Compound: vamorolone
SMILES: O=C1C=C2[C@](C3=CC[C@@]4([C@@](O)(C(=O)CO)[C@@H](C[C@H]4[C@@H]3CC2)C)C)(C)C=C1
InChIKey: ZYTXTXAMMDTYDQ-DGEXFFLYSA-N
Synonyms: vamorolone, 13209-41-1, Agamree, VBP-15 free alcohol, 17,21-Dihydroxy-16alpha-methylpregna-1,4,9(11)-triene-3,20-dione, vamorolona, VBP-15, vamorolonum, 9,11-dehydro dexamethasone, 8XP29XMB43, (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, (16alpha)-17,21-dihydroxy-16-methylpregna-1,4,9(11)-triene-3,20-dione, DTXSID60927527, (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, RefChem:901612, DTXCID601356317, (1R,2R,3aS,3bS,9aS,11aS)-1-hydroxy-1-(2-hydroxyacetyl)-2,9a,11a-trimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,9aH,11H,11aH-cyclopenta(a)phenanthren-7-one, 236-177-8, VBP15, Vamorolone [USAN], Dexamethasone EP Impurity E, VBP 15, CHEMBL2348780, 16a-Methyl-9,11-dehydro Prednisolone, (8S,10S,13S,14S,16R,17R)-17-Hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-3-one, UNII-8XP29XMB43, 17,21-Dihydroxy-16a-methyl-pregna-1,4,9(11)-triene-3,20-dione; Pregna-1,4,9(11)-triene-3,20-dione, 17,21-dihydroxy-16a-methyl- (6CI,7CI,8CI); 17a,21-Dihydroxy-16a-methylpregna-1,4,9(11)-triene-3,20-dione; VBP 15; Dexamethasone Impurity E, Agamree (TN), EINECS 236-177-8, 16alpha-Methyl-9,11-dehydro Prednisolone, VAMOROLONE [INN], Vamorolone (USAN/INN), VAMOROLONE [WHO-DD], SCHEMBL143459, GTPL9247, orb1307625, (16|_)-17,21-Dihydroxy-16-methylpregna-1,4,9(11)-triene-3,20-dione, CHEBI:228304, GLXC-20144, BDBM50432396, VBP15-002, AKOS027430312, DB15114, FM25760, Pregna-1,4,9(11)-triene-3,20-dione, 17,21-dihydroxy-16-methyl-, (16.alpha.)-, BM300100, MS-25588, DB-226160, HY-109017, CS-0030515, NS00052094, DEXAMETHASONE IMPURITY E [EP IMPURITY], D11000, F82162, 16.ALPHA.-METHYL-9,11-DEHYDROPREDNISOLONE, Q27089127, 16a-Methyl-9,11-dehydro prednisolone - Bio-X trade mark, 17alpha,21-Dihydroxy-16alpha-methylpregna-1,4,9(11)-triene-3,20-dione, 17,21-DIHYDROXY-16.ALPHA.-METHYLPREGNA-1,4,9(11)-TRIENE- 3,20-DIONE, DELTA-1,4,9(11)-PREGNATRIENE-17-ALPHA,21-DIHYDROXY-16-ALPHA-METHYL-3,20-DIONE, Pregna-1,4,9(11)-triene-3,20-dione, 17,21-dihydroxy-16-methyl- (6CI,7CI,8CI), 17,21-Dihydroxy-16-methylpregna-1,4,9(11)-triene-3,20-dione,17,21-Dihydroxy-16-methyl-pregna-1,4,9(11)-triene-3,20-dione, VBP 15, VBP 15, 17,21-Dihydroxy-16-methylpregna-1,4,9(11)-triene-3,20-dione, Pregna-1,4,9(11)-triene-3,20-dione, 17,21-dihydroxy-16-methyl- (6CI,7CI,8CI),17,21-Dihydroxy-16-methyl-pregna-1,4,9(11)-triene-3,20-dione
Theoretical properties:
molecular_formula: C22H28O4
molecular_weight: 356.5 g/mol
exact_mass: 356.19875937 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 2
heavy_atom_count: 26
topological_polar_surface_area: 74.6 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Vamorolone is a 3-oxo-1,4-steroid that is pregna-1,4,9(11)-trien-17-ol substituted by oxo, oxo, and hydroxy groups at positions 3, 20, and 21, respectively. It is approved by the FDA for the treatment of patients with Duchenne muscular dystrophy aged 2 years and older. It has a role as an anti-inflammatory drug, an immunosuppressive agent and a glucocorticoid receptor agonist. It is a primary alpha-hydroxy ketone, a tertiary alpha-hydroxy ketone, a 17alpha-hydroxy steroid, a 21-hydroxy steroid, a 20-oxo steroid, a corticosteroid and a 3-oxo-Delta(1),Delta(4)-steroid.
chebi: A 3-oxo-Δ<small><sup>1</small></sup>,Δ<small><sup>4</small></sup>-steroid that is pregna-1,4,9(11)-trien-17-ol substituted by oxo, oxo, and hydroxy groups at positions 3, 20, and 21, respectively. It is approved by the FDA for the treatment of patients with Duchenne muscular dystrophy aged 2 years and older.
chembl: VAMOROLONE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Vamorolone, sold under the brand name Agamree, is a synthetic corticosteroid, which is used for the treatment of Duchenne muscular dystrophy. It is taken by mouth. It is a dual atypical glucocorticoid and antimineralocorticoid.
The most common adverse reactions include cushingoid features, psychiatric disorders, vomiting, increased weight, and vitamin D deficiency.
Vamorolone was approved for medical use in the United States in October 2023, and in the European Union in December 2023.