Hubbry Logo
search button
Sign in
Retroprogesterone
Retroprogesterone
Comunity Hub
MainMain
arrow-down
History
arrow-down
starMore
arrow-down
Sign in
Sign in
bob

Bob

Have a question related to this hub?

bob

Alice

Got something to say related to this hub?
Share it here.

#general is a chat channel to discuss anything related to the hub.
Hubbry Logo
search button
Sign in
Retroprogesterone
Retroprogesterone
Community hub for the Wikipedia article
logoWikipedian hub
Main
Welcome to the community hub built on top of the Retroprogesterone Wikipedia article. Here, you can discuss, collect, and organize anything related to Retroprogesterone. The purpose of the hub is to conne...
Add your contribution
Media Collections
1
Timelines
0
Articles
0
Notes collections
0
Days in Chronicle
0
Retroprogesterone
Retroprogesterone
Clinical data
Other names9β,10α-Progesterone; 9β,10α-Pregn-4-ene-3,20-dione
Drug classProgestin; Progestogen
ATC code
  • None
Identifiers
  • (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
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.018.553 Edit this at Wikidata
Chemical and physical data
FormulaC21H30O2
Molar mass314.469 g·mol−1
3D model (JSmol)
  • CC(=O)C1CCC2C1(CCC3C2CCC4=CC(=O)CCC34C)C
  • 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 progestin which was never marketed.[1][2] It is a stereoisomer of the naturally occurring progestogen progesterone, in which the hydrogen atom at the 9th carbon is in the α-position (below the plane) instead of the β-position (above the plane) and the methyl group at the 10th carbon is in the β-position instead of the α-position.[1][2] In other words, the atom positions at the two carbons have been reversed relative to progesterone, hence the name retroprogesterone. This reversal results in a "bent" configuration in which the plane of rings A and B is orientated at a 60° angle below the rings C and D.[3] This configuration is ideal for interaction with the progesterone receptor, with retroprogesterone binding with high affinity to this receptor.[4] However, the configuration is not as ideal for binding to other steroid hormone receptors, and as a result, retroprogesterone derivatives have increased selectivity for the progesterone receptor relative to progesterone.[5]

Retroprogesterone is the parent compound of a group of progestins consisting of the marketed progestins dydrogesterone (6-dehydroretroprogesterone) and trengestone (1,6-didehydro-6-chlororetroprogesterone) and the never-marketed progestin Ro 6-3129, as well as the active metabolites of these progestins like 20α-dihydrodydrogesterone and 20α-dihydrotrengestone (i.e., the 20α-hydroxylated analogues).[1][2][6][7]

Chemistry

[edit]
See also: List of progestogens

See also

[edit]

References

[edit]
  1. ^ a b c Horský J (6 December 2012). "Therapy of Anovolution". In Horský J, Presl J (eds.). Ovarian Function and its Disorders: Diagnosis and Therapy. Springer Science & Business Media. pp. 305, 329. ISBN 978-94-009-8195-9.
  2. ^ a b c Sindhu SG (18 May 2012). "Endometrial Receptivity and Luteal Support". In Talwar P, Sindhu SG (eds.). Step by Step: Protocols in Clinical Embryology and ART. JP Medical Ltd. pp. 379–. ISBN 978-93-5025-765-4.
  3. ^ Kuhl H (August 2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration". Climacteric. 8 (Suppl 1): 3–63. doi:10.1080/13697130500148875. PMID 16112947. S2CID 24616324.
  4. ^ Litwack G (2 December 2012). Biochemical Actions of Hormones. Elsevier. pp. 193–. ISBN 978-0-323-15189-4.
  5. ^ Rižner TL, Brožič P, Doucette C, Turek-Etienne T, Müller-Vieira U, Sonneveld E, et al. (May 2011). "Selectivity and potency of the retroprogesterone dydrogesterone in vitro". Steroids. 76 (6): 607–615. doi:10.1016/j.steroids.2011.02.043. PMID 21376746. S2CID 31609405.
  6. ^ Padubidri VG, Anand E (January 2005). "Hormonal Therapy in Gynecology". Gynaecology. Elsevier India. pp. 207–. ISBN 978-81-8147-562-6.
  7. ^ Dixon R, Hudson S, Darragh A (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.

This article about a pregnanes is a stub. You can help Wikipedia by expanding it.

Stub icon

This drug article relating to the genito-urinary system is a stub. You can help Wikipedia by expanding it.

Hub tags