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MedKoo Cat#: 318256 | Name: Metipranolol
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Description:

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

Metipranolol is a non-selective beta blocker used in eye drops to treat glaucoma. It is rapidly metabolized into desacetylmetipranolol.

Chemical Structure

Metipranolol
Metipranolol
CAS#22664-55-7 (free)

Theoretical Analysis

MedKoo Cat#: 318256

Name: Metipranolol

CAS#: 22664-55-7 (free)

Chemical Formula: C17H27NO4

Exact Mass: 309.1940

Molecular Weight: 309.40

Elemental Analysis: C, 65.99; H, 8.80; N, 4.53; O, 20.68

Price and Availability

Size Price Availability Quantity
10mg USD 300.00 2 weeks
25mg USD 550.00 2 Weeks
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Related CAS #
36592-77-5 (HCl) 22664-55-7 (free)
Synonym
Metipranolol, OptiPranolol, Betanol, Disorat, Trimepranol
IUPAC/Chemical Name
[4-[2-hydroxy-3-(propan-2-ylamino)propoxy]-2,3,6-trimethylphenyl] acetate
InChi Key
BQIPXWYNLPYNHW-UHFFFAOYSA-N
InChi Code
InChI=1S/C17H27NO4/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
SMILES Code
CC(OC1=C(C)C=C(OCC(O)CNC(C)C)C(C)=C1C)=O
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:
Metipranolol is a nonselective and orally active β-adrenergic receptor antagonist.
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:PBS (pH 7.2) (1:6) 0.1 0.45
DMSO 110.7 357.68
Ethanol 36.0 116.35
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 309.40 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: Chrapek O, Jirkova B, Kandrnal V, Rehak J, Sin M. Treatment of central serous chorioretinopathy with beta-blocker metipranolol. Biomed Pap Med Fac Univ Palacky Olomouc Czech Repub. 2015 Mar;159(1):120-3. doi: 10.5507/bp.2013.015. Epub 2013 Mar 21. PubMed PMID: 23549516. 2: Khanfar MA, AbuKhader MM, Alqtaishat S, Taha MO. Pharmacophore modeling, homology modeling, and in silico screening reveal mammalian target of rapamycin inhibitory activities for sotalol, glyburide, metipranolol, sulfamethizole, glipizide, and pioglitazone. J Mol Graph Model. 2013 May;42:39-49. doi: 10.1016/j.jmgm.2013.02.009. Epub 2013 Mar 13. PubMed PMID: 23545333. 3: 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. PubMed PMID: 16799065. 4: Osborne NN, Wood JP. Metipranolol blunts nitric oxide-induced lipid peroxidation and death of retinal photoreceptors: a comparison with other anti-glaucoma drugs. Invest Ophthalmol Vis Sci. 2004 Oct;45(10):3787-95. PubMed PMID: 15452090. 5: Djanani A, Kaneider NC, Meierhofer C, Sturn D, Dunzendorfer S, Allmeier H, Wiedermann CJ. Inhibition of neutrophil migration and oxygen free radical release by metipranolol and timolol. Pharmacology. 2003 Aug;68(4):198-203. PubMed PMID: 12837974. 6: Wood JP, Schmidt KG, Melena J, Chidlow G, Allmeier H, Osborne NN. The beta-adrenoceptor antagonists metipranolol and timolol are retinal neuroprotectants: comparison with betaxolol. Exp Eye Res. 2003 Apr;76(4):505-16. PubMed PMID: 12634114. 7: Mirza GE, Karaküçük S, Temel E. Comparison of the effects of 0.5% timolol maleate, 2% carteolol hydrochloride, and 0.3% metipranolol on intraocular pressure and perimetry findings and evaluation of their ocular and systemic effects. J Glaucoma. 2000 Feb;9(1):45-50. PubMed PMID: 10708231. 8: Kamalarajah S, Johnston PB. Bilateral anterior uveitis associated with 0.3% minims metipranolol. Eye (Lond). 1999 Jun;13 ( Pt 3a):380-1. PubMed PMID: 10624443. 9: Patel NP, Patel KH, Moster MR, Spaeth GL. Metipranolol-associated nongranulomatous anterior uveitis. Am J Ophthalmol. 1997 Jun;123(6):843-4. PubMed PMID: 9535634. 10: Watanabe TM, Hodes BL. Bilateral anterior uveitis associated with a brand of metipranolol. Arch Ophthalmol. 1997 Mar;115(3):421-2. PubMed PMID: 9076220. 11: Boles Carenini B, Brogliatti B, Dorigo MT, Vadalà G, Protti R, Bellone A. Prepared association of metipranolol 0.1% + pilocarpine 2% and of timolol 0.5% + pilocarpine 2%. Comparison of clinical efficacy and topical tolerability in the treatment of patients affected by POAG tonometrically uncontrolled with beta-blocker alone (two-centre study). Acta Ophthalmol Scand Suppl. 1997;(224):54-5. PubMed PMID: 9589740. 12: Lyden M, Applebaum HJ. Effect of ophthalmic metipranolol and timolol on exerise-induced tachycardia. J Glaucoma. 1995 Apr;4(2):124-9. PubMed PMID: 19920657. 13: KeBler C. Possible bilateral anterior uveitis secondary to metipranolol (OptiPranolol) therapy. Arch Ophthalmol. 1994 Oct;112(10):1277. PubMed PMID: 7945025. 14: Groh MJ, Michelson G, Groh ME, Gründler AE. Ocular macro- and microcirculation after topical application of clonidine and metipranolol. Ger J Ophthalmol. 1994 May;3(3):175-8. PubMed PMID: 7913644. 15: Kessler C, Christ T. Incidence of uveitis in glaucoma patients using metipranolol. J Glaucoma. 1993 Fall;2(3):166-70. PubMed PMID: 19920513. 16: Losa C, Marchal-Heussler L, Orallo F, Vila Jato JL, Alonso MJ. Design of new formulations for topical ocular administration: polymeric nanocapsules containing metipranolol. Pharm Res. 1993 Jan;10(1):80-7. PubMed PMID: 8094245. 17: Tilser I, Martínková J, Chládek J, Zaydlar K. A beneficial effect of metipranolol pretreatment on rat kidney ischemia in vivo. Sb Ved Pr Lek Fak Karlovy Univerzity Hradci Kralove. 1993;36(1-2):31-4. PubMed PMID: 7909376. 18: Lazarová Z. Analysis of ultrastructural changes in the myocardium of rats during withdrawal syndrome after gradual decreasing of metipranolol doses. Cor Vasa. 1992;34(3):283-92. PubMed PMID: 1363978. 19: Akingbehin T, Villada JR. Metipranolol-induced adverse reactions: II. Loss of intraocular pressure control. Eye (Lond). 1992;6 ( Pt 3):280-3. PubMed PMID: 1359979. 20: Steinkraus V, Levenig C, Wachs U. [Psoriasis following metipranolol]. Dtsch Med Wochenschr. 1991 Nov 22;116(47):1814. German. PubMed PMID: 1682123.