20-Dihydroprogesterone

20α-Dihydroprogesterone
Identifiers


CAS Number	145-14-2^Y[yes]
ChemSpider	83725
EC Number	205-649-5
Jmol interactive 3D	Image
MeSH	20-alpha-Dihydroprogesterone
PubChem	8956
InChI InChI=1/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/h12-13,16-19,22H,4-11H2,1-3H3/t13-,16+,17-,18+,19+,20+,21-/m1/s1 Key: RWBRUCCWZPSBFC-SJOKZOANBK
SMILES O=C4\C=C2/[C@]([C@H]1CC[C@@]3([C@H](CC[C@H]3[C@@H]1CC2)[C@H](O)C)C)(C)CC4
Properties
Chemical formula	C₂₁H₃₂O₂
Molar mass	316.478 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is ^YN ?)
Infobox references

20α-Dihydroprogesterone, or 20α-hydroxyprogesterone, is a naturally-occurring, endogenous progestogen.^[1]^[2]^[3] It is a metabolite of progesterone, converted by the 20α-hydroxysteroid dehydrogenases AKR1C1 and AKR1C3, and although still active as a progestogen,^[4] is much less potent in comparison.^[1]^[2]^[3]

References

1 2 Beranič N, Gobec S, Rižner TL (2011). "Progestins as inhibitors of the human 20-ketosteroid reductases, AKR1C1 and AKR1C3". Chem. Biol. Interact. 191 (1-3): 227–33. doi:10.1016/j.cbi.2010.12.012. PMID 21182831.
1 2 Tony M. Plant; Anthony J. Zeleznik (15 November 2014). Knobil and Neill's Physiology of Reproduction: Two-Volume Set. Academic Press. pp. 1–. ISBN 978-0-12-397769-4.
1 2 Cynthia L. Darlington (27 April 2009). The Female Brain. CRC Press. pp. 4–. ISBN 978-1-4200-7745-2.
↑ Marianne J. Legato (29 October 2009). Principles of Gender-Specific Medicine. Academic Press. pp. 617–. ISBN 978-0-08-092150-1.

Endogenous steroids (and metabolic intermediates)

Precursors

Corticosteroids

Glucocorticoids	Corticosterone Cortisol Cortisone DHC Deoxycortisol Deoxycorticosterone 17-Hydroxypregnenolone 17-Hydroxyprogesterone Pregnenolone Progesterone THB

Mineralocorticoids	Aldosterone Corticosterone Cortisol Deoxycortisol Deoxycorticosterone 5α-Dihydroaldosterone 16α,18-Dihydroxy-11-deoxycorticosterone 18-Hydroxy-11-deoxycorticosterone 18-Hydroxycorticosterone 18-Hydroxydeoxycorticosterone

Sex steroids

Androgens	3α-Androstanediol Δ⁵-Androstenediol Δ⁴-Androstenedione Androsterone DHEA DHEA sulfate Dihydrotestosterone Epiandrosterone Epitestosterone 16α-Hydroxyandrostenedione 16α-Hydroxy-DHEA 16α-Hydroxy-DHEA sulfate Testosterone

Estrogens	27-Hydroxycholesterol 3α-Androstanediol 3β-Androstanediol Δ⁴-Androstenedione Δ⁵-Androstenediol DHEA DHEA sulfate 7-Oxo-DHEA 7α-Hydroxy-DHEA 16α-Hydroxy-DHEA 7β-Hydroxyepiandrosterone Estetrol Estradiol Estrone Estriol 2-Hydroxyestrone 16-Hydroxyestrone

Progestogens	Progesterone 17α-Hydroxyprogesterone 20α-Dihydroprogesterone 5α-Dihydroprogesterone Deoxycorticosterone 5α-DHDOC

Neurosteroids

Others

Progestogenics

Receptor
(ligands)

Agonists	3,8-Dihydrodiligustilide 5α-Dihydroprogesterone 20α-Dihydroprogesterone 11-Dehydroprogesterone 11-Deoxycorticosterone 17α-Hydroxyprogesterone 19-Norprogesterone Δ^4-Tibolone Algestone Algestone acetonide Algestone acetophenide Allylestrenol Altrenogest Amadinone Amadinone acetate Anagestone Anagestone acetate Canrenoic acid Canrenone Chlormadinone Chlormadinone acetate Cingestol Cismadinone Cismadinone acetate Clogestone Clogestone acetate Clomegestone Clometerone Cyproterone acetate Danazol Delmadinone Delmadinone acetate Demegestone Desogestrel Dienogest Dimethisterone Diosgenin Drospirenone Dydrogesterone Edogesterone Ethisterone Ethynerone Etonogestrel Etynodiol Etynodiol diacetate Flugestone Flugestone acetate Gestaclone Gestadienol Gestodene Gestonorone Gestonorone caproate Gestovister Gestrinone Gestronol Guggulsterone Haloprogesterone Hydromadinone Hydroxyprogesterone acetate Hydroxyprogesterone caproate Hydroxyprogesterone heptanoate Hydroxyprogesterone hexanoate Levonorgestrel Lutenyl Lynestrenol Medrogestone Medroxyprogesterone Medroxyprogesterone acetate Megestrol Megestrol acetate Melengestrol Melengestrol acetate Mespirenone Methylestrenolone Methynodiol Methynodiol diacetate Mometasone furoate Nandrolone Nestorone Nomegestrol Nomegestrol acetate Norelgestromin Norethisterone (norethindrone) Norethisterone acetate Norethisterone acetate oxime Norethisterone enanthate Noretynodrel Norgesterone Norgestimate Norgestomet Norgestrel Norgestrienone Norvinisterone Org-2058 Oxogestone Oxogestone phenpropionate Pentagestrone Potassium canrenoate Progesterone Proligestone Promegestone Retroprogesterone Riligustilide Quingestanol Quingestanol acetate Quingestrone Segesterone Spironenone Spironolactone Tanaproget Tetrahydrogestrinone Tibolone Tigestol Tosagestin Trengestone Trimegestone ZM-182,345

Mixed (SPRMs)	Apigenin Asoprisnil Asoprisnil ecamate Kaempferol J1042 LG-120,838 Naringenin Syringic acid Telapristone Antagonistic: Mifepristone Org-31710 Org-33628 Ulipristal acetate ZK-137,316

Antagonists	3α-Hydroxytibolone 3β-Hydroxytibolone Aglepristone Lilopristone Lonaprisan Onapristone Toripristone Valproic acid Vilaprisan ZM-150,271 ZM-172,406

Enzyme

Modulators	See here instead (modulators of 20,22-desmolase, 17α-hydroxylase/17,20-lyase, 3β-HSD, and 21-hydroxylase).

Others

Precursors/prohormones	Cholesterol 22R-Hydroxycholesterol 20α,22R-Dihydroxycholesterol Pregnenolone Pregnenolone sulfate 17-Hydroxypregnenolone

Indirect	Antigonadotropins (e.g., estrogens, progestogens, prolactin) GnRH agonists (e,g, GnRH, leuprorelin) GnRH antagonists (e.g., cetrorelix) Gonadotropins (e.g., FSH, hCG, LH) Kisspeptin Plasma proteins (ABP, albumin, SHBG)

See also: Androgenics • Estrogenics • Glucocorticoids • Mineralocorticoids

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