Prasterone sulfate

Last updated
Prasterone sulfate
DHEA sulfate.png
Sulfato de dehidroepiandrosterona3D.png
Clinical data
Trade names Astenile, Dastonil, Di Luo An, Dinistenile, Levospa, Mylis, Sinsurrene, Teloin
Other namesDHEA sulfate; DHEA-S; Sodium prasterone sulfate; Sodium prasterone sulfate hydrate; KYH-3102; NSC-72822; PB-005 [1] [2]
Routes of
administration 		Injection [3]
Drug class Androgen; Anabolic steroid; Androgen ester; Estrogen; Neurosteroid
Identifiers
  • [(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] hydrogen sulfate
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
Chemical and physical data
Formula C19H28O5S
Molar mass 368.49 g·mol−1
3D model (JSmol)
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CC=C4[C@@]3(CC[C@@H](C4)OS(=O)(=O)O)C
  • InChI=1S/C19H28O5S/c1-18-9-7-13(24-25(21,22)23)11-12(18)3-4-14-15-5-6-17(20)19(15,2)10-8-16(14)18/h3,13-16H,4-11H2,1-2H3,(H,21,22,23)/t13-,14-,15-,16-,18-,19-/m0/s1
  • Key:CZWCKYRVOZZJNM-USOAJAOKSA-N

Prasterone sulfate (brand names Astenile, Mylis, Teloin, others), also known as dehydroepiandrosterone sulfate (DHEA-S), is a naturally occurring androstane steroid which is marketed and used in Japan and other countries as a labor inducer in the treatment of insufficient cervical ripening and dilation during childbirth. [3] [1] [4] [5] [6] [7] [8] [9] It is the C3β sulfate ester of prasterone (dehydroepiandrosterone; DHEA), and is known to act as a prohormone of DHEA and by extension of androgens and estrogens, [10] although it also has its own activity as a neurosteroid. [11] Prasterone sulfate is used medically as the sodium salt via injection and is referred to by the name sodium prasterone sulfate (JAN Tooltip Japanese Accepted Name). [9] [12]

Prasterone sulfate is available in Japan, Italy, Portugal, Argentina, and China. [9] [13] Brand names include Astenile, Dastonil, Di Luo An, Dinistenile, Levospa, Mylis, Sinsurrene, and Teloin. [9] [13]

See also

Related Research Articles

<span class="mw-page-title-main">Dehydroepiandrosterone</span> Chemical compound

Dehydroepiandrosterone (DHEA), also known as androstenolone, is an endogenous steroid hormone precursor. It is one of the most abundant circulating steroids in humans. DHEA is produced in the adrenal glands, the gonads, and the brain. It functions as a metabolic intermediate in the biosynthesis of the androgen and estrogen sex steroids both in the gonads and in various other tissues. However, DHEA also has a variety of potential biological effects in its own right, binding to an array of nuclear and cell surface receptors, and acting as a neurosteroid and modulator of neurotrophic factor receptors.

<span class="mw-page-title-main">Adrenal cortex</span> Cortex of the adrenal gland

The adrenal cortex is the outer region and also the largest part of the adrenal gland. It is divided into three separate zones: zona glomerulosa, zona fasciculata and zona reticularis. Each zone is responsible for producing specific hormones. It is also a secondary site of androgen synthesis.

An androgen prohormone, or proandrogen, is a prohormone of an anabolic-androgenic steroid (AAS). They can be prohormones of testosterone or of synthetic AAS, for example, nandrolone (19-nortestosterone). Dehydroepiandrosterone (DHEA), DHEA sulfate (DHEA-S), and androstenedione may all be considered proandrogens of testosterone.

<span class="mw-page-title-main">Pregnenolone</span> Chemical compound

Pregnenolone (P5), or pregn-5-en-3β-ol-20-one, is an endogenous steroid and precursor/metabolic intermediate in the biosynthesis of most of the steroid hormones, including the progestogens, androgens, estrogens, glucocorticoids, and mineralocorticoids. In addition, pregnenolone is biologically active in its own right, acting as a neurosteroid.

<span class="mw-page-title-main">Prasterone</span> Medical usage of the prasterone compound

Prasterone, also known as dehydroepiandrosterone (DHEA) and sold under the brand name Intrarosa among others, is a medication as well as over-the-counter dietary supplement which is used to correct DHEA deficiency due to adrenal insufficiency or old age, as a component of menopausal hormone therapy, to treat painful sexual intercourse due to vaginal atrophy, and to prepare the cervix for childbirth, among other uses. It is taken by mouth, by application to the skin, in through the vagina, or by injection into muscle.

<span class="mw-page-title-main">Androstenediol</span> Chemical compound

Androstenediol, or 5-androstenediol, also known as androst-5-ene-3β,17β-diol, is an endogenous weak androgen and estrogen steroid hormone and intermediate in the biosynthesis of testosterone from dehydroepiandrosterone (DHEA). It is closely related to androstenedione (androst-4-ene-3,17-dione).

<span class="mw-page-title-main">Dehydroepiandrosterone sulfate</span> Chemical compound

Dehydroepiandrosterone sulfate, abbreviated as DHEA sulfate or DHEA-S, also known as androstenolone sulfate, is an endogenous androstane steroid that is produced by the adrenal cortex. It is the 3β-sulfate ester and a metabolite of dehydroepiandrosterone (DHEA) and circulates in far greater relative concentrations than DHEA. The steroid is hormonally inert and is instead an important neurosteroid and neurotrophin.

<span class="mw-page-title-main">Steroid sulfatase</span> Protein-coding gene in the species Homo sapiens

Steroid sulfatase (STS), or steryl-sulfatase, formerly known as arylsulfatase C, is a sulfatase enzyme involved in the metabolism of steroids. It is encoded by the STS gene.

<span class="mw-page-title-main">16α-Hydroxy-DHEA</span> Chemical compound

16α-Hydroxydehydroepiandrosterone is an endogenous metabolite of dehydroepiandrosterone (DHEA). Both 16α-OH-DHEA and its 3β-sulfate ester, 16α-OH-DHEA-S, are intermediates in the biosynthesis of estriol from dehydroepiandrosterone (DHEA). 16α-OH-DHEA has estrogenic activity.

<span class="mw-page-title-main">Pregnenolone sulfate</span> Chemical compound

Pregnenolone sulfate is an endogenous excitatory neurosteroid that is synthesized from pregnenolone. It is known to have cognitive and memory-enhancing, antidepressant, anxiogenic, and proconvulsant effects.

<span class="mw-page-title-main">7-Keto-DHEA</span> Chemical compound

7-Ketodehydroepiandrosterone (7-keto-DHEA,7-oxo-DHEA), also known as 7-oxoprasterone, is a prohormone produced by metabolism of the prohormone dehydroepiandrosterone (DHEA).

A steroidogenesis inhibitor, also known as a steroid biosynthesis inhibitor, is a type of drug which inhibits one or more of the enzymes that are involved in the process of steroidogenesis, the biosynthesis of endogenous steroids and steroid hormones. They may inhibit the production of cholesterol and other sterols, sex steroids such as androgens, estrogens, and progestogens, corticosteroids such as glucocorticoids and mineralocorticoids, and neurosteroids. They are used in the treatment of a variety of medical conditions that depend on endogenous steroids.

<span class="mw-page-title-main">Prasterone enanthate</span> Chemical compound

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.

<span class="mw-page-title-main">1-Androsterone</span> Chemical compound

1-Androsterone is a synthetic, orally active anabolic-androgenic steroid (AAS). It is an androgen prohormone of 1-testosterone (dihydroboldenone), 1-androstenedione, and other 1-dehydrogenated androstanes. The drug has been sold on the Internet as a designer steroid and "dietary supplement". It is a positional isomer of dehydroepiandrosterone.

Adrenal steroids are steroids that are derived from the adrenal glands. They include corticosteroids, which consist of glucocorticoids like cortisol and mineralocorticoids like aldosterone, adrenal androgens like dehydroepiandrosterone (DHEA), DHEA sulfate (DHEA-S), and androstenedione (A4), and neurosteroids like DHEA and DHEA-S, as well as pregnenolone and pregnenolone sulfate (P5-S). Adrenal steroids are specifically produced in the adrenal cortex.

<span class="mw-page-title-main">Sturamustine</span> Chemical compound

Sturamustine, also known as dehydroepiandrosterone (DHEA) 17β-N-(2-chloroethyl)-N-nitrosourea, is a synthetic androstane steroid and a C17β nitrosourea conjugate of dehydroepiandrosterone (DHEA) which was developed as a cytostatic antineoplastic agent for the treatment of hormone-dependent tumors but was never marketed. It was synthesized in 1982.

<span class="mw-page-title-main">Estradiol valerate/prasterone enanthate</span> Combination drug

Estradiol valerate/prasterone enanthate (EV/DHEA-E), sold under the brand name Gynodian Depot among others, is an injectable combination medication of estradiol valerate (EV), an estrogen, and prasterone enanthate (DHEA-E), an androgen, estrogen, and neurosteroid, which is used in menopausal hormone therapy for women. It is provided in the form of 1 mL ampoules containing 4 mg estradiol valerate and 200 mg prasterone enanthate in an oil solution and is administered by intramuscular injection once every 4 to 6 weeks. EV/DHEA-E reportedly has a duration of about 21 days.

<span class="mw-page-title-main">Androstenetriol</span> Chemical compound

Androstenetriol is a steroid produced in the adrenal glands as a metabolite of DHEA. It is believed to have similar effects as DHEA and androstenediol. A study in rodents found that the compound was a weak androgen and estrogen, but did not attach to the androgen, estrogen, progesterone, or glucocorticoid receptors. Synthetic analogs of AET known as HE3286 and NE3107 have been developed.

References

  1. 1 2 Negwer M, Scharnow HG (2001). Organic-chemical drugs and their synonyms: (an international survey). Wiley-VCH. p. 1831. ISBN   978-3-527-30247-5. 3β-Hydroxyandrost-5-en-17-one hydrogen sulfate = (3β)-3-(Sulfooxy)androst-5-en-17-one. R: Sodium salt (1099-87-2). S: Astenile, Dehydroepiandrosterone sulfate sodium, DHA-S, DHEAS, KYH 3102, Mylis, PB 005, Prasterone sodium sulfate, Teloin
  2. ↑ Challener CA (1 December 2001). Chiral Drugs. Wiley. ISBN   978-0-566-08411-9. [...] Mylis; NSC 72822; Prasterone sodium sulfate; Prasterone sodium sulfate; Sodium dehydroepiandrosterone sulfate; [...]
  3. 1 2 Sakaguchi M, Sakai T, Adachi Y, Kawashima T, Awata N (1992). "The biological fate of sodium prasterone sulfate after vaginal administration. I. Absorption and excretion in rats". J. Pharmacobio-Dyn. 15 (2): 67–73. doi: 10.1248/bpb1978.15.67 . PMID   1403604.
  4. ↑ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 641–. ISBN   978-1-4757-2085-3.
  5. ↑ Blunt JW, Munro MH (19 September 2007). "3-hydroxyandrost-5-en-17-one". Dictionary of Marine Natural Products with CD-ROM. CRC Press. pp. 1075–. ISBN   978-0-8493-8217-8.
  6. ↑ Kleemann A, Engel J, Kutscher B, Reichert D (14 May 2014). Pharmaceutical Substances, 5th Edition, 2009: Syntheses, Patents and Applications of the most relevant APIs. Thieme. pp. 2441–2442. ISBN   978-3-13-179525-0.
  7. ↑ Jianqiu Y (1992). "Clinical Application of Prasterone Sodium Sulfate". Chinese Journal of New Drugs. 5: 015.
  8. ↑ Sakai T, Sakaguchi M, Adachi Y, Kawashima T, Awata N (1992). "The Biological Fate of Sodium Prasterone Sulfate after Vaginal Administration II: Distribution after Single and Multiple Administration to Pregnant Rats". 薬物動態 (Pharmacokinetics). 7 (1): 87–101.
  9. 1 2 3 4 "Prasterone (Dehydroepiandrosterone, DHEA) vaginal Uses, Side Effects & Warnings". drugs.com.
  10. ↑ Mueller JW, Gilligan LC, Idkowiak J, Arlt W, Foster PA (2015). "The Regulation of Steroid Action by Sulfation and Desulfation". Endocr. Rev. 36 (5): 526–63. doi:10.1210/er.2015-1036. PMC   4591525 . PMID   26213785.
  11. ↑ Gibbs TT, Russek SJ, Farb DH (2006). "Sulfated steroids as endogenous neuromodulators". Pharmacol. Biochem. Behav. 84 (4): 555–67. doi:10.1016/j.pbb.2006.07.031. PMID   17023038. S2CID   33659983.
  12. ↑ "1099-87-2 - GFJWACFSUSFUOG-ZJTJBYBXSA-M - Sodium prasterone sulfate [JAN] - Similar structures search, synonyms, formulas, resource links, and other chemical information". ChemIDplus. U.S. National Library of Medicine.
  13. 1 2 "Micromedex". Merative US L.P.


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