Estradiol benzoate

Estradiol benzoate
Clinical data
Pronunciation	/ˌɛstrəˈdaɪoʊl ˈbɛnzoʊeɪt/; ES-trə-DY-ohl BEN-zoh-ayt
Trade names	Agofollin Depot, Ben-Ovocylin, Benzofoline, Dimenformon, Ovocyclin M, Progynon-B, many others
Other names	EB; E2B; Oestradiol benzoate; 17β-Estradiol-3-benzoate; NSC-9566; Benzhormovarine, Difollisterol, Follicormon, Follidimyl, Follidrinbensoat, Oestro-Vitis, Oestroform
Routes of; administration	Intramuscular injection, subcutaneous injection, vaginal
Drug class	Estrogen; Estrogen ester
ATC code	G03CA03 (WHO) ;
Legal status
Legal status	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, benzoic acid, and metabolites of estradiol
Elimination half-life	IM: 48–120 hrs (2–5 days)
Duration of action	IM (0.3–1.7 mg): 2–3 days; IM (5 mg): 4–6 days
Excretion	Urine
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;
CAS Number	50-50-0;
PubChem CID	222757;
DrugBank	DB13953;
ChemSpider	193412;
UNII	1S4CJB5ZGN;
KEGG	D01953;
ChEBI	CHEBI:77006;
ChEMBL	ChEMBL282575;
CompTox Dashboard (EPA)	DTXSID9022998 ;
ECHA InfoCard	100.000.040
Chemical and physical data
Formula	C25H28O3
Molar mass	376.496 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=C3C=CC(=C4)OC(=O)C5=CC=CC=C5;
	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), sold under the brand name Progynon-B 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 transgender women, and in the treatment of gynecological disorders. It is also used in the treatment of prostate cancer in men. Estradiol benzoate is used in veterinary medicine as well. When used clinically, the medication is given by injection into muscle usually two to three times per week.

Side effects of estradiol benzoate include breast tenderness, breast enlargement, nausea, headache, and fluid retention. Estradiol benzoate 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 benzoate was discovered in 1933 and was introduced for medical use that same year. It was the first estradiol ester to be discovered or marketed, and was one of the first estrogens to be used in medicine. Along with estradiol dipropionate, estradiol benzoate was among the most widely used esters of estradiol for many years following its introduction. However, in the 1950s, longer-acting estradiol esters that necessitated less frequent injections, such as estradiol valerate and estradiol cypionate, were developed, and have since largely superseded estradiol benzoate. Nonetheless, estradiol benzoate remains widely available throughout the world. It is not available for medical use in the United States, but is available there for use in veterinary medicine.

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