Prasterone sulfate

Overview

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. 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, although it also has its own activity as a neurosteroid. Prasterone sulfate is used medically as the sodium salt via injection and is referred to by the name sodium prasterone sulfate (JAN (Japanese Accepted Name)).[1–11] WP

Prasterone sulfate is available in Japan, Italy, Portugal, Argentina, and China. Brand names include Astenile, Dastonil, Di Luo An, Dinistenile, Levospa, Mylis, Sinsurrene, and Teloin.[8][12] WP

Chemistry

Formula

C19H28O5S PC

CAS number

651-48-9 PC

Molar mass (g/mol)

368.5 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] hydrogen sulfate PC

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 PC

InChIKey

CZWCKYRVOZZJNM-USOAJAOKSA-N PC

PubChem CID

12594

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

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Sources

1. Journal / agency Sakaguchi M, Sakai T, Adachi Y, Kawashima T, Awata N. The biological fate of sodium prasterone sulfate after vaginal administration. I. Absorption and excretion in rats. J. Pharmacobio-Dyn. 1992. doi:10.1248/bpb1978.15.67 · PMID 1403604
2. Other Negwer M, Scharnow HG. Organic-chemical drugs and their synonyms: (an international survey). 2001
3. Other Elks J. The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. 14 November 2014
4. Other Blunt JW, Munro MH. Dictionary of Marine Natural Products with CD-ROM. 19 September 2007
5. 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
6. Journal / agency Jianqiu Y. Clinical Application of Prasterone Sodium Sulfate. Chinese Journal of New Drugs. 1992
7. Journal / agency Sakai T, Sakaguchi M, Adachi Y, Kawashima T, Awata N. 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). 1992
8. Other Prasterone (Dehydroepiandrosterone, DHEA) vaginal Uses, Side Effects & Warnings
9. Journal / agency Mueller JW, Gilligan LC, Idkowiak J, Arlt W, Foster PA. The Regulation of Steroid Action by Sulfation and Desulfation. Endocr. Rev. 2015. doi:10.1210/er.2015-1036 · PMID 26213785 · PMC4591525
10. Journal / agency Gibbs TT, Russek SJ, Farb DH. Sulfated steroids as endogenous neuromodulators. Pharmacol. Biochem. Behav. 2006. doi:10.1016/j.pbb.2006.07.031 · PMID 17023038
11. Journal / agency 1099-87-2 - GFJWACFSUSFUOG-ZJTJBYBXSA-M - Sodium prasterone sulfate [JAN] - Similar structures search, synonyms, formulas, resource links, and other chemical information
12. Other Micromedex

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.