Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C22H28O4 |
Molecular Weight | 356.4553 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12C[C@@H](C)[C@](O)(C(=O)CO)[C@@]1(C)CC=C3[C@@]2([H])CCC4=CC(=O)C=C[C@]34C
InChI
InChIKey=ZYTXTXAMMDTYDQ-DGEXFFLYSA-N
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
Molecular Formula | C22H28O4 |
Molecular Weight | 356.4553 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
VBP-15 FREE ALCOHOL, also known as Vamorolone and VBP-15, is an anti-inflammatory compound used in the treatment of muscular dystrophy. Vamorolone is a dissociative steroid that retains high affinity binding and nuclear translocation of both glucocorticoid (agonist) and mineralocorticoid (antagonist) receptors, but does not show pharmacodynamic safety concerns of existing glucocorticoid drugs at up to 20 mg/kg/day. Vamorolone is a first-in-class steroidal multi-functional drug that shows potent inhibition of pro-inflammatory NFkB pathways via high-affinity binding to the glucocorticoid receptor, high affinity antagonism for the mineralocorticoid receptor, and membrane stabilization properties. Pre-clinical data in multiple mouse models of inflammation showed retention of anti-inflammatory efficacy, but loss of most or all side effects. Vamorolone has received Orphan Drug Designation in the US and Europe and is being developed for chronic treatment of boys with Duchenne Muscular Dystrophy (DMD).
Originator
Approval Year
PubMed
Title | Date | PubMed |
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Vamorolone, a dissociative steroidal compound, reduces pro-inflammatory cytokine expression in glioma cells and increases activity and survival in a murine model of cortical tumor. | 2017 Feb 7 |
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The corticosteroid compounds prednisolone and vamorolone do not alter the nociception phenotype and exacerbate liver injury in sickle cell mice. | 2018 Apr 17 |
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Phase 1 trial of vamorolone, a first-in-class steroid, shows improvements in side effects via biomarkers bridged to clinical outcomes. | 2018 Jun |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/30219580
2-week, open-label Phase IIa multiple ascending dose study (0.25, 0.75, 2.0, and 6.0 mg/kg/day) enrolled 48 boys with Duchenne muscular dystrophy. Vamorolone was safe and well-tolerated through the highest dose tested (6.0 mg/kg/day) and pharmacokinetics of vamorolone were similar to prednisolone.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27261270
Primary human intestinal epithelial cells were treated with VBP-15 (10 uM) for 24 h. VBP-15 significantly reduced the in vitro production of CCL5 , IL-6, IL-8.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 02:12:01 GMT 2023
by
admin
on
Sat Dec 16 02:12:01 GMT 2023
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Record UNII |
8XP29XMB43
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C521
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EU-Orphan Drug |
EU/3/14/1309
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FDA ORPHAN DRUG |
343111
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8XP29XMB43
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CD-141
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DTXSID60927527
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236-177-8
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Vamorolone
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C152825
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13209-41-1
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3035000
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100000174660
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