Synthesis of 2 beta,16 beta-bis-(4'-dimethyl-1'-piperazino)-3 alpha,17 beta-diacetoxy-5 alpha-androstane dibromide and related compounds.
A series of bisquaternary ammonio steroids having androstane skeletons have been prepared some of which possessed high neuromuscular blocking activity. One of the series 2 beta,16 beta-bis-(4'-dimethyl-1'-piperazino)-3 alpha, 17 beta-diacetoxy-5 alpha-androstane-dibromide (9, pipercurium bromide, Arduan) has proved to be a clinically useful agent of medium duration of action without side effects. The preparation of these ammonio steroids and structure-activity relationships within the series are described. The structure of 9 and related compounds was elucidated by spectrometric methods IR, NMR and MS.
D015113:Androstane-3,17-diol / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D000732:Androstanols / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D008968:Molecular Conformation; D009466:Neuromuscular Blocking Agents / Q000138:chemical synthesis*; D017300:Pipecuronium; D010879:Piperazines / Q000138:chemical synthesis*; D013329:Structure-Activity Relationship
D000732:Androstanols; D009466:Neuromuscular Blocking Agents; D010879:Piperazines; D017300:Pipecuronium; D015113:Androstane-3,17-diol