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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
Structure of VAMOROLONE

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

HIDE SMILES / InChI

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).

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: CHEMBL2094258
Sources: patents.google.com/patent/WO2009155056A2
PubMed

PubMed

TitleDatePubMed
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
The corticosteroid compounds prednisolone and vamorolone do not alter the nociception phenotype and exacerbate liver injury in sickle cell mice.
2018 Apr 17
Patents

Patents

Sample Use Guides

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
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 Sat Dec 16 02:12:01 GMT 2023
Edited
by admin
on Sat Dec 16 02:12:01 GMT 2023
Record UNII
8XP29XMB43
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
VAMOROLONE
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
VAMOROLONE [USAN]
Common Name English
17,21-DIHYDROXY-16.ALPHA.-METHYLPREGNA-1,4,9(11)-TRIENE- 3,20-DIONE
Systematic Name English
DEXAMETHASONE IMPURITY E [EP IMPURITY]
Common Name English
DELTA-1,4,9(11)-PREGNATRIENE-17-ALPHA,21-DIHYDROXY-16-ALPHA-METHYL-3,20-DIONE
Common Name English
9,11-DEHYDRO DEXAMETHASONE
Common Name English
vamorolone [INN]
Common Name English
PREGNA-1,4,9(11)-TRIENE-3,20-DIONE, 17,21-DIHYDROXY-16-METHYL-, (16.ALPHA.)-
Systematic Name English
AGAMREE
Brand Name English
Vamorolone [WHO-DD]
Common Name English
16.ALPHA.-METHYL-9,11-DEHYDROPREDNISOLONE
Common Name English
VBP-15 FREE ALCOHOL
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C521
Created by admin on Sat Dec 16 02:12:01 GMT 2023 , Edited by admin on Sat Dec 16 02:12:01 GMT 2023
EU-Orphan Drug EU/3/14/1309
Created by admin on Sat Dec 16 02:12:01 GMT 2023 , Edited by admin on Sat Dec 16 02:12:01 GMT 2023
FDA ORPHAN DRUG 343111
Created by admin on Sat Dec 16 02:12:01 GMT 2023 , Edited by admin on Sat Dec 16 02:12:01 GMT 2023
Code System Code Type Description
FDA UNII
8XP29XMB43
Created by admin on Sat Dec 16 02:12:01 GMT 2023 , Edited by admin on Sat Dec 16 02:12:01 GMT 2023
PRIMARY
USAN
CD-141
Created by admin on Sat Dec 16 02:12:01 GMT 2023 , Edited by admin on Sat Dec 16 02:12:01 GMT 2023
PRIMARY
EPA CompTox
DTXSID60927527
Created by admin on Sat Dec 16 02:12:01 GMT 2023 , Edited by admin on Sat Dec 16 02:12:01 GMT 2023
PRIMARY
ECHA (EC/EINECS)
236-177-8
Created by admin on Sat Dec 16 02:12:01 GMT 2023 , Edited by admin on Sat Dec 16 02:12:01 GMT 2023
PRIMARY
WIKIPEDIA
Vamorolone
Created by admin on Sat Dec 16 02:12:01 GMT 2023 , Edited by admin on Sat Dec 16 02:12:01 GMT 2023
PRIMARY
NCI_THESAURUS
C152825
Created by admin on Sat Dec 16 02:12:01 GMT 2023 , Edited by admin on Sat Dec 16 02:12:01 GMT 2023
PRIMARY
ChEMBL
CHEMBL3707311
Created by admin on Sat Dec 16 02:12:01 GMT 2023 , Edited by admin on Sat Dec 16 02:12:01 GMT 2023
PRIMARY
DRUG BANK
DB15114
Created by admin on Sat Dec 16 02:12:01 GMT 2023 , Edited by admin on Sat Dec 16 02:12:01 GMT 2023
PRIMARY
INN
10419
Created by admin on Sat Dec 16 02:12:01 GMT 2023 , Edited by admin on Sat Dec 16 02:12:01 GMT 2023
PRIMARY
CAS
13209-41-1
Created by admin on Sat Dec 16 02:12:01 GMT 2023 , Edited by admin on Sat Dec 16 02:12:01 GMT 2023
PRIMARY
PUBCHEM
3035000
Created by admin on Sat Dec 16 02:12:01 GMT 2023 , Edited by admin on Sat Dec 16 02:12:01 GMT 2023
PRIMARY
SMS_ID
100000174660
Created by admin on Sat Dec 16 02:12:01 GMT 2023 , Edited by admin on Sat Dec 16 02:12:01 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY