Fluasterone

HCID 133967CAS 112859-71-9

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Grundinformationen

Standard-SMILES: C[C@]12CCCCC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)[C@H](F)C[C@@H]12
InChIKey: VHZXNQKVFDBFIK-NBBHSKLNSA-N
Summenformel: C19H27FO
Durchschnittliche Molmasse: 290,4 g/mol
Monoisotopische Masse: 290,2045937

Überblick

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

Namen und Bezeichner

Bevorzugter Name: Fluasterone
IUPAC: (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
Englischer Name: Fluasterone
Summenformel: C19H27FO
Molmasse: 290.42

Namen und Synonyme

Fluasterone112859-71-916alpha-Fluoroandrost-5-en-17-oneR7M5UGD04GDTXSID90920920RefChem:599317DTXCID401349821Dehydroepiandrosterone Analog 8354(1S,2R,10R,11S,13R,15S)-13-fluoro-2,15-dimethyltetracyclo(8.7.0.0^(2,7).0^(11,15))heptadec-7-en-14-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-one156680-74-9CHEMBL4441355

Weitere Namen anzeigen

16-fluoro-5-androsten-17-oneAndrost-5-en-17-one, 16-fluoro-, (16α)-

16alpha-Fluoro-5-androsten-17-oneUNII-R7M5UGD04G16-fluoro-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-oneCCRIS 4216(8R,9S,10R,13S,14S,16R)-16-Fluoro-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-17H-cyclopenta[a]phenanthren-17-oneVHZXNQKVFDBFIK-NBBHSKLNSA-N8354 compoundHE2500

Datenbank-Bezeichner

CAS: 112859-71-9
PubChem CID: 133967
DTXSID: DTXSID90920920
ChEMBL: CHEMBL4441355
UNII: R7M5UGD04G
Nikkaji: J245.776H

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 5,1
Polarare Oberfläche (TPSA): 17,1 Å²
H-Brücken-Donoren: 0
H-Brücken-Akzeptoren: 2
Frei drehbare Bindungen: 0
Schwere Atome: 21
Formalladung: 0
Komplexität: 510

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15

Physikochemische Eigenschaften

Schmelzpunkt: 165 · 165 - 168oC
Siedepunkt: 382.5 · 382.5±42.0 °C(Predicted)
Dichte: 1.09 · 1.09±0.1 g/cm3(Predicted)
storage temp.: -20 °C · Hygroscopic, -20°C Freezer, Under inert atmosphere
Löslichkeit: Chloroform (Slightly), Methanol (Very Slightly, Heated)
Aggregatzustand: Solid
Farbe: White to Off-White

Chemie und Industrie

Pharmakologische Informationen

Mechanism of Action · 1 Eintrag

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]

Anwendungen · 1 Eintrag

VerwendenFluasterone is a synthetic derivative of Dehydroepiandrosterone. The reduced androgenicity of Fluasterone may obviate toxicities associated with the androgenicity of the parent compound. Antitumor agent. Fluasterone is used in clinical trials for prostate cancer prevention.