Allopregnandione

Allopregnandione

Generel
Chem. formel	C21H32O2 _ _ _ _ _
Fysiske egenskaber
Molar masse	316,48 g/ mol
Klassifikation
Reg. CAS nummer	566-65-4
PubChem	92810
Reg. EINECS nummer	209-297-3
SMIL	CC(=O)C1CCC2C1(CCC3C2CCC4C3(CCC(=O)C4)C)C
InChI	InChI=1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14.2)19(16)9- 11- 21(17,18)3/h14,16-19H,4-12H2,1-3H3/t14-,16-,17+,18-,19-,20-,21+/m0/s1XMRPGKVKISIQBV-BJMCWZGWSA-N
CHEBI	28952
ChemSpider	24823328
Data er baseret på standardbetingelser (25 °C, 100 kPa), medmindre andet er angivet.

Allopregnandion (5α-dihydroprogesteron, 5α-DHP eller 5α-pregnan-3,20-dion) er et endogent gestagen og neurosteroid , der syntetiseres ud fra progesteron . Det er også et mellemprodukt i syntesen af allopregnanolon og isopregnanolon fra progesteron. 5α-DHP er en progesteronreceptoragonist og en positiv allosterisk modulator af GABAA - receptoren (omend med en affinitet til denne receptor, der anses for relativt lav (sammenlignet med 3α-hydroxylerede progesteronmetabolitter såsom allopregnanolon og pregnanolon)). Det har også vist sig at virke som en negativ allosterisk modulator af GABAA - rho-receptoren. Steroidet viste sig at have 82 % af progesterons affinitet til progesteronreceptoren i rhesusabens livmoder. 5α-Dihydroprogesteron er blevet rapporteret at have ca. 33 % af den relative progestogene aktivitet af progesteron. Derudover er det en svag X-pregnan receptor (PXR) agonist (EC50 > 10.000 µM), med ca. 6 gange mindre styrke end dens 5β-isomer, 5β-dihydroprogesteron.

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