Chemistry:Prasterone 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
Routes of; administration	Injection
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;

Short description: Medication

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).^[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]

References

↑ ^1.0 ^1.1 Organic-chemical drugs and their synonyms: (an international survey). Wiley-VCH. 2001. p. 1831. ISBN 978-3-527-30247-5. https://books.google.com/books?id=zmpqAAAAMAAJ. "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"
↑ Chiral Drugs. Wiley. 1 December 2001. ISBN 978-0-566-08411-9. https://books.google.com/books?id=hyhtAAAAMAAJ. "[...] Mylis; NSC 72822; Prasterone sodium sulfate; Prasterone sodium sulfate; Sodium dehydroepiandrosterone sulfate; [...]"
↑ ^3.0 ^3.1 "The biological fate of sodium prasterone sulfate after vaginal administration. I. Absorption and excretion in rats". J. Pharmacobio-Dyn. 15 (2): 67–73. 1992. doi:10.1248/bpb1978.15.67. PMID 1403604.
↑ The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014. pp. 641–. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA641.
↑ "3-hydroxyandrost-5-en-17-one". Dictionary of Marine Natural Products with CD-ROM. CRC Press. 19 September 2007. pp. 1075–. ISBN 978-0-8493-8217-8. https://books.google.com/books?id=w1bLBQAAQBAJ&pg=PA1075.
↑ Pharmaceutical Substances, 5th Edition, 2009: Syntheses, Patents and Applications of the most relevant APIs. Thieme. 14 May 2014. pp. 2441–2442. ISBN 978-3-13-179525-0. https://books.google.com/books?id=fO2IAwAAQBAJ&pg=PT2441.
↑ "Clinical Application of Prasterone Sodium Sulfate". Chinese Journal of New Drugs 5: 015. 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. 1992. https://web.archive.org/web/20181030110302id_/https://www.jstage.jst.go.jp/article/dmpk1986/7/1/7_1_87/_pdf.
↑ ^9.0 ^9.1 ^9.2 ^9.3 "Prasterone (Dehydroepiandrosterone, DHEA) vaginal Uses, Side Effects & Warnings". drugs.com. https://www.drugs.com/international/prasterone.html.
↑ "The Regulation of Steroid Action by Sulfation and Desulfation". Endocr. Rev. 36 (5): 526–63. 2015. doi:10.1210/er.2015-1036. PMID 26213785.
↑ "Sulfated steroids as endogenous neuromodulators". Pharmacol. Biochem. Behav. 84 (4): 555–67. 2006. doi:10.1016/j.pbb.2006.07.031. PMID 17023038.
↑ "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. https://chem.nlm.nih.gov/chemidplus/rn/1099-87-2.
↑ ^13.0 ^13.1 "Micromedex". Merative US L.P.. https://www.micromedexsolutions.com/.

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| group1 = Androgens
(incl. AAS)

| list1 =

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D₂ receptor antagonists (prolactin releasers) (e.g., domperidone, metoclopramide, risperidone, haloperidol, chlorpromazine, sulpiride)
Estrogens (e.g., bifluranol, [[diethylstilbestrol, estradiol, estradiol esters, ethinylestradiol, ethinylestradiol sulfonate, paroxypropione)
GnRH agonists (e.g., leuprorelin)
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Progestogens (incl., chlormadinone acetate, [[cyproterone acetate, hydroxyprogesterone caproate, gestonorone caproate, [[Chemistry:Medroxyprogesterone medroxyprogesterone acetate, Chemistry:Megestrol acetate|megestrol acetate]])

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^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

See also: Androgen receptor modulators; Estrogens and antiestrogens; Progestogens and antiprogestogens; List of androgens/anabolic steroids

}}

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Original source: https://en.wikipedia.org/wiki/Prasterone sulfate. Read more

[NegwerScharnow2001-1] 1.0 ^1.1 Organic-chemical drugs and their synonyms: (an international survey). Wiley-VCH. 2001. p. 1831. ISBN 978-3-527-30247-5. https://books.google.com/books?id=zmpqAAAAMAAJ. "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"

[Challener2001-2] Chiral Drugs. Wiley. 1 December 2001. ISBN 978-0-566-08411-9. https://books.google.com/books?id=hyhtAAAAMAAJ. "[...] Mylis; NSC 72822; Prasterone sodium sulfate; Prasterone sodium sulfate; Sodium dehydroepiandrosterone sulfate; [...]"

[pmid1403604-3] 3.0 ^3.1 "The biological fate of sodium prasterone sulfate after vaginal administration. I. Absorption and excretion in rats". J. Pharmacobio-Dyn. 15 (2): 67–73. 1992. doi:10.1248/bpb1978.15.67. PMID 1403604.

[Elks2014-4] The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014. pp. 641–. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA641.

[BluntMunro2007-5] "3-hydroxyandrost-5-en-17-one". Dictionary of Marine Natural Products with CD-ROM. CRC Press. 19 September 2007. pp. 1075–. ISBN 978-0-8493-8217-8. https://books.google.com/books?id=w1bLBQAAQBAJ&pg=PA1075.

[KleemannEngel2014-6] Pharmaceutical Substances, 5th Edition, 2009: Syntheses, Patents and Applications of the most relevant APIs. Thieme. 14 May 2014. pp. 2441–2442. ISBN 978-3-13-179525-0. https://books.google.com/books?id=fO2IAwAAQBAJ&pg=PT2441.

[Jianqiu1992-7] "Clinical Application of Prasterone Sodium Sulfate". Chinese Journal of New Drugs 5: 015. 1992.

[SakaiSakaguchi1992-8] "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. 1992. https://web.archive.org/web/20181030110302id_/https://www.jstage.jst.go.jp/article/dmpk1986/7/1/7_1_87/_pdf.

[Drugs.com-9] 9.0 ^9.1 ^9.2 ^9.3 "Prasterone (Dehydroepiandrosterone, DHEA) vaginal Uses, Side Effects & Warnings". drugs.com. https://www.drugs.com/international/prasterone.html.

[pmid26213785-10] "The Regulation of Steroid Action by Sulfation and Desulfation". Endocr. Rev. 36 (5): 526–63. 2015. doi:10.1210/er.2015-1036. PMID 26213785.

[pmid17023038-11] "Sulfated steroids as endogenous neuromodulators". Pharmacol. Biochem. Behav. 84 (4): 555–67. 2006. doi:10.1016/j.pbb.2006.07.031. PMID 17023038.

[ChemIDplus-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. https://chem.nlm.nih.gov/chemidplus/rn/1099-87-2.

[Micromedex-13] 13.0 ^13.1 "Micromedex". Merative US L.P.. https://www.micromedexsolutions.com/.

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5α-Reductase	Alfatradiol Dutasteride Epristeride Finasteride Saw palmetto extract
Others	Abiraterone acetate Aminoglutethimide Bifluranol Cyproterone acetate Flutamide Ketoconazole Nilutamide Seviteronel^† Spironolactone

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