Pharmacokinetics of 2-naphthol following intrapericardial administration, and formation of 2-naphthyl-beta-D-glucoside and 2-naphthyl sulphate in the American lobster, Homarus americanus.
1. Following a 0.25-mg/kg intrapericardial dose of the phenolic compound, 2-naphthol, to the American lobster, Homarus americanus, a two-compartment model best described the disposition of parent [14C]-2-naphthol in the haemolymph. Male and female lobsters had similar alpha-phase half lives of 26 +/- 19 min (mean +/- SD, n = 4) and 29 +/- 15 min respectively. The beta-phase half lives were significantly longer in males, 63.9 +/- 30.9 h, than in females, 30.6 +/- 6.8 h (p < 0.05). The total body clearance for females was 26.4 +/- 6.5 ml x h-1 x kg-1 and was higher than that of males, 11.1 +/- 5.9 ml x h-1 x kg-1 (p < 0.05). 2. 2-Naphthol was converted to 2-naphthyl-beta-D-glucoside (major metabolite) and 2-naphthyl sulphate (minor metabolite) such that at 24 h 39-60.6% of the radioactivity in haemolymph was 2-naphthyl-beta-D-glucoside, 38.6-58.9% 2-naphthol and 0.5-4% 2-naphthyl sulphate. 3. The 2-naphthol-derived radioactivity was > 99% bound to haemolymph proteins at 1 min and > 90% bound at 1 day after the dose, indicating that both 2-naphthol and 2-naphthyl-beta-D-glucoside were highly protein bound. 4. 2-Naphthyl-beta-D-glucoside was slowly eliminated from haemolymph in both males and females, with elimination half lives of 34-78 h. 2-Naphthyl-beta-D-glucoside was the major metabolite in urine samples collected at 5 days after the dose. Hepatopancreas and antennal gland contained glucosidase activities, and the long half life of 2-naphthyl-beta-D-glucoside could be explained by conjugation deconjugation cycling. 5. 2-Naphthyl sulphate was eliminated from haemolymph with a half-life < 10 h and was excreted in urine.
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Department of Medicinal Chemistry, University of Florida, Gainesville 32610, USA.
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D000818:Animals; D005260:Female; D005960:Glucosides / Q000008:administration & dosage / Q000493:pharmacokinetics*; D006207:Half-Life; D006458:Hemolymph / Q000378:metabolism; D006868:Hydrolysis; D007267:Injections; D008099:Liver / Q000378:metabolism; D008297:Male; D008954:Models, Biological; D009284:Naphthols / Q000008:administration & dosage / Q000493:pharmacokinetics*; D008121:Nephropidae / Q000378:metabolism*; D010179:Pancreas / Q000378:metabolism; D010496:Pericardium; D011485:Protein Binding; D012679:Sense Organs / Q000378:metabolism; D013463:Sulfuric Acid Esters / Q000378:metabolism*; D014018:Tissue Distribution
D005960:Glucosides; D009284:Naphthols; D013463:Sulfuric Acid Esters; C088461:2-naphthylglucoside; C064313:2-naphthyl sulfate; C028405:2-naphthol