4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}-2,3,6-trimethylphenyl acetate

• ChemBase ID: 1084
• Molecular Formular: C17H27NO4
• Molecular Mass: 309.40058
• Monoisotopic Mass: 309.19400835
• SMILES: O(CC(O)CNC(C)C)c1c(c(c(OC(=O)C)c(c1)C)C)C
• Canonical SMILES: OC(COc1cc(C)c(c(c1C)C)OC(=O)C)CNC(C)C
• InChI: 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
• InChIKey: BQIPXWYNLPYNHW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}-2,3,6-trimethylphenyl acetate
• IUPAC Traditional name: metipranolol
• Brand Name: Disorat; Trimepranol; OptiPranolol
• Synonyms: Metipranololum [INN-Latin]; Metipranolol hydrochloride; Metipranolol

Database IDs

• CAS Number: 22664-55-7
• PubChem SID: 46505935; 160964547
• PubChem CID: 31477
• ATC CODE: S01ED04; C07BA68
• CHEMBL: 1291
• Chemspider ID: 29193
• DrugBank ID: DB01214
• KEGG ID: D02374
• Unique Ingredient Identifier: X39AL81KEB
• Wikipedia Title: Metipranolol
• Medline Plus: a601078

CALCULATED PROPERTIES

JChem

• Acid pKa: 14.087952
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.45148742
• LogD (pH = 7.4): 0.5165057
• Log P: 2.7417443
• Molar Refractivity: 86.6315 cm^3
• Polarizability: 33.92427 Å^3
• Polar Surface Area: 67.79 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.13
• LOG S: -3.25
• Solubility (Water): 1.73e-01 g/l

PROPERTIES

Physical Property

• Solubility: 589 mg/L
• Hydrophobicity(logP): 2.2

DETAILS

DrugBank - DB01214

• Drug Groups: approved
• Description: A beta-adrenergic antagonist effective for both beta-1 and beta-2 receptors. It is used as an antiarrhythmic, antihypertensive, and antiglaucoma agent. [PubChem]
• Indication: Indicated in the treatment of elevated intraocular pressure in patients with ocular hypertension or open angle glaucoma.
• Pharmacology: Metipranolol is a beta1 and beta2 (non-selective) adrenergic receptor-blocking agent that does not have significant intrinsic sympathomimetic, direct myocardial depressant, or local anesthetic (membrane-stabilizing) activity. Metipranolol is indicated in the treatment of elevated intraocular pressure in patients with ocular hypertension or open-angle glaucoma. Metipranolol, when applied topically to the eye, has the action of reducing elevated, as well as normal, intraocular pressure, whether or not accompanied by glaucoma. Elevated intraocular pressure is a major risk factor in the pathogenesis of glaucomatous visual field loss and optic nerve damage. Metipranolol reduces intraocular pressure with little or no effect on pupil size or accommodation in contrast to the miosis which cholinergic agents are known to produce.
• Affected Organisms: Humans and other mammals
• External Links: Wikipedia; RxList; Drugs.com