Azastene

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]

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

Synthesis

Azastene synthesis:^[5]

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.

See also

• Cyanoketone