Estradiol undecylate

Estradiol undecylate

Clinical data
Pronunciation	/ˌɛstrəˈdaɪ.ɒl ənˈdɛsᵻleɪt/ ESS-trə-DYE-ol un-DESS-il-ayt
Trade names	Progynon Depot 100, Delestrec, Depogin, Primogyn Depot, Progynon Depot, Oestradiol-Retard Theramex
Routes of administration	Intramuscular injection
ATC code	G03CA03 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name [(8R,9S,13S,14S,17S)-3-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] undecanoate
Synonyms	RS-1047, SQ-9993
CAS Number	3571-53-7
PubChem CID	19135
ChemSpider	18055
UNII	H3N3A8MFJC
KEGG	D04065
ChEMBL	CHEMBL1697794
ECHA InfoCard	100.020.616
Chemical and physical data
Formula	C29H44O3
Molar mass	440.658 g/mol
3D model (JSmol)	Interactive image
SMILES CCCCCCCCCCC(=O)O[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=C3C=CC(=C4)O)C
InChI InChI=1S/C29H44O3/c1-3-4-5-6-7-8-9-10-11-28(31)32-27-17-16-26-25-14-12-21-20-22(30)13-15-23(21)24(25)18-19-29(26,27)2/h13,15,20,24-27,30H,3-12,14,16-19H2,1-2H3/t24-,25-,26+,27+,29+/m1/s1 Key:TXHUMRBWIWWBGW-GVGNIZHQSA-N

Estradiol undecylate (INN, USAN) (brand name Progynon Depot 100, others), or estradiol undecanoate, is a synthetic, steroidal estrogen and an estrogen ester – specifically, the 17β-undecanoate ester of estradiol – which is or has been marketed in Europe, including in Germany, the Netherlands, Switzerland, and Monaco. It acts as a prodrug of estradiol, and hence, is considered to be a natural, bioidentical form of estrogen.

Estradiol undecylate was formerly often used in very high doses (100 mg intramuscular injection every 3 weeks or once per month) to treat prostate cancer, but has since largely been superseded for this indication by newer agents with fewer adverse effects (e.g., gynecomastia and cardiovascular complications) like GnRH analogues and non-steroidal antiandrogens. Along with estradiol valerate, estradiol cypionate, and estradiol benzoate, estradiol undecylate is or has been used as an intramuscular estrogen in hormone replacement therapy for transgender women.