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
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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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Management ofOcular hypertension••••••••••••
Management ofOpen angle glaucoma••••••••••••
Contraindications & Blackbox Warnings
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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.

TargetActionsOrganism
ABeta-1 adrenergic receptor
antagonist
Humans
ABeta-2 adrenergic receptor
antagonist
Humans
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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Toxicity

Not Available

Pathways
PathwayCategory
Metipranolol Action PathwayDrug 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.
DrugInteraction
AcebutololAcebutolol may increase the arrhythmogenic activities of Metipranolol.
AcetyldigitoxinAcetyldigitoxin may increase the arrhythmogenic activities of Metipranolol.
AdenosineAdenosine may increase the arrhythmogenic activities of Metipranolol.
AjmalineAjmaline may increase the arrhythmogenic activities of Metipranolol.
AliskirenMetipranolol may increase the hypotensive activities of Aliskiren.
Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Metipranolol hydrochlorideFBW237ALKD36592-77-5BLWNYSZZZWQCKO-UHFFFAOYSA-N
International/Other Brands
Betanol / Disorat / Trimepranol
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
MetipranololSolution / drops3 mg/1mLOphthalmicBauch & Lomb Incorporated1989-12-292012-07-31US flag
OptiPranololSolution / drops3 mg/1mLOphthalmicPhysicians Total Care, Inc.1989-12-292010-06-30US flag
OptiPranololSolution / drops3 mg/1mLOphthalmicBauch & Lomb Incorporated1989-12-292012-07-31US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
MetipranololSolution / drops3 mg/1mLOphthalmicSandoz Inc2001-08-092018-03-01US flag

Categories

ATC Codes
S01ED54 — Metipranolol, combinationsC07BA68 — Metipranolol and thiazides, combinationsS01ED04 — Metipranolol
Drug Categories
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
Human Metabolome Database
HMDB0015345
KEGG Drug
D02374
KEGG Compound
C07915
PubChem Compound
31477
PubChem Substance
46505935
ChemSpider
29193
RxNav
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

Clinical Trials
PhaseStatusPurposeConditionsCount

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
FormRouteStrength
Solution / dropsOphthalmic3 mg/1mL
Solution / dropsOphthalmic
Prices
Unit descriptionCostUnit
Optipranolol 0.3% Solution 10ml Bottle42.99USD bottle
Optipranolol 0.3% Solution 5ml Bottle25.99USD bottle
Optipranolol 0.3% eye drops5.08USD ml
Metipranolol 0.3% eye drops3.55USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)105-107 °CPhysProp
water solubility589 mg/LNot Available
logP2.66MANNHOLD,R ET AL. (1990)
Predicted Properties
PropertyValueSource
Water Solubility0.173 mg/mLALOGPS
logP2.13ALOGPS
logP2.74Chemaxon
logS-3.2ALOGPS
pKa (Strongest Acidic)14.09Chemaxon
pKa (Strongest Basic)9.67Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area67.79 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity86.63 m3·mol-1Chemaxon
Polarizability35.85 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8638
Blood Brain Barrier-0.9906
Caco-2 permeable-0.5988
P-glycoprotein substrateSubstrate0.6335
P-glycoprotein inhibitor INon-inhibitor0.7599
P-glycoprotein inhibitor IINon-inhibitor0.8296
Renal organic cation transporterNon-inhibitor0.9097
CYP450 2C9 substrateNon-substrate0.8014
CYP450 2D6 substrateSubstrate0.5086
CYP450 3A4 substrateNon-substrate0.6564
CYP450 1A2 substrateNon-inhibitor0.6333
CYP450 2C9 inhibitorNon-inhibitor0.8721
CYP450 2D6 inhibitorNon-inhibitor0.7104
CYP450 2C19 inhibitorNon-inhibitor0.9547
CYP450 3A4 inhibitorNon-inhibitor0.8282
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9528
Ames testNon AMES toxic0.9219
CarcinogenicityNon-carcinogens0.9205
BiodegradationNot ready biodegradable0.7546
Rat acute toxicity2.1686 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9794
hERG inhibition (predictor II)Non-inhibitor0.7745
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0f6x-9730000000-8e6ca7d3d38723277ec5
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0229000000-3070864fcf2d458b973b
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-6915000000-468ce54a750a0fb6f7c7
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0w9a-3972000000-0705540603c7ede9a0c1
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-9400000000-b9e5c325f12c03e3bf1c
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-9430000000-7b219dcc8ef2e189be58
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-9500000000-7ec76bcea15f8814fc46
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-190.1385334
predicted
DarkChem Lite v0.1.0
[M-H]-179.13623
predicted
DeepCCS 1.0 (2019)
[M+H]+189.7192334
predicted
DarkChem Lite v0.1.0
[M+H]+181.49425
predicted
DeepCCS 1.0 (2019)
[M+Na]+190.1479334
predicted
DarkChem Lite v0.1.0
[M+Na]+187.62242
predicted
DeepCCS 1.0 (2019)

Targets

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Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
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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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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]
  3. 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]
  4. 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]
  5. 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
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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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]
  3. 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]
  4. Noack E: [Antiglaucomatous effectiveness of beta receptor blockers with special reference to metipranolol]. Klin Monbl Augenheilkd. 1986 Jul;189(1):1-3. [Article]
  5. 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]
  6. 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
  1. 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]
  2. Brodde OE, Kroemer HK: Drug-drug interactions of beta-adrenoceptor blockers. Arzneimittelforschung. 2003;53(12):814-22. [Article]
  3. 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 at June 13, 2005 13:24 / Updated at March 03, 2024 02:34