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Prasterone sulfate

Clinical data
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
Routes of administration	Injection
Drug class	Androgen; Anabolic steroid; Androgen ester; Estrogen; Neurosteroid
Identifiers
IUPAC name phenanthren-3-yl] hydrogen sulfate
CAS Number	651-48-9 1099-87-2
PubChem CID	12594
ChemSpider	12074
UNII	57B09Q7FJR
ChEBI	CHEBI:16814
ChEMBL	ChEMBL259898
Chemical and physical data
Formula	C19H28O5S
Molar mass	368.49 g·mol
3D model (JSmol)	Interactive image
SMILES C12CC3(1CCC2=O)CC=C43(CC(C4)OS(=O)(=O)O)C
InChI 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. 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 (JANTooltip Japanese Accepted Name).

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.

See also

• List of androgen esters § Esters of other natural AAS

References

1. ^ 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. ^ 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. Archived from the original on 2018-10-30. Retrieved 2023-12-24.{{cite journal}}: CS1 maint: bot: original URL status unknown (link)
9. ^ "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. ^ "Micromedex". Merative US L.P.

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