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
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]

See also

• 17α-Hydroxyprogesterone
• 19-Norprogesterone
• 17α-Ethynyltestosterone
• 19-Nortestosterone
• 17α-Spirolactone

References

1. 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.
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.
3. Padubidri (1 January 2005). Gynaecology. Elsevier India. pp. 207–. ISBN 978-81-8147-562-6.
4. Gerald Litwack (2 December 2012). Biochemical Actions of Hormones. Elsevier. pp. 193–. ISBN 978-0-323-15189-4.
5. 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.