Prasterone enanthate

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.[3][1][4][5][6][7][8][9][10] It is available only as an injectable preparation in combination with estradiol valerate.[3][11][12][13] The medication is given by injection into muscle typically once ever 4 weeks.[3][1][4]

Prasterone enanthate
Clinical data
Trade namesWith estradiol valerate: Gynodian Depot, others
Other namesDHEA enanthate; Prasterone heptanoate; DHEA heptanoate; DHEA-E; EDHEA; SH-90300-D; SH-70833-D (with EV); Androst-5-en-3β-ol-17-one 3β-heptanoate
Routes of
administration		Intramuscular injection
Drug classAndrogen; Anabolic steroid; Androgen ester; Estrogen; Neurosteroid
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
BioavailabilityIM: 100%[1]
Metabolites• Prasterone (DHEA)[1]
• Others[1]
Elimination half-lifeIM: 9 days[1]
IV: 44 minutes[1]
Duration of action18 days[2]
ExcretionUrine, feces[1]
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ECHA InfoCard100.041.777
Chemical and physical data
FormulaC26H40O3
Molar mass400.603 g·mol−1
3D model (JSmol)

Prasterone enanthate is a synthetic androgen, estrogen, and neurosteroid.[3][1][4] It is a steroid ester and a long-lasting prodrug of prasterone (dehydroepiandrosterone; DHEA) in the body.[3][1][4] 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.[14][15] Prasterone also has a variety of activities of its own, including neurosteroid and other activities.[15] An injection of prasterone enanthate has a duration of action in terms of elevated prasterone levels of about 18 days.[3][1][4]

The combination of estradiol valerate and prasterone enanthate was developed as early as 1966 and was introduced for medical use in 1975.[16][17] The formulation is marketed widely throughout Europe, and is also available in several Latin American countries and in Egypt.[11][12][18][13][19] It is not available in any predominantly English-speaking countries.[11][19]

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.[3][16] Estradiol valerate serves as an estrogen in the preparation, while prasterone enanthate is intended to serve as a weak androgen.[3][16] It is thought that the inclusion of prasterone enanthate in the formulation may provide additional psychotropic benefits.[16][20][21][22]

Androgen replacement therapy formulations and dosages used in women
RouteMedicationMajor brand namesFormDosage
OralTestosterone undecanoateAndriol, JatenzoCapsule40–80 mg 1x/1–2 days
MethyltestosteroneMetandren, EstratestTablet0.5–10 mg/day
FluoxymesteroneHalotestinTablet1–2.5 mg 1x/1–2 days
NormethandroneaGinecosideTablet5 mg/day
TiboloneLivialTablet1.25–2.5 mg/day
Prasterone (DHEA)b–Tablet10–100 mg/day
SublingualMethyltestosteroneMetandrenTablet0.25 mg/day
TransdermalTestosteroneIntrinsaPatch150–300 μg/day
AndroGelGel, cream1–10 mg/day
VaginalPrasterone (DHEA)IntrarosaInsert6.5 mg/day
InjectionTestosterone propionateaTestovironOil solution25 mg 1x/1–2 weeks
Testosterone enanthateDelatestryl, Primodian DepotOil solution25–100 mg 1x/4–6 weeks
Testosterone cypionateDepo-Testosterone, Depo-TestadiolOil solution25–100 mg 1x/4–6 weeks
Testosterone isobutyrateaFemandren M, FolivirinAqueous suspension25–50 mg 1x/4–6 weeks
Mixed testosterone estersClimacteronaOil solution150 mg 1x/4–8 weeks
Omnadren, SustanonOil solution50–100 mg 1x/4–6 weeks
Nandrolone decanoateDeca-DurabolinOil solution25–50 mg 1x/6–12 weeks
Prasterone enanthateaGynodian DepotOil solution200 mg 1x/4–6 weeks
ImplantTestosteroneTestopelPellet50–100 mg 1x/3–6 months
Notes: Premenopausal women produce about 230 ± 70 μg testosterone per day (6.4 ± 2.0 mg testosterone per 4 weeks), with a range of 130 to 330 μg per day (3.6–9.2 mg per 4 weeks). Footnotes: a = Mostly discontinued or unavailable. b = Over-the-counter. Sources: See template.

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.[12][13][11]

Side effects
See also: Prasterone § Side effects

Prasterone enanthate, in combination with estradiol valerate at the dosages used clinically, has no masculinizing side effects.[16] This is in contrast to combinations of estrogens with other androgens, such as testosterone esters.[16]

Pharmacology
See also: Prasterone § Pharmacology

Pharmacodynamics
See also: Dehydroepiandrosterone § Biological activity

Pharmacokinetics
See also: Dehydroepiandrosterone § Biochemistry
Estradiol and DHEA levels after a single intramuscular injection of Gynodian Depot (4 mg estradiol valerate, 200 mg prasterone enanthate in oil) in women.[3][2][23]

The pharmacokinetics of prasterone enanthate have been assessed in a number of studies.[2][2][24]

Prasterone enanthate is a prodrug of prasterone in the body.[3][1][2] It is completely hydrolyzed into prasterone and heptanoic acid (enanthic acid) following absorption from the tissue depot after intramuscular injection.[1]

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

Within 30 days, 91% of a dose of prasterone enanthate is eliminated.[1] Approximatley 94% is excreted in urine and 6% in feces.[1] Prasterone enanthate is eliminated mainly in the form of metabolites and conjugates.[1]

Chemistry
See also: Androgen ester and List of androgen esters § Esters of other natural AAS

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).[25][26][18]

History
See also: Prasterone § History

Prasterone enanthate was patented by Schering in 1968 and 1971.[13][18] 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.[16][17][27][13]

Society and culture

Brand names

The major brand name of the combination of estradiol valerate and prasterone enanthate is Gynodian Depot.[11][12][13][19] Other brand names of this formulation include Binodian Depot, Cidodian Depot, Klimax, and Supligol NF.[11][12][13][19]

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.[11][12][18][13][19] In Europe, it is available in Austria, the Czech Republic, France, Germany, Italy, Poland, Russia, Spain, and Switzerland.[11][12][18][13][19] In Latin America, it is available in Argentina, Chile, Mexico, and Venezuela.[11][19] 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.[11][19]

See also

References
  1. https://web.archive.org/web/20190529041314/https://compendium.ch/FrmMainMonographie.aspx?Id=4a7e55ac-b11f-4d80-96d0-b468ab0eb4e3&lang=de&MonType=fi&start=1
  2. Düsterberg B, Wendt H (1983). "Plasma levels of dehydroepiandrosterone and 17 beta-estradiol after intramuscular administration of Gynodian-Depot in 3 women". Horm. Res. 17 (2): 84–9. doi:10.1159/000179680. PMID 6220949.
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