Gestodene

Gestodene
Clinical data
Trade names	Femodene, Femodette, Gynera, Harmonet, Meliane, Minesse, Minulet, others
Other names	GSD; SHB-331; δ15-Norgestrel; 15-Dehydronorgestrel; 17-hydroxy-18a-homo-19-nor-17α-pregna-4,15-dien-20-yn-3-one; 17α-Ethynyl-18-methyl-19-nor-δ15-testosterone; 17α-Ethynyl-18-methylestra-4,15-dien-17β-ol-3-one; 13β-Ethyl-18,19-dinor-17α-pregna-4,15-dien-20-yn-17β-ol-3-one
AHFS/Drugs.com	International Drug Names
Pregnancy; category	X;
Routes of; administration	By mouth
Drug class	Progestogen; Progestin
ATC code	G03AA10 (WHO) G03AB06 (WHO) (only combinations with estrogens);
Legal status
Legal status	In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	96% (87–111%)
Protein binding	98% (64% to SHBGTooltip sex hormone-binding globulin, 34% to albumin, 2% free)
Metabolism	Liver (reduction, hydroxylation)
Elimination half-life	12–15 hours
Excretion	Urine
Identifiers
	IUPAC name (8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14-decahydrocyclopenta[a]phenanthren-3-one;
CAS Number	60282-87-3 ;
PubChem CID	3033968;
DrugBank	DB06730 ;
ChemSpider	2298532 ;
UNII	1664P6E6MI;
KEGG	D04316 ;
ChEBI	CHEBI:135323 ;
ChEMBL	ChEMBL1213583 ;
CompTox Dashboard (EPA)	DTXSID6046478 ;
ECHA InfoCard	100.056.478
Chemical and physical data
Formula	C21H26O2
Molar mass	310.437 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	197.9 °C (388.2 °F)
	SMILES O=C4\C=C3/[C@@H]([C@H]2CC[C@]1([C@@H](/C=C\[C@]1(C#C)O)[C@@H]2CC3)CC)CC4;
	InChI InChI=1S/C21H26O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,10,12-13,16-19,23H,3,5-9,11H2,1H3/t16-,17+,18+,19-,20-,21-/m0/s1 ; Key:SIGSPDASOTUPFS-XUDSTZEESA-N ;
	(verify)

Gestodene, sold under the brand names Femodene and Minulet among others, is a progestin medication which is used in birth control pills for women. It is also used in menopausal hormone therapy. The medication is available almost exclusively in combination with an estrogen. It is taken by mouth.

Side effects of the combination of an estrogen and gestodene include menstrual irregularities, headaches, nausea, breast tenderness, mood changes, and others. Gestodene is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone. It has weak androgenic activity, weak antimineralocorticoid activity, and weak glucocorticoid activity.

Gestodene was discovered in 1975 and was introduced for medical use, specifically in birth control pills, in 1987. It was subsequently introduced for use in menopausal hormone therapy as well. Gestodene is sometimes referred to as a "third-generation" progestin. It is marketed in birth control pills widely throughout the world, whereas it is available for use in menopausal hormone therapy only a few countries. Gestodene is not approved in the United States.