Estradiol benzoate

Estradiol benzoate
Clinical data
Pronunciation/ˌɛstrəˈdaɪoʊl ˈbɛnzoʊeɪt/
ES-trə-DY-ohl BEN-zoh-ayt
Trade namesAgofollin Depot, Ben-Ovocylin, Benzofoline, Dimenformon, Ovocyclin M, Progynon-B, many others
Other namesEB; 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 classEstrogen; Estrogen ester
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
BioavailabilityIM: High[1]
Protein bindingEstradiol: ~98% (to albumin and SHBGTooltip sex hormone-binding globulin)[2][3]
MetabolismCleavage via esterases in the liver, blood, and tissues[4][5]
MetabolitesEstradiol, benzoic acid, and metabolites of estradiol[4][5]
Elimination half-lifeIM: 48–120 hrs (2–5 days)[6]
Duration of actionIM (0.3–1.7 mg): 2–3 days[7][8]
IM (5 mg): 4–6 days[9][10][11]
ExcretionUrine
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
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.040
Chemical and physical data
FormulaC25H28O3
Molar mass376.496 g·mol−1
3D model (JSmol)
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.[8][12][13] It is also used in the treatment of prostate cancer in men.[8] Estradiol benzoate is used in veterinary medicine as well.[14][15] When used clinically, the medication is given by injection into muscle usually two to three times per week.[8][12][16]

Side effects of estradiol benzoate include breast tenderness, breast enlargement, nausea, headache, and fluid retention.[17] Estradiol benzoate is an estrogen and hence is an agonist of the estrogen receptor, the biological target of estrogens like estradiol.[4][5] It is an estrogen ester and a prodrug of estradiol in the body.[4][5] Because of this, it is considered to be a natural and bioidentical form of estrogen.[4]

Estradiol benzoate was discovered in 1933 and was introduced for medical use that same year.[4][18][19][20][21][22][23] It was the first estradiol ester to be discovered or marketed, and was one of the first estrogens to be used in medicine.[24] Along with estradiol dipropionate, estradiol benzoate was among the most widely used esters of estradiol for many years following its introduction.[25] 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.[9] Nonetheless, estradiol benzoate remains widely available throughout the world.[15] It is not available for medical use in the United States, but is available there for use in veterinary medicine.[26][27]

  1. ^ Düsterberg B, Nishino Y (December 1982). "Pharmacokinetic and pharmacological features of oestradiol valerate". Maturitas. 4 (4): 315–324. doi:10.1016/0378-5122(82)90064-0. PMID 7169965.
  2. ^ Stanczyk FZ, Archer DF, Bhavnani BR (June 2013). "Ethinyl estradiol and 17β-estradiol in combined oral contraceptives: pharmacokinetics, pharmacodynamics and risk assessment". Contraception. 87 (6): 706–727. doi:10.1016/j.contraception.2012.12.011. PMID 23375353.
  3. ^ Falcone T, Hurd WH (2007). Clinical Reproductive Medicine and Surgery. Elsevier Health Sciences. pp. 22, 362, 388. ISBN 978-0-323-03309-1.
  4. ^ a b c d e f Cite error: The named reference Oettel-2012 was invoked but never defined (see the help page).
  5. ^ a b c d Cite error: The named reference pmid16112947 was invoked but never defined (see the help page).
  6. ^ Runnebaum B, Rabe T (17 April 2013). Gynäkologische Endokrinologie und Fortpflanzungsmedizin: Band 1: Gynäkologische Endokrinologie. Springer-Verlag. pp. 86–. ISBN 978-3-662-07635-4.
  7. ^ Cite error: The named reference Buchsbaum-2012 was invoked but never defined (see the help page).
  8. ^ a b c d Cite error: The named reference NNR1949e was invoked but never defined (see the help page).
  9. ^ a b 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.
  10. ^ Knörr K, Knörr-Gärtner H, Beller FK, Lauritzen C (8 March 2013). Lehrbuch der Geburtshilfe und Gynäkologie: Physiologie und Pathologie der Reproduktion. Springer-Verlag. pp. 508–. ISBN 978-3-662-00526-2.
  11. ^ Cite error: The named reference Labhart-2012 was invoked but never defined (see the help page).
  12. ^ a b Cite error: The named reference pmid13638626 was invoked but never defined (see the help page).
  13. ^ Cite error: The named reference Israel-2001 was invoked but never defined (see the help page).
  14. ^ Cite error: The named reference Drugs.com-Estradiol was invoked but never defined (see the help page).
  15. ^ a b Cite error: The named reference IndexNominum2000 was invoked but never defined (see the help page).
  16. ^ IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, World Health Organization, International Agency for Research on Cancer (2007). Combined Estrogen-progestogen Contraceptives and Combined Estrogen-progestogen Menopausal Therapy. World Health Organization. pp. 388–. ISBN 978-92-832-1291-1.
  17. ^ Cite error: The named reference Ghosh-2010 was invoked but never defined (see the help page).
  18. ^ Cite error: The named reference pmid16746750 was invoked but never defined (see the help page).
  19. ^ Cite error: The named reference Kaufman-1933 was invoked but never defined (see the help page).
  20. ^ Cite error: The named reference Buschbeck-1934 was invoked but never defined (see the help page).
  21. ^ Cite error: The named reference Biskind-1935 was invoked but never defined (see the help page).
  22. ^ Cite error: The named reference Novak-1935 was invoked but never defined (see the help page).
  23. ^ Cite error: The named reference Kleemann-2014 was invoked but never defined (see the help page).
  24. ^ Raviña E, Kubinyi H (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.
  25. ^ Cite error: The named reference pmid14388061 was invoked but never defined (see the help page).
  26. ^ Cite error: The named reference Drugs@FDA was invoked but never defined (see the help page).
  27. ^ Cite error: The named reference Witherspoon-1994 was invoked but never defined (see the help page).
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