Androstandion
Androstandion |
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Chem. formel |
C19H28O2 _ _ _ _ _ |
Molar masse |
288,431 g/ mol |
Reg. CAS nummer |
5982-99-0 |
PubChem |
3034809 |
SMIL |
CC12CCC(=O)CC1CCC3C2CCC4(C3CCC4=O)C
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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
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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) |
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Hepatosteroider ( lever ) | (S-30: Lanostanes ) |
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(S-27: Cholestans ) |
- Zymosterol → 7-Dehydrodesmosterol → Desmosterol → Kolesterol
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Galdesyrer (C-24: Cholaner ) |
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Gonadosteroider ( gonader ) | |
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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
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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
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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
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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
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