metipranolol

Also known as TUR695, BM-01004, VUAB-6453, VUAB6453, (+-)-metipranolol, acetic acid 4-(2-hydroxy-3-isopropylamino-propoxy)-2,3,6-trimethyl-phenyl ester

Metipranolol (OptiPranolol, Betanol, Disorat, Trimepranol) is a non-selective beta blocker used in eye drops to treat glaucoma. It is rapidly metabolized into desacetylmetipranolol.

In the Vinony graph

Within Vinony's link graph, metipranolol is referenced by 607 other articles, and connects out to propranolol, atenolol and adrenergic receptor.

Vinony files it under Acetate esters, Beta blockers and Drugs with no legal status.

Its subject is documented across 9 Wikipedia language editions.

Chemical data

Formula: C17H27NO4
Molecular weight: 309.4 g/mol
IUPAC name: [4-[2-hydroxy-3-(propan-2-ylamino)propoxy]-2,3,6-trimethylphenyl] acetate
SMILES: CC1=CC(=C(C(=C1OC(=O)C)C)C)OCC(CNC(C)C)O
InChIKey: BQIPXWYNLPYNHW-UHFFFAOYSA-N
XLogP: 2.7
Polar surface area: 67.8 Å²
H-bond donors: 2
H-bond acceptors: 5
Formal charge: 0

via PubChem

Drug data · ChEMBL

Withdrawn

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 1989
Admin. routes: topical
Indications: glaucoma

via ChEMBL · EBI

Research

323 papers

Metipranolol.2006
Ocular metipranolol. A preliminary review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy in glaucoma and ocular hypertension.Drugs · 1988
Metipranolol promotes structure and function of retinal photoreceptors in the rd10 mouse model of human retinitis pigmentosa.Journal of neurochemistry · 2019
Metipranolol-associated granulomatous anterior uveitis.The British journal of ophthalmology · 1991
Drug-induced uveitis.Expert opinion on drug safety · 2015

via PubMed

Wikidata facts

Subclass of: alkanolamine
Mass: 309.194008

Show 5 more facts

chemical formula: C₁₇H₂₇NO₄
canonical SMILES: CC1=CC(=C(C(=C1OC(=O)C)C)C)OCC(CNC(C)C)O
medical condition treated: ocular hypertension
World Health Organisation international non-proprietary name: metipranolol
subject has role: Sympatholytic

Sources (5)

via Wikidata · CC0

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Encyclopedic overview

1 sections

Contents

References

{{Drugbox | verifiedrevid = 411547542 | IUPAC_name = (RS)-4-{[-2-hydroxy-3-(isopropylamino)propyl]oxy}-2,3,6-trimethylphenyl acetate | image = Metipranolol.svg | image_class = skin-invert-image | width = 200 | chirality = Racemic mixture

Excerpted from Wikipedia’s “metipranolol” article, available under the CC BY-SA 4.0 licence.