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MedKoo Cat#: 598721 | Name: Levobetaxolol

Description:

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

Levobetaxolol,also known as Betaxon and AL-1577A, is a cardioselective β-adrenergic receptor inhibitor that has been demonstrated to reduce intraocular pressure in patients affected with primary open-angle glaucoma and ocular hypertension.

Chemical Structure

Levobetaxolol
CAS#93221-48-8 (S-isomer free base)

Theoretical Analysis

MedKoo Cat#: 598721

Name: Levobetaxolol

CAS#: 93221-48-8 (S-isomer free base)

Chemical Formula: C18H29NO3

Exact Mass: 307.2147

Molecular Weight: 307.43

Elemental Analysis: C, 70.32; H, 9.51; N, 4.56; O, 15.61

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
63659-18-7 (free base) 63659-19-8 (HCl) 93221-48-8 (S-isomer free base) 116209-55-3 (S-isomer HCl)
Synonym
Levobetaxolol; (S)-Betaxolol; (S)-(-)-Betaxolol;
IUPAC/Chemical Name
(S)-1-(4-(2-(cyclopropylmethoxy)ethyl)phenoxy)-3-(isopropylamino)propan-2-ol
InChi Key
NWIUTZDMDHAVTP-KRWDZBQOSA-N
InChi Code
InChI=1S/C18H29NO3/c1-14(2)19-11-17(20)13-22-18-7-5-15(6-8-18)9-10-21-12-16-3-4-16/h5-8,14,16-17,19-20H,3-4,9-13H2,1-2H3/t17-/m0/s1
SMILES Code
O[C@@H](CNC(C)C)COC1=CC=C(CCOCC2CC2)C=C1
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
>3 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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 307.43 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
1: Quaranta L, Turano R, Pizzolante T. Levobetaxolol hydrochloride: a review of its pharmacology and use in the treatment of chronic open-angle glaucoma and ocular hypertension. Clin Ophthalmol. 2007 Jun;1(2):93-7. PubMed PMID: 19668496; PubMed Central PMCID: PMC2704505. 2: Sharif NA, Xu SX, Crider JY, McLaughlin M, Davis TL. Levobetaxolol (Betaxon) and other beta-adrenergic antagonists: preclinical pharmacology, IOP-lowering activity and sites of action in human eyes. J Ocul Pharmacol Ther. 2001 Aug;17(4):305-17. PubMed PMID: 11572462. 3: Whitson JT, Roarty JD, Vijaya L, Robin AL, Gross RD, Landry TA, Dickerson JE, Scheib SA, Scott H, Hua SY, Woodside AM, Bergamini MV; Brinzolamide Pediatric Study Group. Efficacy of brinzolamide and levobetaxolol in pediatric glaucomas: a randomized clinical trial. J AAPOS. 2008 Jun;12(3):239-246.e3. doi: 10.1016/j.jaapos.2007.11.004. Epub 2008 Mar 4. PubMed PMID: 18289898. 4: Sharif NA, Xu SX. Binding affinities of ocular hypotensive beta-blockers levobetaxolol, levobunolol, and timolol at endogenous guinea pig beta-adrenoceptors. J Ocul Pharmacol Ther. 2004 Apr;20(2):93-9. PubMed PMID: 15117564. 5: Agarwal N, Martin E, Krishnamoorthy RR, Landers R, Wen R, Krueger S, Kapin MA, Collier RJ. Levobetaxolol-induced Up-regulation of retinal bFGF and CNTF mRNAs and preservation of retinal function against a photic-induced retinopathy. Exp Eye Res. 2002 Apr;74(4):445-53. PubMed PMID: 12076088. 6: Osborne NN, Wood JP, Chidlow G, Casson R, DeSantis L, Schmidt KG. Effectiveness of levobetaxolol and timolol at blunting retinal ischaemia is related to their calcium and sodium blocking activities: relevance to glaucoma. Brain Res Bull. 2004 Feb 15;62(6):525-8. Review. PubMed PMID: 15036567. 7: 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. 8: Sharif NA, Crider JY, Xu SX, McLaughlin M, Davis TL. Levobetaxolol (Betaxon): in vitro pharmacology, intraocular pressure lowering activity and autoradiographic localization of beta-adrenoceptors in human eyes. Proc West Pharmacol Soc. 2001;44:65-8. PubMed PMID: 11793997. 9: Lele BS, Hoffman AS. Insoluble ionic complexes of polyacrylic acid with a cationic drug for use as a mucoadhesive, ophthalmic drug delivery system. J Biomater Sci Polym Ed. 2000;11(12):1319-31. PubMed PMID: 11261874. 10: Melena J, Osborne NN. Metipranolol attenuates lipid peroxidation in rat brain: a comparative study with other antiglaucoma drugs. Graefes Arch Clin Exp Ophthalmol. 2003 Oct;241(10):827-33. Epub 2003 Jul 29. PubMed PMID: 12898280. 11: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2007 Nov;29(9):625-55. PubMed PMID: 18193114. 12: Crider JY, Sharif NA. Adenylyl cyclase activity mediated by beta-adrenoceptors in immortalized human trabecular meshwork and non-pigmented ciliary epithelial cells. J Ocul Pharmacol Ther. 2002 Jun;18(3):221-30. PubMed PMID: 12099543. 13: Chidlow G, Melena J, Osborne NN. Betaxolol, a beta(1)-adrenoceptor antagonist, reduces Na(+) influx into cortical synaptosomes by direct interaction with Na(+) channels: comparison with other beta-adrenoceptor antagonists. Br J Pharmacol. 2000 Jun;130(4):759-66. PubMed PMID: 10864881; PubMed Central PMCID: PMC1572129.

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