| 词条 | Retroprogesterone |
| 释义 |
| Verifiedfields = | Watchedfields = | verifiedrevid = | 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 | image = Retroprogesterone.svg | width = 225px | tradename = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration = | class = Progestin; Progestogen | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion = | CAS_number_Ref = | CAS_number = 2755-10-4 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = R94ZS616JR | CAS_supplemental = | ATC_prefix = None | ATC_suffix = | PubChem = 92940 | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = 83898 | synonyms = 9β,10α-Progesterone; 9β,10α-Pregn-4-ene-3,20-dione | C=21 | H=30 | O=2 | molecular_weight = 314.462 g/mol | SMILES = CC(=O)C1CCC2C1(CCC3C2CCC4=CC(=O)CCC34C)C | StdInChI = RJKFOVLPORLFTN-HQZYFCCVSA-N | StdInChIKey = 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{{See also|List of progestogens}}See also
References1. ^1 2 {{cite book|author1=J. Horsky|author2=J. Presl|title=Ovarian Function and its Disorders: Diagnosis and Therapy|url=https://books.google.com/books?id=7IrpCAAAQBAJ&pg=PA329|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-009-8195-9|pages=305, 329}} {{Progesterone receptor modulators}}{{Steroid-stub}}{{Genito-urinary-drug-stub}}2. ^1 2 {{cite book|author1=Lt Col Pankaj Talwar|author2=Surveen Ghumann Sindhu|title=Step by Step: Protocols in Clinical Embryology and ART|url=https://books.google.com/books?id=KOP17hRq_YgC&pg=PA379|date=18 May 2012|publisher=JP Medical Ltd|isbn=978-93-5025-765-4|pages=379–}} 3. ^{{cite journal | vauthors = Kuhl H | title = Pharmacology of estrogens and progestogens: influence of different routes of administration | journal = Climacteric | volume = 8 Suppl 1 | issue = | pages = 3–63 | year = 2005 | pmid = 16112947 | doi = 10.1080/13697130500148875 | url = http://hormonebalance.org/images/documents/Kuhl%2005%20%20Pharm%20Estro%20Progest%20Climacteric_1313155660.pdf}} 4. ^{{cite book|author=Gerald Litwack|title=Biochemical Actions of Hormones|url=https://books.google.com/books?id=et3Lq-TitzAC&pg=PA193|date=2 December 2012|publisher=Elsevier|isbn=978-0-323-15189-4|pages=193–}} 5. ^{{cite journal | vauthors = Rižner TL, Brožič P, Doucette C, Turek-Etienne T, Müller-Vieira U, Sonneveld E, van der Burg B, Böcker C, Husen B | title = Selectivity and potency of the retroprogesterone dydrogesterone in vitro | journal = Steroids | volume = 76 | issue = 6 | pages = 607–15 | date = May 2011 | pmid = 21376746 | doi = 10.1016/j.steroids.2011.02.043 | url = }} 6. ^{{cite book|author=Padubidri|title=Gynaecology|url=https://books.google.com/books?id=6mvbRMT3_eoC&pg=PA207|date=1 January 2005|publisher=Elsevier India|isbn=978-81-8147-562-6|pages=207–}} 7. ^{{cite journal|last1=Dixon|first1=Ross|last2=Hudson|first2=Sean|last3=Darragh|first3=Austin|title=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|journal=Contraception|volume=8|issue=1|year=1973|pages=53–65|issn=0010-7824|doi=10.1016/0010-7824(73)90159-5}} 4 : Abandoned drugs|Diketones|Pregnanes|Progestogens |
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