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vamorolone   Click here for help

GtoPdb Ligand ID: 9247

Synonyms: Agamree® | VBP-15 | VBP15
Approved drug Immunopharmacology Ligand
vamorolone is an approved drug (FDA & EMA (2023))
Compound class: Synthetic organic
Comment: Vamorolone (VBP15) is a novel, oral non-hormonal steroid modulator, that was investigated in Duchenne muscular dystrophy. It is a multi-functional drug that exhibits anti-inflammatory, membrane stabilisation, and mineralocorticoid receptor antagonist activities. Vamorolone was proposed as a potential replacement for the corticosteroids that are currently used in DMD, as it appears to cause fewer of the common corticosteroid adverse effects [4].

vamorolone 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 4
Hydrogen bond donors 2
Rotatable bonds 2
Topological polar surface area 74.6
Molecular weight 356.2
XLogP 2.49
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 OCC(=O)C1(O)C(C)CC2C1(C)CC=C1C2CCC2=CC(=O)C=CC12C
Isomeric SMILES OCC(=O)[C@@]1(O)[C@H](C)C[C@@H]2[C@]1(C)CC=C1[C@H]2CCC2=CC(=O)C=C[C@]12C
InChI InChI=1S/C22H28O4/c1-13-10-18-16-5-4-14-11-15(24)6-8-20(14,2)17(16)7-9-21(18,3)22(13,26)19(25)12-23/h6-8,11,13,16,18,23,26H,4-5,9-10,12H2,1-3H3/t13-,16-,18+,20+,21+,22+/m1/s1
InChI Key ZYTXTXAMMDTYDQ-DGEXFFLYSA-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. China NMPA (2024)  |  EU EMA (2023)  |  US FDA (2023)
IUPAC Name Click here for help
(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one
International Nonproprietary Names Click here for help
INN number INN
10419 vamorolone
Synonyms Click here for help
Agamree® | VBP-15 | VBP15
Database Links Click here for help
BindingDB Ligand 50432396
CAS Registry No. 13209-41-1 (source: WHO INN record)
ChEMBL Ligand CHEMBL2348780
GtoPdb PubChem SID 315661322
PubChem CID 3035000
Search Google for chemical match using the InChIKey ZYTXTXAMMDTYDQ-DGEXFFLYSA-N
Search Google for chemicals with the same backbone ZYTXTXAMMDTYDQ
Search PubMed clinical trials vamorolone
Search PubMed titles vamorolone
Search PubMed titles/abstracts vamorolone
UniChem Compound Search for chemical match using the InChIKey ZYTXTXAMMDTYDQ-DGEXFFLYSA-N
UniChem Connectivity Search for chemical match using the InChIKey ZYTXTXAMMDTYDQ-DGEXFFLYSA-N

Product suppliers

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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.

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MedChemExpress
Vamorolone (links to external site)
Cat. No. HY-109017