ABSTRACT
The canine phase I and phase II metabolism of the synthetic anabolic-androgenic steroid stanozolol was investigated following intramuscular injection into a male greyhound. The major phase I biotransformation was hydroxylation to give 6alpha-hydroxystanozolol which was excreted as a glucuronide conjugate and was identified by comparison with synthetically derived reference materials. An analytical procedure was developed for the detection of this stanozolol metabolite in canine urine using solid phase extraction, enzyme hydrolysis of glucuronide conjugates and analysis by positive ion electrospray ionisation ion trap LC-MS.
Subject(s)
Anabolic Agents/pharmacokinetics , Androgens/pharmacokinetics , Chromatography, Liquid/methods , Spectrometry, Mass, Electrospray Ionization/methods , Stanozolol/pharmacokinetics , Anabolic Agents/chemical synthesis , Anabolic Agents/urine , Androgens/chemical synthesis , Androgens/urine , Animals , Crystallography, X-Ray , Dogs , Magnetic Resonance Spectroscopy , Male , Models, Molecular , Stanozolol/chemical synthesis , Stanozolol/urineABSTRACT
The first synthesis of 16,16,20,20,20-pentadeuterio-3'-hydroxystanozolol (8) in 26% yield over nine steps is described using moderately priced starting materials and economic amounts of reagents. Compound 8 can be used as an internal standard in screening procedures for anabolic steroids as well as for the quantification of stanozolol metabolites via mass spectrometric techniques, such as LC-MS or gas chromatography-mass spectrometry (GC-MS).
