Estradiol benzoate

Estradiol benzoate

Systematic (IUPAC) name
(17β)-17-hydroxyestra-1,3,5(10)-trien-3-yl benzoate
Clinical data
Routes of administration	IM
Legal status	℞ (Prescription only)
Identifiers
CAS Number	50-50-0
ATC code	None
PubChem	CID 222757
ChemSpider	193412
ChEBI	CHEBI:77006
Synonyms	17β-Estradiol-3-benzoate
Chemical data
Formula	C25H28O3
Molar mass	376.488 g/mol
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 (INN; brand names Agofollin, Diffolisterol, Progynon-B, many others), or oestradiol benzoate (BAN), is a synthetic ester, specifically the 3-benzoyl ester, of the natural estrogen, estradiol.^[1][2] It was the first form of estrogen to be marketed, patented by Schering-Kahlbaum in 1936 in an oil preparation for injectable use and introduced later that year as Progynon-B.^[3][4] Though it is still in widespread use today, it has been mostly superseded by newer forms of estradiol with improved pharmacokinetics that require less frequent administration such as estradiol cypionate and estradiol valerate.^[5]

A single dose of 2.5 mg estradiol benzoate by intramuscular injection was found to produce plasma estradiol levels of >400 pg/mL, measured 24 hours post-injection, in a group of patients with minimal baseline levels of estradiol (due to GnRH analogue therapy with triptorelin).^[6]

See also

• Estrogen ester

References

1. A. D. Roberts (1991). Dictionary of Steroids: Chemical Data, Structures, and Bibliographies. CRC Press. p. 414. ISBN 978-0-412-27060-4. Retrieved 20 May 2012.
2. Index Nominum 2000: International Drug Directory. Taylor & Francis US. 2000. p. 406. ISBN 978-3-88763-075-1. Retrieved 20 May 2012.
3. Enrique Raviña; Hugo Kubinyi (16 May 2011). The Evolution of Drug Discovery: From Traditional Medicines to Modern Drugs. John Wiley & Sons. p. 175. ISBN 978-3-527-32669-3. Retrieved 20 May 2012.
4. Folley SJ (December 1936). "The effect of oestrogenic hormones on lactation and on the phosphatase of the blood and milk of the lactating cow" (PDF). The Biochemical Journal 30 (12): 2262–72. PMC 1263335. PMID 16746289.
5. Oriowo MA, Landgren BM, Stenström B, Diczfalusy E (April 1980). "A comparison of the pharmacokinetic properties of three estradiol esters". Contraception 21 (4): 415–24. doi:10.1016/s0010-7824(80)80018-7. PMID 7389356.
6. Vizziello G, D'Amato G, Trentadue R, Fanizza G (1993). "[Estradiol benzoate test in the study of pituitary block induced by triptorelin]". Minerva Ginecol (in Italian) 45 (4): 185–9. PMID 8506068.