Schänzer W, Opfermann G, Donike M
Institut für Biochemie, Deutsch Sporthochschule Köln, F.R.G.
J Steroid Biochem. 1990 Jun;36(1-2):153-74. doi: 10.1016/0022-4731(90)90126-d.
Urinary metabolites of stanozolol (17 alpha-methyl-17 beta-hydroxy-5 alpha-androst-2-eno(3,2-c)-pyrazole) following oral administration were isolated by chromatography on XAD-2 and by preparative high-performance liquid chromatography (HPLC) and identified by gas chromatography-mass spectrometry (GC/MS) with electron impact (EI)-ionisation. Stanozolol is excreted as a conjugate but is metabolized to a large extent. All identified metabolites are hydroxylated, namely at C-3' of the pyrazole ring and at C-4 beta, C-16 alpha and C-16 beta of the steroid. Less than 5% of the metabolites are found in the unconjugated urine fraction: 3'-hydroxy-stanozolol (II) and 3'-hydroxy-17-epistanozolol (III). Conjugated excreted metabolites are 3'-hydroxystanozolol (II), stanozolol (I), 4 beta-hydroxy-stanozolol (IV), 16 beta-hydroxystanozolol (V), 16 alpha-hydroxystanozolol (VI), two isomers of 3',16-dihydroxystanozolol (VII, VIII), two isomers of 4 beta, 16-dihydroxystanozolol (IX, X) and a 3',?-dihydroxystanozolol (XI). 3'-Hydroxystanozolol, 4 alpha-hydroxystanozolol, 4 beta-hydroxystanozolol, 16 alpha-hydroxy-, 16 alpha-hydroxy-17-epi- and 16 beta-hydroxystanozolol were synthesised to confirm the structural assignment of the main metabolites.
口服司坦唑醇（17α-甲基-17β-羟基-5α-雄甾-2-烯（3,2-c）-吡唑）后的尿液代谢物通过XAD-2柱色谱和制备型高效液相色谱（HPLC）进行分离，并通过具有电子轰击（EI）电离的气相色谱-质谱联用（GC/MS）进行鉴定。司坦唑醇以缀合物形式排泄，但在很大程度上会发生代谢。所有鉴定出的代谢物均发生了羟基化，即在吡唑环的C-3'以及甾体的C-4β、C-16α和C-16β位。在未结合的尿液组分中发现的代谢物不到5%：3'-羟基司坦唑醇（II）和3'-羟基-17-表司坦唑醇（III）。排泄的结合代谢物有3'-羟基司坦唑醇（II）、司坦唑醇（I）、4β-羟基司坦唑醇（IV）、16β-羟基司坦唑醇（V）、16α-羟基司坦唑醇（VI）、3',16-二羟基司坦唑醇的两种异构体（VII、VIII）、4β,16-二羟基司坦唑醇的两种异构体（IX、X）和一种3',?-二羟基司坦唑醇（XI）。合成了3'-羟基司坦唑醇、4α-羟基司坦唑醇、4β-羟基司坦唑醇、16α-羟基、16α-羟基-17-表-和16β-羟基司坦唑醇，以确认主要代谢物的结构归属。
