Estradiol valerate

Estradiol valerate
Clinical data

Pronunciation	/ˌɛstrəˈdaɪoʊl ˈvæləreɪt/ ES-trə-DYE-ohl VAL-ə-rayt
Trade names	Altadiol, Deladiol, Delestrogen, Estraval, Lastrogen, Progynon Depot, Progynova, Valergen, others
Routes of administration	Oral, intramuscular injection
ATC code	G03CA03 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	Oral: 3–5% Intramuscular: 100%
Metabolism	Cleavage via esterases in the liver, blood, and tissues
Metabolites	Estradiol, valeric acid, and metabolites of estradiol
Biological half-life	Oral: 12–20 hours (as E2) Intramuscular: 4–5 days
Duration of action	Intramuscular (5 mg): 7–8 days
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
Synonyms	Estradiol pentanoate; Estradiol valerianate
CAS Number	979-32-8
PubChem CID	13791
ChemSpider	13194
UNII	OKG364O896
KEGG	D01413
ChEBI	CHEBI:31561
ChEMBL	CHEMBL1511
ECHA InfoCard	100.012.327
Chemical and physical data
Formula	C₂₃H₃₂O₃
Molar mass	356.498 g/mol
3D model (Jmol)	Interactive image
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, E2V) (INN, USAN, JAN) (brand names Progynova, Progynon Depot, Delestrogen, many others), or oestradiol valerate (BAN), is a synthetic, steroidal estrogen and an estrogen ester – specifically, the 17β-valerate 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 cypionate, estradiol valerate is one of the most widely used esters of estradiol.

The medical uses of estradiol valerate 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 valerate is available in combination with a progestogen as an combined estradiol-containing oral contraceptive (with dienogest) and as a combined injectable contraceptive (with hydroxyprogesterone caproate or norethisterone enanthate).

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Wikipedia