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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H27FO
Molecular Weight 290.4155
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLUASTERONE

SMILES

C[C@]12CC[C@H]3[C@@H](CC=C4CCCC[C@]34C)[C@@H]1C[C@@H](F)C2=O

InChI

InChIKey=VHZXNQKVFDBFIK-NBBHSKLNSA-N
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

HIDE SMILES / InChI

Molecular Formula C19H27FO
Molecular Weight 290.4155
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Fluasterone is a fluorinated derivative of an endogenous steroid hormone androstenolone (dehydroepiandrosterone, DHEA). According to in vivo studies, fluasterone possess endocrinologic effects manifested in increased estrous cycle length and decreased the weights of the uterus, prostate, seminal vesicles, and testes. The mechanism of action of fluasterone is not yet fully elucidated, but most likely involve inhibition of glucose-6-phosphate hydrogenase. Fluasterone was developed by Aeson Therapeutics and was investigated in the late 1990s for the treatment of asthma, cancer, cardiovascular and metabolic disorders. The development of fluasterone for discontinued, probably due to a combination of low potency and insufficient oral bioavailability. Later, the development of fluasterone was continued by the company SteroTherapeutics. In 2018 the FDA has granted an orphan drug designation for fluasterone for the treatment of nonalcoholic fatty liver disease, nonalcoholic steatosis, and hyperglycemia in patients with Cushing’s syndrome.

Approval Year

PubMed

Substance Class Chemical
Record UNII
R7M5UGD04G
Record Status Validated (UNII)
Record Version