Vamorolone
(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
Molecular Identity
Vamorolone
(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
PubChem CID: 3035000
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.
2D Structure
Properties
C22H28O4
Molecular Formula
356.50
Molecular Weight
g/mol
356.1988
Exact Mass
Da
2.7
XLogP
Drug-like (Lipinski: < 5)
74.6
TPSA
Good oral absorption (< 140 A²)
2
H-Bond Donors
4
H-Bond Acceptors
775
Complexity
SMILES
Canonical SMILES
SMILES: CC1CC2C3CCC4=CC(=O)C=CC4(C3=CCC2(C1(C(=O)CO)O)C)CIsomeric SMILES
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)CSynonyms(20)
vamorolone13209-41-1AgamreeVBP-15 free alcoholvamorolonaVBP-1517,21-Dihydroxy-16alpha-methylpregna-1,4,9(11)-triene-3,20-dionevamorolonum(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-one9,11-dehydro dexamethasone8XP29XMB43(16alpha)-17,21-dihydroxy-16-methylpregna-1,4,9(11)-triene-3,20-dioneDTXSID60927527(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-oneRefChem:901612
Data from PubChem (NCBI)
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