Metipranolol (CED0012629)

Record Information

Version

1.0

Creation Date

2016-05-22 05:28:35 UTC

Update Date

2026-08-19 22:01:51 UTC

Accession Number

CHEM018720

Identification

Common Name

Metipranolol

Class

Small Molecule

Description

Metipranolol is an organic compound with the formula C17H27NO4 and an average molecular weight of 309.40 g/mol. Metipranolol belongs to the phenol esters, a class of benzenoids within the organic compounds. This compound acts as an antagonist of the Beta-1 adrenergic receptor (ADRB1) and the Beta-2 adrenergic receptor (ADRB2). It is found in or released from three recorded sources: electrically stimulated smoking devices, pharmaceuticals and veterinary products including beta blocking agents and miotics and antiglaucoma preparations, and healthcare. The recorded exposure route for this substance is ophthalmic.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+-)-Metipranolol	ChEBI
Acetic acid 4-(2-hydroxy-3-isopropylamino-propoxy)-2,3,6-trimethyl-phenyl ester	ChEBI
Metipranololum	ChEBI
Acetate 4-(2-hydroxy-3-isopropylamino-propoxy)-2,3,6-trimethyl-phenyl ester	Generator
Methypranol	HMDB
1-(4-Acetoxy-2,3,5-trimethylphenoxy)-3-isopropylamino-2-propanol	HMDB
Disorat	HMDB
Trimepranol	HMDB

Chemical Formula

C₁₇H₂₇NO₄

Average Molecular Mass

309.401 g/mol

Monoisotopic Mass

309.194 g/mol

CAS Registry Number

22664-55-7

IUPAC Name

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

Traditional Name

metipranolol

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 Key

BQIPXWYNLPYNHW-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenol esters

Sub Class

Not Available

Direct Parent

Phenol 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

aromatic ether (CHEBI:6897 )
acetate ester (CHEBI:6897 )
secondary amino compound (CHEBI:6897 )
propanolamine (CHEBI:6897 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.17 g/L	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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0f6x-9730000000-8e6ca7d3d38723277ec5	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-006x-4903000000-5e38ed4777ba52d3c36d	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03xr-2395000000-0d03e930dc66a8b35689	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0g4i-6490000000-fb99a0314a0f032dcc87	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-9500000000-c05787b6509293025f3e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4l-4978000000-20e0ee1bc9e1ec524907	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-2910000000-28808768f7352cab1a4a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0k95-4900000000-ec3591175b411fb621d0	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-0139000000-8e1cbb2b284c563d1cec	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0uxs-3940000000-4faf8d90526a2e3f99cc	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-05fr-9300000000-22491bd77e7bc82b0ad1	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0759000000-057655888cd596e2a556	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0536-9800000000-01257d615411e0e2f4a8	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a5d-9600000000-cf213e29c082583fd640	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
996.0	Log mg/kg	[560:1800]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
293	Beta blocking agents	Healthcare, pharmaceuticals & veterinary products	Not Available
398	Antiglaucoma preparations and miotics	Healthcare, pharmaceuticals & veterinary products	Not Available
518	Electrically Stimulated Smoking Devices	Electrical & Electronic Equipment	Not Available
650	Purses Luggage Hand Bags	Textiles, leather & furnishings	Not Available

Pathways

3 pathways

Metipranolol Action Pathway

Metipranolol Action Pathway (New)

Metipranolol Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Beta-2 adrenergic receptor	Q8K4Z4	Cavia porcellus	Predicted (SEA)	3.81461
Click to view 3D structure	Beta-1 adrenergic receptor	B0FL73	Cavia porcellus	Predicted (SEA)	3.03612
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P19327	Rattus norvegicus	Predicted (SEA)	64.3813
Click to view 3D structure	Beta-1 adrenergic receptor	P08588	Humans	Predicted (SEA)	9.49761
Click to view 3D structure	Beta-2 adrenergic receptor	P07550	Humans	Predicted (SEA)	12.6894
Click to view 3D structure	Beta-3 adrenergic receptor	P13945	Humans	Predicted (SEA)	8.64126
Click to view 3D structure	Beta-1 adrenergic receptor	P18090	Rattus norvegicus	Predicted (SEA)	2.80257
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P08908	Humans	Predicted (SEA)	105.797
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q99720	Humans	Predicted (SEA)	63.6807
Click to view 3D structure	Beta-2 adrenergic receptor	Q28044	Bos taurus	Predicted (SEA)	2.49118
Click to view 3D structure	5-hydroxytryptamine receptor 1B	P28564	Rattus norvegicus	Predicted (SEA)	26.2352
Click to view 3D structure	Sodium-dependent serotonin transporter	P31645	Humans	Predicted (SEA)	93.8862
Click to view 3D structure	Cytochrome P450 2D6	P10635	Humans	Predicted (SEA)	156.944
Click to view 3D structure	5-hydroxytryptamine receptor 2B	P41595	Humans	Predicted (SEA)	102.917
Click to view 3D structure	5-hydroxytryptamine receptor 2C	P28335	Humans	Predicted (SEA)	150.56
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	207.546
Click to view 3D structure	5-hydroxytryptamine receptor 6	P50406	Humans	Predicted (SEA)	103.617
Click to view 3D structure	Beta-2 adrenergic receptor	P54833	Canis lupus familiaris	Predicted (SEA)	2.02408
Click to view 3D structure	5-hydroxytryptamine receptor 1B	P28222	Humans	Predicted (SEA)	106.576
Click to view 3D structure	Beta-1 adrenergic receptor	P34971	Mus musculus	Predicted (SEA)	7.31783
Click to view 3D structure	DNA (cytosine-5)-methyltransferase 1	P13864	Mus musculus	Predicted (SEA)	2.56902
Click to view 3D structure	Beta-2 adrenergic receptor	P10608	Rattus norvegicus	Predicted (SEA)	5.60514
Click to view 3D structure	Sigma intracellular receptor 2	Q5BJF2	Humans	Predicted (SEA)	219.068
Click to view 3D structure	Voltage-gated inwardly rectifying potassium channel KCNH2	Q12809	Humans	Predicted (SEA)	1143.37
Click to view 3D structure	Sodium channel protein type 5 subunit alpha	Q14524	Humans	Predicted (SEA)	160.914