mirabegron   Click here for help

GtoPdb Ligand ID: 7445

Synonyms: Betmiga® | Myrbetriq® | YM-178
Approved drug PDB Ligand
mirabegron is an approved drug (FDA and EMA (2012))
Compound class: Synthetic organic
Comment: Mirabegron is a β3-adrenoceptor agonist muscle relaxant. It has been reported to exert effects on cellular metabolism in adipocytes. This latter action is β3-adrenoceptor-dependent, and improves glucose handling in vivo [5].
Click here for help

Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

✖

View interactive charts of activity data across species

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: mirabegron

mirabegron is commercially available from our sponsors

2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. 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.

✖
Hydrogen bond acceptors 6
Hydrogen bond donors 4
Rotatable bonds 10
Topological polar surface area 128.51
Molecular weight 396.16
XLogP 1.66
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help

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.

✖
Canonical SMILES O=C(Cc1csc(n1)N)Nc1ccc(cc1)CCNCC(c1ccccc1)O
Isomeric SMILES O=C(Cc1csc(n1)N)Nc1ccc(cc1)CCNC[C@@H](c1ccccc1)O
InChI InChI=1S/C21H24N4O2S/c22-21-25-18(14-28-21)12-20(27)24-17-8-6-15(7-9-17)10-11-23-13-19(26)16-4-2-1-3-5-16/h1-9,14,19,23,26H,10-13H2,(H2,22,25)(H,24,27)/t19-/m0/s1
InChI Key PBAPPPCECJKMCM-IBGZPJMESA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA and EMA (2012))
IUPAC Name Click here for help
2-(2-amino-1,3-thiazol-4-yl)-N-[4-[2-[[(2R)-2-hydroxy-2-phenylethyl]amino]ethyl]phenyl]acetamide
International Nonproprietary Names Click here for help
INN number INN
8907 mirabegron
Synonyms Click here for help
Betmiga® | Myrbetriq® | YM-178
Database Links Click here for help
Specialist databases
GPCRdb Ligand mirabegron
Reactome Drug Reactome logo R-ALL-9611838
Reactome Reaction Reactome logo R-HSA-9611839
Other databases
CAS Registry No. 223673-61-8
ChEBI CHEBI:65349
ChEMBL Ligand CHEMBL2095212
DrugBank Ligand DB08893
DrugCentral Ligand 4382
GtoPdb PubChem SID 178104017
PubChem CID 9865528
RCSB PDB Ligand H6U
Search Google for chemical match using the InChIKey PBAPPPCECJKMCM-IBGZPJMESA-N
Search Google for chemicals with the same backbone PBAPPPCECJKMCM
Search PubMed clinical trials mirabegron
Search PubMed titles mirabegron
Search PubMed titles/abstracts mirabegron
UniChem Compound Search for chemical match using the InChIKey PBAPPPCECJKMCM-IBGZPJMESA-N
UniChem Connectivity Search for chemical match using the InChIKey PBAPPPCECJKMCM-IBGZPJMESA-N
Wikipedia Mirabegron

Product suppliers

View disclaimer

Sponsored products disclaimer

Product supplier links are provided as a service to assist in identifying commercial suppliers of reagents that are mentioned on the IUPHAR/BPS Guide to PHARMACOLOGY database website, and do not imply their endorsement by NC-IUPHAR.

Links are provided in return for sponsorship, used to fund improvements to this database. The sponsorship account is managed and audited by the University of Edinburgh, a charitable body registered in Scotland, SC005336. If you are interested in sponsoring the database, please contact us.

✖

Tocris
Mirabegron (links to external site)
Cat. No. 7070