Androstandion

Androstandion

Generel
Chem. formel	C19H28O2 _ _ _ _ _
Fysiske egenskaber
Molar masse	288,431 g/ mol
Klassifikation
Reg. CAS nummer	5982-99-0
PubChem	3034809
SMIL	CC12CCC(=O)CC1CCC3C2CCC4(C3CCC4=O)C
InChI	InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15.2)10-8- 16( 14)18/h12,14-16H,3-11H2,1-2H3/t12a,14-,15-,16-,18-,19-/m0/s1RAJWOBJTTGJROA-RNQTWYFASA-N
CHEBI	22542
ChemSpider	2299204
Data er baseret på standardbetingelser (25 °C, 100 kPa), medmindre andet er angivet.
Mediefiler på Wikimedia Commons

Androstandione, 5α-androstandione eller 5α-androstan-3,17-dion , er et naturligt forekommende androstan (5α-androstane) steroid og en endogen metabolit af androgener , såsom testosteron , dihydrotestosteron (DHT), dehydroepiandrosteron (DHEA), og . Det er C5-epimeren af etiocholandione (5β-androstanedion). Androstenedion dannes ud fra androstenedion af 5α-reduktase og fra DHT af 17β-hydroxysteroid dehydrogenase . Det har en vis androgen aktivitet.

En oralt aktiv syntetisk analog af 3α-androstanediol, 17α-ethynyl-5α-androstane-3α,17β-diol (HE-3235, Apoptone) er tidligere blevet undersøgt til behandling af prostatacancer og brystkræft .

Steroide hormoner (endogene)

Hepatosteroider
( lever )

(S-30: Lanostanes )	Lanosterol
(S-27: Cholestans )	Zymosterol → 7-Dehydrodesmosterol → Desmosterol → Kolesterol
Galdesyrer (C-24: Cholaner )	Cholinsyre • Chenodeoxycholsyre • ‎ Deoxycholsyre • ‎ Lithocholsyre • ‎ Glycocholsyre • ‎ Glycochenodeoxycholsyre • ‎ Taurocholsyre • ‎ Taurochenodeoxycholsyre

Gonadosteroider
( gonader )

Gestogener (C-21: Pregnanes )	17α-AC: Epipregnenolon → Epiprogesteron → Epiallopregnandione → Epiallopregnanolon 17-AC: 17-Pregnenolon → 17-Progesteron → 17-Allopregnanedion → 17-Allopregnanolon 17β-AC: Pregnenolon → Progesteron → Allopregnanedion → Allopregnanolon
Androgener (C-19: Androstanes )	17α-OH: Epiandrostenediol → Epitestosteron → 5α-Dihydroepitestosteron → Epiandrostenediol 17-O: Dehydroepiandrosteron → Androstenedion → Androstenedion → Androsteron 17β-OH: Androstenediol → Testosteron → 5α-Dihydrotestosteron → Androstenediol
Østrogener (C-18: Estranes )	17α-OH: Epiestradiol → Epiestriol → Epiestretrol 17-O: Estron → Estradiolon → Estriolon 17β-OH: Østradiol → Estriol → Estetrol

Adrenosteroider
( binyrerne )

Glumerosteroider (C-21: Pregnanes )	Mineralokortikoider 11-Deoxycorticosteron → Corticosteron → 5α-Dihydrocorticosteron → 3α,5α-Tetrahydrocorticosteron Aldosteron → 5α-dihydroaldosteron → 3α,5α-Tetrahydroaldosteron 5α-Dihydrodeoxycorticosteron → 3α,5α-Tetrahydrodeoxycorticosteron Glukokortikoider 11-Deoxycortisol → Cortisol → 5α-Dihydrocortisol → 3α,5α-Tetrahydrocortisol Cortison → 5α-dihydrocortison → 3α,5α-Tetrahydrocortison 5α-Dihydrodeoxycortisol → 3α,5α-Tetrahydrodeoxycortisol
Fascillosteroider (C-19: Androstanes )	11a-hydroxy 17α-OH: 11α-Hydroxyepiandrostanediol → 11α-Hydroxyepiandrostanediol → 5α-dihydro-11α-hydroxyepistosteron → 11α-hydroxyepiandrostanediol 17-O: 11α-hydroxydehydroepiandrosteron → 11α-hydroxyandrostenedion → 11α-hydroxyandrostenedion → 11α-hydroxyandrostenedion 17β-OH: 11α-hydroxyandrostenediol → 11α-hydroxytestosteron → 5α-dihydro-11α-hydroxytestosteron → 11α-hydroxyandrostenediol 11-keto 17α-OH: 11-ketoepiandrostanediol → 11-ketoepistosteron → 5α-dihydro-11-ketoepitestosteron → 11-ketoepiandrostanediol 17-O: 11-ketodehydroepiandrosteron → 11-ketoandrostenedion → 11-ketoandrostenedion → 11-ketoandrostenedion 17β-OH: 11-ketoandrostenediol → 11-ketotestosteron → 5α-dihydro-11-ketotestosteron → 11-ketoandrostenediol 11β-hydroxy 17α-OH: 11β-hydroxyepiandrostanediol → 11β-hydroxyepitaestosteron → 5α-dihydro-11β-hydroxyepitaestosteron → 11β-hydroxyepiandrostanediol 17-O: 11β-hydroxydehydroepiandrosteron → 11β-hydroxyandrostenedion → 11β-hydroxyandrostenedion → 11β-hydroxyandrostenedion 17β-OH: 11β-hydroxyandrostendiol → 11β-hydroxytestosteron → 5α-dihydro-11β-hydroxytestosteron → 11β-hydroxyandrostenediol
Retikulosteroider (C-18: Estranes )	Katekol-østrogener 17α-OH: 2-Hydroxyepiestradiol og 4-Hydroxyepiestradiol 17-O: 2-Hydroxyestron og 4-Hydroxyestron 17β-OH: 2-hydroxyestradiol og 4-hydroxyestradiol Quinon-østrogener 17α-OH: 2,3-quinonepiestradiol og 4,3-quinonepiestradiol 17-O: 2,3-quinonestron og 4,3-quinonestron 17β-OH: 2,3-quinonestradiol og 4,3-quinonestradiol
Medullosteroider	2,3-OH DOPA → Dopamin → Noradrenalin → Adrenalin 3-OH Tryptophan → 5-hydroxytryptophan → Serotonin → N-acetyl-5-hydroxytryptamin → Melatonin 3,4-OH DOPA → Dopamin → Noradrenalin → Adrenalin