Prasterone enanthate explained

Prasterone enanthate, also known as dehydroepiandrosterone enanthate (DHEA-E) and sold in combination with estradiol valerate under the brand name Gynodian Depot among others, is a weak androgen, estrogen, and neurosteroid medication which is used as a component of menopausal hormone therapy to treat menopausal symptoms in women.[1] [2] [3] [4] [5] [6] [7] [8] It is available only as an injectable preparation in combination with estradiol valerate.[9] The medication is given by injection into muscle typically once every 4 weeks.

Prasterone enanthate is a synthetic androgen, estrogen, and neurosteroid. It is a steroid ester and a long-lasting prodrug of prasterone (dehydroepiandrosterone; DHEA) in the body. Prasterone is a naturally occurring prohormone of androgens and estrogens and hence is an agonist of the androgen and estrogen receptors, the respective biological targets of androgens like testosterone and estrogens like estradiol.[10] [11] Prasterone also has a variety of activities of its own, including neurosteroid and other activities. An injection of prasterone enanthate has a duration of action in terms of elevated prasterone levels of about 18 days.

The combination of estradiol valerate and prasterone enanthate was developed as early as 1966 and was introduced for medical use in 1975. The formulation is marketed widely throughout Europe, and is also available in several Latin American countries and in Egypt. It is not available in any predominantly English-speaking countries.

Medical uses

The combination of estradiol valerate and prasterone enanthate is used in menopausal hormone therapy to treat menopausal symptoms in peri- and postmenopausal women. Estradiol valerate serves as an estrogen in the preparation, while prasterone enanthate is intended to serve as a weak androgen. It is thought that the inclusion of prasterone enanthate in the formulation may provide additional psychotropic benefits.[12] [13] [14]

Available forms

See also: Estradiol valerate/prasterone enanthate.

Prasterone enanthate is available only as a combination formulation of 4 mg estradiol valerate and 200 mg prasterone enanthate in oil for depot intramuscular injection.[15]

Side effects

Prasterone enanthate, in combination with estradiol valerate at the dosages used clinically, has no masculinizing side effects. This is in contrast to combinations of estrogens with other androgens, such as testosterone esters.

The following is a list of possible side-effects that may occur in medicines that contain Estradiol Valerate / Prasterone Enanthate. This is not a comprehensive list. These side-effects are possible, but do not always occur. Some of the side-effects may be rare but serious. Consult your doctor if you observe any of the following side-effects, especially if they do not go away.

DysmenorrheaVaginitisOvarian cancerEndometrial hyperplasiaEndometrial cancerBreast cancerStrokeIncrease in blood pressurePulmonary embolismNauseaVomitingAbdominal crampsBloatingCholestatic jaundicePruritusRashDizziness

Estradiol Valerate / Prasterone Enanthate may also cause side-effects not listed here.[16]

Pharmacology

Pharmacokinetics

The pharmacokinetics of prasterone enanthate have been assessed in a number of studies.[17]

Prasterone enanthate is a prodrug of prasterone in the body. It is completely hydrolyzed into prasterone and heptanoic acid (enanthic acid) following absorption from the tissue depot after intramuscular injection.

Levels of DHEA peak at about 9 ng/mL within 1 to 4 days of an injection of prasterone enanthate. Subsequently, DHEA levels return to baseline by about 18 days following the injection. Prasterone enanthate has an elimination half-life of about 9 days. The plasma half-life of DHEA/prasterone enanthate following an intravenous injection is about 44 minutes. The half-lives of DHEA metabolites range up to 3.6 days.

Within 30 days, 91% of a dose of prasterone enanthate is eliminated. Approximately 94% is excreted in urine and 6% in feces. Prasterone enanthate is eliminated mainly in the form of metabolites and conjugates.

Chemistry

See also: Androgen ester.

Prasterone enanthate, also known as 5-dehydroepiandrosterone 3β-enanthate or as androst-5-en-3β-ol-17-one 3β-heptanoate, is a synthetic androstane steroid and the C3β heptanoate (enanthate) ester of prasterone (5-dehydroepiandrosterone).[18] [19] [20]

History

Prasterone enanthate was patented by Schering in 1968 and 1971. The combination of estradiol valerate and prasterone enanthate was developed and marketed by Schering, was first tested clinically as early as 1966, was first described in the scientific literature in 1972, and was first introduced for medical use in April 1975.[21] [22] [23] [24]

Society and culture

Brand names

The major brand name of the combination of estradiol valerate and prasterone enanthate is Gynodian Depot. Other brand names of this formulation include Binodian Depot, Cidodian Depot, Klimax, and Supligol NF.

Availability

The combination of estradiol valerate and prasterone enanthate is marketed widely throughout Europe, and is also available in several Latin American countries and in Egypt.[25] In Europe, it is available in Austria, the Czech Republic, Germany, Italy, Poland, Russia, Spain, and Switzerland. In Latin America, it is available in Argentina, Chile, Mexico, and Venezuela. The medication is not available in any predominantly English-speaking countries, including the United States, Canada, the United Kingdom, Ireland, Australia, New Zealand, or South Africa.

See also

Notes and References

  1. Web site: Gynodian® Depot . Bayer (Schweiz) AG . 16 October 2017 . compendium.ch . 15 January 2022 . https://web.archive.org/web/20190529041314/https://compendium.ch/FrmMainMonographie.aspx?Id=4a7e55ac-b11f-4d80-96d0-b468ab0eb4e3&lang=de&MonType=fi&start=1 . 29 May 2019 . dead.
  2. Web site: Modern Medicine. 2019-01-08. 2019-01-09. https://web.archive.org/web/20190109011940/http://www.meppo.com/pdf/drugs/859-GYNODIAN-DEPOT-1440663828.pdf. dead.
  3. Web site: Gynodian Depoty . www.sukl.cz . 15 January 2022 . https://web.archive.org/web/20190529041214/http://www.sukl.cz/download/pil/PI23959.pdf . 29 May 2019 . dead.
  4. Book: Horsky J, Presl J . Ovarian Function and its Disorders: Diagnosis and Therapy. 6 December 2012. Springer Science & Business Media. 978-94-009-8195-9. 146–.
  5. Book: Platt D . Geriatrics 3: Gynecology · Orthopaedics · Anesthesiology · Surgery · Otorhinolaryngology · Ophthalmology · Dermatology. 6 December 2012. Springer Science & Business Media. 978-3-642-68976-5. 6–.
  6. Book: Campbell S . The Management of the Menopause & Post-Menopausal Years: The Proceedings of the International Symposium held in London 24–26 November 1975 Arranged by the Institute of Obstetrics and Gynaecology, The University of London. 6 December 2012. Springer Science & Business Media. 978-94-011-6165-7. 395–.
  7. Book: Bagatell C, Bremner WJ . Androgens in Health and Disease. 27 May 2003. Springer Science & Business Media. 978-1-59259-388-0. 277–.
  8. Frigo P, Eppel W, Asseryanis E, Sator M, Golaszewski T, Gruber D, Lang C, Huber J . 6 . The effects of hormone substitution in depot form on the uterus in a group of 50 perimenopausal women--a vaginosonographic study . Maturitas . 21 . 3 . 221–225 . April 1995 . 7616871 . 10.1016/0378-5122(94)00893-c .
  9. Web site: Gynodian Depot.
  10. Book: Cupp MJ, Tracy TS . Dietary Supplements: Toxicology and Clinical Pharmacology. 10 December 2002. Springer Science & Business Media. 978-1-59259-303-3. 123–147.
  11. Prough RA, Clark BJ, Klinge CM . Novel mechanisms for DHEA action . Journal of Molecular Endocrinology . 56 . 3 . R139–R155 . April 2016 . 26908835 . 10.1530/JME-16-0013 . free .
  12. Lauritzen C . . Experience of treatment of climacteric symptoms with depot injections of estradiol valerianate-dehydroandrosterone enantate . Die Therapiewoche . 1980 . 30 . 10 . 1736–1742 . 0040-5973 . https://www.researchgate.net/publication/322473099_Experience_of_treatment_of_climacteric_symptoms_with_depot_injections_of_estradiol_valerianate-dehydroandrosterone_oenantate -->. A trial of estradiol valerianate-dehydroandrosterone oenantate (Gynodian-Depot) was conducted in 68 post-menopausal women. The treatment exerted a very favorable influence on the typical subjective disorders of the climacteric and on the atrophic alterations of the target organs. Owing to its estrogenic and dehydroepiandrosterone components, the compound also exerts a favorable psychotropic effect. It was tolerated well and caused no side effects of any significance..
  13. Jurczok F . [Treatment of the climacteric symptom complex with a new combined hormone preparation] . de . Fortschritte der Medizin . 94 . 9 . 524–527 . March 1976 . 134967 . Treatment of the climacteric symptom complex with a new combined hormone preparation .
  14. Dinulović D, Radonjić G . [Gynodian-depot in the treatment of castration-induced postmenopause] . hr . Jugoslavenska Ginekologija I Perinatologija . 27 . 1–2 . 37–40 . 1987 . 2960859 . Gynodian-depot in the treatment of castration-induced postmenopause .
  15. Book: Muller. European Drug Index: European Drug Registrations, Fourth Edition. 19 June 1998. CRC Press. 978-3-7692-2114-5. 566–.
  16. D. J. Portman, S. R. Goldstein & R. Kagan (2019) Treatment of moderate to severe dyspareunia with intravaginal prasterone therapy: a review, Climacteric, 22（1）, 65-72, https://doi.org/10.1080/13697137.2018.1535583
  17. Nyholm H, Plesner R . Serum testosterone, FSH/LH and urinary excretion of estrogens and corticoids during treatment with an injectable, longacting estrogen-DHEA preparation . Acta Obstetricia et Gynecologica Scandinavica . 58 . 4 . 385–388 . 1979 . 160742 . 10.3109/00016347909154601 . 25606982 .
  18. Book: Elks J . The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. 14 November 2014. Springer. 978-1-4757-2085-3. 641–.
  19. Book: Blunt JW, Munro MH . Dictionary of Marine Natural Products with CD-ROM. 19 September 2007. CRC Press. 978-0-8493-8217-8. 1075–.
  20. Book: William Andrew Publishing. Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. 22 October 2013. Elsevier. 978-0-8155-1856-3. 1208–.
  21. Picha E, Weghaupt K . [Experience with a new hormone combination for menopausal disorders] . de . Medizinische Klinik . 67 . 11 . 382–386 . March 1972 . 4259772 . Experience with a new hormone combination for menopausal disorders . A new hormone combination for menopausal complaints. Since the treatment of menopausal complaints with estrogens as well as with the combination of estrogens and androgens causes undesired side effects such as bleeding, mammary changes and masculinisation, dehydroepiandrosteron (DHEA), a precursor of testosteron, has been synthesised, which has only a low conversion rate to free testosteron and no masculinising effect. The substance has been tested in combination with estrogen (200 mg DHEA-enanthate and 4 mg estradiolvalerianate per 1 ml) in 266 women with menopausal complaints. The duration of treatment has been up to 6 years with an injection interval of 3 to 8 weeks. The therapeutic results were as good as with estrogen-androgen-combinations, but there was no masculinising effect. Changes of voice, hair and libido caused by pretreatment partly disappeared. Side effects [such] as acne, mastodynia, and sensation of repletion were of transitory nature. This preparation seems to be a true alternative to the traditional estrogen-androgen-combinations. .
  22. Book: Sauer F . Erfolgsfaktoren für das marktorientierte Management patentgeschützter Arzneimittel: eine Analyse der Produktwahrnehmung niedergelassener Vertragsärzte unter der Berücksichtigung unsicherer Therapieergebnisse . February 2008. BoD – Books on Demand. 978-3-936863-12-3. 37,346.
  23. Book: Kaufmann M, Costa SD, Scharl A . Die Gynäkologie. 27 November 2013. Springer-Verlag. 978-3-662-11496-4. 917–.
  24. Book: Kleemann A, Engel J, Kutscher B, Reichert D . Pharmaceutical Substances, 5th Edition, 2009: Syntheses, Patents and Applications of the most relevant APIs. 14 May 2014. Thieme. 978-3-13-179525-0. 1172–1174, 2441–2442.
  25. Web site: Micromedex products . 2024-02-19.

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