Promegestone

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Promegestone
Clinical data
Other namesR-5020; RU-5020
ATC code
Identifiers
  • (8S,13S,14S,17S)-13,17-dimethyl-17-propionyl-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
ECHA InfoCard100.207.681 Edit this at Wikidata
Chemical and physical data
FormulaC22H30O2
Molar mass326.472 g/mol g·mol−1
3D model (JSmol)
  • CCC(=O)[C@]1(CC[C@@H]2[C@@]1(CCC3=C4CCC(=O)C=C4CC[C@@H]23)C)C
  • InChI=1S/C22H30O2/c1-4-20(24)22(3)12-10-19-18-7-5-14-13-15(23)6-8-16(14)17(18)9-11-21(19,22)2/h13,18-19H,4-12H2,1-3H3/t18-,19+,21+,22-/m1/s1
  • Key:QFFCYTLOTYIJMR-XMGTWHOFSA-N

Promegestone (INN) (brand name Surgestone), also known as 17α,21-dimethyl-19-nor-Δ4,9-pregnadiene-3,20-dione, is a 19-norprogesterone derivative and steroidal progestin which was introduced in 1983 and is marketed in France, Portugal, and Argentina.[1][2][3][4] Indications include gynaecological conditions caused by luteal insufficiency, including premenopausal disorders, dysmenorrhea, and premenstrual syndrome.[4] Promegestone has weak glucocorticoid activity, but does not bind to the androgen receptor or possess antimineralocorticoid activity.[4][5] In addition, promegestone has also been found to act as a non-competitive antagonist of the nicotinic acetylcholine receptor.[6] The drug is mainly bound to albumin; it does not bind to sex hormone-binding globulin, and binds only weakly to transcortin.[5]

See also

References

  1. ^ R.A. Hill; H.L.J. Makin; D.N. Kirk; G.M. Murphy (23 May 1991). Dictionary of Steroids. CRC Press. pp. 759–. ISBN 978-0-412-27060-4.
  2. ^ William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 2935–. ISBN 978-0-8155-1856-3.
  3. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 883–. ISBN 978-3-88763-075-1.
  4. ^ a b c Cain (11 September 1984). ANNUAL REPORTS IN MED CHEMISTRY V19 PPR. Academic Press. pp. 323–. ISBN 978-0-08-058363-1.
  5. ^ a b Kuhl, H (2009). "Pharmacology of estrogens and progestogens: influence of different routes of administration" (PDF). Climacteric. 8 (sup1): 3–63. doi:10.1080/13697130500148875. ISSN 1369-7137.
  6. ^ Blanton MP, Xie Y, Dangott LJ, Cohen JB (February 1999). "The steroid promegestone is a noncompetitive antagonist of the Torpedo nicotinic acetylcholine receptor that interacts with the lipid-protein interface". Mol. Pharmacol. 55 (2): 269–78. PMID 9927618.


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