Dienogest

Dienogest
Clinical data
Trade names	Visanne, others
Other names	DNG; Dienogestril; Cyanomethyldienolone; BAY 86-5258; Endometrion; M-18575; MJR-35; SH-660; SH-T00660AA; STS-557; ZK-37659; δ9-17α-Cyanomethyl-19-nortestosterone; 17α-Cyanomethylestra-4,9(10)-dien-17β-ol-3-one; 17β-Hydroxy-3-oxo-19-nor-17α-pregna-4,9-diene-21-nitrile
AHFS/Drugs.com	International Drug Names
Pregnancy; category	AU: B3; ;
Routes of; administration	By mouth
Drug class	Progestogen; Progestin; Steroidal antiandrogen
ATC code	G03DB08 (WHO) ; G03AB08 (WHO) G03FA15 (WHO) (combinations with estrogens);
Legal status
Legal status	AU: S4 (Prescription only);
Pharmacokinetic data
Bioavailability	90%
Protein binding	Albumin: 90%; Free: 10%
Metabolism	Liver (reduction, hydroxylation via CYP3A4, removal of cyanomethyl group, conjugation)
Metabolites	• 9α,10β-Dihydro-DNG; • 3,5α-Tetrahydro-DNG; (Both said to be inactive)
Elimination half-life	7.5–10.7 hours
Excretion	Urine
Identifiers
	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;
CAS Number	65928-58-7 [pubchem];
PubChem CID	68861;
IUPHAR/BPS	7654;
DrugBank	DB09123 ;
ChemSpider	62093 ;
UNII	46M3EV8HHE;
KEGG	D03799 ;
ChEBI	CHEBI:70708 ;
ChEMBL	ChEMBL1201864 ;
CompTox Dashboard (EPA)	DTXSID80891478 ;
ECHA InfoCard	100.167.087
Chemical and physical data
Formula	C20H25NO2
Molar mass	311.425 g·mol−1
3D model (JSmol)	Interactive image;
Density	1.2 g/cm3
Melting point	210 to 218 °C (410 to 424 °F) (experimental)
Boiling point	549 °C (1,020 °F)
	SMILES C[C@]12CCC3=C4CCC(=O)C=C4CC[C@H]3[C@@H]1CC[C@]2(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 [pubchem]; Key:AZFLJNIPTRTECV-FUMNGEBKSA-N [pubchem];
	(verify)

Dienogest, sold under the brand name Visanne (manufactured by Bayer AG) among others, is a progestin medication which is used in birth control pills and in the treatment of endometriosis. It is also used in menopausal hormone therapy and to treat heavy periods. Dienogest is available both alone and in combination with estrogens. It is taken by mouth.

Side effects of dienogest include menstrual irregularities, headaches, nausea, breast tenderness, depression, and acne, among others. Dienogest is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone. It is a unique progestogen, with strong effects in the uterus. The medication has some antiandrogenic activity, which may help to improve androgen-dependent symptoms like acne, and has no other important hormonal activity.

Dienogest was discovered in 1979 and was introduced for medical use in 1995. Additional formulations of dienogest were approved between 2007 and 2010. It is sometimes referred to as a "fourth-generation" progestin. Dienogest is marketed widely throughout the world. It is available as a generic medication.