Estradiol valerate

From Wikipedia, the free encyclopedia
Jump to: navigation, search
See also: estradiol and estrogen
Estradiol valerate
Estradiol valerate.svg
Systematic (IUPAC) name
(17β)-3-hydroxyestra-1,3,5(10)-trien-17-yl valerate
Clinical data
Legal status Prescription only
Routes Oral, IM[1]
Identifiers
CAS number 979-32-8
ATC code None
PubChem CID 13791
ChemSpider 13194
Synonyms

17β-Estradiol-17-valerate

pentanoate d'estra-1,3,5(10)-triène-3-ol-17β-yle
Chemical data
Formula C23H32O3 
Mol. mass 356.498 g/mol

Estradiol valerate (INN, USAN; brand names Altadiol, Deladiol, Delestrogen, Estraval, Progynova, Valergen, many others), or oestradiol valerate (BAN), is a synthetic ester, specifically the 17-pentanoyl ester, of the natural estrogen, 17β-estradiol.[2][3] It was introduced in the 1950s, and along with estradiol benzoate and estradiol cypionate, has since become one of the most widely used esters of estradiol.[4]

Upon ingestion, regardless of the route of administration, estradiol valerate behaves as a prodrug, being cleaved by esterases in blood plasma and the liver into 17β-estradiol and valeric acid.[5][6] However, compared to estradiol itself, estradiol valerate is absorbed more slowly and possesses a longer duration, especially when given in an oil solution via intramuscular injection (in which it acts as a depot). As a result, it can be administered less frequently.[7][8]

See also[edit]

References[edit]

  1. ^ Christoph Zink (1 January 1988). Dictionary of Obstetrics and Gynecology. Walter de Gruyter. p. 86. ISBN 978-3-11-085727-6. Retrieved 20 May 2012. 
  2. ^ A. D. Roberts (1991). Dictionary of Steroids: Chemical Data, Structures, and Bibliographies. CRC Press. p. 415. ISBN 978-0-412-27060-4. Retrieved 20 May 2012. 
  3. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis US. 2000. p. 405. ISBN 978-3-88763-075-1. Retrieved 20 May 2012. 
  4. ^ Samuel S. C. Yen (1991). Reproductive endocrinology: physiology, pathophysiology, and clinical management. Saunders. ISBN 978-0-7216-3206-3. Retrieved 20 May 2012. 
  5. ^ Düsterberg B, Nishino Y (December 1982). "Pharmacokinetic and pharmacological features of oestradiol valerate". Maturitas 4 (4): 315–24. doi:10.1016/0378-5122(82)90064-0. PMID 7169965. 
  6. ^ "Progynova 1mg (SPC) | Drugs.com" (HTML). Retrieved 2012-09-06. 
  7. ^ Sriram. Medicinal Chemistry. Pearson Education India. p. 427. ISBN 978-81-317-0031-0. Retrieved 20 May 2012. 
  8. ^ 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.