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metipranolol   Click here for help

GtoPdb Ligand ID: 7239

Synonyms: BM-01004 | Optipranolol® | VUAB-6453 | VUAB6453
Approved drug
metipranolol is an approved drug (FDA (1989))
Compound class: Synthetic organic
Comment: Metipranolol is a β-blocker. The drug's active metabolite is desacetylmetipranolol (CHEMBL1201363).

metipranolol is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 67.79
Molecular weight 309.19
XLogP 2.23
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES OC(COc1cc(C)c(c(c1C)C)OC(=O)C)CNC(C)C
Isomeric SMILES OC(COc1cc(C)c(c(c1C)C)OC(=O)C)CNC(C)C
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
InChI Key BQIPXWYNLPYNHW-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. US FDA (1989)
IUPAC Name Click here for help
4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}-2,3,6-trimethylphenyl acetate
International Nonproprietary Names Click here for help
INN number INN
4372 metipranolol
Synonyms Click here for help
BM-01004 | Optipranolol® | VUAB-6453 | VUAB6453
Database Links Click here for help
CAS Registry No. 22664-55-7
ChEMBL Ligand CHEMBL1291
DrugBank Ligand DB01214
DrugCentral Ligand 1779
GtoPdb PubChem SID 178103813
PubChem CID 31477
Search Google for chemical match using the InChIKey BQIPXWYNLPYNHW-UHFFFAOYSA-N
Search Google for chemicals with the same backbone BQIPXWYNLPYNHW
Search PubMed clinical trials metipranolol
Search PubMed titles metipranolol
Search PubMed titles/abstracts metipranolol
UniChem Compound Search for chemical match using the InChIKey BQIPXWYNLPYNHW-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey BQIPXWYNLPYNHW-UHFFFAOYSA-N
Wikipedia Metipranolol

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MedChemExpress
Metipranolol (links to external site)
Cat. No. HY-121567