Estradiol cypionate

Estradiol cypionate
Clinical data

Pronunciation	ESS-tra-DYE-ole sip-eye-oh-nate
Trade names	Depo-Estradiol, Depofemin, Estradep, many others
Routes of administration	Intramuscular injection, subcutaneous injection
ATC code	G03CA03 (WHO)
Legal status
Legal status	℞ (Prescription only)
Pharmacokinetic data
Bioavailability	Intramuscular: 100%
Metabolism	Cleavage via esterases in the liver, blood, and tissues
Metabolites	Estradiol, cypionic acid, and metabolites of estradiol
Biological half-life	Intramuscular: 8–10 days
Duration of action	Intramuscular (5 mg): 11 days or 14–24 days
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] 3-cyclopentylpropanoate
CAS Number	313-06-4
PubChem (CID)	9403
DrugBank	DBSALT000067
ChemSpider	9033
UNII	7E1DV054LO
KEGG	D04063
ChEBI	CHEBI:34745
ChEMBL	CHEMBL1200973
ECHA InfoCard	100.005.672
Chemical and physical data
Formula	C₂₆H₃₆O₃
Molar mass	396.562 g/mol
3D model (Jmol)	Interactive image
SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2OC(=O)CCC4CCCC4)CCC5=C3C=CC(=C5)O
InChI InChI=1S/C26H36O3/c1-26-15-14-21-20-10-8-19(27)16-18(20)7-9-22(21)23(26)11-12-24(26)29-25(28)13-6-17-4-2-3-5-17/h8,10,16-17,21-24,27H,2-7,9,11-15H2,1H3/t21-,22-,23+,24+,26+/m1/s1 Key:UOACKFBJUYNSLK-XRKIENNPSA-N

Estradiol cypionate (EC, E2C) (INN, USAN) (brand name Depo-Estradiol, many others), or estradiol cipionate, also known as estradiol 17β-cyclopentylpropionate or estradiol 17β-cyclopentanepropionate, is a synthetic, steroidal estrogen and an estrogen ester – specifically, the 17β-cypionate (cyclopentylpropionate) ester of estradiol – which is marketed in the United States, Canada, Europe, and throughout much of the rest of the world. It acts as a prodrug of estradiol, and hence, is considered to be a natural, bioidentical form of estrogen. Along with estradiol valerate, estradiol cypionate is one of the most widely used esters of estradiol.

The medical uses of estradiol cypionate are the same as those of estradiol and other estrogens. Examples of indications for the drug include hormone replacement therapy and hormonal contraception. In regards to the latter, estradiol cypionate is available as a combined injectable contraceptive in combination with medroxyprogesterone acetate. Along with estradiol valerate, estradiol undecylate, and estradiol benzoate, estradiol undecylate is or has been used as an intramuscular estrogen in hormone replacement therapy for transgender women.

...
Wikipedia