Medication
This article is about DHEA sulfate as a medication. For as a natural hormone, see
DHEA sulfate .
Prasterone sulfate Trade names Astenile, Dastonil, Di Luo An, Dinistenile, Levospa, Mylis, Sinsurrene, Teloin Other names DHEA 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
[(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 Formula C 19 H 28 O 5 S 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]
^ a b 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
^ 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; [...]
^ a b 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 .
^ 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 .
^ 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 .
^ 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 .
^ Jianqiu Y (1992). "Clinical Application of Prasterone Sodium Sulfate". Chinese Journal of New Drugs . 5 : 015.
^ 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.
^ a b c d "Prasterone (Dehydroepiandrosterone, DHEA) vaginal Uses, Side Effects & Warnings" . drugs.com .
^ 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 .
^ 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 .
^ "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.
^ a b "Micromedex" . Merative US L.P.