Estradiol cypionate

Estradiol cypionate
Clinical data
Pronunciation	/ˌɛstrəˈdaɪoʊl sɪˈpaɪoʊneɪt/; ES-trə-DY-ohl sih-PY-oh-nate
Trade names	Depo-Estradiol, Depofemin, Estradep, many others
Other names	EC; E2C; Estradiol cipionate; Estradiol cyclopentylpropionate; ECP; Estradiol 17β-cyclopentylpropionate; Estradiol 17β-cyclopentanepropionate
Routes of; administration	Intramuscular injection, subcutaneous injection
Drug class	Estrogen; Estrogen ester
ATC code	G03CA03 (WHO) ;
Legal status
Legal status	US: WARNING; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	IM: High
Protein binding	Estradiol: ~98% (to albumin and SHBGTooltip sex hormone-binding globulin)
Metabolism	Cleavage via esterases in the liver, blood, and tissues
Metabolites	Estradiol, cypionic acid, and metabolites of estradiol
Elimination half-life	IM (aqueous suspension): 8–10 days
Duration of action	IM (oil): 5 mg ≈ 11–14 days; IM (aqueous suspension): 5 mg ≈ 14–24 days
Excretion	Urine
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	DB13954;
ChemSpider	9033;
UNII	7E1DV054LO;
KEGG	D04063;
ChEBI	CHEBI:34745;
ChEMBL	ChEMBL1200973;
CompTox Dashboard (EPA)	DTXSID4022999 ;
ECHA InfoCard	100.005.672
Chemical and physical data
Formula	C26H36O3
Molar mass	396.571 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	151 to 152 °C (304 to 306 °F)
	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), sold under the brand name Depo-Estradiol among others, is an estrogen medication which is used in hormone therapy for menopausal symptoms and low estrogen levels in women, in hormone therapy for trans women, and in hormonal birth control for women. It is given by injection into muscle once every 1 to 4 weeks.

Side effects of estradiol cypionate include breast tenderness, breast enlargement, nausea, headache, and fluid retention. Estradiol cypionate is an estrogen and hence is an agonist of the estrogen receptor, the biological target of estrogens like estradiol. Estradiol cypionate is an estrogen ester and a long-lasting prodrug of estradiol in the body. Because of this, it is considered to be a natural and bioidentical form of estrogen.

Estradiol cypionate was first described as well as introduced for medical use in 1952. Along with estradiol valerate, it is one of the most commonly used esters of estradiol. Estradiol cypionate has mostly been used in the United States, but is also marketed in a few other countries. The medication is not available in Europe. It is not currently available as a generic medication in the United States.

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