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m sockvasion, with typical RS fail
 
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{{Short description|Chemical compound}}
{{Chembox
{{Drugbox
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| ImageFile = Epostane.svg
| ImageSize = 200px
| Verifiedfields =
| ImageAlt =
| Watchedfields =
| IUPACName =
| verifiedrevid =
| IUPAC_name = 4α,5α-Epoxy-3,17β-dihydroxy-4β,17α-dimethylandrost-2-ene-2-carbonitrile
⚫
| OtherNames = Win-32729
⚫
| image = Epostane.svg
|Section1={{Chembox Identifiers
| CASNo =
| width = 250px

<!--Clinical data-->
| tradename =
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA =
| legal_UK =
| legal_US =
| legal_status =
| routes_of_administration =

<!--Pharmacokinetic data-->
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =

<!-- Identifiers -->
| CAS_number_Ref =
| CAS_number = 80471-63-2
| CAS_supplemental =
⚫
| class =
| ATC_prefix =
| ATC_suffix =
| ATC_supplemental =
| PubChem = 6917713
| PubChem = 6917713
| IUPHAR_ligand =
⚫
| InChI=1S/C22H31NO3/c1-18-8-6-16-14(15(18)7-9-20(18,3)25)5-10-22-19(16,2)11-13(12-23)17(24)21(22,4)26-22/h14-16,24-25H,5-11H2,1-4H3/t14-,15-,16-,18-,19+,20-,21+,22-/m0/s1
| DrugBank_Ref =
⚫
| InChIKey= CETKWEWBSMKADK-GSXVSZIWSA-N
| DrugBank =
⚫
| SMILES =C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C)O)CC[C@]45[C@@]3(CC(=C([C@]4(O5)C)O)C#N)C }}
| ChemSpiderID_Ref =
|Section2={{Chembox Properties
| ChemSpiderID = 5292942
| UNII = 6375T36951
| KEGG =
| ChEBI =
| ChEMBL = 2106218

<!--Chemical data-->
| C=22 | H=31 | N=1 | O=3
| C=22 | H=31 | N=1 | O=3
⚫
| SMILES = C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C)O)CC[C@]45[C@@]3(CC(=C([C@]4(O5)C)O)C#N)C
| Appearance =
| Density =
| StdInChI_Ref =
⚫
| StdInChI = 1S/C22H31NO3/c1-18-8-6-16-14(15(18)7-9-20(18,3)25)5-10-22-19(16,2)11-13(12-23)17(24)21(22,4)26-22/h14-16,24-25H,5-11H2,1-4H3/t14-,15-,16-,18-,19+,20-,21+,22-/m0/s1
| MeltingPt =
| BoilingPt =
| StdInChIKey_Ref =
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| StdInChIKey = CETKWEWBSMKADK-GSXVSZIWSA-N
| Solubility = }}
⚫
| synonyms = WIN-32729
|Section3={{Chembox Hazards
| MainHazards =
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| FlashPt =
| AutoignitionPt = }}
}}
}}


'''Epostane''' ([[International Nonproprietary Name|INN]], [[United States Adopted Name|USAN]], [[British Approved Name|BAN]]) (developmental code name '''WIN-32729''') is an [[enzyme inhibitor|inhibitor]] of [[3β-hydroxysteroid dehydrogenase]] (3β-HSD) that was developed as an [[contraceptive]], [[abortifacient]], and [[oxytocic]] [[drug]] but was never marketed.<ref name="Elks2014">{{cite book|author=J. Elks|title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA492|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=492–}}</ref><ref name="MortonHall2012">{{cite book|author1=I.K. Morton|author2=Judith M. Hall|title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms|url=https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA113|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-4439-1|pages=113–}}</ref> By inhibiting 3β-HSD, epostane blocks the [[biosynthesis]] of [[progesterone]] from [[pregnenolone]] (and also the conversion of [[dehydroepiandrosterone]] to [[androstenedione]]), thereby functioning as an [[antiprogestogen]] and terminating [[pregnancy]].<ref name="Elks2014" /> The drug was trialed and in a study was found to be slightly more effective at inducing [[medical abortion|abortion]] relative to [[mifepristone]].<ref name="Lachelin2013">{{cite book|author=Gillian C. L. Lachelin|title=Introduction to Clinical Reproductive Endocrinology|url=https://books.google.com/books?id=RaHpAgAAQBAJ&pg=PA198|date=11 September 2013|publisher=Elsevier Science|isbn=978-1-4831-9380-9|pages=198–}}</ref>
'''Epostane''' ([[International Nonproprietary Name|INN]], [[United States Adopted Name|USAN]], [[British Approved Name|BAN]]) (developmental code name '''WIN-32729''') is an [[enzyme inhibitor|inhibitor]] of [[3β-hydroxysteroid dehydrogenase]] (3β-HSD) that was developed as a [[contraceptive]], [[abortifacient]], and [[oxytocic]] [[drug]] but was never marketed.<ref name="Elks2014">{{cite book | vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA492|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=492–}}</ref><ref name="MortonHall2012">{{cite book| vauthors = Morton IK, Hall JM |title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms|url=https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA113|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-4439-1|pages=113–}}</ref><ref name="Milne2018">{{cite book| vauthors = Milne GW |title=Drugs: Synonyms and Properties: Synonyms and Properties|url=https://books.google.com/books?id=xUlaDwAAQBAJ&pg=PT23|date=8 May 2018|publisher=Taylor & Francis|isbn=978-1-351-78989-9|pages=23–}}</ref> By inhibiting 3β-HSD, epostane blocks the [[biosynthesis]] of [[progesterone]] from [[pregnenolone]] (and also the conversion of [[dehydroepiandrosterone]] to [[androstenedione]]), thereby functioning as an [[antiprogestogen]] and terminating [[pregnancy]].<ref name="Elks2014" /> The drug was trialed and in a study was found to be slightly more effective at inducing [[medical abortion|abortion]] relative to [[mifepristone]].<ref name="Lachelin2013">{{cite book| vauthors = Lachelin GC |title=Introduction to Clinical Reproductive Endocrinology|url=https://books.google.com/books?id=RaHpAgAAQBAJ&pg=PA198|date=11 September 2013|publisher=Elsevier Science|isbn=978-1-4831-9380-9|pages=198–}}</ref>
<!--

==Synthesis==
==Synthesis==
[[File:Epostane synthesis.png|thumb|center|500px|Epostane synthesis: [[Sterling Drug]], R. G. Christiansen, {{Cite patent|DE|2855091}} (1979).]]
[[File:Epostane synthesis.png|thumb|center|500px|Epostane synthesis: [[Sterling Drug]], R. G. Christiansen, {{Cite patent|DE|2855091}} (1979).]]-->

==See also==
* [[Nisterime]]
* [[Trilostane]]


==References==
==References==
{{Reflist|2}}
{{Reflist|2}}


[[Category:3β-Hydroxysteroid dehydrogenase inhibitors]]

⚫
[[Category:Androstanes]]
{{Steroid hormone metabolism modulators}}

[[Category:Antiprogestogens]]
[[Category:Antiprogestogens]]
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[[Category:Steroids]]
[[Category:Nitriles]]
[[Category:Nitriles]]
[[Category:Epoxides]]
[[Category:Epoxides]]
[[Category:Enzyme inhibitors]]
[[Category:1-Methylcyclopentanols]]
[[Category:Enols]]

[[Category:Cyclohexenols]]
[[Category:Sterols]]


{{steroid-stub}}
{{steroid-stub}}

Latest revision as of 10:07, 9 January 2023

Epostane
Clinical data
Other namesWIN-32729
Identifiers
  • 4α,5α-Epoxy-3,17β-dihydroxy-4β,17α-dimethylandrost-2-ene-2-carbonitrile
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC22H31NO3
Molar mass357.494 g·mol−1
3D model (JSmol)
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C)O)CC[C@]45[C@@]3(CC(=C([C@]4(O5)C)O)C#N)C
  • InChI=1S/C22H31NO3/c1-18-8-6-16-14(15(18)7-9-20(18,3)25)5-10-22-19(16,2)11-13(12-23)17(24)21(22,4)26-22/h14-16,24-25H,5-11H2,1-4H3/t14-,15-,16-,18-,19+,20-,21+,22-/m0/s1
  • Key:CETKWEWBSMKADK-GSXVSZIWSA-N

Epostane (INN, USAN, BAN) (developmental code name WIN-32729) is an inhibitor of 3β-hydroxysteroid dehydrogenase (3β-HSD) that was developed as a contraceptive, abortifacient, and oxytocic drug but was never marketed.[1][2][3] By inhibiting 3β-HSD, epostane blocks the biosynthesis of progesterone from pregnenolone (and also the conversion of dehydroepiandrosterone to androstenedione), thereby functioning as an antiprogestogen and terminating pregnancy.[1] The drug was trialed and in a study was found to be slightly more effective at inducing abortion relative to mifepristone.[4]

See also

[edit]

References

[edit]
  1. ^ a b Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 492–. ISBN 978-1-4757-2085-3.
  2. ^ Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 113–. ISBN 978-94-011-4439-1.
  3. ^ Milne GW (8 May 2018). Drugs: Synonyms and Properties: Synonyms and Properties. Taylor & Francis. pp. 23–. ISBN 978-1-351-78989-9.
  4. ^ Lachelin GC (11 September 2013). Introduction to Clinical Reproductive Endocrinology. Elsevier Science. pp. 198–. ISBN 978-1-4831-9380-9.
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