Estradiol valerate

Estradiol valerate
Clinical data
Pronunciation/ˌɛstrəˈdaɪoʊl ˈvæləreɪt/ ⓘ
ES-trə-DY-ohl VAL-ə-rayt[1]
Trade namesDelestrogen, Progynon Depot, Progynova, many others
Other namesEV; E2V; Oestradiol valerate; Estradiol pentanoate; Estradiol valerianate
Routes of
administration		By mouth, sublingual, intramuscular injection,[2] subcutaneous injection
Drug classEstrogen; Estrogen ester
ATC code
Legal status
Legal status
  • US: ℞-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
BioavailabilityOral: 3–5%[3][4]
IM injection: 100%[5][3]
Protein bindingEstradiol: ~98% (to albumin and SHBGTooltip sex hormone-binding globulin)[6][7]
MetabolismCleavage via esterases in the liver, blood, and tissues[3]
MetabolitesEstradiol, valeric acid, and metabolites of estradiol[3]
Elimination half-lifeOral: 12–20 hours (as E2)[3][6]
IM injection: 3.5 (1.2–7.2) days[8]
Duration of actionIM injection:
• 5 mg: 7–8 days[9]
• 10 mg: 10–14 days[10][11]
• 40 mg: 2–3 weeks[10]
• 100 mg: 3–4 weeks[10]
ExcretionUrine (80%)[3]
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
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.012.327
Chemical and physical data
FormulaC23H32O3
Molar mass356.506 g·mol−1
3D model (JSmol)
Melting point144 to 145 °C (291 to 293 °F)
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), sold for use by mouth under the brand name Progynova and for use by injection under the brand names Delestrogen and Progynon Depot among others, is an estrogen medication. It is used in hormone therapy for menopausal symptoms and low estrogen levels, hormone therapy for transgender people, and in hormonal birth control.[4][3][12][13] It is also used in the treatment of prostate cancer.[12] The medication is taken by mouth or by injection into muscle or fat once every 1 to 4 weeks.[12][13]

Side effects of estradiol valerate include breast tenderness, breast enlargement, nausea, headache, and fluid retention.[14][12][13] Estradiol valerate is an estrogen and hence is an agonist of the estrogen receptor, the biological target of estrogens like estradiol.[4][3][15] It is an estrogen ester and a prodrug of estradiol in the body.[15][4][3] Because of this, it is considered to be a natural and bioidentical form of estrogen.[15][16][3][17]

Estradiol valerate was first described in 1940 and was introduced for medical use in 1954.[18][19][20] Along with estradiol cypionate, it is one of the most widely used esters of estradiol.[21] Estradiol valerate is used in the United States, Canada, Europe, and throughout much of the rest of the world.[22][23] It is available as a generic medication.[24]

  1. ^ "Estradiol and dienogest Advanced Patient Information". Drugs.com.
  2. ^ Zink C (1 January 1988). Dictionary of Obstetrics and Gynecology. Walter de Gruyter. p. 86. ISBN 978-3-11-085727-6. Retrieved 20 May 2012.
  3. ^ a b c d e f g h i j Cite error: The named reference pmid7169965 was invoked but never defined (see the help page).
  4. ^ a b c d Kuhl H (August 2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration". Climacteric. 8 (Suppl 1): 3–63. doi:10.1080/13697130500148875. PMID 16112947. S2CID 24616324.
  5. ^ Seibert B, Günzel P (April 1994). "Animal toxicity studies performed for risk assessment of the once-a-month injectable contraceptive Mesigyna". Contraception. 49 (4): 303–333. doi:10.1016/0010-7824(94)90030-2. PMID 8013217.
  6. ^ a b 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.
  7. ^ Falcone T, Hurd WW (2007). Clinical Reproductive Medicine and Surgery. Elsevier Health Sciences. pp. 22, 362, 388. ISBN 978-0-323-03309-1.
  8. ^ Cite error: The named reference pmid22257576 was invoked but never defined (see the help page).
  9. ^ Cite error: The named reference pmid7389356 was invoked but never defined (see the help page).
  10. ^ a b c Cite error: The named reference Lauritzen-1988 was invoked but never defined (see the help page).
  11. ^ Labhart A (6 December 2012). Clinical Endocrinology: Theory and Practice. Springer Science & Business Media. pp. 551–. ISBN 978-3-642-96158-8.
  12. ^ a b c d Cite error: The named reference Delestrogen-Label was invoked but never defined (see the help page).
  13. ^ a b c Cite error: The named reference Progynova-Label was invoked but never defined (see the help page).
  14. ^ Cite error: The named reference Ghosh-2010 was invoked but never defined (see the help page).
  15. ^ a b c Oettel M, Schillinger E (6 December 2012). Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen. Springer Science & Business Media. p. 261. ISBN 978-3-642-60107-1. Natural estrogens considered here include: [...] Esters of 17β-estradiol, such as estradiol valerate, estradiol benzoate and estradiol cypionate. Esterification aims at either better absorption after oral administration or a sustained release from the depot after intramuscular administration. During absorption, the esters are cleaved by endogenous esterases and the pharmacologically active 17β-estradiol is released; therefore, the esters are considered as natural estrogens.
  16. ^ Cirigliano M (June 2007). "Bioidentical hormone therapy: a review of the evidence". Journal of Women's Health. 16 (5): 600–631. doi:10.1089/jwh.2006.0311. PMID 17627398.
  17. ^ Seth S, Nagrath A, Deoghare R (15 December 2012). "Injectable Contraceptives Till Date". In Arun N, Narendra M, Shikha S (eds.). Progress in Obstetrics and Gynecology--3. Jaypee Brothers Medical Publishers Pvt. Ltd. pp. 419–. ISBN 978-93-5090-575-3.
  18. ^ Cite error: The named reference Kleemann-2014 was invoked but never defined (see the help page).
  19. ^ Cite error: The named reference Publishing2013 was invoked but never defined (see the help page).
  20. ^ Cite error: The named reference Duetsch-1969 was invoked but never defined (see the help page).
  21. ^ Cite error: The named reference Yen-1991 was invoked but never defined (see the help page).
  22. ^ Cite error: The named reference Elks-2014 was invoked but never defined (see the help page).
  23. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis US. 2000. p. 405. ISBN 978-3-88763-075-1. Retrieved 20 May 2012.
  24. ^ "Generic Delestrogen Availability". Drugs.com.
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