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Fluasterone

Fluasterone

Synopsis, Chemistry

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Also known as: 112859-71-9, R7m5ugd04g, 156680-74-9, Chembl4441355, 16alpha-fluoro-5-androsten-17-one, (8r,9s,10r,13s,14s,16r)-16-fluoro-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one

Molecular Formula

C₁₉H₂₇FO

Molecular Weight

290.4 g/mol

InChI Key

VHZXNQKVFDBFIK-NBBHSKLNSA-N

FDA UNII

R7M5UGD04G

Has antiproliferative effects on HIV-1 and reduces HIV-1 replication.

1 2D Structure

Fluasterone

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(8R,9S,10R,13S,14S,16R)-16-fluoro-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one

2.1.2 InChI

InChI=1S/C19H27FO/c1-18-9-4-3-5-12(18)6-7-13-14(18)8-10-19(2)15(13)11-16(20)17(19)21/h6,13-16H,3-5,7-11H2,1-2H3/t13-,14+,15+,16-,18+,19+/m1/s1

2.1.3 InChI Key

VHZXNQKVFDBFIK-NBBHSKLNSA-N

2.1.4 Canonical SMILES

CC12CCCCC1=CCC3C2CCC4(C3CC(C4=O)F)C

2.1.5 Isomeric SMILES

C[C@]12CCCCC1=CC[C@@H]3[C@@H]2CC[C@]4([C@H]3C[C@H](C4=O)F)C

2.2 Other Identifiers

2.2.1 UNII

R7M5UGD04G

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 5-androstene-16-fluoro-17-one

2. 5-androstene-16alpha-fluoro-17-one

3. Dhea Analog 8354

4. He2500

2.3.2 Depositor-Supplied Synonyms

1. 112859-71-9

2. R7m5ugd04g

3. 156680-74-9

4. Chembl4441355

5. 16alpha-fluoro-5-androsten-17-one

6. (8r,9s,10r,13s,14s,16r)-16-fluoro-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one

7. 16-fluoro-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one

8. 16-fluoro-5-androsten-17-one

9. He2500

10. Unii-r7m5ugd04g

11. Ccris 4216

12. 8354 Compound

13. Schembl1418930

14. Niosh/bv8387230

15. Dtxsid90920920

16. Zinc3778181

17. Bdbm50507597

18. 16-alpha-fluoro-5-androsten-17-one

19. Db06250

20. Bv83872300

21. 16.alpha.-fluoroandrost-5-en-17-one

22. Androst-5-en-17-one, 16-fluoro-, (16alpha)-

23. Androst-5-en-17-one, 16-fluoro-, (16-alpha)-

24. J-002855

25. Androst-5-en-17-one, 16-fluoro-, (16.alpha.)-

26. Q27287895

27. (2r,3as,3br,9ar,9bs,11as)-2-fluoro-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9ah,9bh,10h,11h,11ah-cyclopenta[a]phenanthren-1-one

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₂₇FO
Molecular Weight	290.4 g/mol
XLogP3	5.1
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	0
Exact Mass	290.20459364 g/mol
Monoisotopic Mass	290.20459364 g/mol
Topological Polar Surface Area	17.1 Å²
Heavy Atom Count	21
Formal Charge	0
Complexity	510
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

4 Drug and Medication Information

4.1 Drug Indication

Investigated for use/treatment in psoriasis and psoriatic disorders, hyperlipidemia, metabolic disease, cancer/tumors (unspecified), and obesity.

5 Pharmacology and Biochemistry

5.1 Mechanism of Action

Fluasterone is a synthetically stable adrenocortical steroid fluorinated analogue of dehydroepiandrosterone (DHEA), a powerful anti-inflammatory molecule with androgenic or estrogenic side effects. It is proposed that fluasterone inhibits NF-kB activation and reduces oxidative stress, but other mechanisms may play a role. Fluasterone suppresses inflammation and is effective in preclinical models of chronic inflammatory disease including psoriasis, asthma, rheumatoid arthritis, multiple sclerosis and lupus erythematosus. Fluasterone has anti-inflammatory effects inpreclinical models of chronic inflammatory disease including psoriasis, asthma, rheumatoid arthritis, multiple sclerosis and lupus erythematosus. [Aeson Pharmaceuticals Executive Report]