Retroprogesterone

Retroprogesterone
Clinical data

ATC code	None
Identifiers
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
Synonyms	9β,10α-Progesterone, 9β,10α-pregn-4-ene-3,20-dione
CAS Number	2755-10-4
PubChem (CID)	92940
ChemSpider	83898
UNII	R94ZS616JR^Y
Chemical and physical data
Formula	C₂₁H₃₀O₂
Molar mass	314.4617 g/mol
3D model (Jmol)	Interactive image
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]

Ro 6-3129 (6-16-ethylthioretroprogesterone) is a retroprogesterone derivative that was never marketed.^[5]

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.
↑ Dixon, Ross; Hudson, Sean; Darragh, Austin (1973). "Pharmacokinetics of the retro-steroid progestogen, 16α-ethylthio-9β,10α-pregna-4, 6-diene-3, 20-dione (Ro 6-3129), in man and the sheep". Contraception. 8 (1): 53–65. doi:10.1016/0010-7824(73)90159-5. ISSN 0010-7824.

Progesterone receptor modulators

Agonists	Progesterone derivatives: 5α-Dihydroprogesterone 9α-Bromo-11-ketoprogesterone 11-Dehydroprogesterone 11-Deoxycorticosterone 16α-Hydroxyprogesterone 20α-Dihydroprogesterone Dimepregnen Diosgenin Progesterone Quingestrone Retroprogesterone derivatives: Dydrogesterone Retroprogesterone Ro 6-3129 Trengestone 17α-Substituted progesterone derivatives: 17α-Hydroxyprogesterone (hydroxyprogesterone) 17α-Methylprogesterone Acetomepregenol (mepregenol diacetate) Algestone Algestone acetonide Algestone acetophenide Amadinone Amadinone acetate Anagestone Anagestone acetate Butagest (buterol) Chlormadinone Chlormadinone acetate Cismadinone Cismadinone acetate Clogestone Clogestone acetate Clomegestone Clomegestone acetate Cyproterone acetate Delmadinone Delmadinone acetate Edogestrone Flugestone Flugestone acetate Flumedroxone Flumedroxone acetate Gestaclone Haloprogesterone Hydromadinone (hydromadinone acetate) Hydroxyprogesterone acetate Hydroxyprogesterone caproate (hydroxyprogesterone hexanoate) Hydroxyprogesterone heptanoate (hydroxyprogesterone enanthate) Mecigestone (pentarane B) Medrogestone Medroxyprogesterone Medroxyprogesterone acetate Megestrol Megestrol acetate Melengestrol Melengestrol acetate Mometasone Mometasone furoate Osaterone Osaterone acetate Pentagestrone Pentagestrone acetate Pentarane A Proligestone 19-Norprogesterone derivatives: 19-Norprogesterone Demegestone Gestadienol Gestonorone caproate (gestronol hexanoate) Gestronol (gestonorone) Nomegestrol Nomegestrol acetate Norgestomet Org-2058 Oxogestone Oxogestone phenpropionate Promegestone Segesterone Segesterone acetate (nestorone) Trimegestone Testosterone derivatives: 6,6-Difluoronorethisterone 11β-Methyl-19-nortestosterone 11β-Methyl-19-nortestosterone dodecylcarbonate 19-Nor-5-androstenediol 19-Nor-5-androstenedione Δ^4-Tibolone Allylestrenol Altrenogest Bolandiol Bolandiol dipropionate Bolandione Chloroethynyl norgestrel Cingestol Danazol Desogestrel Dienedione Dienogest Dienolone Dimethandrolone Dimethandrolone buciclate Dimethandrolone dodecylcarbonate Dimethandrolone undecanoate Dimethisterone Dimethyltrienolone Ethisterone Ethyldienolone Ethylestrenol (ethylnandrol) Ethynerone Etonogestrel Etynodiol Etynodiol diacetate Gestodene Gestrinone Levonorgestrel Levonorgestrel butanoate Lynestrenol Methyldienolone Metribolone (R-1881) Metynodiol Metynodiol diacetate Methoxydienone (methoxygonadiene) Mibolerone Nandrolone Nandrolone esters (e.g., nandrolone decanoate, nandrolone phenylpropionate) Norelgestromin Norethisterone (norethindrone) Norethisterone acetate Norethisterone acetate oxime Norethisterone enanthate Noretynodrel Norgesterone Norgestimate Norgestrel Norgestrienone Normethandrone (methylestrenolone, normethandrolone, normethisterone) Norvinisterone Oxendolone Quingestanol Quingestanol acetate Tetrahydrogestrinone Tibolone Tigestol Tosagestin Trenbolone (trienolone) Trestolone Trestolone acetate Spirolactone derivatives: Canrenoic acid Canrenone Drospirenone Mespirenone Potassium canrenoate SC-5233 SC-8109 Spironolactone Spirorenone Non-steroidal: 3,8-Dihydrodiligustilide Riligustilide Tanaproget ZM-182345

Mixed (SPRMs)	Apigenin Asoprisnil Asoprisnil ecamate Guggulsterone Kaempferol J1042 LG-120838 Naringenin PRA-910 Syringic acid Telapristone Antagonistic: Mifepristone Org-31710 Org-33628 Ulipristal acetate ZK-137316

Antagonists	3α-Hydroxytibolone 3β-Hydroxytibolone Aglepristone Lilopristone Lonaprisan Onapristone Toripristone Valproic acid Vilaprisan Zanoterone ZM-150271 ZM-172406

mPRs
(PAQRs)

Agonists	5α-Dihydroprogesterone 5β-Dihydroprogesterone 11-Deoxycorticosterone 17α-Hydroxyprogesterone 17α,21-Dihydroxyprogesterone 21-Hydroxyprogesterone Allopregnanolone Mifepristone Pregnenolone Progesterone

Antagonists	Mifepristone

See also: Androgenics • Estrogenics • Glucocorticoidics • Mineralocorticoidics • Steroid hormone metabolism modulators

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