10.1007/s11259-009-9273-9. PubMed PMID: 19626454. 5: Karataş A, Sonakin O, Kiliçarslan M, Baykara T. Poly (epsilon-caprolactone) microparticles containing Levobunolol HCl prepared by a multiple emulsion (W/O/W) solvent evaporation technique: effects of some formulation parameters on microparticle characteristics. J Microencapsul. 2009 Feb;26(1):63-74. doi: 10.1080/02652040802141039. PubMed PMID: 18608798. 6: Ciancaglini M, Carpineto P, Agnifili L, Nubile M, Fasanella V, Lanzini M, Calienno R, Mastropasqua L. An in vivo confocal microscopy and impression cytology analysis of preserved and unpreserved levobunolol-induced conjunctival changes. Eur J Ophthalmol. 2008 May-Jun;18(3):400-7. PubMed PMID: 18465723. 7: Dong Y, Ishikawa H, Wu Y, Yoshitomi T. Vasodilatory mechanism of levobunolol on vascular smooth muscle cells. Exp Eye Res. 2007 Jun;84(6):1039-46. Epub 2007 Jan 27. PubMed PMID: 17459374. 8: Hashimoto Y, Aragane Y, Kawada A. Allergic contact dermatitis due to levobunolol in an ophthalmic preparation. J Dermatol. 2006 Jul;33(7):507-9. PubMed PMID: 16848829. 9: Ishibashi T, Yokoi N, Kinoshita S. Comparison of the effects of topical levobunolol and timolol solution on the human ocular surface. Cornea. 2003 Nov;22(8):709-15. PubMed PMID: 14576520. 10: Halper LK, Johnson-Pratt L, Dobbins T, Hartenbaum D. A comparison of the efficacy and tolerability of 0.5% timolol maleate ophthalmic gel-forming solution QD and 0.5% levobunolol hydrochloride BID in patients with ocular hypertension or open-angle glaucoma. J Ocul Pharmacol Ther. 2002 Apr;18(2):105-13. PubMed PMID: 12002664. 11: Wilkinson SM. False-negative patch test with levobunolol. Contact Dermatitis. 2001 Apr;44(4):264. PubMed PMID: 11260243. 12: Doyle E, Liu C. A case of acquired iris depigmentation as a possible complication of levobunolol eye drops. Br J Ophthalmol. 1999 Dec;83(12):1405-6. PubMed PMID: 10660314; PubMed Central PMCID: PMC1722884. 13: Garcia F, Blanco J, Juste S, Garces MM, Alonso L, Marcos ML, Carretero P, Perez R. Contact dermatitis due to levobunolol in eyedrops. Contact Dermatitis. 1997 Apr;36(4):230. PubMed PMID: 9165213. 14: Bloom AH, Grunwald JE, DuPont JC. Effect of one week of levobunolol HCl 0.5% on the human retinal circulation. Curr Eye Res. 1997 Mar;16(3):191-6. PubMed PMID: 9088734. 15: Tang M, Chen L, Wei W, Yang L, Wang T, Liu Z, Hu X, Sun H, Luo H. The effect of levobunolol hydrochloride on the calcium and potassium channels in isolated ventricular myocytes of guinea pig. J Tongji Med Univ. 1997;17(2):90-3. PubMed PMID: 9639797. 16: Akafo SK, Thompson JR, Rosenthal AR. A cross-over trial comparing once daily levobunolol with once and twice daily timolol. Eur J Ophthalmol. 1995 Jul-Sep;5(3):172-6. PubMed PMID: 8845685. 17: Zucchelli V, Silvani S, Vezzani C, Lorenzi S, Tosti A. Contact dermatitis from levobunolol and befunolol. Contact Dermatitis. 1995 Jul;33(1):66-7. PubMed PMID: 7493479. 18: di Lernia V, Albertini G, Bisighini G. Allergic contact dermatitis from levobunolol eyedrops. Contact Dermatitis. 1995 Jul;33(1):57. PubMed PMID: 7493471. 19: Lewis SE. Controlled comparison of the cardiovascular effects of levobunolol 0.25% ophthalmic solution and betaxolol 0.25% ophthalmic suspension. J Glaucoma. 1994 Winter;3(4):308-14. PubMed PMID: 19920615. 20: Tang-Liu DD, Richman JB. The effect of pilocarpine on ocular levobunolol absorption from ophthalmic solutions. J Ocul Pharmacol. 1994 Winter;10(4):605-15. PubMed PMID: 7714404.