Estradiol valerate

Estradiol valerate
Clinical data
Pronunciation	/ˌɛstrəˈdaɪoʊl ˈvæləreɪt/; ES-trə-DY-ohl VAL-ə-rayt
Trade names	Delestrogen, Progynon Depot, Progynova, many others
Other names	EV; E2V; Oestradiol valerate; Estradiol pentanoate; Estradiol valerianate
Routes of; administration	By mouth, sublingual, 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	Oral: 3–5%; IM injection: 100%
Protein binding	Estradiol: ~98% (to albumin and SHBGTooltip sex hormone-binding globulin)
Metabolism	Cleavage via esterases in the liver, blood, and tissues
Metabolites	Estradiol, valeric acid, and metabolites of estradiol
Elimination half-life	Oral: 12–20 hours (as E2); IM injection: 3.5 (1.2–7.2) days
Duration of action	IM injection:; • 5 mg: 7–8 days; • 10 mg: 10–14 days; • 40 mg: 2–3 weeks; • 100 mg: 3–4 weeks
Excretion	Urine (80%)
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] pentanoate;
CAS Number	979-32-8;
PubChem CID	13791;
DrugBank	DB13956;
ChemSpider	13194;
UNII	OKG364O896;
KEGG	D01413;
ChEBI	CHEBI:31561;
ChEMBL	ChEMBL1511;
CompTox Dashboard (EPA)	DTXSID8023004 ;
ECHA InfoCard	100.012.327
Chemical and physical data
Formula	C23H32O3
Molar mass	356.506 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	144 to 145 °C (291 to 293 °F)
	SMILES CCCCC(=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/C23H32O3/c1-3-4-5-22(25)26-21-11-10-20-19-8-6-15-14-16(24)7-9-17(15)18(19)12-13-23(20,21)2/h7,9,14,18-21,24H,3-6,8,10-13H2,1-2H3/t18-,19-,20+,21+,23+/m1/s1; Key:RSEPBGGWRJCQGY-RBRWEJTLSA-N;

Estradiol valerate (EV), sold for use by mouth under the brand name Progynova and for use by injection under the brand names Delestrogen and Progynon Depot among others, is an estrogen medication. It is used in hormone therapy for menopausal symptoms and low estrogen levels, hormone therapy for transgender people, and in hormonal birth control. It is also used in the treatment of prostate cancer. The medication is taken by mouth or by injection into muscle or fat once every 1 to 4 weeks.

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

Estradiol valerate was first described in 1940 and was introduced for medical use in 1954. Along with estradiol cypionate, it is one of the most widely used esters of estradiol. Estradiol valerate is used in the United States, Canada, Europe, and throughout much of the rest of the world. It is available as a generic medication.

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