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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

[H][C@@]12C[C@@H](F)C(=O)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CC=C4CCCC[C@]34C

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
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

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

PubMed

TitleDatePubMed
Inhibition of carcinogen-activating enzymes by 16alpha-fluoro-5-androsten-17-one.
2002 Jul 1
Dehydroepiandrosterone inhibits the progression phase of mammary carcinogenesis by inducing cellular senescence via a p16-dependent but p53-independent mechanism.
2005
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:54:42 UTC 2023
Edited
by admin
on Fri Dec 15 15:54:42 UTC 2023
Record UNII
R7M5UGD04G
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FLUASTERONE
Common Name English
16.ALPHA.-FLUOROANDROST-5-EN-17-ONE
Systematic Name English
HE-2500
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 527116
Created by admin on Fri Dec 15 15:54:42 UTC 2023 , Edited by admin on Fri Dec 15 15:54:42 UTC 2023
NCI_THESAURUS C1636
Created by admin on Fri Dec 15 15:54:42 UTC 2023 , Edited by admin on Fri Dec 15 15:54:42 UTC 2023
Code System Code Type Description
FDA UNII
R7M5UGD04G
Created by admin on Fri Dec 15 15:54:42 UTC 2023 , Edited by admin on Fri Dec 15 15:54:42 UTC 2023
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CAS
112859-71-9
Created by admin on Fri Dec 15 15:54:42 UTC 2023 , Edited by admin on Fri Dec 15 15:54:42 UTC 2023
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EVMPD
SUB34022
Created by admin on Fri Dec 15 15:54:42 UTC 2023 , Edited by admin on Fri Dec 15 15:54:42 UTC 2023
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DRUG BANK
DB06250
Created by admin on Fri Dec 15 15:54:42 UTC 2023 , Edited by admin on Fri Dec 15 15:54:42 UTC 2023
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EPA CompTox
DTXSID90920920
Created by admin on Fri Dec 15 15:54:42 UTC 2023 , Edited by admin on Fri Dec 15 15:54:42 UTC 2023
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WIKIPEDIA
Fluasterone
Created by admin on Fri Dec 15 15:54:42 UTC 2023 , Edited by admin on Fri Dec 15 15:54:42 UTC 2023
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SMS_ID
100000127841
Created by admin on Fri Dec 15 15:54:42 UTC 2023 , Edited by admin on Fri Dec 15 15:54:42 UTC 2023
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NCI_THESAURUS
C63639
Created by admin on Fri Dec 15 15:54:42 UTC 2023 , Edited by admin on Fri Dec 15 15:54:42 UTC 2023
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PUBCHEM
133967
Created by admin on Fri Dec 15 15:54:42 UTC 2023 , Edited by admin on Fri Dec 15 15:54:42 UTC 2023
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