Estradiol enanthate

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Estradiol enanthate
Estradiol enanthate.png
Clinical data
Trade names Anafertin, Deladroxate, Perlutan, Topasel (all in combination with a progestin)
Synonyms Estradiol enantate; Estradiol heptanoate; SQ-16150
Routes of
administration
Intramuscular injection
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
ECHA InfoCard 100.023.272
Chemical and physical data
Formula C25H36O3
Molar mass 384.56 g/mol
3D model (JSmol)

Estradiol enanthate (INN, USAN), or estradiol heptanoate, is a synthetic, steroidal estrogen and an estrogen ester – specifically, the 17β-enanthate ester of estradiol – which is used as a component of hormonal contraception.[1][2][3][4] It acts as a prodrug of estradiol, and hence, is considered to be a natural, bioidentical form of estrogen.[5] Estradiol enanthate is used in combination with the progestogen dihydroxyprogesterone acetophenide as a once-monthly combined injectable contraceptive in Spain and Latin America under brand names including Anafertin, Deladroxate, Perlutan, and Topasel.[1][2][3][6] This combination has been marketed since the mid-1960s.[7] Estradiol enanthate does not appear to be available as a standalone drug (i.e., by itself).[2]

When estradiol enanthate is administered in oil via intramuscular injection, a depot effect occurs, and the drug has a very long duration of effect.[8] A single 10 mg intramuscular dose of estradiol enanthate has been found to result in significantly elevated levels of estradiol for at least 31 days.[5] The duration of estradiol enanthate is considerably longer than that of various other commonly used estradiol esters like estradiol valerate and estradiol cypionate.[8]

See also[edit]

References[edit]

  1. ^ a b J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 898–. ISBN 978-1-4757-2085-3. 
  2. ^ a b c Index Nominum 2000: International Drug Directory. Taylor & Francis US. 2000. p. 405. ISBN 978-3-88763-075-1. Retrieved 20 May 2012. 
  3. ^ a b Newton JR, D'arcangues C, Hall PE (1994). "A review of "once-a-month" combined injectable contraceptives". J Obstet Gynaecol (Lahore). 4 Suppl 1: S1–34. PMID 12290848. doi:10.3109/01443619409027641. 
  4. ^ Kuhnz, W.; Blode, H.; Zimmermann, H. (1993). "Pharmacokinetics of Exogenous Natural and Synthetic Estrogens and Antiestrogens". 135 / 2: 261–322. ISSN 0171-2004. doi:10.1007/978-3-642-60107-1_15. 
  5. ^ a b Michael Oettel; Ekkehard Schillinger (6 December 2012). Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen. Springer Science & Business Media. pp. 261, 271. ISBN 978-3-642-60107-1. 
  6. ^ Zutshi (1 January 2005). Hormones in Obstetrics and Gynaecology. Jaypee Brothers Publishers. p. 138. ISBN 978-81-8061-427-9. Retrieved 20 May 2012. 
  7. ^ Rizkallah TH, Taymor ML (January 1966). "Ovulation inhibition with a log-acting injectable. II. The cycling effects of varying progestagen-estrogen combinations". American Journal of Obstetrics and Gynecology. 94 (2): 161–4. PMID 5900652. 
  8. ^ a b Oriowo MA, Landgren BM, Stenström B, Diczfalusy E (1980). "A comparison of the pharmacokinetic properties of three estradiol esters". Contraception. 21 (4): 415–24. PMID 7389356.