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Spiroxasone

Spiroxasone (INN, USAN) is a synthetic, steroidal antimineralocorticoid of the spirolactone group which was developed as a diuretic and antihypertensive agent but was never marketed.[1][2] It was synthesized and assayed in 1963.[1] The drug is 7α-acetylthiospirolactone with the ketone group removed from the C17α spirolactone ring.[1] Similarly to other spirolactones like spironolactone, spiroxasone also possesses antiandrogen activity.[3][4]

Spiroxasone
Clinical data
Routes of
administration
By mouth
Identifiers
  • S-[(7R,8R,9S,10R,13S,14S,17R)-10,13-dimethyl-3-oxospiro[2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-17,2'-oxolane]-7-yl] ethanethioate
CAS Number
  • 6673-97-8
PubChem CID
  • 23141
ChemSpider
  • 21652
UNII
  • 8P0U2ZA1NQ
KEGG
  • D05912
ChEMBL
  • ChEMBL2105514
Chemical and physical data
FormulaC24H34O3S
Molar mass402.59 g·mol−1
3D model (JSmol)
  • Interactive image
  • CC(=O)S[C@@H]1CC2=CC(=O)CC[C@@]2([C@@H]3[C@@H]1[C@@H]4CC[C@]5([C@]4(CC3)C)CCCO5)C
  • InChI=1S/C24H34O3S/c1-15(25)28-20-14-16-13-17(26)5-9-22(16,2)18-6-10-23(3)19(21(18)20)7-11-24(23)8-4-12-27-24/h13,18-21H,4-12,14H2,1-3H3/t18-,19-,20+,21+,22-,23-,24-/m0/s1
  • Key:XKCGICBTWRNUCL-KIEAKMPYSA-N

References

  1. ^ a b c J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 1114–. ISBN 978-1-4757-2085-3.
  2. ^ I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 261–. ISBN 978-94-011-4439-1.
  3. ^ Progress in Medicinal Chemistry. Elsevier. 1 January 1979. pp. 69–. ISBN 978-0-08-086264-4. Spiroxasone [...] is also an anti-androgen [379].
  4. ^ Rasmusson GH, Chen A, Reynolds GF, Patanelli DJ, Patchett AA, Arth GE (1972). "Antiandrogens. 2',3' -Tetrahydrofuran-2'spiro-17-(1,2 -methylene-4-androsten-3-ones)". J. Med. Chem. 15 (11): 1165–8. doi:10.1021/jm00281a018. PMID 4654667.



spiroxasone, usan, synthetic, steroidal, antimineralocorticoid, spirolactone, group, which, developed, diuretic, antihypertensive, agent, never, marketed, synthesized, assayed, 1963, drug, acetylthiospirolactone, with, ketone, group, removed, from, c17α, spiro. Spiroxasone INN USAN is a synthetic steroidal antimineralocorticoid of the spirolactone group which was developed as a diuretic and antihypertensive agent but was never marketed 1 2 It was synthesized and assayed in 1963 1 The drug is 7a acetylthiospirolactone with the ketone group removed from the C17a spirolactone ring 1 Similarly to other spirolactones like spironolactone spiroxasone also possesses antiandrogen activity 3 4 SpiroxasoneClinical dataRoutes ofadministrationBy mouthIdentifiersIUPAC name S 7R 8R 9S 10R 13S 14S 17R 10 13 dimethyl 3 oxospiro 2 6 7 8 9 11 12 14 15 16 decahydro 1H cyclopenta a phenanthrene 17 2 oxolane 7 yl ethanethioateCAS Number6673 97 8PubChem CID23141ChemSpider21652UNII8P0U2ZA1NQKEGGD05912ChEMBLChEMBL2105514Chemical and physical dataFormulaC 24H 34O 3SMolar mass402 59 g mol 13D model JSmol Interactive imageSMILES CC O S C H 1CC2 CC O CC C 2 C H 3 C H 1 C H 4CC C 5 C 4 CC3 C CCCO5 CInChI InChI 1S C24H34O3S c1 15 25 28 20 14 16 13 17 26 5 9 22 16 2 18 6 10 23 3 19 21 18 20 7 11 24 23 8 4 12 27 24 h13 18 21H 4 12 14H2 1 3H3 t18 19 20 21 22 23 24 m0 s1Key XKCGICBTWRNUCL KIEAKMPYSA NReferences Edit a b c J Elks 14 November 2014 The Dictionary of Drugs Chemical Data Chemical Data Structures and Bibliographies Springer pp 1114 ISBN 978 1 4757 2085 3 I K Morton Judith M Hall 6 December 2012 Concise Dictionary of Pharmacological Agents Properties and Synonyms Springer Science amp Business Media pp 261 ISBN 978 94 011 4439 1 Progress in Medicinal Chemistry Elsevier 1 January 1979 pp 69 ISBN 978 0 08 086264 4 Spiroxasone is also an anti androgen 379 Rasmusson GH Chen A Reynolds GF Patanelli DJ Patchett AA Arth GE 1972 Antiandrogens 2 3 Tetrahydrofuran 2 spiro 17 1 2 methylene 4 androsten 3 ones J Med Chem 15 11 1165 8 doi 10 1021 jm00281a018 PMID 4654667 This article about a steroid is a stub You can help Wikipedia by expanding it vte This drug article relating to the cardiovascular system is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Spiroxasone amp oldid 1120886284, wikipedia, wiki, book, books, library,

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