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Abandoned drugs
Nisterime acetate
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    Nisterime acetate

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    Nisterime acetate
    Nisterime acetate.svg
    Clinical data
    Other names 2α-Chloro-5α-androstan-17β-ol-3-one O-(p-nitrophenyl)oxime 17β-acetate; 2α-Chloro-4,5α-dihydrotestosterone O-(p-nitrophenyl)oxime 17β-acetate; 2α-Chloro-3-(p-nitrophenoxy)imino-5α-androstan-17β-ol 17β-acetate
    Routes of
    administration    		 Oral
    Identifiers
    • [(2R,3Z,5S,8R,9S,10S,13S,14S,17S)-2-Chloro-10,13-dimethyl-3-(4-nitrophenoxy)imino-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl] acetate
    CAS Number
    PubChem CID
    ChemSpider
    UNII
    KEGG
    ChEMBL
    CompTox Dashboard (EPA)
    Chemical and physical data
    Formula C27H35ClN2O5
    Molar mass 503.04 g·mol−1
    3D model (JSmol)
    • CC(=O)O[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@@H]4[C@@]3(C[C@H](/C(=N\OC5=CC=C(C=C5)[N+](=O)[O-])/C4)Cl)C)C
    • InChI=1S/C27H35ClN2O5/c1-16(31)34-25-11-10-21-20-9-4-17-14-24(29-35-19-7-5-18(6-8-19)30(32)33)23(28)15-27(17,3)22(20)12-13-26(21,25)2/h5-8,17,20-23,25H,4,9-15H2,1-3H3/b29-24-/t17-,20-,21-,22-,23+,25-,26-,27-/m0/s1
    • Key:NNFGKFKPLQYECP-BYXNGVTISA-N

    Nisterime acetate (USAN) (developmental code name ORF-9326), also known as 2α-chloro-4,5α-dihydrotestosterone O-(p-nitrophenyl)oxime 17β-acetate or as 2α-chloro-5α-androstan-17β-ol-3-one O-(p-nitrophenyl)oxime 17β-acetate, is a synthetic, orally active anabolic-androgenic steroid (AAS) and a derivative of dihydrotestosterone (DHT) that was developed as a postcoital contraceptive but was never marketed. It is an androgen ester – specifically, the C17α acetate ester of nisterime. Unlike antiprogestogens like mifepristone, nisterime acetate does not prevent implantation and instead induces embryo resorption as well as interrupts the post-implantation stage of pregnancy.

    Nisterime acetate is described as an androgen by some sources. However, it has also been reported that the drug lacks hormonal activity in bioassays, including androgenic, estrogenic, or progestogenic activity (as well as antagonistic activity). This finding has been described as puzzling in light of the potent abortifacient activity of the drug in animals and it has been said that its mechanism of action remains unknown.

    See also



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