| IUPAC name | 2-[(8S,13S,14S,17R)-17-hydroxy-13-methyl-3-oxo-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl]acetonitrile |
| canonical smiles | CC12CCC3=C4CCC(=O)C=C4CCC3C1CCC2(CC#N)O |
| inchi | InChI=1S/C20H25NO2/c1-19-8-6-16-15-5-3-14(22)12-13(15)2-4-17(16)18(19)7-9-20(19,23)10-11-21/h12,17-18,23H,2-10H2,1H3/t17-,18+,19+,20-/m1/s1 |
| inchi key | AZFLJNIPTRTECV-FUMNGEBKSA-N |
| molecular formula | C20H25NO2 |
| synonyms | Dienogest65928-58-7DienogestrelDienogestrilDienogestum |
| Compound Description | Dienogest is a steroid hormone that is 17beta-hydroxy-3-oxoestra-4,9-diene substituted at position 17 by a cyanomethyl group. Used as an oral contraceptive. It has a role as a synthetic oral contraceptive, a progesterone receptor agonist and a progestin. It is a 17beta-hydroxy steroid, a 3-oxo-Delta steroid, a steroid hormone and an aliphatic nitrile. It derives from a hydride of an estrane.Dienogest is an orally-active semisynthetic progestogen which also possesses the properties of 17α-hydroxyprogesterone. It is a derivative of 19-nortestosterone and has antiandrogenic properties. It is primarily used as a contraceptive in combination with ethinylestradiol, or in other combination form pills approved in United States and Europe however it is not available in the US by itself. In Europe, Australia, Malaysia, Singapore and Japan, dienogest single therapy is an approved treatment for endometriosis to alleviate painful symptoms of endometriosis and reduce endometriotic lesions. Dienogest is commonly marketed as Visanne, Natazia and Qlaira.Dienogest is a Progestin.Dienogest is an orally-active, semisynthetic, fourth generation, nonethinylated progestogen with antiproliferative, antiandrogenic, anti-inflammatory and antiangiogenic activities that is used in hormone therapy and as a female contraceptive. Upon oral administration, dienogest binds intracellular progesterone receptors which then translocate to the nucleus where the drug-receptor complex interacts with progesterone response elements, thus altering the expression of target genes. Dienogest reduces the production of estradiol, prevents ovulation and alters the cervical mucus and endometrium. In addition, dienogest appears to suppress the expression of cell cycle regulator cyclin D1. Altogether, this may prevent the growth of endometrial epithelial cells and may reduce symptoms associated with leiomyoma. |
