prasterone sulfate

{{About|DHEA sulfate as a medication|as a natural hormone|DHEA sulfate}}

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| IUPAC_name = [(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

| image = DHEA sulfate.png

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| image2 = Sulfato de dehidroepiandrosterona3D.png

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| tradename = Astenile, Dastonil, Di Luo An, Dinistenile, Levospa, Mylis, Sinsurrene, Teloin

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| routes_of_administration = Injection

| class = Androgen; Anabolic steroid; Androgen ester; Estrogen; Neurosteroid

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| CAS_number_Ref =

| CAS_number = 651-48-9

| CAS_supplemental =
1099-87-2

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| PubChem = 12594

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| ChemSpiderID_Ref =

| ChemSpiderID = 12074

| UNII = 57B09Q7FJR

| KEGG =

| ChEBI = 16814

| ChEMBL = 259898

| synonyms = DHEA sulfate; DHEA-S; Sodium prasterone sulfate; Sodium prasterone sulfate hydrate; KYH-3102; NSC-72822; PB-005{{cite book| vauthors = Challener CA |title=Chiral Drugs |url=https://books.google.com/books?id=hyhtAAAAMAAJ |date=1 December 2001|publisher=Wiley|isbn=978-0-566-08411-9|quote=[...] Mylis; NSC 72822; Prasterone sodium sulfate; Prasterone sodium sulfate; Sodium dehydroepiandrosterone sulfate; [...]}}

| C=19 | H=28 | O=5 | S=1

| SMILES = 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

| StdInChI_Ref =

| StdInChI = 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

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| StdInChIKey = CZWCKYRVOZZJNM-USOAJAOKSA-N

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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.{{cite journal | vauthors = Sakaguchi M, Sakai T, Adachi Y, Kawashima T, Awata N | title = The biological fate of sodium prasterone sulfate after vaginal administration. I. Absorption and excretion in rats | journal = J. Pharmacobio-Dyn. | volume = 15 | issue = 2 | pages = 67–73 | year = 1992 | pmid = 1403604 | doi = 10.1248/bpb1978.15.67| doi-access = free }}{{cite book| vauthors = Negwer M, Scharnow HG |title=Organic-chemical drugs and their synonyms: (an international survey)|url=https://books.google.com/books?id=zmpqAAAAMAAJ|year=2001|publisher=Wiley-VCH|isbn=978-3-527-30247-5|page=1831|quote=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}}{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA641|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=641–}}{{cite book| vauthors = Blunt JW, Munro MH | chapter = 3-hydroxyandrost-5-en-17-one |title=Dictionary of Marine Natural Products with CD-ROM| chapter-url = https://books.google.com/books?id=w1bLBQAAQBAJ&pg=PA1075|date=19 September 2007|publisher=CRC Press|isbn=978-0-8493-8217-8|pages=1075–}}{{cite book|vauthors = Kleemann A, Engel J, Kutscher B, Reichert D|title=Pharmaceutical Substances, 5th Edition, 2009: Syntheses, Patents and Applications of the most relevant APIs|url=https://books.google.com/books?id=fO2IAwAAQBAJ&pg=PT2441|date=14 May 2014|publisher=Thieme|isbn=978-3-13-179525-0|pages=2441–2442}}{{cite journal | vauthors = Jianqiu Y | year = 1992 | title = Clinical Application of Prasterone Sodium Sulfate | journal = Chinese Journal of New Drugs | volume = 5 | page = 015 }}{{cite journal | vauthors = Sakai T, Sakaguchi M, Adachi Y, Kawashima T, Awata N | date = 1992 | title = The Biological Fate of Sodium Prasterone Sulfate after Vaginal Administration II: Distribution after Single and Multiple Administration to Pregnant Rats. | journal = 薬物動態 (Pharmacokinetics) | volume = 7 | issue = 1 | pages = 87–101 | url = https://www.jstage.jst.go.jp/article/dmpk1986/7/1/7_1_87/_pdf | access-date = 2023-12-24 | archive-date = 2018-10-30 | archive-url = https://web.archive.org/web/20181030110302/https://www.jstage.jst.go.jp/article/dmpk1986/7/1/7_1_87/_pdf | url-status = bot: unknown }}{{Cite web|url=https://www.drugs.com/international/prasterone.html|title=Prasterone (Dehydroepiandrosterone, DHEA) vaginal Uses, Side Effects & Warnings | work = drugs.com }} 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,{{cite journal | vauthors = Mueller JW, Gilligan LC, Idkowiak J, Arlt W, Foster PA | title = The Regulation of Steroid Action by Sulfation and Desulfation | journal = Endocr. Rev. | volume = 36 | issue = 5 | pages = 526–63 | year = 2015 | pmid = 26213785 | pmc = 4591525 | doi = 10.1210/er.2015-1036 }} although it also has its own activity as a neurosteroid.{{cite journal | vauthors = Gibbs TT, Russek SJ, Farb DH | title = Sulfated steroids as endogenous neuromodulators | journal = Pharmacol. Biochem. Behav. | volume = 84 | issue = 4 | pages = 555–67 | year = 2006 | pmid = 17023038 | doi = 10.1016/j.pbb.2006.07.031 | s2cid = 33659983 }} Prasterone sulfate is used medically as the sodium salt via injection and is referred to by the name sodium prasterone sulfate ({{abbrlink|JAN|Japanese Accepted Name}}).{{Cite web|url=https://chem.nlm.nih.gov/chemidplus/rn/1099-87-2| work = ChemIDplus | publisher = U.S. National Library of Medicine | title = 1099-87-2 - GFJWACFSUSFUOG-ZJTJBYBXSA-M - Sodium prasterone sulfate [JAN] - Similar structures search, synonyms, formulas, resource links, and other chemical information}}

Prasterone sulfate is available in Japan, Italy, Portugal, Argentina, and China.{{cite web | title = Micromedex | url = https://www.micromedexsolutions.com/ | publisher = Merative US L.P. }} Brand names include Astenile, Dastonil, Di Luo An, Dinistenile, Levospa, Mylis, Sinsurrene, and Teloin.