Azastene

Azastene
Clinical data
Other names	WIN-17625; 4,4,17α-Trimethylandrosta-2,5-dieno(2,3-d)isoxazol-17β-ol
Identifiers
	IUPAC name (1S,3aS,3bR,10aR,10bS,12aS)-1,6,6,10a,12a-Pentamethyl-2,3,3a,3b,4,6,10,10a,10b,11,12,12a-dodecahydro-1H-cyclopenta[7,8]phenanthro[3,2-d][1,2]oxazol-1-ol;
CAS Number	13074-00-5;
PubChem CID	11725766;
ChemSpider	9900482;
UNII	1XA84ITL1H;
ChEMBL	ChEMBL2103987;
CompTox Dashboard (EPA)	DTXSID801180403 ;
Chemical and physical data
Formula	C23H33NO2
Molar mass	355.522 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C)O)CC=C4[C@@]3(CC5=C(C4(C)C)ON=C5)C;
	InChI InChI=1S/C23H33NO2/c1-20(2)18-7-6-15-16(21(18,3)12-14-13-24-26-19(14)20)8-10-22(4)17(15)9-11-23(22,5)25/h7,13,15-17,25H,6,8-12H2,1-5H3/t15-,16+,17+,21-,22+,23+/m1/s1; Key:AXLOCHLTNQDFFS-BESJYZOMSA-N;

Azastene (INN, USAN) (developmental code name WIN-17625) is a steroidogenesis inhibitor described as a contraceptive, luteolytic, and abortifacient which was never marketed.^[1]^[2] It acts as a competitive inhibitor of 3β-hydroxysteroid dehydrogenase (IC₅₀ = 1 μM), and thereby inhibiting the formation of progesterone, corticosteroids, androgens, and estrogens.^[3]^[4] Due to inhibition of corticosteroid synthesis, azastene is immunosuppressive.^[2]

Synthesis

One synthesis of this compound involves initial alkylation of methyl testosterone by means of strong base and methyl iodide to afford the 4,4-dimethyl derivative. Formylation with alkoxide and methyl formate leads to the 2-hydroxymethyl derivative. Reaction of this last with hydroxylamine leads to formation of an isoxazole ring. There is then obtained azastene.

References

^ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 113–. ISBN 978-1-4757-2085-3.
^ ^a ^b Milne GW (8 May 2018). Drugs: Synonyms and Properties: Synonyms and Properties. Taylor & Francis. pp. 1457–. ISBN 978-1-351-78989-9.
^ Runnebaum B, Rabe T, Kiesel L (6 December 2012). Future Aspects in Contraception: Proceeding of an International Symposium held in Heidelberg, 5–8 September 1984 Part 1 Male Contraception. Springer Science & Business Media. pp. 74–. ISBN 978-94-009-4910-2.
^ Singh H, Jindal DP, Yadav MR, Kumar M (1991). "Heterosteroids and drug research". Progress in Medicinal Chemistry. 28: 233–300. doi:10.1016/s0079-6468(08)70366-7. ISBN 978-0-08-086276-7. PMID 1843548.
^ US 3966926, Potts, Gordon O., "Composition of a steroidal[2,3-d]-isoxazole and method of use thereof", published 1976-06-29, assigned to Sterling Drug Inc. .

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[Elks2014-1] Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 113–. ISBN 978-1-4757-2085-3.

[Milne2018-2] Milne GW (8 May 2018). Drugs: Synonyms and Properties: Synonyms and Properties. Taylor & Francis. pp. 1457–. ISBN 978-1-351-78989-9.

[RunnebaumRabe2012-3] Runnebaum B, Rabe T, Kiesel L (6 December 2012). Future Aspects in Contraception: Proceeding of an International Symposium held in Heidelberg, 5–8 September 1984 Part 1 Male Contraception. Springer Science & Business Media. pp. 74–. ISBN 978-94-009-4910-2.

[pmid1843548-4] Singh H, Jindal DP, Yadav MR, Kumar M (1991). "Heterosteroids and drug research". Progress in Medicinal Chemistry. 28: 233–300. doi:10.1016/s0079-6468(08)70366-7. ISBN 978-0-08-086276-7. PMID 1843548.

[5] US 3966926, Potts, Gordon O., "Composition of a steroidal[2,3-d]-isoxazole and method of use thereof", published 1976-06-29, assigned to Sterling Drug Inc. .

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Synthesis

See also

References