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{{See also|Estrogen ester|List of estrogen esters}}
{{See also|Estrogen ester|List of estrogen esters}}


Estradiol enanthate is a [[synthetic compound|synthetic]] [[estrane]] [[steroid]] and the C17β [[heptanoic acid|enanthate]] (or heptanoate) [[fatty acid]] [[ester]] of [[estradiol (medication)|estradiol]].<ref name="Elks2014" /><ref name="IndexNominum2000" /> It is also known as estradiol 17β-enanthate or as estra-1,3,5(10)-triene-3,17β-diol 17β-enanthate.<ref name="Elks2014" /><ref name="IndexNominum2000" /> Other common esters of estradiol in use include [[estradiol cypionate]], [[estradiol undecylate]], and [[estradiol valerate]].<ref name="IndexNominum2000" />
Estradiol enanthate, also known as estradiol 17β-enanthate or estra-1,3,5(10)-triene-3,17β-diol 17β-heptanoate, is a [[synthetic compound|synthetic]] [[estrane]] [[steroid]] and the C17β [[heptanoic acid|enanthate]] (heptanoate) [[fatty acid]] [[ester]] of [[estradiol (medication)|estradiol]].<ref name="Elks2014" /><ref name="IndexNominum2000" /> Other common esters of estradiol used clinically include [[estradiol benzoate]], [[estradiol cypionate]], [[estradiol undecylate]], and [[estradiol valerate]].<ref name="IndexNominum2000" /> [[Estradiol dienanthate]] (component of [[Climacteron]]), or estradiol 3,17β-dienanthate, has also been used.<ref name="Elks2014" /><ref name="Ginsburg1999">{{cite book |last1=Ginsburg |first1=Elizabeth S. |editor-first=David B. |editor-last=Seifer |editor-first2=Elizabeth A. |editor-last2=Kennard |title=Menopause |date=1999 |volume=18 |pages=209–219 |doi=10.1007/978-1-59259-246-3_13 |chapter=Androgen Replacement in Postmenopausal Women |isbn=978-1-61737-129-5}}</ref><ref name="pmid13901504">{{cite journal | title=The treatment of the menopause | journal=Can Med Assoc J | author=Robert B. Greenblatt | author2=William E. Barfield | author3=Edwin C. Jungck | date=January 1962 | volume=86 | issue=3 | pages=113–4 | pmc=1848811 | pmid=13901504}}</ref><ref name="Seifer1999">{{cite book | url=https://books.google.com/books?id=t0zMBgAAQBAJ&pg=PT183 | title=Menopause: Endocrinology and Management | publisher=Springer Science & Business Media | date=27 July 1999 | author=David B. Seifer | pages=183– | isbn=978-1-59259-246-3 | doi=10.1007/978-1-59259-246-3}}</ref>


==History==
==History==
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===Brand names===
===Brand names===
Estradiol enanthate is marketed in combination with DHPA under the brand names Anafertin, Deladroxate, Patector, Perlutal, Perlutan, and Topasel, among many others.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="Micromedex" />
Estradiol enanthate is marketed in combination with DHPA under the brand names Anafertin, Patector, Perlutal, Perlutan, and Topasel, among many others.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="Micromedex" />


===Availability===
===Availability===

Revision as of 11:54, 18 September 2018

Not to be confused with Ethinylestradiol.
Estradiol enantate
Clinical data
Trade namesPerlutal, Topasel, Unalmes, Yectames, others
Other namesEE; E2E; E2-EN; Estradiol enantate; Estradiol heptanoate; SQ-16150
Routes of
administration		Intramuscular injection[1][2]
Drug classEstrogen; Estrogen ester
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
BioavailabilityIM: High
MetabolismCleavage via esterases in the liver, blood, and tissues[3][4]
MetabolitesEstradiol, heptanoic acid, and metabolites of estradiol[3][4]
Elimination half-lifeIM: 5.6–7.5 days[5][1][6][7]
ExcretionUrine[1]
Identifiers
  • [(8R,9S,13S,14S,17S)-3-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] heptanoate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.023.272 Edit this at Wikidata
Chemical and physical data
FormulaC25H36O3
Molar mass384.56 g/mol g·mol−1
3D model (JSmol)
  • CCCCCCC(=O)O[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=C3C=CC(=C4)O)C
  • InChI=1S/C25H36O3/c1-3-4-5-6-7-24(27)28-23-13-12-22-21-10-8-17-16-18(26)9-11-19(17)20(21)14-15-25(22,23)2/h9,11,16,20-23,26H,3-8,10,12-15H2,1-2H3/t20-,21-,22+,23+,25+/m1/s1
  • Key:RFWTZQAOOLFXAY-BZDYCCQFSA-N

Estradiol enanthate, sold in a combination preparation under the brand names Perlutal and Topasel among others, is an estrogen medication which is used in hormonal birth control.[1][2] It is formulated in combination with dihydroxyprogesterone acetophenide (DHPA; algestone acetophenide), a progestin, and is used as a once-monthly combined injectable contraceptive.[1][2] It is given by injection into muscle once a month.[1][2]

Side effects of estradiol enanthate include breast tenderness, breast enlargement, nausea, headache, and fluid retention.[8] The drug is a synthetic estrogen and hence is an agonist of the estrogen receptor (ER), the biological target of estrogens like estradiol.[4][3] Estradiol enanthate is an estrogen ester and a long-lasting prodrug of estradiol in the body.[3][4] Because of this, it is considered to be a natural and bioidentical form of estrogen.[3][9]

Estradiol enanthate was first described by 1954,[10] and was first studied in combination with DHPA as a combined injectable contraceptive in 1964.[11][12] The combination was introduced for clinical use by the mid-1970s.[13][14][15] Estradiol enanthate is not available as a standalone medication (i.e., by itself without DHPA).[16] The combination is available in Latin America and Hong Kong, and was also previously marketed in Spain and Portugal.[16][2][17]

Medical uses

See also: Estradiol (medication) § Medical uses, and High-dose estrogen

Estradiol enanthate is used in combination with the progestin DHPA as a once-monthly combined injectable contraceptive in Latin America and Hong Kong.[1][2][18][16] This combination has been said to also be used by "travestis" (a term for transgender women in some cultures, especially in South America) as a means of feminizing hormone therapy.[19]

There have been concerns about possible accumulation of estradiol enanthate and consequent estrogenic overexposure with once-monthly injection due to its long duration, and this may have limited its use.[6][20] However, in spite of this, clinical studies have found that there is very limited or no accumulation of estradiol enanthate when used as a once-a-month injectable contraceptive in combination with DHPA.[6][21][2]

Side effects

Main article: Estradiol (medication) § Side effects

The side effects of estradiol enanthate are the same as those of estradiol. Examples of such side effects include breast tenderness and enlargement, nausea, bloating, edema, headache, and melasma.[8] The combination of estradiol enanthate and DHPA has shown no adverse effects on liver function, lipid metabolism, or coagulation.[21][2]

Pharmacology

See also: Pharmacology of estradiol

Pharmacodynamics

Estradiol enanthate is an estradiol ester, or a prodrug of estradiol.[3][4] As such, it is an estrogen, or an agonist of the estrogen receptors.[3][4] Estradiol enanthate is of about 41% higher molecular weight than estradiol due to the presence of its C17β enanthate ester.[22][16] Because estradiol enanthate is a prodrug of estradiol, it is considered to be a natural and bioidentical form of estrogen.[3][9]

The combination of 10 mg estradiol enanthate and 150 mg DHPA as a once-monthly combined injectable contraceptive (which achieves levels of estradiol of around 350 pg/mL)[20][23][24] has been found to have little to no effect on many markers of estrogen-modulated liver protein synthesis including circulating levels of HDL and LDL cholesterol, copper, ceruloplasmin, total and free cortisol, corticosteroid-binding globulin, and sex hormone-binding globulin.[25] However, it was found to significantly increase levels of triglycerides and significantly decrease levels of total and free testosterone.[25] In contrast to the combined injectable contraceptive, an ethinylestradiol-containing birth control pill produced highly significant changes in all of the preceding parameters.[25]

Pharmacokinetics

Idealized curves of estradiol levels over a period of 30 days after injection of different estradiol esters in women.[20] Four data points were used to generate the curves (day 0, peak day, a third day, and day 30).[20] The measurements from which the points were drawn were taken at 24-hour intervals.[20] The estradiol esters were given mostly as combined injectable contraceptives together with a progestin.[20]

When estradiol enanthate is administered in an oil solution by intramuscular injection, a depot effect occurs, and this results in it having a long duration of action.[20][4][26] The duration of action of estradiol enanthate is considerably longer than that of various other estradiol esters such as estradiol benzoate, estradiol valerate, and estradiol cypionate, whereas its duration is shorter than that of estradiol undecylate.[20][27][28] In general, the longer the fatty acid ester chain, the more lipophilic the estradiol ester, the more slowly it is released from the depot and absorbed into the circulation, and the longer its duration of action.[4][26]

The pharmacokinetics of estradiol enanthate have been assessed in a number of studies.[20][29][23][5][24][30] It has usually been studied in combination with algestone acetophenide.[20][29][23][24] Following an intramuscular injection of estradiol enanthate, levels of estradiol have been found to peak after 4 to 8 days.[20][24] Maximal levels of estradiol after a 5 mg injection of estradiol enanthate have been found to be about 163 to 209 pg/mL and after a 10 mg injection about 283 to 445 pg/mL.[20][23][24] Estradiol levels have been found to return to baseline levels of about 50 pg/mL after around 30 days.[23][5][3][30] However, a metabolic study found that traces of radiolabeled estradiol enanthate remained detectable in blood for at least 30 to 40 days and as long as 60 days.[29] Studies have reported that the elimination half-life of estradiol enanthate after a single 10 mg intramuscular injection was 5.6 to 7.5 days.[5][1][6] The volume of distribution of estradiol enanthate has been reported to be 5.087 L.[7] Estradiol enanthate is excreted preferentially in urine.[14]

Chemistry

See also: Estrogen ester and List of estrogen esters

Estradiol enanthate, also known as estradiol 17β-enanthate or estra-1,3,5(10)-triene-3,17β-diol 17β-heptanoate, is a synthetic estrane steroid and the C17β enanthate (heptanoate) fatty acid ester of estradiol.[22][16] Other common esters of estradiol used clinically include estradiol benzoate, estradiol cypionate, estradiol undecylate, and estradiol valerate.[16] Estradiol dienanthate (component of Climacteron), or estradiol 3,17β-dienanthate, has also been used.[22][31][32][33]

History

Estradiol enanthate was first described in the literature by 1954.[10][34][35][28][36][37] The first clinical study of estradiol enanthate and DHPA as a combined injectable contraceptive was conducted in 1964.[11][12] The combination was marketed by the mid-1970s.[13][14][15]

Society and culture

Generic names

Estradiol enantate is the generic name of the drug and its INNMTooltip International Nonproprietary Name and BANMTooltip British Approved Name, while estradiol enanthate is its USANTooltip United States Adopted Name.[22][16][38] It is also known by its former developmental code name SQ-16150.[39]

Brand names

Estradiol enanthate is marketed in combination with DHPA under the brand names Anafertin, Patector, Perlutal, Perlutan, and Topasel, among many others.[22][16][17]

Availability

Known availability of estradiol enanthate in countries throughout the world (as of September 2018).

Estradiol enanthate is available in combination with DHPA widely throughout Latin America, and also in Hong Kong.[17] The combination was also previously available in Spain and Portugal, but has been discontinued in these countries.[17] It is available in Canada in combination with estradiol benzoate and testosterone enanthate for veterinary use as Uni-Bol.[40]

See also

References

  1. ^ a b c d e f g h Jarquín González JD, Elda de Aguirre L, Rodríguez C, Abrego de Aguilar M, Carrillo F, León DA, Lima M, Trigueros S, Acosta R (September 1996). "Dihydroxyprogesterone acetophenide 150 mg + estradiol enantate 10 mg as monthly injectable contraceptives". Adv Contracept. 12 (3): 213–25. doi:10.1007/BF01849664. PMID 8910663.
  2. ^ a b c d e f g h 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. doi:10.3109/01443619409027641. PMID 12290848.
  3. ^ a b c d e f g h i 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. 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. [...] Wiemeyer et al. (1986) measured elevated estradiol levels up to 31 days after an intramuscular dose of 10mg estradiol enanthate.
  4. ^ a b c d e f g h Kuhl H (2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration" (PDF). Climacteric. 8 Suppl 1: 3–63. doi:10.1080/13697130500148875. PMID 16112947.
  5. ^ a b c d Wiemeyer JC, Fernandez M, Moguilevsky JA, Sagasta CL (1986). "Pharmacokinetic studies of estradiol enantate in menopausic women". Arzneimittelforschung. 36 (11): 1674–7. PMID 3814225.
  6. ^ a b c d Sang GW (April 1994). "Pharmacodynamic effects of once-a-month combined injectable contraceptives". Contraception. 49 (4): 361–85. doi:10.1016/0010-7824(94)90033-7. PMID 8013220.
  7. ^ a b "Bula do Algestona Acetofenida + Enantato de Estradiol". Consulta Remédios. Archived from the original (HTML) on 2018-09-18. Retrieved 2018-09-18.
  8. ^ a b Amit K. Ghosh (23 September 2010). Mayo Clinic Internal Medicine Board Review. OUP USA. pp. 222–. ISBN 978-0-19-975569-1.
  9. ^ a b Nagrath Arun; Malhotra Narendra; Seth Shikha (15 December 2012). Progress in Obstetrics and Gynecology--3. Jaypee Brothers Medical Publishers Pvt. Ltd. pp. 419–. ISBN 978-93-5090-575-3.
  10. ^ a b International Neurochemical Symposium (1954). Proceedings. Academic Press. p. 453.
  11. ^ a b Rutherford RN, Banks AL, Coburn WA (1964). "Deladroxate for the Prevention of Ovulation". Fertil. Steril. 15: 648–52. doi:10.1016/s0015-0282(16)35410-3. PMID 14236841.
  12. ^ a b Taymor ML, Planck S, Yahia C (1964). "Ovulation Inhibition with a Long-acting Parenteral Progestogen-Estrogen Combination". Fertil. Steril. 15: 653–60. doi:10.1016/s0015-0282(16)35411-5. PMID 14236842.
  13. ^ a b J. Bringer; B. Hedon (15 September 1995). Fertility and Sterility: A Current Overview. CRC Press. pp. 47–. ISBN 978-1-85070-694-6.
  14. ^ a b c Toppozada M (June 1977). "The clinical use of monthly injectable contraceptive preparations". Obstet Gynecol Surv. 32 (6): 335–47. doi:10.1097/00006254-197706000-00001. PMID 865726.
  15. ^ a b Toppozada MK (April 1994). "Existing once-a-month combined injectable contraceptives". Contraception. 49 (4): 293–301. doi:10.1016/0010-7824(94)90029-9. PMID 8013216.
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  17. ^ a b c d https://www.micromedexsolutions.com/
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  21. ^ a b De Aguilar MA, Altamirano L, Leon DA, De Fung RC, Grillo AE, Gonzalez JD, Canales JR, Sanchez Jdel C, Pozuelos JL, Ramirez L, Rigionni R, Salgado JS, Torres L, Vallecillos G, Zambrano EJ, Zea C (December 1997). "Current status of injectable hormonal contraception, with special reference to the monthly method". Adv Contracept. 13 (4): 405–17. doi:10.1023/A:1006501526018. PMID 9404550.
  22. ^ a b c d e 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.
  23. ^ a b c d e Recio R, Garza-Flores J, Schiavon R, Reyes A, Diaz-Sanchez V, Valles V, Luz de la Cruz D, Oropeza G, Perez-Palacios G (June 1986). "Pharmacodynamic assessment of dihydroxyprogesterone acetophenide plus estradiol enanthate as a monthly injectable contraceptive". Contraception. 33 (6): 579–89. doi:10.1016/0010-7824(86)90046-6. PMID 3769482.
  24. ^ a b c d e Schiavon R, Benavides S, Oropeza G, Garza-Flores J, Recio R, Díaz-Sanchez V, Pérez-Palacios G (June 1988). "Serum estrogens and ovulation return in chronic users of a once-a-month injectable contraceptive". Contraception. 37 (6): 591–8. doi:10.1016/0010-7824(88)90005-4. PMID 3396358.
  25. ^ a b c Wiemeyer JC, Sagasta CL, Roncales Mateo JM, Lavarello AC, Angel de Toro LA, Salas Diaz R (July 1990). "Multicentred clinical study of the metabolic effect of the monthly injectable contraceptive containing dihydroxyprogesterone acetophenide 150 mg + estradiol enanthate 10 mg". Contraception. 42 (1): 13–28. doi:10.1016/0010-7824(90)90088-D. PMID 2117515.
  26. ^ a b Vermeulen A (1975). "Longacting steroid preparations". Acta Clin Belg. 30 (1): 48–55. doi:10.1080/17843286.1975.11716973. PMID 1231448.
  27. ^ Oriowo MA, Landgren BM, Stenström B, Diczfalusy E (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.
  28. ^ a b Percy Roberts Wilde; Carey Franklin Coombs; Arthur J. Rendle Short (1959). The Medical Annual: A Year Book of Treatment and Practitioner's Index ... Publishing Science Group. As in the case of progestogens the esters of oestradiol vary in the duration of their effect. Oestradiol benzoate is short-acting (three days to a week). Oestradiol valerianate is somewhat longer-acting, and oestradiol enanthate and undecylate have considerably more prolonged duration of effectiveness. The undecylate may remain effective for some months, and should not be employed, [...]
  29. ^ a b c Gual, C.; Pérez-Palacios, G.; Pérez, A.E.; Ruiz, M.R.; Solis, J.; Cervantes, A.; Iramain, C.; Schreiber, E.C. (1973). "Metabolic fate of a long-acting injectable estrogen-progestogen contraceptive 1,2". Contraception. 7 (4): 271–287. doi:10.1016/0010-7824(73)90145-5. ISSN 0010-7824.
  30. ^ a b Garza-Flores J, Alba VM, Cravioto MC, Hernandez L, Perez-Palacios G, Alvarado G, Rivera R, Recio R, Bassol S (May 1989). "Estrogen-progestogen once-a-month injectable contraceptives and serum prolactin". Contraception. 39 (5): 519–29. doi:10.1016/0010-7824(89)90107-8. PMID 2524362.
  31. ^ Ginsburg, Elizabeth S. (1999). "Androgen Replacement in Postmenopausal Women". In Seifer, David B.; Kennard, Elizabeth A. (eds.). Menopause. Vol. 18. pp. 209–219. doi:10.1007/978-1-59259-246-3_13. ISBN 978-1-61737-129-5.
  32. ^ Robert B. Greenblatt; William E. Barfield; Edwin C. Jungck (January 1962). "The treatment of the menopause". Can Med Assoc J. 86 (3): 113–4. PMC 1848811. PMID 13901504.
  33. ^ David B. Seifer (27 July 1999). Menopause: Endocrinology and Management. Springer Science & Business Media. pp. 183–. doi:10.1007/978-1-59259-246-3. ISBN 978-1-59259-246-3.
  34. ^ Heinrich Waelsch (1955). Biochemistry of the Developing Nervous System: Proceedings. Academic Press. p. 453.
  35. ^ Acta Cytologica. International Academy of Cytology. 1958. p. 378.
  36. ^ Gauthier, B; Le Dreff, L; Aubry, R (1958). "Hormone derivatives of long-lasting action. I. Esters of estradiol". Annales Pharmaceutiques Francaises. 16: 757–66. ISSN 0003-4509. Treating 10 g. estradiol benzoate in 30 cc.dry C5H5N dropwise with 4.3 g. n-C6H13COCl (b20 71-2°), heating 1 hr. at 50-60°, pouring into 100 cc. 10% H2SO4, sepg. the oil after its solidification, washing with petr. ether, heating with 50 cc. MeOH, and cooling gave 10 g. 17-heptoyl-3β-benzoylestradiol, m. 95-8°. Dissolving 10 g. of this in 210 cc. 0.1N NaOH in MeOH and 40 cc. Me2CO with stirring, adding HCl to pH 7, filtering, evapg. in vacuo, and stirring the residue with petr. ether gave 7.9 g. 17-heptoyl-β-estradiol, m. 94-6° (iso-Pr2O). Adding to 5 g. estradiol stirred in 10 cc. anhyd. pyridine 8 g. n-C10H21COCl (b20 135-6°), keeping 1 hr. at 100°, cooling, adding 50 cc. 10% H2SO4, dissolving the sepd. ester in 50 cc. iso-Pr2O, washing with satd. NaHCO3 soln. and H2O, drying, and evapg. at room temp. gave 10.7 g. 3,17-diundecanoylestradiol, m. 48-9° (MeOH-Me2CO, then Me2O-Et2O), λmax. (0.005% in MeOH contg. 4% iso-Pr2O) 268 mμ, λmin. 282 and 250 mμ, inflexion 215 mμ. Stirring 8.8 g. estradiol divalerate in 90 cc. MeOH and 0.4 g. NaOH under N 210 min. to soln., adding 20% HCl to pH 7, evapg. in vacuo to 10 cc., keeping overnight at a low temp., and washing with H2O, MeOH, and petr. ether gave 4.4 g. 17-valeryl-β-estradiol, m. 145-6°, λmax. (0.005% in EtOH) 282 mμ, λmin. 248 mμ, inflexion 215 mμ. A single dose of 25 mg. of the diundecanate gave a therapeutic effect lasting 3 weeks.
  37. ^ 241206 ES 241206, "Esters of cortical hormones, androgens, or esterogens by transesterification and alcoholysis" 
  38. ^ Sweetman, Sean C., ed. (2009). "Sex hormones and their modulators". Martindale: The Complete Drug Reference (36th ed.). London: Pharmaceutical Press. p. 2097. ISBN 978-0-85369-840-1.
  39. ^ George W.A Milne (8 May 2018). Drugs: Synonyms and Properties: Synonyms and Properties. Taylor & Francis. pp. 1404–. ISBN 978-1-351-78989-9.
  40. ^ https://health-products.canada.ca/dpd-bdpp/info.do?lang=en&code=11012


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