Metipranolol
Identification
- Summary
Metipranolol is a beta-adrenergic antagonist used for the reduction of elevated intraocular pressure in patients with ocular hypertension or open-angle glaucoma.
- Generic Name
- Metipranolol
- DrugBank Accession Number
- DB01214
- Background
A beta-adrenergic antagonist effective for both beta-1 and beta-2 receptors. It is used as an antiarrhythmic, antihypertensive, and antiglaucoma agent.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Metipranolol (DB01214)
- Weight
- Average: 309.4006
Monoisotopic: 309.194008357 - Chemical Formula
- C17H27NO4
- Synonyms
- (±)-metipranolol
- Acetic acid 4-(2-hydroxy-3-isopropylamino-propoxy)-2,3,6-trimethyl-phenyl ester
- Metipranolol
- Metipranololum
- External IDs
- BM-01.004
- BM01.004
- VUAB-6453
- VUAB6453
Pharmacology
- Indication
Indicated in the treatment of elevated intraocular pressure in patients with ocular hypertension or open angle glaucoma.
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- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
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.
- Mechanism of action
Although it is known that metipranolol binds the beta1 and beta2 adrenergic receptors, the mechanism of metipranolol's action is not known. It has no significant intrinsic sympathomimetic activity, and has only weak local anesthetic (membrane-stabilizing) and myocardial depressant activity. It appears that the ophthalmic beta-adrenergic blocking agents reduce aqueous humor production, as demonstrated by tonography and fluorophotometry. A slight increase in aqueous humor outflow may be an additional mechanism.
Target Actions Organism ABeta-2 adrenergic receptor antagonistHumans ABeta-1 adrenergic receptor antagonistHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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Not Available
- Pathways
Pathway Category Metipranolol Action Pathway Drug action - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcebutolol Acebutolol may increase the arrhythmogenic activities of Metipranolol. Acetyldigitoxin Acetyldigitoxin may increase the arrhythmogenic activities of Metipranolol. Adenosine Adenosine may increase the arrhythmogenic activities of Metipranolol. Ajmaline Ajmaline may increase the arrhythmogenic activities of Metipranolol. Aliskiren Metipranolol may increase the hypotensive activities of Aliskiren. Ambrisentan Metipranolol may increase the hypotensive activities of Ambrisentan. Amiodarone The risk or severity of adverse effects can be increased when Amiodarone is combined with Metipranolol. Amlodipine Amlodipine may increase the arrhythmogenic activities of Metipranolol. Atenolol Atenolol may increase the arrhythmogenic activities of Metipranolol. Atropine Atropine may increase the arrhythmogenic activities of Metipranolol. 
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- No interactions found.
Products
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Ingredient UNII CAS InChI Key Metipranolol hydrochloride FBW237ALKD 36592-77-5 BLWNYSZZZWQCKO-UHFFFAOYSA-N - International/Other Brands
- Betanol / Disorat / Trimepranol
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Metipranolol Solution / drops 3 mg/1mL Ophthalmic Bauch & Lomb Incorporated 1989-12-29 2012-07-31 US 
OptiPranolol Solution / drops 3 mg/1mL Ophthalmic Physicians Total Care, Inc. 1989-12-29 2010-06-30 US OptiPranolol Solution / drops 3 mg/1mL Ophthalmic Bauch & Lomb Incorporated 1989-12-29 2012-07-31 US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Metipranolol Solution / drops 3 mg/1mL Ophthalmic Sandoz Inc 2001-08-09 2018-03-01 US
Categories
- ATC Codes
- S01ED54 — Metipranolol, combinations
- S01ED — Beta blocking agents
- S01E — ANTIGLAUCOMA PREPARATIONS AND MIOTICS
- S01 — OPHTHALMOLOGICALS
- S — SENSORY ORGANS
- C07BA — Beta blocking agents, non-selective, and thiazides
- C07B — BETA BLOCKING AGENTS AND THIAZIDES
- C07 — BETA BLOCKING AGENTS
- C — CARDIOVASCULAR SYSTEM
- Drug Categories
- Adrenergic Agents
- Adrenergic Antagonists
- Adrenergic beta-Antagonists
- Agents causing hyperkalemia
- Alcohols
- Amines
- Amino Alcohols
- Antiarrhythmic agents
- Antiglaucoma Preparations and Miotics
- Antihypertensive Agents
- Autonomic Agents
- Beta Blocking Agents and Thiazides
- Beta Blocking Agents, Non-Selective, and Thiazides
- Bradycardia-Causing Agents
- Cardiovascular Agents
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 Substrates
- Hypotensive Agents
- Neurotransmitter Agents
- Ophthalmologicals
- Peripheral Nervous System Agents
- Phenoxypropanolamines
- Propanolamines
- Propanols
- Sensory Organs
- Sympatholytics
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Phenol esters
- Sub Class
- Not Available
- Direct Parent
- Phenol esters
- Alternative Parents
- Phenoxy compounds / Phenol ethers / Alkyl aryl ethers / Secondary alcohols / Carboxylic acid esters / Amino acids and derivatives / 1,2-aminoalcohols / Monocarboxylic acids and derivatives / Dialkylamines / Organopnictogen compounds show 3 more
- Substituents
- 1,2-aminoalcohol / Alcohol / Alkyl aryl ether / Amine / Amino acid or derivatives / Aromatic homomonocyclic compound / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Ether show 15 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- aromatic ether, acetate ester, secondary amino compound, propanolamine (CHEBI:6897)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- X39AL81KEB
- CAS number
- 22664-55-7
- InChI Key
- BQIPXWYNLPYNHW-UHFFFAOYSA-N
- 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
- IUPAC Name
- 4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}-2,3,6-trimethylphenyl acetate
- SMILES
- CC(C)NCC(O)COC1=C(C)C(C)=C(OC(C)=O)C(C)=C1
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015345
- KEGG Drug
- D02374
- KEGG Compound
- C07915
- PubChem Compound
- 31477
- PubChem Substance
- 46505935
- ChemSpider
- 29193
- 10824
- ChEBI
- 6897
- ChEMBL
- CHEMBL1291
- Therapeutic Targets Database
- DAP000480
- PharmGKB
- PA164748727
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Metipranolol
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Alcon Laboratories
- Bausch & Lomb Inc.
- Dispensing Solutions
- Doctor Gerhard Mann Chemisch Pharmazeutische Fabrik GmbH
- Falcon Pharmaceuticals Ltd.
- Physicians Total Care Inc.
- Dosage Forms
Form Route Strength Solution / drops Ophthalmic 3 mg/1mL Solution / drops Ophthalmic - Prices
Unit description Cost Unit Optipranolol 0.3% Solution 10ml Bottle 42.99USD bottle Optipranolol 0.3% Solution 5ml Bottle 25.99USD bottle Optipranolol 0.3% eye drops 5.08USD ml Metipranolol 0.3% eye drops 3.55USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 105-107 °C PhysProp water solubility 589 mg/L Not Available logP 2.66 MANNHOLD,R ET AL. (1990) - Predicted Properties
Property Value Source Water Solubility 0.173 mg/mL ALOGPS logP 2.13 ALOGPS logP 2.74 ChemAxon logS -3.2 ALOGPS pKa (Strongest Acidic) 14.09 ChemAxon pKa (Strongest Basic) 9.67 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 67.79 Å2 ChemAxon Rotatable Bond Count 8 ChemAxon Refractivity 86.63 m3·mol-1 ChemAxon Polarizability 35.85 Å3 ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.8638 Blood Brain Barrier - 0.9906 Caco-2 permeable - 0.5988 P-glycoprotein substrate Substrate 0.6335 P-glycoprotein inhibitor I Non-inhibitor 0.7599 P-glycoprotein inhibitor II Non-inhibitor 0.8296 Renal organic cation transporter Non-inhibitor 0.9097 CYP450 2C9 substrate Non-substrate 0.8014 CYP450 2D6 substrate Substrate 0.5086 CYP450 3A4 substrate Non-substrate 0.6564 CYP450 1A2 substrate Non-inhibitor 0.6333 CYP450 2C9 inhibitor Non-inhibitor 0.8721 CYP450 2D6 inhibitor Non-inhibitor 0.7104 CYP450 2C19 inhibitor Non-inhibitor 0.9547 CYP450 3A4 inhibitor Non-inhibitor 0.8282 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9528 Ames test Non AMES toxic 0.9219 Carcinogenicity Non-carcinogens 0.9205 Biodegradation Not ready biodegradable 0.7546 Rat acute toxicity 2.1686 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9794 hERG inhibition (predictor II) Non-inhibitor 0.7745
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Protein homodimerization activity
- Specific Function
- Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately ...
- Gene Name
- ADRB2
- Uniprot ID
- P07550
- Uniprot Name
- Beta-2 adrenergic receptor
- Molecular Weight
- 46458.32 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Drimal J, Knezl V, Magna D, Strizova K: External transport of beta-adrenergic binding sites in ischemic myocardium. Gen Physiol Biophys. 1987 Dec;6(6):583-91. [Article]
- Noack E: [Antiglaucomatous effectiveness of beta receptor blockers with special reference to metipranolol]. Klin Monbl Augenheilkd. 1986 Jul;189(1):1-3. [Article]
- Arai K, Wood JP, Osborne NN: Beta-adrenergic receptor agonists and antagonists counteract LPS-induced neuronal death in retinal cultures by different mechanisms. Brain Res. 2003 Sep 26;985(2):176-86. [Article]
- Bilcikova L, Bauer V, Kolena J: The action of adrenoceptor agonists and antagonists on the guinea pig and dog trachea. Gen Physiol Biophys. 1987 Feb;6(1):87-101. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Receptor signaling protein activity
- Specific Function
- Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately e...
- Gene Name
- ADRB1
- Uniprot ID
- P08588
- Uniprot Name
- Beta-1 adrenergic receptor
- Molecular Weight
- 51322.1 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Drimal J, Knezl V, Magna D, Strizova K: External transport of beta-adrenergic binding sites in ischemic myocardium. Gen Physiol Biophys. 1987 Dec;6(6):583-91. [Article]
- Arai K, Wood JP, Osborne NN: Beta-adrenergic receptor agonists and antagonists counteract LPS-induced neuronal death in retinal cultures by different mechanisms. Brain Res. 2003 Sep 26;985(2):176-86. [Article]
- Bilcikova L, Bauer V, Kolena J: The action of adrenoceptor agonists and antagonists on the guinea pig and dog trachea. Gen Physiol Biophys. 1987 Feb;6(1):87-101. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Sternieri E, Coccia CP, Pinetti D, Guerzoni S, Ferrari A: Pharmacokinetics and interactions of headache medications, part II: prophylactic treatments. Expert Opin Drug Metab Toxicol. 2006 Dec;2(6):981-1007. doi: 10.1517/17425255.2.6.981 . [Article]
- Brodde OE, Kroemer HK: Drug-drug interactions of beta-adrenoceptor blockers. Arzneimittelforschung. 2003;53(12):814-22. [Article]
- Iwaki M, Niwa T, Bandoh S, Itoh M, Hirose H, Kawase A, Komura H: Application of substrate depletion assay to evaluation of CYP isoforms responsible for stereoselective metabolism of carvedilol. Drug Metab Pharmacokinet. 2016 Dec;31(6):425-432. doi: 10.1016/j.dmpk.2016.08.007. Epub 2016 Sep 2. [Article]
Drug created on June 13, 2005 13:24 / Updated on August 07, 2021 00:40