Prasterone sulfate

This article is about DHEA sulfate as a medication. For as a natural hormone, see DHEA sulfate.

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 [1] [2]
Routes of administration	Injection [3]
Drug class	Androgen; Anabolic steroid; Androgen ester; Estrogen; Neurosteroid
Identifiers
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
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−1
3D model (JSmol)	Interactive image
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
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. ^{[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

• 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.
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.