Estradiol benzoate

Estradiol benzoate

Clinical data
Pronunciation	/ˌɛstrəˈdaɪoʊl ˈbɛnzoʊeɪt/ ES-trə-DYE-ohl BEN-zoh-ayt
Trade names	Agofollin, Benovocyclin, Benzofoline, Dimenformon, Progynon-B, many others
Routes of administration	Intramuscular injection
ATC code	G03CA03 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	Intramuscular: 100%
Metabolism	Cleavage via esterases in the liver, blood, and tissues
Metabolites	Estradiol, benzoic acid, and metabolites of estradiol
Duration of action	4–5 days (5 mg i.m.)
Identifiers
IUPAC name [(8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] benzoate
Synonyms	17β-Estradiol-3-benzoate; NSC-9566; Benzhormovarine, Difollisterol, Follicormon, Follidimyl, Follidrinbensoat, Oestro-Vitis, Oestroform
CAS Number	50-50-0
PubChem CID	222757
DrugBank	DBSALT000066
ChemSpider	193412
UNII	1S4CJB5ZGN
KEGG	D01953
ChEBI	CHEBI:77006
ChEMBL	CHEMBL282575
ECHA InfoCard	100.000.040
Chemical and physical data
Formula	C25H28O3
Molar mass	376.488 g/mol
3D model (Jmol)	Interactive image
SMILES O=C(Oc1cc3c(cc1)[C@H]2CC[C@@]4([C@@H](O)CC[C@H]4[C@@H]2CC3)C)c5ccccc5
InChI InChI=1S/C25H28O3/c1-25-14-13-20-19-10-8-18(28-24(27)16-5-3-2-4-6-16)15-17(19)7-9-21(20)22(25)11-12-23(25)26/h2-6,8,10,15,20-23,26H,7,9,11-14H2,1H3/t20-,21-,22+,23+,25+/m1/s1 Key:UYIFTLBWAOGQBI-BZDYCCQFSA-N

Estradiol benzoate (EB, E2B) (INN) (brand name Progynon-B, many others), or oestradiol benzoate (BAN), is a synthetic, steroidal estrogen and an estrogen ester – specifically, the 3-benzoate ester of estradiol – which is marketed in Europe and elsewhere throughout the world. It acts as a prodrug of estradiol, and hence, is considered to be a natural, bioidentical form of estrogen. Estradiol benzoate was introduced in 1936 and was one of the first forms of estrogen to be marketed. Along with estradiol dipropionate, it was one of the most widely used estradiol esters prior to the 1950s. However, estradiol benzoate is now little used, having largely been superseded by longer-acting esters of estradiol like estradiol valerate and estradiol cypionate that require less frequent administration.

The medical uses of estradiol benzoate are the same as those of estradiol and other estrogens. An example of an indication for the drug is hormone replacement therapy for menopausal symptoms or hypoestrogenism.

The side effects of estradiol benzoate are the same as those of estradiol. Examples of such side effects include breast tenderness and enlargement, nausea, bloating, edema, headache, and melasma.