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].
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/)

For advanced searching click here to open chemical structure editor

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