Prasterone enanthate

Overview

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. It is available only as an injectable preparation in combination with estradiol valerate. The medication is given by injection into muscle typically once every 4 weeks.[1–12] WP

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. 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.[1][2][3][13][14] WP

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.[10][11][12][15–18] WP

Uses, dosage and effects

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.[1][15][19][20][21] WP

Available forms

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.[10][11][12] WP

Risks and side effects

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.[15] WP

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. WP

Dysmenorrhea Vaginitis Ovarian cancer Endometrial hyperplasia Endometrial cancer Breast cancer Stroke Increase in blood pressure Pulmonary embolism Nausea Vomiting Abdominal cramps Bloating Cholestatic jaundice Pruritus Rash Dizziness WP

Estradiol Valerate / Prasterone Enanthate may also cause side-effects not listed here.[22] WP

Pharmacology

Pharmacokinetics

The pharmacokinetics of prasterone enanthate have been assessed in a number of studies.[23][24] WP

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.[1][2][23] WP

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.[2] WP

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.[2] WP

History

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.[12][15][16][17][25] WP

Legal status

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.[10][11][12][18] WP

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. 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.[10][11][12][17][18] WP

Chemistry

Formula

C26H40O3 PC

CAS number

23983-43-9 PC

Molar mass (g/mol)

400.6 PC

IUPAC name (computed by PubChem)

[(3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-oxo-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-yl] heptanoate PC

SMILES

CCCCCCC(=O)O[C@H]1CC[C@@]2([C@H]3CC[C@]4([C@H]([C@@H]3CC=C2C1)CCC4=O)C)C PC

InChIKey

HHENOUDBWKNPAB-BNCSLUSBSA-N PC

PubChem CID

163331

Harm reduction information

No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.

User reports

Pop culture

No references added yet.

Sources

1. Other Kuhl H, Taubert HD. Das Klimakterium – Pathophysiologie, Klinik, Therapie. 1987
2. Other Gynodian® Depot. 16 October 2017
3. Other Modern Medicine
4. Other Gynodian Depoty
5. Other Horsky J, Presl J. Ovarian Function and its Disorders: Diagnosis and Therapy. 6 December 2012
6. Other Platt D. Geriatrics 3: Gynecology · Orthopaedics · Anesthesiology · Surgery · Otorhinolaryngology · Ophthalmology · Dermatology. 6 December 2012
7. Other 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
8. Other Bagatell C, Bremner WJ. Androgens in Health and Disease. 27 May 2003
9. Journal / agency Frigo P, Eppel W, Asseryanis E, Sator M, Golaszewski T, Gruber D, Lang C, Huber J. The effects of hormone substitution in depot form on the uterus in a group of 50 perimenopausal women--a vaginosonographic study. Maturitas. April 1995. doi:10.1016/0378-5122(94)00893-c · PMID 7616871
10. Other Gynodian Depot
11. Other Muller. European Drug Index: European Drug Registrations, Fourth Edition. 19 June 1998
12. Other 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
13. Other Cupp MJ, Tracy TS. Dietary Supplements: Toxicology and Clinical Pharmacology. 10 December 2002
14. Journal / agency Prough RA, Clark BJ, Klinge CM. Novel mechanisms for DHEA action. Journal of Molecular Endocrinology. April 2016. doi:10.1530/JME-16-0013 · PMID 26908835
15. Journal / agency Picha E, Weghaupt K. Experience with a new hormone combination for menopausal disorders. Medizinische Klinik. March 1972. PMID 4259772
16. Other Sauer F. Erfolgsfaktoren für das marktorientierte Management patentgeschützter Arzneimittel: eine Analyse der Produktwahrnehmung niedergelassener Vertragsärzte unter der Berücksichtigung unsicherer Therapieergebnisse. February 2008
17. Other William Andrew Publishing. Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. 22 October 2013
18. Other Micromedex products
19. Journal / agency Lauritzen C. Erfahrungen in der Behandlung klimakterischer Beschwerden mit Depot-Injektionen von Östradiolvalerianat-Dehydroepiandrosteronönanthat. Die Therapiewoche. 1980
20. Journal / agency Jurczok F. Treatment of the climacteric symptom complex with a new combined hormone preparation. Fortschritte der Medizin. March 1976. PMID 134967
21. Journal / agency Dinulović D, Radonjić G. Gynodian-depot in the treatment of castration-induced postmenopause. Jugoslavenska Ginekologija I Perinatologija. 1987. PMID 2960859
22. Journal / agency 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
23. Journal / agency Düsterberg B, Wendt H. Plasma levels of dehydroepiandrosterone and 17 beta-estradiol after intramuscular administration of Gynodian-Depot in 3 women. Hormone Research. 1983. doi:10.1159/000179680 · PMID 6220949
24. Journal / agency 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. 1979. doi:10.3109/00016347909154601 · PMID 160742
25. Other Kaufmann M, Costa SD, Scharl A. Die Gynäkologie. 27 November 2013

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