A 26-year-old male bodybuilder self-administering stanozolol tablets presents with pruritus, pale stools and conjugated hyperbilirubinaemia. Liver biopsy shows canalicular bile plugs without inflammation or necrosis. The chemical property of his anabolic steroid most responsible for this picture is:

• A Reduction to dihydrotestosterone, generating toxic metabolites in hepatocytes
• B Esterification at the 17-beta position, prolonging half-life and accumulating in liver
• C Aromatisation to oestradiol, causing canalicular membrane injury
• D 17-alpha alkylation, which impairs hepatic metabolism and causes cholestasis ✓

Explanation

Orally active anabolic steroids such as methyltestosterone, oxandrolone and stanozolol carry a 17-alpha alkyl group that resists first-pass hepatic metabolism. This same substitution is associated with intrahepatic cholestasis and, with prolonged use, peliosis hepatis and hepatocellular adenoma or carcinoma. Injectable testosterone esters are esterified at the 17-beta position instead and are far less hepatotoxic, making option B the key distractor to eliminate.

Reference: Katzung Basic and Clinical Pharmacology, 15th ed.

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Written and medically reviewed by the StethoPrep medical team.