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MedKoo Cat#: 525322 | Name: Levobunolol Hydrochloride
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Description:

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

Levobunolol Hydrochloride is a non-cardioselective adrenergic beta-receptor antagonist with anti-glaucoma activity.

Chemical Structure

Levobunolol Hydrochloride
CAS#27912-14-7 (HCl)

Theoretical Analysis

MedKoo Cat#: 525322

Name: Levobunolol Hydrochloride

CAS#: 27912-14-7 (HCl)

Chemical Formula: C17H26ClNO3

Exact Mass: 327.1601

Molecular Weight: 327.85

Elemental Analysis: C, 62.28; H, 7.99; Cl, 10.81; N, 4.27; O, 14.64

Price and Availability

Size Price Availability Quantity
50mg USD 300.00 2 Weeks
100mg USD 550.00 2 Weeks
250mg USD 950.00 2 Weeks
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Related CAS #
47141-42-4 27912-14-7 (HCl)
Synonym
Levobunolol Hydrochloride
IUPAC/Chemical Name
5-[(2S)-3-(tert-Butylamino)-2-hydroxypropoxy]-3,4-dihydro-2H-naphthalen-1-one hydrochloride
InChi Key
DNTDOBSIBZKFCP-YDALLXLXSA-N
InChi Code
InChI=1S/C17H25NO3.ClH/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;1H/t12-;/m0./s1
SMILES Code
O=C1CCCC2=C1C=CC=C2OC[C@@H](O)CNC(C)(C)C.[H]Cl
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
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
Certificate of Analysis
View CoA: current batch, Lot#C8M10C24
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction
Biological target:
Levobunolol (l-Bunolol) hydrochloride 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/
Solvent mg/mL mM comments
Solubility
DMF 14.0 42.70
DMSO 39.3 119.72
Ethanol 11.0 33.55
PBS (pH 7.2) 5.0 15.25
Water 50.0 152.51
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 327.85 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.

Recalculate based on batch purity %
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:
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.
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: Argikar UA, Dumouchel JL, Dunne CE, Saran C, Cirello AL, Gunduz M. Ocular Metabolism of Levobunolol: Historic and Emerging Metabolic Pathways. Drug Metab Dispos. 2016 Aug;44(8):1304-12. doi: 10.1124/dmd.116.070458. Epub 2016 May 17. PubMed PMID: 27190057. 2: Li T, Lindsley K, Rouse B, Hong H, Shi Q, Friedman DS, Wormald R, Dickersin K. Comparative Effectiveness of First-Line Medications for Primary Open-Angle Glaucoma: A Systematic Review and Network Meta-analysis. Ophthalmology. 2016 Jan;123(1):129-40. doi: 10.1016/j.ophtha.2015.09.005. Epub 2015 Oct 31. Review. PubMed PMID: 26526633; PubMed Central PMCID: PMC4695285. 3: 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. 4: Li N, Shi HM, Cong L, Lu ZZ, Ye W, Zhang YY. Outflow facility efficacy of five drugs in enucleated porcine eyes by a method of constant-pressure perfusion. Int J Clin Exp Med. 2015 May 15;8(5):7184-91. eCollection 2015. PubMed PMID: 26221257; PubMed Central PMCID: PMC4509202. 5: Krishnamurthy R, Senthil S, Garudadri CS. Late postoperative choroidal detachment following an uneventful cataract surgery in a patient on topical latanoprost. BMJ Case Rep. 2015 Jul 14;2015. pii: bcr2015211408. doi: 10.1136/bcr-2015-211408. PubMed PMID: 26174734. 6: Kochar B, Shan SJ, Anand G, Zinreich SJ, Gelber AC. Totally one-sided: painless unilateral proptosis. Am J Med. 2015 Apr;128(4):361-3. doi: 10.1016/j.amjmed.2014.12.005. Epub 2015 Jan 5. PubMed PMID: 25572713. 7: 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. 8: Mohamed N, Meyer D. Intraocular pressure-lowering effect of oral paracetamol and its in vitro corneal penetration properties. Clin Ophthalmol. 2013;7:219-27. doi: 10.2147/OPTH.S38473. Epub 2013 Jan 30. PubMed PMID: 23390358; PubMed Central PMCID: PMC3564461. 9: Choi H, Lee Y, Yeon S, Lee H, Lee H. Effects of anti-glaucoma drugs on resistive index of the medial long posterior ciliary artery using color Doppler imaging in Beagle dogs. J Vet Sci. 2011 Mar;12(1):99-101. PubMed PMID: 21368570; PubMed Central PMCID: PMC3053475. 10: 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. 11: 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. 12: Bussières JF, Therrien R, Hamel P, Barret P, Prot-Labarthe S. Retrospective cohort study of 163 pediatric glaucoma patients. Can J Ophthalmol. 2009 Jun;44(3):323-7. doi: 10.3129/i09-065. PubMed PMID: 19491991. 13: Ayaki M, Noda Y, Yaguchi S, Koide R, Iwasawa A, Inoue T, Inoue Y. [Cytotoxicity of antiglaucoma ophthalmic solutions for human corneal endothelial cells]. Nippon Ganka Gakkai Zasshi. 2009 May;113(5):576-82. Japanese. PubMed PMID: 19489448. 14: 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. 15: 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. 16: Gao Y, Wu L, Li A. Daily cost of glaucoma medications in China. J Glaucoma. 2007 Oct-Nov;16(7):594-7. PubMed PMID: 18091176. 17: Ramadan NK, Zaazaa HE. Membrane electrodes for determination of some beta-blocker drugs. J AOAC Int. 2007 Jul-Aug;90(4):987-94. PubMed PMID: 17760336. 18: 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. 19: Wu KY, Wang HZ, Hong SJ. Cellular cytotoxicity of antiglaucoma drugs in cultured corneal endothelial cells. Kaohsiung J Med Sci. 2007 Mar;23(3):105-11. PubMed PMID: 17389174. 20: Blumetti B, Brodell RT, Helms SE, Brodell LP, Bredle DL. Contact dermatitis to levobunolol eyedrops superimposed on IgE-mediated rhinoconjunctivitis. Ann Allergy Asthma Immunol. 2006 Dec;97(6):817-8. PubMed PMID: 17201244.

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