ChEMBL logo

ChEMBL

spacer
ChEMBL Statistics
  Loading Statistics...
spacer

Compound Report Card

Compound Name and Classification

Compound ID CHEMBL1291
CHEMBL1291
Compound Name METIPRANOLOL
ChEMBL Synonyms BM01.004 | VUAB6453 (SPOFA) | VUAB-6453 | GLAULINE | METIPRANOLOL | OPTIPRANOLOL | METIPRANOLOL HYDROCHLORIDE
Max Phase 4 (Approved)
Withdrawn Yes
Trade Names OPTIPRANOLOL | GLAULINE | METIPRANOLOL
Molecular Formula C17H27NO4

Additional synonyms for CHEMBL1291 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CC(C)NCC(O)COc1cc(C)c(OC(=O)C)c(C)c1C
Standard InChI InChI=1S/C17H27NO4/c1-10(2)18-8-15(20)9-21-16-7-11(3)17(22-1 ...
Download InChI
Standard InChI Key BQIPXWYNLPYNHW-UHFFFAOYSA-N

Sources

  • British National Formulary
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification
  • Withdrawn Drugs

Alternate Forms of Compound in ChEMBL


CHEMBL1291

Molecule Features

CHEMBL1291 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Racemic Mixture Prodrug:N Oral:N Parenteral:N Topical:Y Black Box:N Availability Type:Prescription-only

Withdrawal Information

Year 1990
Country United Kingdom
Reason Uveitis
Class Opthalmic toxicity

Mechanism of Action

Mechanism of Action ChEMBL Target References
Beta-1 adrenergic receptor antagonist Beta-1 adrenergic receptor DailyMed
Beta-2 adrenergic receptor antagonist Beta-2 adrenergic receptor DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
GlaucomaD005901EFO:0000516glaucoma4ATC
ATC

Clinical Data

ClinicalTrials.gov METIPRANOLOL
The Cochrane Collaboration METIPRANOLOL

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL1291. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL3373 Beta-2 adrenergic receptor Bos taurus 1.000
CHEMBL210 Beta-2 adrenergic receptor Homo sapiens 1.000
CHEMBL213 Beta-1 adrenergic receptor Homo sapiens 1.000
CHEMBL3252 Beta-1 adrenergic receptor Rattus norvegicus 0.994
CHEMBL4302 P-glycoprotein 1 Homo sapiens 0.991
CHEMBL3892 Sphingosine 1-phosphate receptor Edg-3 Homo sapiens 0.981
CHEMBL1878 Calcium sensing receptor Homo sapiens 0.963
CHEMBL5414 Beta-2 adrenergic receptor Cavia porcellus 0.676
CHEMBL3251 Nuclear factor NF-kappa-B p105 subunit Homo sapiens 0.394
CHEMBL312 Arachidonate 5-lipoxygenase Rattus norvegicus 0.386
CHEMBL1075138 Tyrosyl-DNA phosphodiesterase 1 Homo sapiens 0.296



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL3373 Beta-2 adrenergic receptor Bos taurus 1.000
CHEMBL210 Beta-2 adrenergic receptor Homo sapiens 1.000
CHEMBL3252 Beta-1 adrenergic receptor Rattus norvegicus 1.000
CHEMBL213 Beta-1 adrenergic receptor Homo sapiens 0.997
CHEMBL3892 Sphingosine 1-phosphate receptor Edg-3 Homo sapiens 0.938
CHEMBL3251 Nuclear factor NF-kappa-B p105 subunit Homo sapiens 0.857
CHEMBL2289 Beta-2 adrenergic receptor Canis lupus familiaris 0.770
CHEMBL1878 Calcium sensing receptor Homo sapiens 0.738
CHEMBL4302 P-glycoprotein 1 Homo sapiens 0.702
CHEMBL5414 Beta-2 adrenergic receptor Cavia porcellus 0.489
CHEMBL246 Beta-3 adrenergic receptor Homo sapiens 0.228

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
309.4 309.194 2.27 7 67.79 BASE


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
5 2 0 5 2 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
13.91 9.58 2.28 .05 1 22 0.6

Structural Alerts

There are 5 structural alerts for CHEMBL1291. To view alerts please click here.

Compound Cross References

ATC S - SENSORY ORGANS
S01 - OPHTHALMOLOGICALS
S01E - ANTIGLAUCOMA PREPARATIONS AND MIOTICS
S01ED - Beta blocking agents 1)
S01ED54 - metipranolol, combinations

S - SENSORY ORGANS
S01 - OPHTHALMOLOGICALS
S01E - ANTIGLAUCOMA PREPARATIONS AND MIOTICS
S01ED - Beta blocking agents 1)
S01ED04 - metipranolol

ChemSpider ChemSpider:BQIPXWYNLPYNHW-UHFFFAOYSA-N
DailyMed metipranolol hydrochloride
PubChem SID: 144205272 SID: 29215465
Wikipedia Metipranolol

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL1291



ACToR 22664-55-7
ChEBI 6897
DrugBank DB01214
DrugCentral 1779
eMolecules 670661
EPA CompTox Dashboard DTXSID4046078
Guide to Pharmacology 7239
Human Metabolome Database HMDB0015345
IBM Patent System FF8540E5868D9C1F1899F6F03BB203BE
KEGG Ligand C07915
Mcule MCULE-4113586715
MolPort MolPort-001-801-890
Nikkaji J11.486C
PharmGKB PA164748727
PubChem 31477
PubChem: Thomson Pharma 14923317
SureChEMBL SCHEMBL24324

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/BQIPXWYNLPYNHW-UHFFFAOYSA-N spacer
spacer