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Abandoned drugs
BMS-641988
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    BMS-641988

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    BMS-641988
    BMS-641988.svg
    Clinical data
    Routes of
    administration    		 By mouth
    Drug class Nonsteroidal antiandrogen
    Identifiers
    • N-[(3aR,4R,5R,7R,7aS)-2-[4-cyano-3-(trifluoromethyl)phenyl]-4,7-dimethyl-1,3-dioxo-3a,5,6,7a-tetrahydro-octahydro-1H-4,7-epoxyisoindol-5-yl]ethanesulfonamide
    CAS Number
    PubChem CID
    UNII
    ChEBI
    ChEMBL
    CompTox Dashboard (EPA)
    Chemical and physical data
    Formula C20H20F3N3O5S
    Molar mass 471.45 g·mol−1
    3D model (JSmol)
    • CCS(=O)(=O)N[C@@H]1C[C@@]2([C@@H]3[C@H]([C@]1(O2)C)C(=O)N(C3=O)C4=CC(=C(C=C4)C#N)C(F)(F)F)C
    • InChI=1S/C20H20F3N3O5S/c1-4-32(29,30)25-13-8-18(2)14-15(19(13,3)31-18)17(28)26(16(14)27)11-6-5-10(9-24)12(7-11)20(21,22)23/h5-7,13-15,25H,4,8H2,1-3H3/t13-,14-,15+,18-,19+/m1/s1
    • Key:HYNANJUKEMCYEQ-HIGHGGLBSA-N

    BMS-641988 is a nonsteroidal antiandrogen which was developed by Bristol-Myers Squibb for the treatment of prostate cancer but was never marketed. It acts as a potent competitive antagonist of the androgen receptor (AR) (Ki = 10 nM; IC50 = 56 nM). The drug was found to have 20-fold higher affinity for the AR than bicalutamide in MDA-MB-453 cells, and showed 3- to 7-fold the antiandrogenic activity of bicalutamide in vitro. It may have some weak partial agonist activity at the androgen receptor. BMS-641988 is transformed by CYP3A4 into BMS-570511, and this metabolite is then reduced to BMS-501949 by cytosolic reductases. All three compounds show similar antiandrogenic activity. In addition to its antiandrogenic activity, BMS-641988 shows activity as a negative allosteric modulator of the GABAA receptor, and can produce seizures in animals at sufficiently high doses. It also shows some drug-induced QT prolongation. BMS-641988 reached phase I clinical trials prior to the discontinuation of its development. The clinical development of BMS-641988 was terminated due to the occurrence of a seizure in a patient during a phase I study.

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