Nisterime acetate

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.^[2][3][1] It is an androgen ester – specifically, the C17α acetate ester of nisterime.^[2] 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.^[4]

Nisterime acetate

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[1]
Identifiers
IUPAC name [(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	51354-31-5
PubChem CID	10006270
ChemSpider	16741388
UNII	7M1ALD652F
KEGG	D05174
ChEMBL	ChEMBL2104712
CompTox Dashboard (EPA)	DTXSID60965626
Chemical and physical data
Formula	C27H35ClN2O5
Molar mass	503.04 g·mol−1
3D model (JSmol)	Interactive image
SMILES 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 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 is described as an androgen by some sources.^[2][5] 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).^[1][6] 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.^[6]