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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:57 UTC
HMDB IDHMDB0015345
Secondary Accession Numbers
  • HMDB15345
Metabolite Identification
Common NameMetipranolol
DescriptionMetipranolol is only found in individuals that have used or taken this drug. It is a beta-adrenergic antagonist effective for both beta-1 and beta-2 receptors. It is used as an antiarrhythmic, antihypertensive, and antiglaucoma agent. [PubChem]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.
Structure
Data?1582753287
Synonyms
ValueSource
(+-)-MetipranololChEBI
Acetic acid 4-(2-hydroxy-3-isopropylamino-propoxy)-2,3,6-trimethyl-phenyl esterChEBI
MetipranololumChEBI
Acetate 4-(2-hydroxy-3-isopropylamino-propoxy)-2,3,6-trimethyl-phenyl esterGenerator
MethypranolHMDB
1-(4-Acetoxy-2,3,5-trimethylphenoxy)-3-isopropylamino-2-propanolHMDB
DisoratHMDB
TrimepranolHMDB
Chemical FormulaC17H27NO4
Average Molecular Weight309.4006
Monoisotopic Molecular Weight309.194008357
IUPAC Name4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}-2,3,6-trimethylphenyl acetate
Traditional Namemetipranolol
CAS Registry Number22664-55-7
SMILES
CC(C)NCC(O)COC1=C(C)C(C)=C(OC(C)=O)C(C)=C1
InChI Identifier
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
InChI KeyBQIPXWYNLPYNHW-UHFFFAOYSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol esters
Sub ClassNot Available
Direct ParentPhenol esters
Alternative Parents
Substituents
  • Phenol ester
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • 1,2-aminoalcohol
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Secondary aliphatic amine
  • Ether
  • Monocarboxylic acid or derivatives
  • Secondary amine
  • Alcohol
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Amine
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point105 - 107 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.17 g/LNot Available
LogP2.2Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.17 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity86.63 m³·mol⁻¹ChemAxon
Polarizability35.85 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+174.33131661259
DarkChem[M-H]-170.18731661259
DeepCCS[M+H]+181.49430932474
DeepCCS[M-H]-179.13630932474
DeepCCS[M-2H]-212.02230932474
DeepCCS[M+Na]+187.62230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MetipranololCC(C)NCC(O)COC1=C(C)C(C)=C(OC(C)=O)C(C)=C12822.3Standard polar33892256
MetipranololCC(C)NCC(O)COC1=C(C)C(C)=C(OC(C)=O)C(C)=C12286.4Standard non polar33892256
MetipranololCC(C)NCC(O)COC1=C(C)C(C)=C(OC(C)=O)C(C)=C12268.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Metipranolol,1TMS,isomer #1CC(=O)OC1=C(C)C=C(OCC(CNC(C)C)O[Si](C)(C)C)C(C)=C1C2217.5Semi standard non polar33892256
Metipranolol,1TMS,isomer #2CC(=O)OC1=C(C)C=C(OCC(O)CN(C(C)C)[Si](C)(C)C)C(C)=C1C2359.1Semi standard non polar33892256
Metipranolol,2TMS,isomer #1CC(=O)OC1=C(C)C=C(OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C)C(C)=C1C2402.5Semi standard non polar33892256
Metipranolol,2TMS,isomer #1CC(=O)OC1=C(C)C=C(OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C)C(C)=C1C2458.7Standard non polar33892256
Metipranolol,2TMS,isomer #1CC(=O)OC1=C(C)C=C(OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C)C(C)=C1C2683.7Standard polar33892256
Metipranolol,1TBDMS,isomer #1CC(=O)OC1=C(C)C=C(OCC(CNC(C)C)O[Si](C)(C)C(C)(C)C)C(C)=C1C2443.9Semi standard non polar33892256
Metipranolol,1TBDMS,isomer #2CC(=O)OC1=C(C)C=C(OCC(O)CN(C(C)C)[Si](C)(C)C(C)(C)C)C(C)=C1C2638.6Semi standard non polar33892256
Metipranolol,2TBDMS,isomer #1CC(=O)OC1=C(C)C=C(OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(C)=C1C2871.4Semi standard non polar33892256
Metipranolol,2TBDMS,isomer #1CC(=O)OC1=C(C)C=C(OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(C)=C1C2861.3Standard non polar33892256
Metipranolol,2TBDMS,isomer #1CC(=O)OC1=C(C)C=C(OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(C)=C1C2896.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Metipranolol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6x-9730000000-8e6ca7d3d38723277ec52017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Metipranolol GC-MS (1 TMS) - 70eV, Positivesplash10-006x-4903000000-5e38ed4777ba52d3c36d2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Metipranolol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metipranolol 10V, Positive-QTOFsplash10-03xr-2395000000-0d03e930dc66a8b356892016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metipranolol 20V, Positive-QTOFsplash10-0g4i-6490000000-fb99a0314a0f032dcc872016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metipranolol 40V, Positive-QTOFsplash10-00di-9500000000-c05787b6509293025f3e2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metipranolol 10V, Negative-QTOFsplash10-0a4l-4978000000-20e0ee1bc9e1ec5249072016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metipranolol 20V, Negative-QTOFsplash10-0006-2910000000-28808768f7352cab1a4a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metipranolol 40V, Negative-QTOFsplash10-0k95-4900000000-ec3591175b411fb621d02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metipranolol 10V, Positive-QTOFsplash10-03di-0139000000-8e1cbb2b284c563d1cec2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metipranolol 20V, Positive-QTOFsplash10-0uxs-3940000000-4faf8d90526a2e3f99cc2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metipranolol 40V, Positive-QTOFsplash10-05fr-9300000000-22491bd77e7bc82b0ad12021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metipranolol 10V, Negative-QTOFsplash10-0a4i-0759000000-057655888cd596e2a5562021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metipranolol 20V, Negative-QTOFsplash10-0536-9800000000-01257d615411e0e2f4a82021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metipranolol 40V, Negative-QTOFsplash10-0a5d-9600000000-cf213e29c082583fd6402021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01214 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01214 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01214
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID29193
KEGG Compound IDC07915
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMetipranolol
METLIN IDNot Available
PubChem Compound31477
PDB IDNot Available
ChEBI ID6897
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
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 equal affinity
Gene Name:
ADRB1
Uniprot ID:
P08588
Molecular weight:
51322.1
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. [PubMed:17139284 ]
  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. [PubMed:17016423 ]
  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. [PubMed:2895037 ]
  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. [PubMed:12967722 ]
  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. [PubMed:2885244 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
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 30-fold greater affinity than it does norepinephrine
Gene Name:
ADRB2
Uniprot ID:
P07550
Molecular weight:
46458.3
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. [PubMed:17139284 ]
  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. [PubMed:17016423 ]
  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. [PubMed:2895037 ]
  4. Noack E: [Antiglaucomatous effectiveness of beta receptor blockers with special reference to metipranolol]. Klin Monbl Augenheilkd. 1986 Jul;189(1):1-3. [PubMed:2876128 ]
  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. [PubMed:12967722 ]
  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. [PubMed:2885244 ]