Promegestone

Promegestone

Clinical data
ATC code	G03DB07 (WHO)
Identifiers
IUPAC name (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
Synonyms	R-5020; RU-5020
CAS Number	34184-77-5
PubChem (CID)	36709
ChemSpider	33716
KEGG	D08431
Chemical and physical data
Formula	C22H30O2
Molar mass	326.472 g/mol
3D model (Jmol)	Interactive image
SMILES CCC(=O)[C@]1(CC[C@@H]2[C@@]1(CCC3=C4CCC(=O)C=C4CC[C@@H]23)C)C
InChI 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-Δ⁹-19-norprogesterone or 17α,21-dimethyl-19-norpregna-4,9-diene-3,20-dione,^[1] is a steroidal progestin of the 19-norprogesterone group 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 been found to act as a non-competitive antagonist of the nicotinic acetylcholine receptor, similarly to progesterone.^[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

• Demegestone
• Gestonorone caproate
• Medrogestone
• Nomegestrol acetate
• Segesterone acetate
• Trimegestone

References

1. J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 1026–. ISBN 978-1-4757-2085-3.
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. Cain (11 September 1984). ANNUAL REPORTS IN MED CHEMISTRY V19 PPR. Academic Press. pp. 323–. ISBN 978-0-08-058363-1.
5. 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.