Vamorolone

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Also known as: 13209-41-1, Vamorolone [usan], Vbp-15 free alcohol, 17,21-dihydroxy-16alpha-methylpregna-1,4,9(11)-triene-3,20-dione, 16alpha-methyl-9,11-dehydro prednisolone, 8xp29xmb43

Molecular Formula

C₂₂H₂₈O₄

Molecular Weight

356.5 g/mol

InChI Key

ZYTXTXAMMDTYDQ-DGEXFFLYSA-N

FDA UNII

8XP29XMB43

Vamorolone is under investigation in clinical trial NCT03439670 (A Study to Assess the Efficacy and Safety of Vamorolone in Boys With Duchenne Muscular Dystrophy (DMD)).

1 2D Structure

Vamorolone

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(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

2.1.2 InChI

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

2.1.3 InChI Key

ZYTXTXAMMDTYDQ-DGEXFFLYSA-N

2.1.4 Canonical SMILES

CC1CC2C3CCC4=CC(=O)C=CC4(C3=CCC2(C1(C(=O)CO)O)C)C

2.1.5 Isomeric 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)C

2.2 Other Identifiers

2.2.1 UNII

8XP29XMB43

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Vbp15 Compound

2.3.2 Depositor-Supplied Synonyms

1. 13209-41-1

2. Vamorolone [usan]

3. Vbp-15 Free Alcohol

4. 17,21-dihydroxy-16alpha-methylpregna-1,4,9(11)-triene-3,20-dione

5. 16alpha-methyl-9,11-dehydro Prednisolone

6. 8xp29xmb43

7. (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

8. Chembl2348780

9. Vbp15

10. (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

11. Unii-8xp29xmb43

12. Vbp 15

13. Einecs 236-177-8

14. 16

15. A-methyl-9,11-dehydro Prednisolone

16. Vamorolone [inn]

17. Vamorolone (usan/inn)

18. Vamorolone [who-dd]

19. Vbp15vbp15

20. Schembl143459

21. Gtpl9247

22. Amy7535

23. Dtxsid60927527

24. Bdbm50432396

25. Zinc33650317

26. Db15114

27. Pregna-1,4,9(11)-triene-3,20-dione, 17,21-dihydroxy-16-methyl-, (16.alpha.)-

28. Hy-109017

29. Cs-0030515

30. Dexamethasone Impurity E [ep Impurity]

31. D11000

32. 16.alpha.-methyl-9,11-dehydroprednisolone

33. J-006120

34. Q27089127

35. 17,21-dihydroxy-16.alpha.-methylpregna-1,4,9(11)-triene- 3,20-dione

36. 17.alpha.,21-dihydroxy-16.alpha.-methylpregna-1,4,9(11)-triene-3,20-dione

37. Delta-1,4,9(11)-pregnatriene-17-alpha,21-dihydroxy-16-alpha-methyl-3,20-dione

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₂₈O₄
Molecular Weight	356.5 g/mol
XLogP3	2.7
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	2
Exact Mass	356.19875937 g/mol
Monoisotopic Mass	356.19875937 g/mol
Topological Polar Surface Area	74.6 Å²
Heavy Atom Count	26
Formal Charge	0
Complexity	775
Isotope Atom Count	0
Defined Atom Stereocenter Count	6
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1