MedKoo Cat#: 584448 | Name: Metipranolol hydrochloride
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Description:

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

Metipranolol hydrochloride is a non-selective β-adrenergic receptor (β-AR) antagonist. Formulations containing metipranolol have been used in the treatment of elevated IOP in patients with ocular hypertension or glaucoma.

Chemical Structure

Metipranolol hydrochloride
Metipranolol hydrochloride
CAS#36592-77-5 (HCl)

Theoretical Analysis

MedKoo Cat#: 584448

Name: Metipranolol hydrochloride

CAS#: 36592-77-5 (HCl)

Chemical Formula: C17H28ClNO4

Exact Mass: 345.1707

Molecular Weight: 345.86

Elemental Analysis: C, 59.04; H, 8.16; Cl, 10.25; N, 4.05; O, 18.50

Price and Availability

Size Price Availability Quantity
5mg USD 365.00 2 weeks
10mg USD 650.00 2 weeks
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Synonym
Metipranolol hydrochloride; OptiPranolol; Metipranolol; Metipranolol HCl
IUPAC/Chemical Name
4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]-2,3,6-trimethyl-phenol, 1-acetate, monohydrochloride
InChi Key
BLWNYSZZZWQCKO-UHFFFAOYSA-N
InChi Code
InChI=1S/C17H27NO4.ClH/c1-10(2)18-8-15(20)9-21-16-7-11(3)17(22-14(6)19)13(5)12(16)4;/h7,10,15,18,20H,8-9H2,1-6H3;1H
SMILES Code
CC1=C(OC(C)=O)C(C)=C(C)C(OCC(O)CNC(C)C)=C1.[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
Biological target:
Metipranolol hydrochloride is a non-selective β adrenergic receptor blocking agent.
In vitro activity:
Immunohistochemistry, immunoblot analysis and the terminal-deoxynucleotidyl transferase dUTP-linked nick-end labeling (TUNEL) procedure determined the effects of zinc with or without trolox or metipranolol on photoreceptor death in situ. Zinc-induced apoptosis of cultured RPE cells and photoreceptors were attenuated only by metipranolol and trolox. Reference: Invest Ophthalmol Vis Sci. 2006 Jul;47(7):3178-86. https://pubmed.ncbi.nlm.nih.gov/16799065/
In vivo activity:
This study tested the hypothesis that metipranolol protects photoreceptor structure and function in the mouse model rd10. At P50, metipranolol-treated rd10 mice had decreased 3-nitrotyrosine staining in the retina, increased immunostaining for cone arrestin, a marker for cone photoreceptors, and significantly higher scotopic and photopic b-wave amplitudes at the highest stimulus intensity compared with vehicle-treated mice. Reference: J Neurochem. 2019 Jan;148(2):307-318. https://pubmed.ncbi.nlm.nih.gov/30315650/
Solvent mg/mL mM comments
Solubility
DMF 50.0 144.57
DMSO 75.0 216.85
Ethanol 10.0 28.91
PBS (pH 7.2) 5.0 14.46
Water 100.0 289.13
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 345.86 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. Osborne NN, Wood JP. The beta-adrenergic receptor antagonist metipranolol blunts zinc-induced photoreceptor and RPE apoptosis. Invest Ophthalmol Vis Sci. 2006 Jul;47(7):3178-86. doi: 10.1167/iovs.05-1370. PMID: 16799065. 2. Kanan Y, Khan M, Lorenc VE, Long D, Chadha R, Sciamanna J, Green K, Campochiaro PA. Metipranolol promotes structure and function of retinal photoreceptors in the rd10 mouse model of human retinitis pigmentosa. J Neurochem. 2019 Jan;148(2):307-318. doi: 10.1111/jnc.14613. Epub 2018 Dec 3. PMID: 30315650. 3. 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. doi: 10.1007/s00417-003-0726-5. Epub 2003 Jul 29. PMID: 12898280.
In vitro protocol:
1. Osborne NN, Wood JP. The beta-adrenergic receptor antagonist metipranolol blunts zinc-induced photoreceptor and RPE apoptosis. Invest Ophthalmol Vis Sci. 2006 Jul;47(7):3178-86. doi: 10.1167/iovs.05-1370. PMID: 16799065.
In vivo protocol:
1. Kanan Y, Khan M, Lorenc VE, Long D, Chadha R, Sciamanna J, Green K, Campochiaro PA. Metipranolol promotes structure and function of retinal photoreceptors in the rd10 mouse model of human retinitis pigmentosa. J Neurochem. 2019 Jan;148(2):307-318. doi: 10.1111/jnc.14613. Epub 2018 Dec 3. PMID: 30315650. 2. 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. doi: 10.1007/s00417-003-0726-5. Epub 2003 Jul 29. PMID: 12898280.
1. Sugrue, M.F., Armstrong, J.M., Gautheron, P.D., et al. A study on the ocular and extraocular pharmacology of metipranolol. Graefes. Arch. Clin. Exp. Ophthalmol. 222(3), 123-127 (1985). 2. Wood, J.P.M., Schmidt, K.-G., Melena, J., et al. The β-adrenoceptor antagonists metipranolol and timolol are retinal neuroprotectants: comparison with betaxolo. Exp. Eye Res. 76(4), 505-516 (2003). 3. Osborne, N.N.W., J.P.M. Metipranolol blunts nitric oxide-induced lipid peroxidation and death of retinal photoreceptors: a comparison with other anti-glaucoma drugs. Invest. Ophthalmol. Vis. Sci. 45(10), 3787-3795 (2004).