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Merck
CN

SML3275

Vamorolone

≥95% (HPLC)

Synonym(s):

(16α)-17,21-Dihydroxy-16-methylpregna-1,4,9(11)-triene-3,20-dione, (16α)-17,21-Dihydroxy-16-methylpregna-1,4,9(11)-triene-3,20-dione;, VBP 15, VBP15

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About This Item

Empirical Formula (Hill Notation):
C22H28O4
CAS Number:
13209-41-1
Molecular Weight:
356.46
MDL number:
MFCD18452727
UNSPSC Code:
12352200
NACRES:
NA.84

Key Documents

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Quality Level

100

Assay

≥95% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

SMILES string

O[C@]1([C@@]2([C@H]([C@@H]3CCC4=CC(=O)C=C[C@@]4(C3=CC2)C)C[C@H]1C)C)C(=O)CO

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

InChI key

ZYTXTXAMMDTYDQ-DGEXFFLYSA-N

Biochem/physiol Actions

Orally available dissociative steroid with anti-inflammatory efficacy
Vamorolone, a synthetic steroid, is an orally available dissociative steroid with anti-inflammatory efficacy. It is a partial agonist of the glucocorticoid receptor (NR3C1) that appear to be safe and well tolerated. Also, vamorolone is a potent antagonist of the mineralocorticoid receptor (NR3C2). It is under development for children with Duchenne muscular dystrophy.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H317,H319

Hazard Classifications

Eye Irrit. 2 - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000184388
0000184389
0000176721
0000176721
0000184389

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Xu Liu et al.
Proceedings of the National Academy of Sciences of the United States of America, 117(39), 24285-24293 (2020-09-13)
Duchenne muscular dystrophy is a genetic disorder that shows chronic and progressive damage to skeletal and cardiac muscle leading to premature death. Antiinflammatory corticosteroids targeting the glucocorticoid receptor (GR) are the current standard of care but drive adverse side effects
Christopher R Heier et al.
Life science alliance, 2(1) (2019-02-13)
Cardiomyopathy is a leading cause of death for Duchenne muscular dystrophy. Here, we find that the mineralocorticoid receptor (MR) and glucocorticoid receptor (GR) can share common ligands but play distinct roles in dystrophic heart and skeletal muscle pathophysiology. Comparisons of

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