Details of the Drug

General Information of Drug (ID: DM047HI)

Drug Name
VBP15
Synonyms
vamorolone; Vamorolone; 13209-41-1; UNII-8XP29XMB43; VBP-15; 8XP29XMB43; CHEMBL2348780; 17,21-Dihydroxy-16alpha-methylpregna-1,4,9(11)-triene-3,20-dione; A-Methyl-9,11-dehydro Prednisolone; (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; Vamorolone [USAN]; VBP-15 free alcohol; VBP 15; EINECS 236-177-8; AC1MHYKY; Vamorolone (USAN/INN); SCHEMBL143459; GTPL9247; A)-17,21-dihydroxy-16-methylpregna-1,4,9(11)-triene-3,20-dione; ZINC33650317
Indication
Disease Entry ICD 11 Status REF
Duchenne dystrophy 8C70 Phase 2 [1], [2]
Inflammatory bowel disease DD72 Phase 1 [3]
Multiple sclerosis 8A40 Phase 1 [3]
Rheumatoid arthritis FA20 Phase 1 [3]
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 356.5
Topological Polar Surface Area (xlogp) 2.7
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 4
Chemical Identifiers
Formula
C22H28O4
IUPAC Name
(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
Canonical SMILES
C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@@]4(C3=CC[C@@]2([C@]1(C(=O)CO)O)C)C
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
InChIKey
ZYTXTXAMMDTYDQ-DGEXFFLYSA-N
Cross-matching ID
PubChem CID
3035000
CAS Number
13209-41-1
TTD ID
D0F6YM

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Glucocorticoid receptor messenger RNA (GCR mRNA) TTOZRK6 GCR_HUMAN Agonist [3], [1]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Duchenne dystrophy
ICD Disease Classification 8C70
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Glucocorticoid receptor messenger RNA (GCR mRNA) DTT NR3C1 3.19E-02 0.54 1.67
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
2 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
3 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
4 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
5 Clinical pipeline report, company report or official report of ISIS Pharmaceuticals (2011).
6 Synthesis and activity of novel bile-acid conjugated glucocorticoid receptor antagonists. Bioorg Med Chem Lett. 2006 Dec 1;16(23):6086-90.
7 Discovery of N-{1-[3-(3-oxo-2,3-dihydrobenzo[1,4]oxazin-4-yl)propyl]piperidin-4-yl}-2-phenylacetamide (Lu AE51090): an allosteric muscarinic M1 rec... J Med Chem. 2010 Sep 9;53(17):6386-97.
8 Functional probing of the human glucocorticoid receptor steroid-interacting surface by site-directed mutagenesis. Gln-642 plays an important role in steroid recognition and binding. J Biol Chem. 2000Jun 23;275(25):19041-9.
9 Antiinflammatory glucocorticoid receptor ligand with reduced side effects exhibits an altered protein-protein interaction profile. Proc Natl Acad Sci U S A. 2007 Dec 4;104(49):19244-9.
10 Differentiation of in vitro transcriptional repression and activation profiles of selective glucocorticoid modulators. Bioorg Med Chem Lett. 2004 Apr 5;14(7):1721-7.