Retroprogesterone

Retroprogesterone
Systematic (IUPAC) name

(8S,9R,10S,13S,14S,17S)-17-Acetyl-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
Identifiers
CAS Number	2755-10-4
ATC code	None
PubChem	CID 92940
ChemSpider	83898
Synonyms	9β,10α-Progesterone, 9β,10α-pregn-4-ene-3,20-dione
Chemical data
Formula	C₂₁H₃₀O₂
Molar mass	314.4617 g/mol
SMILES CC(=O)C1CCC2C1(CCC3C2CCC4=CC(=O)CCC34C)C
InChI InChI=RJKFOVLPORLFTN-HQZYFCCVSA-N Key:1S/C21H30O2/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/h12,16-19H,4-11H2,1-3H3/t16-,17+,18-,19+,20+,21+/m0/s1

Retroprogesterone, also known as 9β,10α-progesterone or as 9β,10α-pregn-4-ene-3,20-dione, is a synthetic steroid and stereoisomer of the natural progestogen, progesterone.^[1]^[2] It is the parent compound of a group of progestins consisting of dydrogesterone (6-dehydroretroprogesterone) and trengestone (1,6-bis-dehydro-6-chloro-retroprogesterone).^[1]^[2]^[3] Retroprogesterone itself binds with high affinity to the progesterone receptor as well.^[4]

References

1 2 J. Horsky; J. Presl (6 December 2012). Ovarian Function and its Disorders: Diagnosis and Therapy. Springer Science & Business Media. pp. 305, 329. ISBN 978-94-009-8195-9.
1 2 Lt Col Pankaj Talwar; Surveen Ghumann Sindhu (18 May 2012). Step by Step: Protocols in Clinical Embryology and ART. JP Medical Ltd. pp. 379–. ISBN 978-93-5025-765-4.
↑ Padubidri (1 January 2005). Gynaecology. Elsevier India. pp. 207–. ISBN 978-81-8147-562-6.
↑ Gerald Litwack (2 December 2012). Biochemical Actions of Hormones. Elsevier. pp. 193–. ISBN 978-0-323-15189-4.

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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